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76-09-5,MFCD00149294
Catalog No.:AA0035EU

76-09-5 | Pinacol

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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA0035EU
Chemical Name:
Pinacol
CAS Number:
76-09-5
Molecular Formula:
C6H14O2
Molecular Weight:
118.1742
MDL Number:
MFCD00149294
SMILES:
CC(C(O)(C)C)(O)C
NSC Number:
25943
Properties
Properties
 
BP:
174.4°C at 760 mmHg  
Form:
Solid  
MP:
40-43 °C(lit.)  
Refractive Index:
1.4347 (estimate)  
Solubility:
alcohol: freely soluble  
Stability:
Hygroscopic  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
72.5  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
8  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
1  
XLogP3:
0.1  

Literature

Title: Frustrated Lewis pair inspired carbon dioxide reduction by a ruthenium tris(aminophosphine) complex.

Journal: Angewandte Chemie (International ed. in English) 20121105

Title: Pinacolborane as the boron source in nitrogen-directed borylations of aromatic N,N-dimethylhydrazones.

Journal: The Journal of organic chemistry 20121102

Title: Taking the F out of FLP: simple Lewis acid-base pairs for mild reductions with neutral boranes via borenium ion catalysis.

Journal: Journal of the American Chemical Society 20121024

Title: Ruthenium catalyzed hydroboration of terminal alkynes to Z-vinylboronates.

Journal: Journal of the American Chemical Society 20120905

Title: Synthesis and antimitotic and tubulin interaction profiles of novel pinacol derivatives of podophyllotoxins.

Journal: Journal of medicinal chemistry 20120809

Title: Beyond benzyl grignards: facile generation of benzyl carbanions from styrenes.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20120723

Title: Aerobic oxidation reactions catalyzed by vanadium complexes of bis(phenolate) ligands.

Journal: Inorganic chemistry 20120702

Title: Synthesis of taxane ABC tricyclic skeleton from lycoctonine.

Journal: Natural product communications 20120601

Title: Total syntheses of hopeanol and hopeahainol A empowered by a chiral Brønsted acid induced pinacol rearrangement.

Journal: Angewandte Chemie (International ed. in English) 20120423

Title: Regioselective synthesis of 1,2-dihydropyridines by rhodium-catalyzed hydroboration of pyridines.

Journal: Journal of the American Chemical Society 20120227

Title: Palladium-catalyzed synthesis of terminal acetals via highly selective anti-Markovnikov nucleophilic attack of pinacol on vinylarenes, allyl ethers, and 1,5-dienes.

Journal: Chemical communications (Cambridge, England) 20120128

Title: Catalytic non-conventional trans-hydroboration: a theoretical and experimental perspective.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20120127

Title: Ionic crystals [M3O(OOCC6H5)6(H2O)3]4[α-SiW12O40] (M = Cr, Fe) as heterogeneous catalysts for pinacol rearrangement.

Journal: Inorganic chemistry 20120116

Title: Highly selective trifluoromethylation of 1,3-disubstituted arenes through iridium-catalyzed arene borylation.

Journal: Angewandte Chemie (International ed. in English) 20120109

Title: Transition-metal-catalyzed synthesis of diboranes(4).

Journal: Angewandte Chemie (International ed. in English) 20111223

Title: Hydride as a leaving group in the reaction of pinacolborane with halides under ambient Grignard and Barbier conditions. One-pot synthesis of alkyl, aryl, heteroaryl, vinyl, and allyl pinacolboronic esters.

Journal: The Journal of organic chemistry 20111202

Title: Completing the puzzle of aurachin biosynthesis in Stigmatella aurantiaca Sg a15.

Journal: Molecular bioSystems 20111201

Title: Stereoselective construction of quaternary carbon stereocenters via a semipinacol rearrangement strategy.

Journal: Accounts of chemical research 20111115

Title: 1,2-Bis(benz-yloxy)-1,2-bis-(4-chloro-phen-yl)-3,8-dimeth-oxy-acenaphthene.

Journal: Acta crystallographica. Section E, Structure reports online 20111001

Title: Alkoxide-catalyzed reduction of ketones with pinacolborane.

Journal: The Journal of organic chemistry 20110805

Title: An efficient copper(I)-catalyst system for the asymmetric hydroboration of β-substituted vinylarenes with pinacolborane.

Journal: Chemistry, an Asian journal 20110801

Title: 4,4,5,5-Tetra-methyl-1,3,2λ-dioxa-phospho-lan-2-one.

Journal: Acta crystallographica. Section E, Structure reports online 20110801

Title: Structure-based design of novel boronic acid-based inhibitors of autotaxin.

Journal: Journal of medicinal chemistry 20110714

Title: Silver-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with β-boryl acrylates.

Journal: The Journal of organic chemistry 20110318

Title: New developments in aromatic halogenation, borylation, and cyanation.

Journal: Chimia 20110101

Title: Chiral Brønsted acid catalyzed pinacol rearrangement.

Journal: Angewandte Chemie (International ed. in English) 20101210

Title: Diols and anions can control the formation of an exciplex between a pyridinium boronic acid with an aryl group connected via a propylene linker.

Journal: Chemical communications (Cambridge, England) 20101121

Title: Catalytic activity of phosphine-copper complexes for hydroboration of styrene with pinacolborane: experiment and theory.

Journal: The journal of physical chemistry. A 20101118

Title: 1-Bromo-3-(1',1'-dimethylalkyl)-1-deoxy-Δ(8)-tetrahydrocannabinols: New selective ligands for the cannabinoid CB(2) receptor.

Journal: Bioorganic & medicinal chemistry 20101115

Title: An opportunity for Mg-catalyzed Grignard-type reactions: direct coupling of benzylic halides with pinacolborane with 10 mol % of magnesium.

Journal: Journal of the American Chemical Society 20100901

Title: Isolation and reactivity of palladium hydrido complexes: intermediates in the hydrodefluorination of pentafluoropyridine.

Journal: Dalton transactions (Cambridge, England : 2003) 20100828

Title: C-H bond activation/borylation of furans and thiophenes catalyzed by a half-sandwich iron N-heterocyclic carbene complex.

Journal: Chemistry, an Asian journal 20100705

Title: The synthesis and NMR investigation on novel boron derivatives of stavudine.

Journal: Bioorganic chemistry 20100601

Title: Synthesis of notoamide J: a potentially pivotal intermediate in the biosynthesis of several prenylated indole alkaloids.

Journal: The Journal of organic chemistry 20100507

Title: Borinium cations as sigma-B-H ligands in osmium complexes.

Journal: Journal of the American Chemical Society 20100428

Title: Catalytic asymmetric conjugate addition of alpha-cyanoketones for the construction of a quaternary stereogenic center.

Journal: Organic letters 20100402

Title: Regio- and stereoselective Ni-catalyzed 1,4-hydroboration of 1,3-dienes: access to stereodefined (Z)-allylboron reagents and derived allylic alcohols.

Journal: Journal of the American Chemical Society 20100303

Title: Dramatic effect of Lewis acids on the rhodium-catalyzed hydroboration of olefins.

Journal: Journal of the American Chemical Society 20100113

Title: Highly regio- and stereoselective synthesis of (Z)-trisubstituted alkenes via propyne bromoboration and tandem Pd-catalyzed cross-coupling.

Journal: Organic letters 20090917

Title: Rationally improved chiral Brønsted acid for catalytic enantioselective allylboration of aldehydes with an expanded reagent scope.

Journal: The Journal of organic chemistry 20090605

Title: Synthesis of 1-borylisoindoles via palladium-catalyzed dehydrogenation/C-H borylation of isoindolines.

Journal: Journal of the American Chemical Society 20090506

Title: Unexpected Ti(III)/Mn-promoted pinacol coupling of ketones.

Journal: The Journal of organic chemistry 20090501

Title: Reduction of benzophenones with SmI2. Post electron transfer processes.

Journal: The Journal of organic chemistry 20090306

Title: Demonstration that CobG, the monooxygenase associated with the ring contraction process of the aerobic cobalamin (vitamin B12) biosynthetic pathway, contains an Fe-S center and a mononuclear non-heme iron center.

Journal: The Journal of biological chemistry 20090220

Title: Diastereoselective intramolecular pinacol couplings of sulfinyl iron(0) diene complexes.

Journal: The Journal of organic chemistry 20090220

Title: Aerobic oxidation of pinacol by vanadium(V) dipicolinate complexes: evidence for reduction to vanadium(III).

Journal: Journal of the American Chemical Society 20090121

Title: Selectivity control in Lewis acid catalyzed regiodivergent tandem cationic cyclization/ring expansion terminated by pinacol rearrangement.

Journal: Angewandte Chemie (International ed. in English) 20090101

Title: Activation of B-H bonds by an oxo-rhenium complex.

Journal: Dalton transactions (Cambridge, England : 2003) 20081221

Title: Asymmetric reductive Mannich reaction to ketimines catalyzed by a Cu(I) complex.

Journal: Journal of the American Chemical Society 20081203

Title: Diastereoselective addition of zincated hydrazones to alkenylboronates and stereospecific trapping of boron/zinc bimetallic intermediates by carbon electrophiles.

Journal: Journal of the American Chemical Society 20081119

Title: Diastereoselective synthesis of cyclopentanediols by InCl 3/Al mediated intramolecular pinacol coupling reaction in aqueous media.

Journal: Molecules (Basel, Switzerland) 20081027

Title: Ionic-liquid-promoted decaborane olefin-hydroboration: a new efficient route to 6-R-B10H13 derivatives.

Journal: Inorganic chemistry 20081020

Title: Total syntheses of (+)- and (-)-peribysin E.

Journal: Journal of the American Chemical Society 20081015

Title: Synthesis, characterization, and reactivity of rhodium(I) acetylacetonato complexes containing pyridinecarboxaldimine ligands.

Journal: Inorganic chemistry 20081006

Title: Analysis of recognition of fructose by imprinted polymers.

Journal: Talanta 20080915

Title: Pinacol macrocyclization-based route to the polyfused medium-sized CDE ring system of lancifodilactone G.

Journal: Organic letters 20080904

Title: Sigma-borane complexes of iridium: synthesis and structural characterization.

Journal: Journal of the American Chemical Society 20080813

Title: 9,9-Dioctyl-2,7-bis-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene.

Journal: Acta crystallographica. Section E, Structure reports online 20080801

Title: An expeditious one-step entry to the tetracyclic core of integrastatins.

Journal: Chemical communications (Cambridge, England) 20080721

Title: An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane.

Journal: The Journal of organic chemistry 20080718

Title: Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol x SnCl4 complexes. optimization, substrate scope and mechanistic investigations.

Journal: Journal of the American Chemical Society 20080702

Title: rac-(2R,3S)-2-Phenyl-3-(3-phenyl-1,2,3,4-tetra-hydro-quinoxalin-2-yl)quinoxaline.

Journal: Acta crystallographica. Section E, Structure reports online 20080701

Title: Gold(I)-catalyzed divergence in the reactivity of 3-silyloxy 1,6-enynes: pinacol-terminated vs claisen-terminated cyclization cascades.

Journal: Organic letters 20080619

Title: Sequential Ni-catalyzed borylation and cross-coupling of aryl halides via in situ prepared neopentylglycolborane.

Journal: Organic letters 20080619

Title: Stereochemical nonrigidity of a chiral rhodium boryl hydride complex: a sigma-borane complex as transition state for isomerization.

Journal: Journal of the American Chemical Society 20080402

Title: Efficient amide-directed catalytic asymmetric hydroboration.

Journal: Journal of the American Chemical Society 20080326

Title: On the role of samarium/HMPA in the post electron-transfer steps in SmI2 reductions.

Journal: Organic letters 20080306

Title: Thermometric MIP sensor for fructosyl valine.

Journal: Biosensors & bioelectronics 20080227

Title: Stepwise oxygenation of pinacolborane by a rhodiumperoxo complex: detection of an intermediate metal borate and perborate.

Journal: Angewandte Chemie (International ed. in English) 20080101

Title: Enantioselective pinacol coupling of aryl aldehydes catalyzed by chiral Salan-Mo(IV) complexes.

Journal: The Journal of organic chemistry 20071221

Title: The skeletal rearrangement of gold- and platinum-catalyzed cycloisomerization of cis-4,6-dien-1-yn-3-ols: pinacol rearrangement and formation of bicyclo[4.1.0]heptenone and reorganized styrene derivatives.

Journal: Journal of the American Chemical Society 20071219

Title: Samarium(ii) iodide-mediated intramolecular pinacol coupling reactions with cyclopropyl ketones.

Journal: Chemical communications (Cambridge, England) 20071207

Title: Room temperature-stable electride as a synthetic organic reagent: application to pinacol coupling reaction in aqueous media.

Journal: Organic letters 20071011

Title: Theoretical study of the role of solvent H2O in neopentyl and pinacol rearrangements.

Journal: Journal of computational chemistry 20070715

Title: Palladium-catalyzed cyclization of 1,omega-dienols: multiple ways to intramolecularly trap a carbocation.

Journal: The Journal of organic chemistry 20070622

Title: Development of fructosyl valine binding polymers by covalent imprinting.

Journal: Biosensors & bioelectronics 20070615

Title: One-pot synthesis of arylboronic acids and aryl trifluoroborates by Ir-catalyzed borylation of arenes.

Journal: Organic letters 20070301

Title: Catalyzed tandem reaction of 3-silyloxy-1,5-enynes consisting of cyclization and pinacol rearrangement.

Journal: Angewandte Chemie (International ed. in English) 20070101

Title: Synthetic studies toward (-)-FR901483 using a conjugate allylation to install the C-1 quaternary carbon.

Journal: The Journal of organic chemistry 20061208

Title: Luminescence tuning of organoboron quinolates through substituent variation at the 5-position of the quinolato moiety.

Journal: Organic letters 20061109

Title: TADDOL-derived phosphites and phosphoramidites for efficient rhodium-catalyzed asymmetric hydroboration.

Journal: Organic letters 20060706

Title: Mechanisms of glycerol dehydration.

Journal: The journal of physical chemistry. A 20060511

Title: Novel calixarene hemisphere synthesized via pinacol rearrangement of [2.1.2.1]metacyclophane.

Journal: Organic letters 20060511

Title: The uptake of methyl vinyl ketone, methacrolein, and 2-methyl-3-butene-2-ol onto sulfuric acid solutions.

Journal: The journal of physical chemistry. A 20060223

Title: Studies of low-coordinate iron dinitrogen complexes.

Journal: Journal of the American Chemical Society 20060125

Title: Formation of arylboronates by a CuI-catalyzed coupling reaction of pinacolborane with aryl iodides at room temperature.

Journal: Organic letters 20060119

Title: New enantioselective entry to cycloheptane amino acid polyols.

Journal: The Journal of organic chemistry 20060106

Title: Stereoselective pinacol coupling of chiral formylferrocene using divalent samarium triflate: preparation of a new chiral bisferrocenyl oxazoline ligand and its application to asymmetric Diels-Alder reactions.

Journal: Organic letters 20051222

Title: The unusual phases of anhydrous and hydrated pinacol.

Journal: Acta crystallographica. Section B, Structural science 20051201

Title: A density functional study of propylene glycol conversion to propanal and propanone of various acid-catalyzed reaction models: a water-addition effect.

Journal: Journal of computational chemistry 20051130

Title: Samarium diiodide-induced intramolecular pinacol coupling of dinitrones: synthesis of cyclic cis-vicinal diamines.

Journal: Chemical communications (Cambridge, England) 20051121

Title: Novel multichiral diols and diamines by highly stereoselective pinacol coupling of planar chiral [2.2]paracyclophane derivatives.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20051118

Title: Nickel-catalyzed trans-alkynylboration of alkynes via activation of a boron-chlorine bond.

Journal: Journal of the American Chemical Society 20051116

Title: Vanadium-catalyzed pinacol coupling reaction in water.

Journal: The Journal of organic chemistry 20051014

Title: Preparation and Suzuki-Miyaura coupling reactions of tetrahydropyridine-2-boronic acid pinacol esters.

Journal: The Journal of organic chemistry 20050902

Title: Tetracyanoanthraquinodimethanes with a chiral amide group: preparation, properties, and charge-transfer photochirogenetic reaction with 1,2-dianisylacenaphthene-1,2-diol.

Journal: The Journal of organic chemistry 20050708

Title: Syntheses and reactions of the bis-boryloxide O(Bpin)2(pin = O2C2Me4).

Journal: Dalton transactions (Cambridge, England : 2003) 20050621

Title: Steric effects in metathesis and reduction reactions of phosphinimines with catechol- and pinacolboranes.

Journal: Inorganic chemistry 20050613

Title: Synthesis of planar-chiral paracyclophanes via samarium(II)-catalyzed intramolecular pinacol coupling.

Journal: Organic letters 20050609

Title: Highly functionalised cyclobutanols via samarium(II) iodide-induced pinacol cyclisations of carbohydrate-derived 1,4-diketones.

Journal: Carbohydrate research 20050523

Title: Ketone-imide versus ketone-oxime reductive cross-coupling promoted by samarium diiodide: new mechanistic insight gained from a failed aminocyclopentitol synthesis.

Journal: The Journal of organic chemistry 20050513

Title: Samarium diiodide-catalyzed diastereoselective pinacol couplings.

Journal: Organic letters 20050512

Title: A chelation effect on the pathway between intramolecular hydrodimerization and pinacol coupling.

Journal: Organic letters 20050414

Title: Pinacol coupling of aromatic aldehydes and ketones using TiCl3-Mg under ultrasound irradiation.

Journal: Ultrasonics sonochemistry 20050401

Title: Rhodium boryl complexes in the catalytic, terminal functionalization of alkanes.

Journal: Journal of the American Chemical Society 20050302

Title: Six- and eightfold palladium-catalyzed cross-coupling reactions of hexa- and octabromoarenes.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20041217

Title: Ring expansion-annulation strategy for the synthesis of substituted azulenes and oligoazulenes. 2. Synthesis of azulenyl halides, sulfonates, and azulenylmetal compounds and their application in transition-metal-mediated coupling reactions.

Journal: The Journal of organic chemistry 20041210

Title: In quest of factors that control the enantioselective catalytic Markovnikov hydroboration/oxidation of vinylarenes.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20041203

Title: Efficient analyte oxidation in an electrospray ion source using a porous flow-through electrode emitter.

Journal: Journal of the American Society for Mass Spectrometry 20041201

Title: Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis.

Journal: Organic letters 20041125

Title: Catalytic, highly enantio- and diastereoselective pinacol coupling reaction with a new tethered bis(8-quinolinolato) ligand.

Journal: Journal of the American Chemical Society 20041020

Title: The potential of photochemical transition metal reactions in prebiotic organic synthesis. I. Observed conversion of methanol into ethylene glycol as possible prototype for sugar alcohol formation.

Journal: Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life 20041001

Title: Regio- and enantiocontrol in the room-temperature hydroboration of vinyl arenes with pinacol borane.

Journal: Journal of the American Chemical Society 20040804

Title: Theoretical study of reaction pathways for the rhodium phosphine-catalysed borylation of C-H bonds with pinacolborane.

Journal: Dalton transactions (Cambridge, England : 2003) 20040521

Title: Reaction of tin porphyrins with vicinal diols.

Journal: Inorganic chemistry 20040405

Title: Photochemical pinacol rearrangements of unsymmetrical diols.

Journal: The Journal of organic chemistry 20040319

Title: Palladium-catalyzed cross-coupling of stereospecific potassium cyclopropyl trifluoroborates with aryl bromides.

Journal: Organic letters 20040205

Title: Metal-catalyzed reactions of diborons for synthesis of organoboron compounds.

Journal: Chemical record (New York, N.Y.) 20040101

Title: Room temperature borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane catalyzed by iridium complexes in an inert solvent.

Journal: Chemical communications (Cambridge, England) 20031207

Title: Synthesis of 2,3-substituted thienylboronic acids and esters.

Journal: The Journal of organic chemistry 20031128

Title: Synthesis of arylboronates by the palladium catalysed cross-coupling reaction in ionic liquids.

Journal: Organic & biomolecular chemistry 20031007

Title: Waste-free and facile solid-state protection of diamines, anthranilic acid, diols, and polyols with phenylboronic acid.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20030905

Title: Truly catalytic and enantioselective pinacol coupling of aryl aldehydes mediated by chiral Ti(III) complexes.

Journal: The Journal of organic chemistry 20030711

Title: New mixed phosphonate esters by transesterification of pinacol phosphonates and their use in aldehyde and ketone coupling reactions with nonstabilized phosphonates.

Journal: The Journal of organic chemistry 20030221

Title: A novel, solventless reductive coupling of carbonyl compounds by alkali metals, catalysed by bromobenzene.

Journal: Chemical communications (Cambridge, England) 20030221

Title: Pinacol coupling reaction of beta-halo-alpha,beta-unsaturated aldehydes promoted by TiI4.

Journal: Organic letters 20021114

Title: Mechanistic insight into fragmentation reactions of titanapinacolate complexes.

Journal: Journal of the American Chemical Society 20021016

Title: A sigma 4, lambda 5-phosphinine palladium complex: a new type of phosphorus ligand and catalyst. Application to the Pd-catalyzed formation of arylboronic esters.

Journal: Chemical communications (Cambridge, England) 20020807

Title: Novel Brønsted acidic ionic liquids and their use as dual solvent-catalysts.

Journal: Journal of the American Chemical Society 20020529

Title: sigma-Borane and dihydroborate complexes of ruthenium.

Journal: Journal of the American Chemical Society 20020522

Title: Efficient synthesis and hydrolysis of cyclic oxalate esters of glycols.

Journal: Chemical & pharmaceutical bulletin 20020301

Title: Microwave-assisted synthesis of pinacol boronates from aryl chlorides catalyzed by a palladium/imidazolium salt system.

Journal: Organic letters 20020221

Title: Rhodium-catalyzed, regiospecific functionalization of polyolefins in the melt.

Journal: Journal of the American Chemical Society 20020220

Title: Enantioselective pinacol coupling of aldehydes mediated and catalyzed by chiral titanium complexes.

Journal: Organic letters 20011129

Title: Synthesis of novel, potent, diol-based HIV-1 protease inhibitors via intermolecular pinacol homocoupling of (2S)-2-benzyloxymethyl-4-phenylbutanal.

Journal: Journal of medicinal chemistry 20011011

Title: Photochemical reactions and on-line UV detection in microfabricated reactors.

Journal: Lab on a chip 20010901

Title: Reactions of aliphatic ketones R2CO (R=Me, Et, iPr and tBu) with the MCI4/Li(Hg) system (M=U or Ti): mechanistic analogies between the McMurry, Wittig, and Clemmensen reactions.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20010716

Title: Diastereoselective inter- and intramolecular pinacol coupling of aldehydes promoted by monomeric titanocene(II) complex Cp(2)TiPh.

Journal: The Journal of organic chemistry 20010601

Title: Hydroboration of unsaturated phosphonic esters: synthesis of boronophosphonates and trisubstituted vinylphosphonates.

Journal: Organic letters 20010125

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Tags:76-09-5 Molecular Formula|76-09-5 MDL|76-09-5 SMILES|76-09-5 Pinacol |Organic_Building_Blocks