634-97-9,MFCD00005219
Catalog No.:AA0035H7

634-97-9 | Pyrrole-2-carboxylic acid

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Purity
Availability
Price(USD)
Quantity
  
1g
>97%
in stock  
$10.00   $7.00
- +
5g
>97%
in stock  
$16.00   $11.00
- +
25g
98%
in stock  
$28.00   $19.00
- +
  • Technical Information
  • Properties
  • Literature
  • Application
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA0035H7
Chemical Name:
Pyrrole-2-carboxylic acid
CAS Number:
634-97-9
Molecular Formula:
C5H5NO2
Molecular Weight:
111.0987
MDL Number:
MFCD00005219
SMILES:
OC(=O)c1ccc[nH]1
NSC Number:
48130
Properties
Properties
 
BP:
340.3°C at 760 mmHg  
Form:
Solid  
MP:
204-208 °C(dec.)(lit.)  
Refractive Index:
1.441-1.445  
Solubility:
Soluble in methanol.  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
103  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
8  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0  
Rotatable Bond Count:
1  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
0.8  

Literature

Title: Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics.

Journal: Scientific reports 20180101

Title: Functionalized polypyrrole nanotube arrays as electrochemical biosensor for the determination of copper ions.

Journal: Analytica chimica acta 20121009

Title: Molecular structure, spectral studies, intra and intermolecular interactions analyses in a novel ethyl 4-[3-(2-chloro-phenyl)-acryloyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate and its dimer: A combined DFT and AIM approach.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20120801

Title: An in vivo highly antitumor-active tetrazolato-bridged dinuclear platinum(II) complex largely circumvents in vitro cisplatin resistance: two linkage isomers yield the same product upon reaction with 9-ethylguanine but exhibit different cytotoxic profiles.

Journal: Metallomics : integrated biometal science 20120701

Title: Dichloridobis(4-pyridylmethyl 1H-pyrrole-2-carboxyl-ate-κN)zinc.

Journal: Acta crystallographica. Section E, Structure reports online 20120301

Title: Total syntheses of (-)-hanishin, (-)-longamide B, and (-)-longamide B methyl ester via a novel preparation of N-substituted pyrrole-2-carboxylates [corrected].

Journal: Organic letters 20120217

Title: 2-(4-Chloro-N-{2-[(1H-pyrrol-2-yl)carbon-yloxy]eth-yl}anilino)ethyl 1H-pyrrole-2-carboxyl-ate.

Journal: Acta crystallographica. Section E, Structure reports online 20120201

Title: Biosynthesis of the nargenicin A1 pyrrole moiety from Nocardia sp. CS682.

Journal: Applied microbiology and biotechnology 20120101

Title: Labelless impedance immunosensor based on polypyrrole-pyrolecarboxylic acid copolymer for hCG detection.

Journal: Talanta 20111015

Title: Large-scale conformational changes of Trypanosoma cruzi proline racemase predicted by accelerated molecular dynamics simulation.

Journal: PLoS computational biology 20111001

Title: Production of anticancer polyenes through precursor-directed biosynthesis.

Journal: Organic & biomolecular chemistry 20110921

Title: Identifying chelators for metalloprotein inhibitors using a fragment-based approach.

Journal: Journal of medicinal chemistry 20110127

Title: In vitro secretion and activity profiles of matrix metalloproteinases, MMP-9 and MMP-2, in human term extra-placental membranes after exposure to Escherichia coli.

Journal: Reproductive biology and endocrinology : RB&E 20110101

Title: Sulfur-containing constituents and one 1H-pyrrole-2-carboxylic acid derivative from pineapple [Ananas comosus (L.) Merr.] fruit.

Journal: Phytochemistry 20101201

Title: Theoretical description of hydrogen bonding in oxalic acid dimer and trimer based on the combined extended-transition-state energy decomposition analysis and natural orbitals for chemical valence (ETS-NOCV).

Journal: Journal of molecular modeling 20101101

Title: Polypyrrole nanowire modified with Gly-Gly-His tripeptide for electrochemical detection of copper ion.

Journal: Biosensors & bioelectronics 20101015

Title: Hydrolytic decarboxylation of carboxylic acids and the formation of protonated carbonic acid.

Journal: Journal of the American Chemical Society 20100224

Title: Metabolomic analysis in severe childhood pneumonia in the Gambia, West Africa: findings from a pilot study.

Journal: PloS one 20100101

Title: A submarine journey: the pyrrole-imidazole alkaloids.

Journal: Marine drugs 20091201

Title: Inhibition of Trypanosoma cruzi proline racemase affects host-parasite interactions and the outcome of in vitro infection.

Journal: Memorias do Instituto Oswaldo Cruz 20091201

Title: Synthesis of an amine-oleate derivative using an ionic liquid catalyst.

Journal: Journal of agricultural and food chemistry 20090923

Title: Experimental and computational study on the molecular energetics of 2-pyrrolecarboxylic acid and 1-methyl-2-pyrrolecarboxylic acid.

Journal: The journal of physical chemistry. A 20090903

Title: Decarboxylation via addition of water to a carboxyl group: acid catalysis of pyrrole-2-carboxylic acid.

Journal: Journal of the American Chemical Society 20090826

Title: Proline racemases are conserved mitogens: characterization of a Trypanosoma vivax proline racemase.

Journal: Molecular and biochemical parasitology 20090601

Title: 1H-Pyrrole-2-carboxylic acid.

Journal: Acta crystallographica. Section E, Structure reports online 20090501

Title: Biosynthesis of pyrrolylpolyenes in Auxarthron umbrinum.

Journal: Organic & biomolecular chemistry 20090107

Title: GPR12 selections of the metabolites from an endophytic Streptomyces sp. associated with Cistanches deserticola.

Journal: Archives of pharmacal research 20080901

Title: Pyrrole-2-carboxylic acid as a ligand for the Cu-catalyzed reactions of primary anilines with aryl halides.

Journal: The Journal of organic chemistry 20080704

Title: The discovery of fused pyrrole carboxylic acids as novel, potent D-amino acid oxidase (DAO) inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20080601

Title: 2-(1H-pyrrolyl)carboxylic acids as pigment precursors in garlic greening.

Journal: Journal of agricultural and food chemistry 20080227

Title: Suppression of blood lipid concentrations by volatile Maillard reaction products.

Journal: Nutrition (Burbank, Los Angeles County, Calif.) 20080101

Title: Structurally unique inhibitors of human mitogen-activated protein kinase phosphatase-1 identified in a pyrrole carboxamide library.

Journal: The Journal of pharmacology and experimental therapeutics 20070901

Title: SmI(2)-promoted radical addition reactions with N-(2-Indolylacyl)oxazolidinones: synthesis of bisindole compounds.

Journal: The Journal of organic chemistry 20070525

Title: Molecular and structural discrimination of proline racemase and hydroxyproline-2-epimerase from nosocomial and bacterial pathogens.

Journal: PloS one 20070101

Title: 4,5-Diaryl-1H-pyrrole-2-carboxylates as combretastatin A-4/lamellarin T hybrids: synthesis and evaluation as anti-mitotic and cytotoxic agents.

Journal: Bioorganic & medicinal chemistry 20060701

Title: Ionization of zwitterionic amine substrates bound to monomeric sarcosine oxidase.

Journal: Biochemistry 20051227

Title: Crystal structures of Delta1-piperideine-2-carboxylate/Delta1-pyrroline-2-carboxylate reductase belonging to a new family of NAD(P)H-dependent oxidoreductases: conformational change, substrate recognition, and stereochemistry of the reaction.

Journal: The Journal of biological chemistry 20051209

Title: Acyl transfer in clorobiocin biosynthesis: involvement of several proteins in the transfer of the pyrrole-2-carboxyl moiety to the deoxysugar.

Journal: Chembiochem : a European journal of chemical biology 20051201

Title: Dimers of formic acid, acetic acid, formamide and pyrrole-2-carboxylic acid: an ab initio study.

Journal: The journal of physical chemistry. A 20050728

Title: Weak carbon-hydrogen-nitrogen interactions affect the heterocyclic ligand bonding modes in barium complexes containing eta2-tetrazolato and eta2-pentazolato ligands.

Journal: Inorganic chemistry 20050711

Title: A guided inquiry experiment for the measurement of activation energies in the biophysical chemistry laboratory: Decarboxylation of pyrrole-2-carboxylate.

Journal: Biochemistry and molecular biology education : a bimonthly publication of the International Union of Biochemistry and Molecular Biology 20050301

Title: New synthetic equivalent of nitromalonaldehyde treatable in organic media.

Journal: The Journal of organic chemistry 20041126

Title: Oxidation of 3,4-dehydro-D-proline and other D-amino acid analogues by D-alanine dehydrogenase from Escherichia coli.

Journal: FEMS microbiology letters 20040915

Title: A likely biogenetic gateway linking 2-aminoimidazolinone metabolites of sponges to proline: spontaneous oxidative conversion of the pyrrole-proline-guanidine pseudo-peptide to dispacamide A.

Journal: Journal of the American Chemical Society 20040825

Title: Brominated pyrrole alkaloids from marine Agelas sponges reduce depolarization-induced cellular calcium elevation.

Journal: Toxicon : official journal of the International Society on Toxinology 20040701

Title: CloN6, a novel methyltransferase catalysing the methylation of the pyrrole-2-carboxyl moiety of clorobiocin.

Journal: Chembiochem : a European journal of chemical biology 20030804

Title: CloN2, a novel acyltransferase involved in the attachment of the pyrrole-2-carboxyl moiety to the deoxysugar of clorobiocin.

Journal: Microbiology (Reading, England) 20030801

Title: Polynuclear palladium complexes with 3,5-dimethylpyrazolate exhibiting three different coordination modes.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20030721

Title: Genetic analysis of the biosynthesis of the pyrrole and carbamoyl moieties of coumermycin A1 and novobiocin.

Journal: Molecular genetics and genomics : MGG 20021101

Title: Monomeric sarcosine oxidase: role of histidine 269 in catalysis.

Journal: Biochemistry 20020806

Title: Vibrational spectrum of methyl pyrrole-2-carboxylate.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20020101

Title: Conversion of pyrrole to pyrrole-2-carboxylate by cells of Bacillus megaterium in supercritical CO2.

Journal: Chemical communications (Cambridge, England) 20011107

Title: Inhibition of Escherichia coli CTP synthase by glutamate gamma-semialdehyde and the role of the allosteric effector GTP in glutamine hydrolysis.

Journal: The Biochemical journal 20010515

Title: Characterization of the FAD-containing N-methyltryptophan oxidase from Escherichia coli.

Journal: Biochemistry 20010206

Title: Computer-assisted design, synthesis and biological evaluation of novel pyrrolyl heteroaryl sulfones targeted at HIV-1 reverse transcriptase as non-nucleoside inhibitors.

Journal: Bioorganic & medicinal chemistry 20000901

Title: He XX, et al. Pelopuradazole, a new imidazole derivative alkaloid from the marine bacteria Pelomonas puraquae sp. nov. Nat Prod Res. 2014;28(9):680-2.

Application
Pyrrole-2-carboxylic acid is utilized in the synthesis of cholecystokinin antagonists, benzopyran antihypertensives, and azepinediones.
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Tags:634-97-9 Molecular Formula|634-97-9 MDL|634-97-9 SMILES|634-97-9 Pyrrole-2-carboxylic acid
Catalog No.: AA0035H7
634-97-9,MFCD00005219
634-97-9 | Pyrrole-2-carboxylic acid
Pack Size: 1g
Purity: >97%
in stock
$10.00 $7.00
Pack Size: 5g
Purity: >97%
in stock
$16.00 $11.00
Pack Size: 25g
Purity: 98%
in stock
$28.00 $19.00
Quantity
- +
Add to Card
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Technical Information
Catalog Number: AA0035H7
Chemical Name: Pyrrole-2-carboxylic acid
CAS Number: 634-97-9
Molecular Formula: C5H5NO2
Molecular Weight: 111.0987
MDL Number: MFCD00005219
SMILES: OC(=O)c1ccc[nH]1
NSC Number: 48130
Properties
BP: 340.3°C at 760 mmHg  
Form: Solid  
MP: 204-208 °C(dec.)(lit.)  
Refractive Index: 1.441-1.445  
Solubility: Soluble in methanol.  
Storage: Keep in dry area;Room Temperature;  
Complexity: 103  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 8  
Hydrogen Bond Acceptor Count: 2  
Hydrogen Bond Donor Count: 2  
Isotope Atom Count: 0  
Rotatable Bond Count: 1  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 0.8  
Literature fold

Title: Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics.

Journal: Scientific reports20180101

Title: Functionalized polypyrrole nanotube arrays as electrochemical biosensor for the determination of copper ions.

Journal: Analytica chimica acta20121009

Title: Molecular structure, spectral studies, intra and intermolecular interactions analyses in a novel ethyl 4-[3-(2-chloro-phenyl)-acryloyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate and its dimer: A combined DFT and AIM approach.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy20120801

Title: An in vivo highly antitumor-active tetrazolato-bridged dinuclear platinum(II) complex largely circumvents in vitro cisplatin resistance: two linkage isomers yield the same product upon reaction with 9-ethylguanine but exhibit different cytotoxic profiles.

Journal: Metallomics : integrated biometal science20120701

Title: Dichloridobis(4-pyridylmethyl 1H-pyrrole-2-carboxyl-ate-κN)zinc.

Journal: Acta crystallographica. Section E, Structure reports online20120301

Title: Total syntheses of (-)-hanishin, (-)-longamide B, and (-)-longamide B methyl ester via a novel preparation of N-substituted pyrrole-2-carboxylates [corrected].

Journal: Organic letters20120217

Title: 2-(4-Chloro-N-{2-[(1H-pyrrol-2-yl)carbon-yloxy]eth-yl}anilino)ethyl 1H-pyrrole-2-carboxyl-ate.

Journal: Acta crystallographica. Section E, Structure reports online20120201

Title: Biosynthesis of the nargenicin A1 pyrrole moiety from Nocardia sp. CS682.

Journal: Applied microbiology and biotechnology20120101

Title: Labelless impedance immunosensor based on polypyrrole-pyrolecarboxylic acid copolymer for hCG detection.

Journal: Talanta20111015

Title: Large-scale conformational changes of Trypanosoma cruzi proline racemase predicted by accelerated molecular dynamics simulation.

Journal: PLoS computational biology20111001

Title: Production of anticancer polyenes through precursor-directed biosynthesis.

Journal: Organic & biomolecular chemistry20110921

Title: Identifying chelators for metalloprotein inhibitors using a fragment-based approach.

Journal: Journal of medicinal chemistry20110127

Title: In vitro secretion and activity profiles of matrix metalloproteinases, MMP-9 and MMP-2, in human term extra-placental membranes after exposure to Escherichia coli.

Journal: Reproductive biology and endocrinology : RB&E20110101

Title: Sulfur-containing constituents and one 1H-pyrrole-2-carboxylic acid derivative from pineapple [Ananas comosus (L.) Merr.] fruit.

Journal: Phytochemistry20101201

Title: Theoretical description of hydrogen bonding in oxalic acid dimer and trimer based on the combined extended-transition-state energy decomposition analysis and natural orbitals for chemical valence (ETS-NOCV).

Journal: Journal of molecular modeling20101101

Title: Polypyrrole nanowire modified with Gly-Gly-His tripeptide for electrochemical detection of copper ion.

Journal: Biosensors & bioelectronics20101015

Title: Hydrolytic decarboxylation of carboxylic acids and the formation of protonated carbonic acid.

Journal: Journal of the American Chemical Society20100224

Title: Metabolomic analysis in severe childhood pneumonia in the Gambia, West Africa: findings from a pilot study.

Journal: PloS one20100101

Title: A submarine journey: the pyrrole-imidazole alkaloids.

Journal: Marine drugs20091201

Title: Inhibition of Trypanosoma cruzi proline racemase affects host-parasite interactions and the outcome of in vitro infection.

Journal: Memorias do Instituto Oswaldo Cruz20091201

Title: Synthesis of an amine-oleate derivative using an ionic liquid catalyst.

Journal: Journal of agricultural and food chemistry20090923

Title: Experimental and computational study on the molecular energetics of 2-pyrrolecarboxylic acid and 1-methyl-2-pyrrolecarboxylic acid.

Journal: The journal of physical chemistry. A20090903

Title: Decarboxylation via addition of water to a carboxyl group: acid catalysis of pyrrole-2-carboxylic acid.

Journal: Journal of the American Chemical Society20090826

Title: Proline racemases are conserved mitogens: characterization of a Trypanosoma vivax proline racemase.

Journal: Molecular and biochemical parasitology20090601

Title: 1H-Pyrrole-2-carboxylic acid.

Journal: Acta crystallographica. Section E, Structure reports online20090501

Title: Biosynthesis of pyrrolylpolyenes in Auxarthron umbrinum.

Journal: Organic & biomolecular chemistry20090107

Title: GPR12 selections of the metabolites from an endophytic Streptomyces sp. associated with Cistanches deserticola.

Journal: Archives of pharmacal research20080901

Title: Pyrrole-2-carboxylic acid as a ligand for the Cu-catalyzed reactions of primary anilines with aryl halides.

Journal: The Journal of organic chemistry20080704

Title: The discovery of fused pyrrole carboxylic acids as novel, potent D-amino acid oxidase (DAO) inhibitors.

Journal: Bioorganic & medicinal chemistry letters20080601

Title: 2-(1H-pyrrolyl)carboxylic acids as pigment precursors in garlic greening.

Journal: Journal of agricultural and food chemistry20080227

Title: Suppression of blood lipid concentrations by volatile Maillard reaction products.

Journal: Nutrition (Burbank, Los Angeles County, Calif.)20080101

Title: Structurally unique inhibitors of human mitogen-activated protein kinase phosphatase-1 identified in a pyrrole carboxamide library.

Journal: The Journal of pharmacology and experimental therapeutics20070901

Title: SmI(2)-promoted radical addition reactions with N-(2-Indolylacyl)oxazolidinones: synthesis of bisindole compounds.

Journal: The Journal of organic chemistry20070525

Title: Molecular and structural discrimination of proline racemase and hydroxyproline-2-epimerase from nosocomial and bacterial pathogens.

Journal: PloS one20070101

Title: 4,5-Diaryl-1H-pyrrole-2-carboxylates as combretastatin A-4/lamellarin T hybrids: synthesis and evaluation as anti-mitotic and cytotoxic agents.

Journal: Bioorganic & medicinal chemistry20060701

Title: Ionization of zwitterionic amine substrates bound to monomeric sarcosine oxidase.

Journal: Biochemistry20051227

Title: Crystal structures of Delta1-piperideine-2-carboxylate/Delta1-pyrroline-2-carboxylate reductase belonging to a new family of NAD(P)H-dependent oxidoreductases: conformational change, substrate recognition, and stereochemistry of the reaction.

Journal: The Journal of biological chemistry20051209

Title: Acyl transfer in clorobiocin biosynthesis: involvement of several proteins in the transfer of the pyrrole-2-carboxyl moiety to the deoxysugar.

Journal: Chembiochem : a European journal of chemical biology20051201

Title: Dimers of formic acid, acetic acid, formamide and pyrrole-2-carboxylic acid: an ab initio study.

Journal: The journal of physical chemistry. A20050728

Title: Weak carbon-hydrogen-nitrogen interactions affect the heterocyclic ligand bonding modes in barium complexes containing eta2-tetrazolato and eta2-pentazolato ligands.

Journal: Inorganic chemistry20050711

Title: A guided inquiry experiment for the measurement of activation energies in the biophysical chemistry laboratory: Decarboxylation of pyrrole-2-carboxylate.

Journal: Biochemistry and molecular biology education : a bimonthly publication of the International Union of Biochemistry and Molecular Biology20050301

Title: New synthetic equivalent of nitromalonaldehyde treatable in organic media.

Journal: The Journal of organic chemistry20041126

Title: Oxidation of 3,4-dehydro-D-proline and other D-amino acid analogues by D-alanine dehydrogenase from Escherichia coli.

Journal: FEMS microbiology letters20040915

Title: A likely biogenetic gateway linking 2-aminoimidazolinone metabolites of sponges to proline: spontaneous oxidative conversion of the pyrrole-proline-guanidine pseudo-peptide to dispacamide A.

Journal: Journal of the American Chemical Society20040825

Title: Brominated pyrrole alkaloids from marine Agelas sponges reduce depolarization-induced cellular calcium elevation.

Journal: Toxicon : official journal of the International Society on Toxinology20040701

Title: CloN6, a novel methyltransferase catalysing the methylation of the pyrrole-2-carboxyl moiety of clorobiocin.

Journal: Chembiochem : a European journal of chemical biology20030804

Title: CloN2, a novel acyltransferase involved in the attachment of the pyrrole-2-carboxyl moiety to the deoxysugar of clorobiocin.

Journal: Microbiology (Reading, England)20030801

Title: Polynuclear palladium complexes with 3,5-dimethylpyrazolate exhibiting three different coordination modes.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)20030721

Title: Genetic analysis of the biosynthesis of the pyrrole and carbamoyl moieties of coumermycin A1 and novobiocin.

Journal: Molecular genetics and genomics : MGG20021101

Title: Monomeric sarcosine oxidase: role of histidine 269 in catalysis.

Journal: Biochemistry20020806

Title: Vibrational spectrum of methyl pyrrole-2-carboxylate.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy20020101

Title: Conversion of pyrrole to pyrrole-2-carboxylate by cells of Bacillus megaterium in supercritical CO2.

Journal: Chemical communications (Cambridge, England)20011107

Title: Inhibition of Escherichia coli CTP synthase by glutamate gamma-semialdehyde and the role of the allosteric effector GTP in glutamine hydrolysis.

Journal: The Biochemical journal20010515

Title: Characterization of the FAD-containing N-methyltryptophan oxidase from Escherichia coli.

Journal: Biochemistry20010206

Title: Computer-assisted design, synthesis and biological evaluation of novel pyrrolyl heteroaryl sulfones targeted at HIV-1 reverse transcriptase as non-nucleoside inhibitors.

Journal: Bioorganic & medicinal chemistry20000901

Title: He XX, et al. Pelopuradazole, a new imidazole derivative alkaloid from the marine bacteria Pelomonas puraquae sp. nov. Nat Prod Res. 2014;28(9):680-2.

Application fold
Pyrrole-2-carboxylic acid is utilized in the synthesis of cholecystokinin antagonists, benzopyran antihypertensives, and azepinediones.
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