Home Carboxes 3740-52-1
3740-52-1,MFCD00007190
Catalog No.:AA003HQ5

3740-52-1 | 2-Nitrophenylacetic acid

Pack Size
Purity
Availability
Price(USD)
Quantity
  
10g
98%
in stock  
$12.00   $8.00
- +
25g
98%
in stock  
$15.00   $11.00
- +
100g
98%
in stock  
$39.00   $28.00
- +
500g
98%
in stock  
$124.00   $87.00
- +
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003HQ5
Chemical Name:
2-Nitrophenylacetic acid
CAS Number:
3740-52-1
Molecular Formula:
C8H7NO4
Molecular Weight:
181.1455
MDL Number:
MFCD00007190
SMILES:
OC(=O)Cc1ccccc1[N+](=O)[O-]
NSC Number:
16624
Properties
Properties
 
BP:
345.1°C at 760 mmHg  
Form:
Solid  
MP:
137-140 °C(lit.)  
Refractive Index:
1.5468 (estimate)  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
211  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
2  
XLogP3:
1.6  

Upstream Synthesis Route

[1]Heterocycles,1996,vol.43,#12,p.2701-2712

[1]Patent:US2015/197511,2015,A1,

[1]JournalofMedicinalChemistry,1994,vol.37,#15,p.2308-2314

[1]Patent:US2017/165166,2017,A1,

[1]JournalofMedicinalChemistry,1994,vol.37,#15,p.2308-2314

Downstream Synthesis Route

[1]EuropeanJournalofOrganicChemistry,2013,p.3232-3240

[2]AustralianJournalofChemistry,2013,vol.66,p.864-873

[3]Heterocycles,1996,vol.43,p.2701-2712

[4]Patent:US2015/182491,2015,A1.Locationinpatent:Paragraph0069

[5]ChemischeBerichte,1898,vol.31,p.394

[6]JournalofMedicinalChemistry,1994,vol.37,p.2308-2314

[7]Patent:EP3456711,2019,A1.Locationinpatent:Paragraph0300;0301

[1]MonatsheftefurChemie,1958,vol.89,p.211,218

[1]Sestito,Simona;Nesi,Giulia;Daniele,Simona;Martelli,Alma;Digiacomo,Maria;Borghini,Alice;Pietra,Daniele;Calderone,Vincenzo;Lapucci,Annalina;Falasca,Marco;Parrella,Paola;Notarangelo,Angelantonio;Breschi,MariaC.;Macchia,Marco;Martini,Claudia;Rapposelli,Simona[EuropeanJournalofMedicinalChemistry,2015,vol.105,p.274-288]

[2]Naik,NileshH.;Urmode,TukaramD.;Sikder,ArunK.;Kusurkar,RadhikaS.[AustralianJournalofChemistry,2013,vol.66,#9,p.1112-1114]

[3]CurrentPatentAssignee:HENKELAG&CO.KGAA-US2017/165166,2017,A1Locationinpatent:Paragraph0218;0219;0220;0221;0222;0223

[4]Locationinpatent:experimentalpartDinesh,BhimaReddy;Baba,A.Ramesha;Sankar,K.Udaya;Gowda,D.Channe[JournalofChemicalResearch,2008,#5,p.287-288]

[5]Locationinpatent:schemeortableKammasud,Naparat;Boonyarat,Chantana;Sanphanya,Kingkan;Utsintong,Maleeruk;Tsunoda,Satoshi;Sakurai,Hiroaki;Saiki,Ikuo;André,Isabelle;Grierson,DavidS.;Vajragupta,Opa[BioorganicandMedicinalChemistryLetters,2009,vol.19,#3,p.745-750]

[6]Heller[ChemischeBerichte,1916,vol.49,p.2769]

[7]Neber[ChemischeBerichte,1922,vol.55,p.839]

[8]DiCarlo[JournaloftheAmericanChemicalSociety,1944,vol.66,p.1420]

[9]Hahn;Tulus[ChemischeBerichte,1941,vol.74,p.500,517]

[10]Heacocketal.[AnnalsofAppliedBiology,1958,vol.46,p.352,357]

[11]Baeyer[ChemischeBerichte,1878,vol.11,p.583]

[12]Koenig;Reissert[ChemischeBerichte,1899,vol.32,p.793]

[13]Koenig;Reissert[ChemischeBerichte,1899,vol.32,p.793]

[14]MarquezRuiz,JuanF.;Kedziora,Kinga;Pigott,Maria;Keogh,Brian;Windle,Henry;Gavin,Jason;Kelleher,DermotP.;Gilmer,JohnF.[BioorganicandMedicinalChemistryLetters,2013,vol.23,#6,p.1693-1698]

[15]CurrentPatentAssignee:APOLLOMICS-WO2014/418,2014,A1

[16]CurrentPatentAssignee:APOLLOMICS-US2015/197511,2015,A1

[17]Braun,Max;Esposito,Davide[ChemCatChem,2017,vol.9,#3,p.393-397]

[1]Peet,NortonP.;Sunder,Shyam[JournalofHeterocyclicChemistry,1983,vol.20,p.1355-1357]

[2]Muth,C.W.etal.[JournalofOrganicChemistry,1960,vol.25,p.736-740]

[3]Tomisek;Christensen[JournaloftheAmericanChemicalSociety,1948,vol.70,p.1701]

[4]Muth,C.W.etal.[JournalofOrganicChemistry,1960,vol.25,p.736-740]Lee;Mayer;Wiegrebe;Lauber;Schlunegger[ArchivderPharmazie,1988,vol.321,#5,p.265-272]

[5]Moody,ChristopherJ.;Rahimtoola,KulsumF.[JournaloftheChemicalSociety.PerkintransactionsI,1990,p.673-679]

[6]Goetz,FrederickJ.;Hirsch,JerryA.;Augustine,RobertL.[JournalofOrganicChemistry,1983,vol.48,#15,p.2468-2472]

[7]Vecchietti;Clarke;Colle;Giardina;Petrone;Sbacchi[JournalofMedicinalChemistry,1991,vol.34,#8,p.2624-2633]

[8]Shah,ShrenikK.;Dorn,ConradP.;Finke,PaulE.;Hale,JeffreyJ.;Hagmann,WilliamK.;etal.[JournalofMedicinalChemistry,1992,vol.35,#21,p.3745-3754]

[9]Alazard.Jean-Pierre;Terrier,Corinne;Mary,Aude;Thal,Claude[Tetrahedron,1994,vol.50,#21,p.6287-6298]

[10]Gee,KyleR.;Wieboldt,Raymond;Hess,GeorgeP.[JournaloftheAmericanChemicalSociety,1994,vol.116,#18,p.8366-8367]

[11]Moody,ChristopherJ.;Mprrell,AndrewI.[JournaloftheIndianChemicalSociety,1994,vol.71,#6-8,p.309-314]

[12]Taga,Masanao;Ohtsuka,Hisao;Inoue,Isao;Kawaguchi,Takayuki;Nomura,Sumihiro;Yamada,Koichiro;Date,Tadamasa;Hiramatsu,Hajime;Sato,Yasuhiko[Heterocycles,1996,vol.42,#1,p.251-263]

[13]Cruces,Jacobo;Estévez,JuanC.;Estévez,RamónJ.;Castedo,Luis[Heterocycles,2000,vol.53,#5,p.1041-1050]

[14]Peng,Lizeng;Zhang,Tao;Li,Ying;Li,Yulin[SyntheticCommunications,2002,vol.32,#5,p.785-791]

[15]Haines,LisaA.;Rajagopal,Karthikan;Ozbas,Bulent;Salick,DaphneA.;Pochan,DarrinJ.;Schneider,JoelP.[JournaloftheAmericanChemicalSociety,2005,vol.127,#48,p.17025-17029]

[16]CurrentPatentAssignee:3MCO-WO2006/107771,2006,A2Locationinpatent:Page/Pagecolumn64-65

[17]Yoneyama,Hiroki;Shimoda,Ayako;Araki,Lisa;Hatano,Kouta;Sakamoto,Yasuhiko;Kurihara,Takushi;Yamatodani,Atsushi;Harusawa,Shinya[JournalofOrganicChemistry,2008,vol.73,#6,p.2096-2104]

[18]Royer,Daniel;Wong,Yung-Sing;Plé,Sophie;Chiaroni,Angèle;Diker,Khalid;Lévy,Jean[Tetrahedron,2008,vol.64,#40,p.9607-9618]

[19]Martin,ConnorL.;Overman,LarryE.;Rohde,JasonM.[JournaloftheAmericanChemicalSociety,2008,vol.130,#24,p.7568-7569]

[20]CurrentPatentAssignee:BAYERAG-EP1204323,2004,B1Locationinpatent:Page15;16

[21]Martin,ConnorL.;Overman,LarryE.;Rohde,JasonM.[JournaloftheAmericanChemicalSociety,2010,vol.132,#13,p.4894-4906]

[22]Locationinpatent:experimentalpartOkuro,Kazumi;Gurnham,Joanna;Alper,Howard[JournalofOrganicChemistry,2011,vol.76,#11,p.4715-4720]

[23]Locationinpatent:experimentalpartZervosen,Astrid;Bouillez,Andre;Herman,Alexandre;Amoroso,Ana;Joris,Bernard;Sauvage,Eric;Charlier,Paulette;Luxen,Andre[BioorganicandMedicinalChemistry,2012,vol.20,#12,p.3915-3924]

[24]Zhang,Yu-Mo;Li,Minjie;Li,Wen;Huang,Zhiyuan;Zhu,Shaoyin;Yang,Bing;Wang,Xiao-Chun;Zhang,SeanXiao-An[JournalofMaterialsChemistryC,2013,vol.1,#34,p.5309-5314]

[25]Du,Wei;Gu,Qiangshuai;Li,Zhongliang;Yang,Dan[JournaloftheAmericanChemicalSociety,2015,vol.137,#3,p.1130-1135]

[26]Higuchi,Kazuhiro;Suzuki,Shin;Ueda,Reeko;Oshima,Norifumi;Kobayashi,Emiko;Tayu,Masanori;Kawasaki,Tomomi[OrganicLetters,2015,vol.17,#1,p.154-157]

[27]Örkényi,Róbert;Beke,Gyula;Riethmüller,Eszter;Szakács,Zoltán;Kóti,János;Faigl,Ferenc;Éles,János;Greiner,István[EuropeanJournalofOrganicChemistry,2017,vol.2017,#44,p.6525-6532]

[28]Zheng,Bo;Qu,Hui-Ya;Meng,Tian-Zhuo;Lu,Xia;Zheng,Jie;He,Yun-Gang;Fan,Qi-Qi;Shi,Xiao-Xin[RSCAdvances,2018,vol.8,#51,p.28997-29007]

[29]Mellini,Paolo;Itoh,Yukihiro;Elboray,ElghareebE.;Tsumoto,Hiroki;Li,Ying;Suzuki,Miki;Takahashi,Yukari;Tojo,Toshifumi;Kurohara,Takashi;Miyake,Yuka;Miura,Yuri;Kitao,Yuki;Kotoku,Masayuki;Iida,Tetsuya;Suzuki,Takayoshi[JournalofMedicinalChemistry,2019,vol.62,#12,p.5844-5862]

[30]Fang,Hai-Lian;He,Jie-Ling;Li,Wei-Yi;Liu,Shan-Shan;Ni,Wei-Wei;Pan,Xing-Ming;Xiao,Zhu-Ping;Ye,Ya-Xi;Yi,Juan;Zhou,Mi;Zhou,Tian-Li;Zhu,Hai-Liang[JournalofEnzymeInhibitionandMedicinalChemistry,2020,vol.35,#1,p.404-413]

[31]Borgert,Sebastian;Daniliuc,ConstantinG.;Ensan,Deeba;Jose,Joachim;Kröger,Lukas;Lauwers,Miriam;Nienberg,Christian;Pietsch,Markus;Steinkrüger,Michaela;Wünsch,Bernhard[ChemMedChem,2020,vol.15,#10,p.871-881]

[32]Aydın,HaticeGülten;Ekmekci,Zeynep;Kaya,Serdal;Keskin,Selbi;Menges,Nurettin[JournalofPhotochemistryandPhotobiologyA:Chemistry,2021,vol.420]

[33]Deflon,VictorM.;DosSantos,CaioY.;Gallo,RafaelD.C.;Jurberg,IgorD.;Munaretto,LaiéliS.;Okada,CelsoY.[OrganicLetters,2021,vol.23,#23,p.9292-9296]

[34]Wang,Zhuo;Ye,Xiaohan;Jin,Meina;Tang,Qi;Fan,Shengyu;Song,Zhiguang;Shi,Xiaodong[OrganicLetters,2022,vol.24,#17,p.3107-3112]

[1]CurrentPatentAssignee:TAKEDAPHARMACEUTICALCOMPANYLIMITED-WO2004/46107,2004,A1Locationinpatent:Page241-242

[2]Pschorr;Hoppe[ChemischeBerichte,1910,vol.43,p.2550]

[3]Muth,C.W.etal.[JournalofOrganicChemistry,1960,vol.25,p.736-740]Lee;Mayer;Wiegrebe;Lauber;Schlunegger[ArchivderPharmazie,1988,vol.321,#5,p.265-272]

[4]CurrentPatentAssignee:CHINAPETROCHEMICALCORPORATION-CN104557610,2018,BLocationinpatent:Paragraph0138;0139;0140;0147;0148

[5]Mellini,Paolo;Itoh,Yukihiro;Elboray,ElghareebE.;Tsumoto,Hiroki;Li,Ying;Suzuki,Miki;Takahashi,Yukari;Tojo,Toshifumi;Kurohara,Takashi;Miyake,Yuka;Miura,Yuri;Kitao,Yuki;Kotoku,Masayuki;Iida,Tetsuya;Suzuki,Takayoshi[JournalofMedicinalChemistry,2019,vol.62,#12,p.5844-5862]

Literature

Title: Inhibition of human carboxylesterases hCE1 and hiCE by cholinesterase inhibitors.

Journal: Chemico-biological interactions 20130325

Title: Molecular mechanism of uncaging CO2 from nitrophenylacetate provides general guidelines for improved ortho-nitrobenzyl cages.

Journal: Chemphyschem : a European journal of chemical physics and physical chemistry 20110801

Title: (2-Nitrophenyl)acetyl: a new, selectively removable hydroxyl protecting group.

Journal: Organic letters 20100507

Title: Total synthesis of (+/-)- and (-)-actinophyllic acid.

Journal: Journal of the American Chemical Society 20100407

Title: Delta9-tetrahydrocannabinol is a full agonist at CB1 receptors on GABA neuron axon terminals in the hippocampus.

Journal: Neuropharmacology 20100101

Title: The α,5-dicarboxy-2-nitrobenzyl caging group, a tool for biophysical applications with improved hydrophilicity: synthesis, photochemical properties and biological characterization.

Journal: Photochemistry and photobiology 20100101

Title: Leveraging a small-molecule modification to enable the photoactivation of rho GTPases.

Journal: Chembiochem : a European journal of chemical biology 20091214

Title: 5-(3-Nitro-benz-yl)-1,3,4-thia-diazol-2-amine.

Journal: Acta crystallographica. Section E, Structure reports online 20091201

Title: Competition between cleavage and decarboxylation in photolysis of alpha-carboxy-2-nitrobenzyl protected cysteine derivatives.

Journal: Chemical communications (Cambridge, England) 20090614

Title: Studies of decarboxylation in photolysis of alpha-carboxy-2-nitrobenzyl (CNB) caged compounds.

Journal: Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20080101

Title: Mechanisms of cholinesterase inhibition by inorganic mercury.

Journal: The FEBS journal 20070401

Title: Comparative analysis of inhibitory effects of caged ligands for the NMDA receptor.

Journal: Journal of neuroscience methods 20050315

Title: Synthesis and characterization of photolabile o-nitrobenzyl derivatives of urea.

Journal: The Journal of organic chemistry 20021213

Title: Studies on the catalytic behaviour of a cholinesterase-like abzyme in an AOT microemulsion system.

Journal: Journal of biotechnology 20020807

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Tags:3740-52-1 Molecular Formula|3740-52-1 MDL|3740-52-1 SMILES|3740-52-1 2-Nitrophenylacetic acid