4-Cyanophenylacetic acid

Base Information

• Chemical Name: 4-Cyanophenylacetic acid
• CAS No.: 5462-71-5
• Molecular Formula: C9H7NO2
• Molecular Weight: 161.16
• Hs Code.: 29269090
• European Community (EC) Number: 226-753-7
• NSC Number: 14104
• UNII: YJK6AE7K3P
• DSSTox Substance ID: DTXSID00203054
• Nikkaji Number: J210.527F
• Wikidata: Q72458718
• Mol file: 5462-71-5.mol

Synonyms:4-Cyanophenylacetic acid;5462-71-5;2-(4-cyanophenyl)acetic acid;(4-Cyanophenyl)acetic acid;Benzeneacetic acid, 4-cyano-;(4-Cyano-phenyl)-acetic acid;333406-09-0;4-Cyanobenzeneacetic acid;4-Cyanophenyl acetic acid;(p-Cyanophenyl)acetic acid;Acetic acid, (p-cyanophenyl)-;MFCD06798066;YJK6AE7K3P;EINECS 226-753-7;NSC-14104;p-cyanophenylacetic acid;2-(4-Cyanophenyl)aceticacid;UNII-YJK6AE7K3P;4-cyano-phenylacetic acid;4-cyano phenyl acetic acid;SCHEMBL335492;(4-Cyanophenyl)acetic acid #;4-Cyanophenylacetic acid, 97%;DTXSID00203054;BCP15472;NSC14104;NSC 14104;AKOS008118611;AM83006;CS-W004704;FS-3473;AC-22906;SY007137;BB 0305894;FT-0649787;EN300-62024;A24322;D72888;AE-641/00004032;F2167-4980;Z362118788

Chemical Property of 4-Cyanophenylacetic acid

Chemical Property:

• Vapor Pressure: 1.17E-05mmHg at 25°C
• Melting Point: 150-154 ºC
• Refractive Index: 1.576
• Boiling Point: 355.2°C at 760mmHg
• PKA: 3.93±0.10(Predicted)
• Flash Point: 168.6°C
• PSA: 61.09000
• Density: 1.26g/cm³
• LogP: 1.18538
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in CHCl3, THF, dioxane.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 161.047678466
• Heavy Atom Count: 12
• Complexity: 208

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Cyanophenylacetic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(=O)O)C#N
• Uses: 4-Cyanophenylacetic acid can be used as a nitrile precursor to synthesize 1,2,4,5-tetrazines by reacting with aliphatic nitriles and hydrazine in the presence of Lewis acid metal catalysts.It can also be used as a reactant to prepare: 4-pyrrolo[1,2-a]quinoxalin-4-ylbenzonitrile by copper-catalyzed reaction with 1-(2-aminoaryl)pyrrole in the presence of 2,2′-bipyridyl as the ligand.4-(1,2-Diphenyl-1H-imidazol-4-yl)benzonitrile by one-pot three-component reaction with N-phenylbenzamidine and nitromethane via activation of C-H and N-H bonds.4-Cyano-N,N-di-2-propen-1-ylbenzeneacetamide by reacting with diallylamine.

Technology Process of 4-Cyanophenylacetic acid

There total 30 articles about 4-Cyanophenylacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

carbon dioxide (124-38-9,18923-20-1) + 1-cyano-4-(fluoromethyl)benzene (16473-21-5) → 4-cyanophenylacetic acid (5462-71-5)

Guidance literature:

With triethylsilane; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate; In dimethyl sulfoxide; at 25 - 30 ℃; for 11h; under 760.051 Torr; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation;

DOI:10.1016/j.chempr.2021.08.004

Reference yield: 89.0%

potassium ferrocyanide + 2-(4-bromophenyl)-acetic acid (1878-68-8) → 4-cyanophenylacetic acid (5462-71-5)

Guidance literature:

With 2C₆H₁₅N*C₄₉H₄₇Cl₂Fe₂N₂O₈P₂PdS₂; potassium carbonate; In 1,4-dioxane; water; at 100 ℃; Inert atmosphere;

DOI:10.1021/om2011529

Reference yield: 89.0%

carbon dioxide (124-38-9,18923-20-1) + 4-((phenylsulfonyl)methyl)benzonitrile (51229-59-5) → 4-cyanophenylacetic acid (5462-71-5)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 30 ℃; for 6h; Electrolysis;

DOI:10.1021/acs.joc.1c01261

upstream raw materials:

4-(cyanomethyl)benzonitrile

4-aminophenylacetic acid

potassium cyanide

methanol

Downstream raw materials:

(E)-1-cyano-4-styryl-benzene

(S)-2-((S)-3-tert-Butoxycarbonyl-2-{2-[2-(4-cyano-phenyl)-acetylamino]-acetylamino}-propionylamino)-3-methyl-butyric acid tert-butyl ester

(4-Cyan-2-nitrophenyl)essigsaeure

(E)-4-stilbenecarboxylic acid

Refernces

• 1、 Zhong, Jun-Song,Yang, Zi-Xin,Ding, Cheng-Lin,Huang, Ya-Feng,Zhao, Yi,Yan, Hong,Ye, Ke-Yin. "Desulfonylative Electrocarboxylation with Carbon Dioxide". supporting information. p. 16162 - 16170. Retrieved 2021/09/02.
• 2、 Wakuluk-Machado, Anne-Marie,Dewez, Damien F.,Baguia, Hajar,Imbratta, Miguel,Echeverria, Pierre-Georges,Evano, Gwilherm. "Pd(OH)2/C, a Practical and Efficient Catalyst for the Carboxylation of Benzylic Bromides with Carbon Monoxide". . p. 713 - 723. Retrieved 2020/02/04.