4-Cyanobenzoic acid

Base Information

• Chemical Name: 4-Cyanobenzoic acid
• CAS No.: 619-65-8
• Molecular Formula: C8H5NO2
• Molecular Weight: 147.133
• Hs Code.: 29269095
• European Community (EC) Number: 210-606-9
• NSC Number: 6306
• UNII: 50Z9A3423Z
• DSSTox Substance ID: DTXSID9041659
• Nikkaji Number: J41.150G
• Wikidata: Q27260843
• ChEMBL ID: CHEMBL101772
• Mol file: 619-65-8.mol

Synonyms:4-cyanobenzoate;4-cyanobenzoic acid;p-cyanobenzoic acid

Chemical Property of 4-Cyanobenzoic acid

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 3.19E-05mmHg at 25°C
• Melting Point: 219-221 °C (dec.)(lit.)
• Refractive Index: 1.592
• Boiling Point: 341 °C at 760 mmHg
• PKA: 3.55(at 25℃)
• Flash Point: 160 °C
• PSA: 61.09000
• Density: 1.32 g/cm³
• LogP: 1.25648
• Storage Temp.: Room temperature.
• Sensitive.: Air Sensitive
• Solubility.: Soluble in methanol.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 147.032028402
• Heavy Atom Count: 11
• Complexity: 195

Purity/Quality:

99% ^*data from raw suppliers

4-Cyanobenzoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#N)C(=O)O
• Uses: An inhibitor. The studies show that 4-cyanobenzaldehyde and 4-cyanobenzoic acid can inhibit both the monophenolase activity and the diphenolase activity of mushroom tyrosinase. 4-Cyanobenzoic acid is used as an inhibitor. 4-cyanobenzaldehyde and 4-cyanobenzoic acid can inhibit both the monophenolase activity and the diphenolase activity of mushroom tyrosinase.

Technology Process of 4-Cyanobenzoic acid

There total 160 articles about 4-Cyanobenzoic 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: 99.0%

4-cyanobenzoic acid methyl ester (1129-35-7) → 4-cyanobenzoic Acid (619-65-8,333406-09-0)

Guidance literature:

With iodine; aluminium; In acetonitrile; at 80 ℃; for 18h;

DOI:10.1021/acs.joc.1c00034

Reference yield: 97.0%

2-(4-cyanophenyl)-5,5-dimethyl[1,3,2]dioxaborinane (214360-44-8) + carbon dioxide (124-38-9,18923-20-1) → 4-cyanobenzoic Acid (619-65-8,333406-09-0)

Guidance literature:

2-(4-cyanophenyl)-5,5-dimethyl[1,3,2]dioxaborinane; carbon dioxide; With [Ni(N,N'-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene)(allyl)Cl]; potassium tert-butylate; In toluene; at 100 ℃; for 15h; under 760.051 Torr; Schlenk technique; Inert atmosphere;

With hydrogenchloride; In water; ethyl acetate; toluene; at 20 ℃;

DOI:10.1039/c4cc03650f

Reference yield: 94.0%

potassiumhexacyanoferrate(II) trihydrate + para-chlorobenzoic acid (74-11-3) → 4-cyanobenzoic Acid (619-65-8,333406-09-0)

Guidance literature:

potassiumhexacyanoferrate(II) trihydrate; para-chlorobenzoic acid; With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate; palladium diacetate; potassium carbonate; In water; at 120 ℃; for 12h; Inert atmosphere; Sealed tube;

potassiumhexacyanoferrate(II) trihydrate; para-chlorobenzoic acid; With potassium carbonate; In water; at 120 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1007/s10562-021-03864-6

upstream raw materials:

potassium cyanide

4-amino-benzoic acid

para-methylbenzonitrile

4-cyanobenzaldehyde

Downstream raw materials:

para-methylbenzonitrile

benzyl 4-cyanobenzoate

R,S-α-p-Cyano-benzoyloxy-valeriansaeure

2-(4-cyano-phenyl)-3-phenyl-5-thioxo-4,5-dihydro-[1,3,4]thiadiazolium betaine

Refernces

• 1、 Wang, Chang-Cheng,Zhang, Guo-Xiang,Zuo, Zhi-Wei,Zeng, Rong,Zhai, Dan-Dan,Liu, Feng,Shi, Zhang-Jie. "Photo-induced deep aerobic oxidation of alkyl aromatics". . p. 1487 - 1492. Retrieved 2021/07/10.
• 2、 -. "PREPARATION OF AROMATIC CARBONYL COMPOUNDS BY CATALYTIC OXIDATION WITH MOLECULAR OXYGEN". Page/Page column 11-12. . Retrieved 2021/08/20.