Methyl 4-cyanobenzoate

Base Information

• Chemical Name: Methyl 4-cyanobenzoate
• CAS No.: 1129-35-7
• Molecular Formula: C9H7NO2
• Molecular Weight: 161.16
• Hs Code.: 29269090
• European Community (EC) Number: 214-443-4
• UNII: F8FMS7O8XG
• DSSTox Substance ID: DTXSID9022150
• Nikkaji Number: J41.149C
• Wikidata: Q27277813
• Mol file: 1129-35-7.mol

Synonyms:Methyl 4-cyanobenzoate;1129-35-7;4-Cyanobenzoic acid methyl ester;Benzoic acid, 4-cyano-, methyl ester;Methyl p-cyanobenzoate;Benzoic acid, p-cyano-, methyl ester;methyl4-cyanobenzoate;4-cyano-benzoic acid methyl ester;EINECS 214-443-4;UNII-F8FMS7O8XG;F8FMS7O8XG;p-Cyanobenzoic acid methyl ester;MFCD00001823;4-(Methoxycarbonyl)benzonitrile;methyl-4-cyanobenzoate;4-CYAN-BENZOIC ACID-METHYL ESTER;4-cyanobenzoic acid methyl;SCHEMBL7393;Methyl 4-cyanobenzoate, 99%;4-cyanobenzoic acid methylester;DTXSID9022150;BENZOATE, 4-CYANO-, METHYL;AKOS000278861;AC-7339;CS-W019823;TS-02142;LS-184908;BENZOIC ACID, 4-CYANO, METHYLESTER-;C1119;FT-0618281;EN300-60642;A802703;AC-907/25014377;W-108631;Q27277813;Z18372983

Chemical Property of Methyl 4-cyanobenzoate

Chemical Property:

• Appearance/Colour: white crystal
• Vapor Pressure: 0.00526mmHg at 25°C
• Melting Point: 65-67 °C(lit.)
• Refractive Index: 1.535
• Boiling Point: 274.9 °C at 760 mmHg
• Flash Point: 131.2 °C
• PSA: 50.09000
• Density: 1.18 g/cm³
• LogP: 1.34488
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: Insoluble in water. Soluble in chloroform and ethyl acetate.
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 161.047678466
• Heavy Atom Count: 12
• Complexity: 208

Purity/Quality:

99% ^*data from raw suppliers

Methyl 4-cyanobenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Hazard Codes: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-60-36/37-26-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(C=C1)C#N
• Uses: Methyl 4-Cyanobenzoate (cas# 1129-35-7) is a compound useful in organic synthesis.

Technology Process of Methyl 4-cyanobenzoate

There total 176 articles about Methyl 4-cyanobenzoate 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%

methyl 4-[(1E)-(hydroxyimino)methyl]benzoate (168699-41-0) → 4-cyanobenzoic acid methyl ester (1129-35-7)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In tetrahydrofuran; ethyl acetate; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.12.090

Reference yield: 96.0%

4-methoxycarbonylphenyl bromide (619-42-1) + potassium ferrocyanide → 4-cyanobenzoic acid methyl ester (1129-35-7)

Guidance literature:

With dichloro[bis{1-(dicyclohexylphosphanyl)piperidine}]palladium; sodium carbonate; In 1-methyl-pyrrolidin-2-one; at 140 ℃; for 6h; Inert atmosphere;

DOI:10.1002/chem.201102936

Reference yield: 95.0%

zinc(II) cyanide (557-21-1) + Methyl 4-chlorobenzoate (1126-46-1) → 4-cyanobenzoic acid methyl ester (1129-35-7)

Guidance literature:

zinc(II) cyanide; With aluminum oxide; Ni(xantphos)(o-tolyl)Cl; for 1h; Schlenk technique; Inert atmosphere; Sealed tube;

Methyl 4-chlorobenzoate; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1039/c7ob00892a

upstream raw materials:

potassium cyanide

4-methoxycarbonyl aniline

terephthalonitrile

methanol

Downstream raw materials:

1-Methyl-1-methoxycyclohexane

trans-1-Methoxy-2-methylcyclohexane

cis-1-methoxy-2-methylcyclohexane

acetic acid methyl ester

Refernces

• 1、 Martin, Michael T.,Liu, Bing,Cooley Jr., Bobby E.,Eaddy, John F.. "Open air palladium catalyzed cyanation-the use of PMHS to protect from oxygen". . p. 2555 - 2557. Retrieved 2007.
• 2、 Tsuji, Chiho,Miyazawa, Etsuko,Sakamoto, Takeshi,Kikugawa, Yasuo. "New method for the synthesis of nitriles from o-arylaldoximes with ZrCl4". . p. 3871 - 3879. Retrieved 2002.
• 3、 Sakamoto, Takao,Ohsawa, Kazutoshi. "Palladium-catalyzed cyanation of aryl and heteroaryl iodides with copper(i) cyanide". . p. 2323 - 2326. Retrieved 1999.
• 4、 Wen, Qiaodong,Jin, Jisong,Mei, Yuncai,Lu, Ping,Wang, Yanguang. "Copper-mediated cyanation of aryl halides by activation of benzyl cyanide as the cyanide source". . p. 4032 - 4036. Retrieved 2013.
• 5、 Zhang, Zhihui,Liebeskind, Lanny S.. "Palladium-catalyzed, copper(I)-mediated coupling of boronic acids and benzylthiocyanate. A cyanide-free cyanation of boronic acids". . p. 4331 - 4333. Retrieved 2006.
• 6、 Pawar, Amit B.,Chang, Sukbok. "Catalytic cyanation of aryl iodides using DMF and ammonium bicarbonate as the combined source of cyanide: A dual role of copper catalysts". . p. 448 - 450. Retrieved 2014.
• 7、 Xu, Jian-Xing,Franke, Robert,Wu, Xiao-Feng. "Phosphite-catalyzed alkoxycarbonylation of aryl diazonium salts". . p. 6180 - 6182. Retrieved 2018.
• 8、 Ano, Yusuke,Chatani, Naoto,Higashino, Masaya,Yamada, Yuki. "Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones". supporting information. p. 3799 - 3802. Retrieved 2022/04/07.
• 9、 Sakurai, Shun,Tobisu, Mamoru. "Palladium-catalyzed decarbonylative cyanation of acyl fluorides and chlorides". supporting information. . Retrieved 2021/01/25.