Methyl 4-(cyanomethyl)benzoate

Base Information

• Chemical Name: Methyl 4-(cyanomethyl)benzoate
• CAS No.: 76469-88-0
• Molecular Formula: C10H9 N O2
• Molecular Weight: 175.187
• Hs Code.: 2926907090
• European Community (EC) Number: 616-338-2
• DSSTox Substance ID: DTXSID00357248
• Nikkaji Number: J502.665B
• Wikidata: Q72489605
• Mol file: 76469-88-0.mol

Synonyms:Methyl 4-(cyanomethyl)benzoate;76469-88-0;4-Cyanomethylbenzoic acid methyl ester;4-(Cyanomethyl)benzoic Acid Methyl Ester;MFCD00060695;Benzoic acid, 4-(cyanomethyl)-, methyl ester;METHYL4-(CYANOMETHYL)BENZOATE;Methyl 4-Cyanomethylbenzoate;Methyl 4-(Cyanomethyl) Benzoate;methyl p-cyanomethylbenzoate;SCHEMBL378575;DTXSID00357248;4-(carbomethoxy)phenylacetonitrile;BBL103202;CL9297;STL557012;AKOS001430834;Methyl 4-(cyanomethyl)benzoate, 96%;CS-W007933;Water Supply QC Check Sample: Cyanide;4-cyanomethyl benzoic acid methyl ester;4-cyanomethyl-benzoic acid methyl ester;4-cyanomethylbenzoic acid, methyl ester;AC-25706;AS-15415;SY005217;Water Pollution QC Check Sample: Cyanide;AM20041135;Benzoic acid,4-(cyanomethyl)-, methyl ester;FT-0618303;M2341;EN300-29522;A24724;Cyanide (CN-) @ 1000 mg/L in 0.1% NaOH;J-650115;Z283862222

Chemical Property of Methyl 4-(cyanomethyl)benzoate

Chemical Property:

• Vapor Pressure: 0.000513mmHg at 25°C
• Melting Point: 64 ºC
• Boiling Point: 110 °C0.2 mm Hg(lit.)
• Flash Point: 145.9°C
• PSA: 50.09000
• Density: 1.141g/cm³
• LogP: 1.53928
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 220

Purity/Quality:

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

Methyl 4-(cyanomethyl)benzoate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(C=C1)CC#N
• Uses: The key intermediate of Fexofenadine (F322490).

Technology Process of Methyl 4-(cyanomethyl)benzoate

There total 25 articles about Methyl 4-(cyanomethyl)benzoate 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: 90.0%

2-aminoacetonitrile hydrochloride (6011-14-9) + 4-methoxycarbonylphenylboronic acid (99768-12-4) → methyl 4-(cyanomethyl)benzoate (76469-88-0)

Guidance literature:

With sodium nitrite; In water; 1,2-dichloro-ethane; at 100 ℃; for 24h; Schlenk technique;

DOI:10.1002/anie.201406765

Reference yield: 87.0%

chloroacetonitrile (107-14-2) + 4-methoxycarbonylphenylboronic acid (99768-12-4) → methyl 4-(cyanomethyl)benzoate (76469-88-0)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate; In 1,4-dioxane; water; at 60 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1021/ol503213z

Reference yield: 86.0%

4-(methoxycarbonyl)benzyl alcohol (6908-41-4,58590-49-1) + potassium cyanide (151-50-8) → methyl 4-(cyanomethyl)benzoate (76469-88-0)

Guidance literature:

4-(methoxycarbonyl)benzyl alcohol; With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 - 20 ℃; for 15h;

potassium cyanide; With 18-crown-6 ether; In acetonitrile; at 20 ℃; for 40h;

upstream raw materials:

Methyl 4-(bromomethyl)benzoate

4-(cyanomethyl)benzoic acid

sodium methylate

4-Bromophenylacetonitrile

Downstream raw materials:

γ-cyano-γ-(p-carbomethoxyphenyl)pimelonitrile

methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate

4-(cyanomethyl)benzoic acid

{4-[5-(butylamino)-1,3,4-thiadiazol-2-yl]phenyl}acetonitrile

Refernces

• 1、 Saraswati, A. Prasanth,Relitti, Nicola,Brindisi, Margherita,Osko, Jeremy D.,Chemi, Giulia,Federico, Stefano,Grillo, Alessandro,Brogi, Simone,McCabe, Niamh H.,Turkington, Richard C.,Ibrahim, Ola,O'Sullivan, Jeffrey,Lamponi, Stefania,Ghanim, Magda,Kelly, Vincent P.,Zisterer, Daniela,Amet, Rebecca,Hannon Barroeta, Patricia,Vanni, Francesca,Ulivieri, Cristina,Herp, Daniel,Sarno, Federica,Di Costanzo, Antonella,Saccoccia, Fulvio,Ruberti, Giovina,Jung, Manfred,Altucci, Lucia,Gemma, Sandra,Butini, Stefania,Christianson, David W.,Campiani, Giuseppe. "Spiroindoline-Capped Selective HDAC6 Inhibitors: Design, Synthesis, Structural Analysis, and Biological Evaluation". supporting information. p. 2268 - 2276. Retrieved 2020/12/17.
• 2、 Chen, Tiffany Q.,MacMillan, David W. C.. "A Metallaphotoredox Strategy for the Cross-Electrophile Coupling of α-Chloro Carbonyls with Aryl Halides". supporting information. p. 14584 - 14588. Retrieved 2019/09/17.