Ethyl 4-(cyanomethyl)benzoate

Base Information

• Chemical Name: Ethyl 4-(cyanomethyl)benzoate
• CAS No.: 83901-88-6
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID80475297
• Nikkaji Number: J502.666K
• Wikidata: Q72458503
• Mol file: 83901-88-6.mol

Synonyms:ethyl 4-(cyanomethyl)benzoate;83901-88-6;Ethyl 4-cyanomethylbenzoate;Ethyl4-(cyanomethyl)benzoate;Benzoic acid, 4-(cyanomethyl)-, ethyl ester;ethyl 4-cyanomethyl-benzoate;SCHEMBL3967293;DTXSID80475297;IOZDJXZPSPNHRS-UHFFFAOYSA-N;4-cyanomethylbenzoic acid ethyl ester;MFCD14544840;4-cyanomethyl benzoic acid ethyl ester;AKOS015838695;NS-01732;4-(cyano-methyl)-benzoic acid ethyl ester

Chemical Property of Ethyl 4-(cyanomethyl)benzoate

Chemical Property:

• Melting Point: 28 °C
• Boiling Point: 325.971 °C at 760 mmHg
• Flash Point: 153.252 °C
• PSA: 50.09000
• Density: 1.113 g/cm³
• LogP: 1.92938
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 233

Purity/Quality:

99% ^*data from raw suppliers

Ethyl4-(Cyanomethyl)benzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC=C(C=C1)CC#N

Technology Process of Ethyl 4-(cyanomethyl)benzoate

There total 10 articles about Ethyl 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: 93.0%

4-(cyanomethyl)phenyl 4-methylbenzenesulfonate (175135-39-4) + ethanol (64-17-5) + carbon monoxide (201230-82-2) → 4-cyanomethylbenzoic acid ethyl ester (83901-88-6)

Guidance literature:

With Josiphos Et₂P-Fc-PtBu₂ ligand; sodium acetate; palladium diacetate; at 130 - 135 ℃; for 20h; under 2068.59 Torr;

DOI:10.1021/ol062208g

Reference yield: 88.0%

Ethyl 4-bromobenzoate (5798-75-4) + ethyl 2-cyanoacetate (105-56-6) → 4-cyanomethylbenzoic acid ethyl ester (83901-88-6)

Guidance literature:

Ethyl 4-bromobenzoate; ethyl 2-cyanoacetate; With potassium phosphate; N-(2-methylnaphthalen-1-yl)-N’-(pyridin-2-ylmethyl)oxalamide; copper(l) chloride; In ethanol; at 80 ℃; for 24h; Schlenk technique; Inert atmosphere;

With hydrogenchloride; In ethanol; water; at 80 ℃; Schlenk technique; Inert atmosphere; Cooling;

DOI:10.1002/anie.202014638

Reference yield: 84.0%

2-trimethylsilylacetonitrile (18293-53-3) + Ethyl 4-bromobenzoate (5798-75-4) → 4-cyanomethylbenzoic acid ethyl ester (83901-88-6)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; zinc(II) fluoride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 90 ℃; for 8h;

DOI:10.1021/ja053027x

upstream raw materials:

Ethyl 4-(bromomethyl)benzoate

2-trimethylsilylacetonitrile

Ethyl 4-bromobenzoate

4-(cyanomethyl)phenyl 4-methylbenzenesulfonate

Downstream raw materials:

4-cyanomethyl-3-nitro-benzoic acid ethyl ester

{4-[(ethyloxy)carbonyl]phenyl}acetic acid

ethyl 4-<2-<<1-<2-methoxy-phenyl>butyl>amino>-2-oxoethyl>-benzoate

ethyl 4-<2-<<1-<2-(phenyl)-phenyl>butyl>amino>-2-oxoethyl>-benzoate

Refernces

• 1、 Czerwiński, Pawe? J.,Furman, Bart?omiej. "Overcoming inaccessibility of fluorinated imines-synthesis of functionalized amines from readily available fluoroacetamides". supporting information. p. 9436 - 9439. Retrieved 2019/08/15.
• 2、 Shang, Rui,Ji, Dong-Sheng,Chu, Ling,Fu, Yao,Liu, Lei. "Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates". supporting information; experimental part. p. 4470 - 4474. Retrieved 2011/06/24.