Ethyl 2-bromo-2-cyanoacetate

Base Information

• Chemical Name: Ethyl 2-bromo-2-cyanoacetate
• CAS No.: 1187-46-8
• Molecular Formula: C5H6 Br N O2
• Molecular Weight: 192.012
• Hs Code.: 2926909090
• NSC Number: 77072
• DSSTox Substance ID: DTXSID401030252
• Nikkaji Number: J54.183D
• Mol file: 1187-46-8.mol

Synonyms:ethyl 2-bromo-2-cyanoacetate;1187-46-8;Acetic acid, bromocyano-, ethyl ester;ethyl bromocyanoacetate;C5H6BrNO2;Ethyl alpha-bromo-alpha-cyanoacetate;NSC 77072;ETHYL 2-BROMO-2-CYANO-ACETATE;BRN 1761604;ACETIC ACID, 2-BROMO-2-CYANO-, ETHYL ESTER;Bromocyanoacetic acid ethyl ester;4-02-00-01905 (Beilstein Handbook Reference);NSC77072;ethylbromocyanoacetate;ethyl 2-bromocyanoacetate;ethyl bromo(cyano)acetate;WLN: NCYEVO2;ethyl2-bromo-2-cyanoacetate;C5-H6-Br-N-O2;SCHEMBL9918669;DTXSID401030252;NSC-77072;AKOS016007209;Ethyl .alpha.-bromo-.alpha.-cyanoacetate;Acetic acid, bromocyano-, ethyl ester (8CI);A892936

Chemical Property of Ethyl 2-bromo-2-cyanoacetate

Chemical Property:

• Vapor Pressure: 0.212mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 208.6°C at 760 mmHg
• Flash Point: 79.9°C
• PSA: 50.09000
• Density: 1.58g/cm³
• LogP: 0.83658
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 190.95819
• Heavy Atom Count: 9
• Complexity: 148

Purity/Quality:

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

ETHYL-2-BROMO-2-CYANOACETATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C#N)Br

Technology Process of Ethyl 2-bromo-2-cyanoacetate

There total 6 articles about Ethyl 2-bromo-2-cyanoacetate 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: 94.0%

ethyl 2-cyanoacetate (105-56-6) → ethyl bromocyanoacetate (1187-46-8)

Guidance literature:

With bromine; In tetrachloromethane; at 100 ℃; for 1h; Irradiation;

DOI:10.1055/s-1990-27009

Reference yield: 89.0%

ethyl 2,2-dibromo-2-cyanoacetate (13280-85-8) → ethyl bromocyanoacetate (1187-46-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 28 ℃; for 19h; Irradiation; Inert atmosphere;

DOI:10.1021/acs.orglett.9b03848

Reference yield: 6.0%

ethyl 2,2-dibromo-2-cyanoacetate (13280-85-8) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → ethyl bromocyanoacetate (1187-46-8) + ethyl 1-cyano-2-carbomethoxycyclopropanecarboxylate (125117-25-1) + ethyl 2-cyanoacetate (105-56-6)

Guidance literature:

With tributylstibine; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80128-9

upstream raw materials:

sodium cyanoacetic acid ethyl ester

ethyl 2-cyanoacetate

ethyl 2,2-dibromo-2-cyanoacetate

acrylic acid methyl ester

Downstream raw materials:

4-amino-3-(3-chloro-phenyl)-2-imino-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester

4-amino-3-(4-ethoxy-phenyl)-2-imino-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester

4-amino-3-(4-bromo-phenyl)-2-imino-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester

ethyl (E)-3-(4-chlorophenyl)-2-cyanoacrylate

Refernces

• 1、 Hosseinzadeh, Rahman,Tajbakhsh, Mahmood,Mohadjerani, Maryam,Lasemi, Zahra. "Ethylenebis(N-methylimidazolium) ditribromide (EBMIDTB): An efficient reagent for the monobromination of 1,3-diketones and β-ketoesters". . p. 57 - 60. Retrieved 2009.
• 2、 Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Tehrani, Shahram Shahriari. "Selective monobromination of 1,3-diones with N-bromosaccharin/Mg(ClO 4)2 system in solution and under solvent-free conditions". experimental part. p. 1543 - 1546. Retrieved 2011/12/04.