5-BROMO-A,2-DICYANOBENZENEACETIC ACID METHYL ESTER

Base Information

• Chemical Name: 5-BROMO-A,2-DICYANOBENZENEACETIC ACID METHYL ESTER
• CAS No.: 925672-87-3
• Molecular Formula: C11H7BrN2O2
• Molecular Weight: 0
• Hs Code.: 2926909090
• Mol file: 925672-87-3.mol

Synonyms:5-BROMO-A,2-DICYANOBENZENEACETIC ACID METHYL ESTER;Methyl 2-(5-broMo-2-cyanophenyl)-2-cyanoacetate

Chemical Property of 5-BROMO-A,2-DICYANOBENZENEACETIC ACID METHYL ESTER

Chemical Property:

• PSA: 73.88000
• LogP: 2.10096

Purity/Quality:

Methyl2-(5-bromo-2-cyanophenyl)-2-cyanoacetate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-BROMO-A,2-DICYANOBENZENEACETIC ACID METHYL ESTER

There total 1 articles about 5-BROMO-A,2-DICYANOBENZENEACETIC ACID METHYL ESTER 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: 74.0%

4-bromo-6-fluorobenzonitrile (105942-08-3) + methyl 2-cyanoacetate (105-34-0) → C11H7BrN2O2 (925672-87-3)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide; at 90 ℃;

DOI:10.1016/j.tetlet.2006.11.035

Reference yield: 93.0%

C11H7BrN2O2 (925672-87-3) → 4-bromo-2-(cyanomethyl)benzonitrile (925672-88-4)

Guidance literature:

With water; In dimethyl sulfoxide; at 115 ℃; for 1h;

DOI:10.1016/j.tetlet.2006.11.035

Reference yield:

C11H7BrN2O2 (925672-87-3) → C22H23N3O

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / H₂O / dimethylsulfoxide / 1 h / 115 °C

2: 59 percent / HBr; dichloroacetic acid / 0 - 20 °C

3: dioxane / 170 °C / microwave irradiation

4: Et₃N

5: P(t-Bu)3; KF / Pd₂(dba)3 / dioxane / 65 °C

With dichloro-acetic acid; potassium fluoride; tri-tert-butyl phosphine; water; hydrogen bromide; triethylamine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In 1,4-dioxane; dimethyl sulfoxide; 5: Suzuki coupling reaction;

DOI:10.1016/j.tetlet.2006.11.035

upstream raw materials:

4-bromo-6-fluorobenzonitrile

methyl 2-cyanoacetate

Downstream raw materials:

4-bromo-2-(cyanomethyl)benzonitrile

1,6-dibromoisoquinolin-3-amine

C₁₇H₁₅BrN₂O

C₁₉H₁₇BrN₂O₂

Refernces

• 1、 Frohn, Mike,Bürli, Roland W.,Riahi, Bobby,Hungate, Randall W.. "An efficient synthesis of 1,6- and 1,7-dibromo-3-aminoisoquinolines: versatile templates for the preparation of functionalized isoquinolines". . p. 487 - 489. Retrieved 2008/02/04.