Methyl 2-amino-5-cyanobenzoate

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Methyl 2-amino-5-cyanobenzoate Basic information
Product Name:Methyl 2-amino-5-cyanobenzoate
Synonyms:2-Amino-5-cyanobenzoic acid methyl ester;Methyl 2-amino-5-cyanobenzoate≥ 97% (HPLC);Benzoic acid, 2-amino-5-cyano-, methyl ester;Methyl 2-amino-5-cyanobenzoate
CAS:159847-81-1
MF:C9H8N2O2
MW:176.17
EINECS:
Product Categories:
Mol File:159847-81-1.mol
Methyl 2-amino-5-cyanobenzoate Structure
Methyl 2-amino-5-cyanobenzoate Chemical Properties
Boiling point 334.1±32.0 °C(Predicted)
density 1.26±0.1 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
pka0.95±0.10(Predicted)
AppearanceOff-white to brown Solid
Safety Information
HS Code 2916399090
MSDS Information
Methyl 2-amino-5-cyanobenzoate Usage And Synthesis
Chemical PropertiesPale yellow crystalline powder
Synthesis
Copper(I) Cyanide

544-92-3

METHYL 2-AMINO-5-BROMOBENZOATE

52727-57-8

METHYL 2-AMINO-5-CYANOBENZOATE

159847-81-1

A mixture of methyl 2-amino-5-bromobenzoate (50 g, 217 mmol) and cuprous cyanide (19.7 g, 220 mmol) was heated to reflux (ca. 200 °C) in 200 mL of N-methyl-2-pyrrolidinone and reacted overnight, followed by cooling to room temperature. The dark reaction mixture was slowly poured into 1800 mL of ether under vigorous stirring. The dark viscous oily material at the bottom was separated and discarded, and the upper turbid solution was washed sequentially with 200 mL of saturated saline, 200 mL of 1 M sodium hydroxide solution, and twice with 200 mL of saturated saline (total 2000 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure to give about 20 g of a yellow solid, methyl 2-amino-5-cyanobenzoate crude, in 52% yield.

References[1] Patent: WO2005/9967, 2005, A2. Location in patent: Page/Page column 78-79
[2] Patent: WO2004/2940, 2004, A1. Location in patent: Page 41; 42
[3] Patent: WO2004/18414, 2004, A2. Location in patent: Page 58
Methyl 2-amino-5-cyanobenzoate Preparation Products And Raw materials
Raw materialsMethanol-->Copper(I) Cyanide-->Methyl 2-amino-5-bromobenzoate-->carbon monoxide-->4-Amino-2-iodobenzonitrile 98
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