4-amino-2-methylbenzonitrile

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4-amino-2-methylbenzonitrile Basic information
Product Name:4-amino-2-methylbenzonitrile
Synonyms:4-amino-2-methylbenzonitrile;Benzonitrile, 4-amino-2-methyl-;2-methyl-4-aminobenzonitrile
CAS:72115-06-1
MF:C8H8N2
MW:132.16
EINECS:
Product Categories:
Mol File:72115-06-1.mol
4-amino-2-methylbenzonitrile Structure
4-amino-2-methylbenzonitrile Chemical Properties
storage temp. Keep in dark place,Inert atmosphere,Room temperature
form solid
AppearanceBrown to black Solid
InChI1S/C8H8N2/c1-6-4-8(10)3-2-7(6)5-9/h2-4H,10H2,1H3
InChIKeyRGHJWZADAWEIFE-UHFFFAOYSA-N
SMILESCc1cc(N)ccc1C#N
Safety Information
WGK Germany WGK 3
HS Code 2926907090
Storage Class11 - Combustible Solids
MSDS Information
4-amino-2-methylbenzonitrile Usage And Synthesis
Synthesis
2-METHYL-4-NITROBENZONITRILE  98

89001-53-6

4-amino-2-methylbenzonitrile

72115-06-1

(b) Synthesis of 4-amino-2-methylbenzonitrile: Tin chloride dihydrate (18.5 g, 82.0 mmol) was added to a solution of 2-methyl-4-nitrobenzonitrile (3.80 g, 23.4 mmol) in ethanol (140 mL). The reaction mixture was stirred under reflux conditions for 3 hours. After completion of the reaction, the solvent was removed by distillation. The residue was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution. The precipitate produced during washing was removed by filtration through diatomaceous earth. The filtrate was extracted with ethyl acetate and the combined organic phases were dried with anhydrous magnesium sulfate, filtered and concentrated to give 4-amino-2-methylbenzonitrile (2.89 g, 94% yield).

References[1] Patent: EP1500643, 2005, A1. Location in patent: Page 32
[2] Chemische Berichte, 1919, vol. 52, p. 1083
[3] Journal of Organic Chemistry, 1962, vol. 27, p. 1426 - 1430
[4] Journal of Medicinal Chemistry, 2001, vol. 44, # 23, p. 3856 - 3871
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 1926 - 1930
4-amino-2-methylbenzonitrile Preparation Products And Raw materials
Raw materials2-Methyl-4-nitrobenzonitrile 98-->2-Propanesulfinamide, N-(4-cyano-3-methylphenyl)-2-methyl--->Tin(IV) chloride-->Ethanol
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