56043-01-7

Basic information

• Product Name: 2-AMINO-6-METHYLBENZONITRILE
• Synonyms: 6-AMINO-O-TOLUNITRILE;2-AMINO-6-METHYLBENZONITRILE;2-Amino-6-methylbenzonitrilepurum;2-AMINO-6-METHYLBENZONITRILE PURUM 97%;2-azanyl-6-methyl-benzenecarbonitrile;2-Amino-6-methylbenzonitrile,6-Amino-o-tolunitrile;2-AMino-6-Methylbenzonitrile >=97.0%
• CAS NO: 56043-01-7
• Molecular Formula: C₈H₈N₂
• Molecular Weight: 132.16
• Mol File: 56043-01-7.mol

Chemical Properties

• Melting Point: 127-132 °C
• Boiling Point: 287.6 °C at 760 mmHg
• Flash Point: 127.7 °C
• Appearance: /
• Density: 1.1 g/cm³
• Vapor Pressure: 0.00246mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 1.94±0.10(Predicted)
• BRN: 2082175
• CAS DataBase Reference: 2-AMINO-6-METHYLBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-6-METHYLBENZONITRILE(56043-01-7)
• EPA Substance Registry System: 2-AMINO-6-METHYLBENZONITRILE(56043-01-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 56043-01-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H8N2/c1-6-3-2-4-8(10)7(6)5-9/h2-4H,10H2,1H3

Upstream product

• 1885-76-3 2-cyano-3-nitrotoluene 
• 545-06-2 trichloroacetonitrile 
• 108-44-1 1-amino-3-methylbenzene 
• 10034-85-2 hydrogen iodide 
• 1192690-76-8 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-6-methylbenzonitrile 
• 1210035-03-2 2-(cyanothioformamido)-6-methylbenzonitrile 
• 603-35-0 triphenylphosphine 
• 570-24-1 2-Methyl-6-nitroaniline 

Downstream Products

• 858004-66-7 2-mercapto-6-methylbenzonitrile 
• 411236-72-1 (2-cyano-3-methyl-phenylsulfanyl)-acetic acid 
• 36715-97-6 3-methylphthalonitrile 
• 6575-09-3 2-chloro-6-methyl-benzonitrile 
• 54454-12-5 (3-chloro-2-methylphenyl)carbonitrile 
• 73289-66-4 2-hydroxy-6-methylbenzonitrile 
• 72618-70-3 2-(imino(o-tolyl)methyl)-3-methylaniline 
• 27018-14-0 2,4-diamino-5-methylquinazoline 
• 77326-29-5 N-(2-Cyano-3-methyl-phenyl)-oxalamic acid ethyl ester 
• 52107-69-4 2-iodo-6-methylbenzonitrile 
• 212369-51-2 2-Dibenzylamino-6-methyl-benzonitrile 
• 606145-78-2 N-(2-cyano-3-methylphenyl)benzonitrile 
• 862595-58-2 2-methyl-6-pyrrol-1-yl-benzylamine 
• 819793-33-4 (2-methoxyethyl)-(5-methylquinazolin-4-yl)amine 

Relevant articles and documents

The conversion of 2-cyano cyanothioformanilides into 3-aminoindole-2- carbonitriles using triphenylphosphine

2-Cyano cyanothioformanilide 3a reacts with triphenylphosphine in the presence of water to give 2-(cyanomethyleneamino)benzonitrile 4a, 2-(cyanomethylamino)benzonitrile 5, 3-aminoindole-2-carbonitrile 2a and (2-cyanoindol-3-yl)iminotriphenylphosphorane 6a. In the presence of p-toluenesulfonic acid in MeOH the reaction between 2-cyano cyanothioformanilide 3a and triphenylphosphine (2 equiv) gives 3-aminoindole-2-carbonitrile 2a in 90% yield. Under the same conditions 2-(cyanomethyleneamino)benzonitrile 4a gives anthranilonitrile 8a, 3-aminoindole-2-carbonitrile 2a and N-(2-cyanophenyl)formamide 9. In addition, substituted 2-cyano cyanothioformanilides 3b-f react with triphenylphosphine and p-toluenesulfonic acid in MeOH to give 3-aminoindole-2-carbonitriles 2b-f in 63-75% yields. Under analogous conditions 2-cyano-4,5-dimethoxyphenyl cyanothioformanilide 2g gives only 4,5-dimethoxyanthranilonitrile 8g and 4,6,7-trimethoxyquinazoline-2- carbonitrile 14g, but in refluxing dry PhMe in the absence of p-toluenesulfonic acid 2-cyano-4,5-dimethoxyphenyl cyanothioformanilide 3g, (2-cyano-5,6- dimethoxyindol-3-yl)iminotriphenylphosphorane 6g and 2-(cyanomethyleneamino)-4, 5-dimethoxybenzonitrile 4g are obtained. The structure of 2- (cyanomethyleneamino)-4,5-dimethoxybenzonitrile 4g is supported unambiguously via independent synthesis and comparison to the isomeric 6,7- dimethoxyquinazoline-2-carbonitrile 15. All new compounds are fully characterised and a tentative mechanism for the transformation of 2-cyano cyanothioformanilides to indoles is proposed.

The conversion of 2-(4-chloro-5H-1,2,3-dithiazolylideneamino)benzonitriles into 3-aminoindole-2-carbonitriles using triphenylphosphine

2-(4-Chloro-5H-1,2,3-dithiazolylideneamino)benzonitrile 1a reacts with triphenylphosphine (4 equiv) in the presence of water (2 equiv) to afford anthranilonitrile 2a, 3-aminoindole-2-carbonitrile 3a and (2-cyanoindol-3-yl)iminotriphenylphosphorane 4a, tog

Design, synthesis, and evaluation of potential GAR and AICAR transformylase inhibitors

The synthesis and evaluation of 1 4 as potential inhibitors of GAR Tfase and AICAR Tfase are detailed. Copyright (C) 1998 Elsevier Science Ltd.

Insecticidal substituted-2,4-diaminoquinazolines

An insecticidal composition comprising, in admixture with an agriculturally acceptable carrier, an insecticidally effective amount of a 2,4-diaminoquinazoline compound of the formula: STR1 wherein R1, R2, R6, R7, W, X, Y, and Z are as defined herein; methods of using the same; novel 2,4-diaminoquinazolines per se; and intermediates in the preparation thereof.

EXLUSIVE ORTHO CYANATION AND ALKYLTHIOCARBONYLATION OF ANILINES AND PHENOLS USING BORON TRICHLORIDE

Use of boron trichloride with or without an aditional Lewis acid makes possible a one-step synthesis of 2-cyano and 2-alkylthiocarbonyl anilines and phenols.

Antifolate and Antibacterial Activities of 5-Substituted 2,4-Diaminoquinazolines

A series of 5-substituted 2,4-diaminoquinazolines (3) has been synthesized and evaluated as inhibitors of the enzyme dihydrofolate reductase (DHFR) from both bacterial and mammalian sources.The best compounds (e.g. 53) show good activity against Escherichia coli DHFR, but there is no significant selectivity for the bacterial over the mammalian enzyme.The structure-activity relationships for enzyme inhibition appear to be complex and not amenable to simple analysis; a hypotesis to explain the observed qualitative structure-activity relationships is proposed.The inhibitory activities of the compounds against the growth of intact bacterial cells in vitro closely parallel those for the inhibition of the isolated bacterial enzymes, suggesting that their antifolate action is responsible for their antibacterial effects.Five of the compounds were tested for their ability to cure a systemic E. coli infection in the mouse, but they showed no therapeutic effects at their maximum tolerated doses.

N-(Aminophenyl)oxamic Acids and Esters as Potent, Orally Active Antiallergy Agents

A series of N-(2-cyano-substituted-phenyl)oxamates was prepared by acylation of the appropriate anthranilonitrile with ethyloxalyl chloride.Hydrolysis with sodium hydroxide gave the corresponding oxamic acid sodium salts.These compounds were extremely potent when tested in the rat passive cutaneous anaphylaxis (PCA assay either by the ip or the po route of administration).One of the sodium salts, oxoacetic acid sodium salt (11a, Wy-41 195), has ED50 value of 0.07 mg/kg po and has been selected for further evaluation.

Compositions and process of treatment

This invention relates to pharmaceutical compositions containing known compounds of the formula SPC1 Wherein M is selected from the group consisting of hydrogen, aluminum, ammonium, sodium, potassium, calcium, tris(hydroxymethyl)methylammonium and lower alkyl of 1 through 4 carbon atoms, R is selected from the group consisting of hydrogen and lower alkyl of 1 through 4 carbon atoms, and R1 and R2 are selected from the group consisting of hydrogen, fluorine, chlorine, bromine, trifluoromethyl, lower alkoxy of 1 through 4 carbon atoms and lower alkyl of 1 through 4 carbon atoms. The compounds (1) above are formulated with pharmaceutical carriers for inhalation or for oral, parenteral or rectal administration, with insufflation being the preferred method. The compositions are useful in the prophylactic treatment of sensitized humans and mammals for allergic and all anaphylactic reactions of a reaginmediated and non-reagin-mediated nature.