289686-80-2

Basic information

• Product Name: 2-AMINO-4-CHLORO-5-METHYL-BENZONITRILE
• Synonyms: 2-AMINO-4-CHLORO-5-METHYL-BENZONITRILE
• CAS NO: 289686-80-2
• Molecular Formula: C₈H₇ClN₂
• Molecular Weight: 166.61
• Mol File: 289686-80-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-AMINO-4-CHLORO-5-METHYL-BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-CHLORO-5-METHYL-BENZONITRILE(289686-80-2)
• EPA Substance Registry System: 2-AMINO-4-CHLORO-5-METHYL-BENZONITRILE(289686-80-2)

Safety Data

• Hazardous Substances Data: 289686-80-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-4-CHLORO-5-METHYL-BENZONITRILE is used as a building block for the synthesis of pharmaceuticals due to its unique chemical structure, which allows for the creation of a wide range of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical industry, 2-AMINO-4-CHLORO-5-METHYL-BENZONITRILE is utilized as a building block for the synthesis of agrochemicals, contributing to the development of effective crop protection agents.
Used in Dye and Pigment Production:
2-AMINO-4-CHLORO-5-METHYL-BENZONITRILE is used as a key intermediate in the production of dyes and pigments, thanks to its chemical properties that facilitate the creation of diverse colorants.
Used in Heterocyclic Compound Synthesis:
As an intermediate, 2-AMINO-4-CHLORO-5-METHYL-BENZONITRILE is employed in the synthesis of various heterocyclic compounds, which are important in numerous chemical and pharmaceutical applications.

Upstream product

• 102170-52-5 2-bromo-5-chloro-4-methylaniline 
• 544-92-3 copper(I) cyanide 
• 95-74-9 3-chloro-p-toluidine 
• 116010-06-1 N-(2-bromo-5-chloro-4-methylphenyl)acetamide 
• 7149-79-3 N-(3-chloro-4-methylphenyl)acetamide 

Downstream Products

• 155184-81-9 2-amino-5-methyl-4-chlorobenzoic acid 
• 458533-69-2 methyl 2-amino-4-chloro-5-methylbenzoate 
• 289686-83-5 7-chloro-2-chloromethyl-6-methyl-3,4-dihydroquinazolin-4-one 
• 458533-71-6 methyl 2-methoxyacetamido-4-chloro-5-methylbenzoate 
• 458533-73-8 2-methoxyacetamido-4-chloro-5-methyl N-methylbenzamide 
• 289686-85-7 2-acetoxymethyl-7-chloro-3,6-dimethyl-3,4-dihydroquinazolin-4-one 
• 289686-86-8 2-acetoxymethyl-6-bromomethyl-7-chloro-3-methyl-3,4-dihydroquinazolin-4-one 
• 289687-02-1 tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-88-0 tert-butyl 4-[N-[7-chloro-2-hydroxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289687-01-0 tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-89-1 tert-butyl 4-[N-[7-chloro-2-methanesulfonyloxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-87-9 tert-butyl 4-[N-[2-acetoxymethyl-7-chloro-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289687-03-2 tert-butyl 4-[N-[7-chloro-2-methanesulfonyloxymethyl-4-oxo-3,4-dihydroxyquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 
• 289686-91-5 tert-butyl4-[N-[2-diethylaminomethyl-7-chloro-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 

Relevant articles and documents

Anti-quinazoline compounds

Dihydroquinazoline derivatives of the formula where R3is —(CH2)p—A where p is from 1 to 4 and A is a 5- or 6-membered N-containing heterocyclic ring attached via the N atom or A is —NA′A″ wherein A′ and A″ are the same or different and are each a C1-C4alkyl group or their pharmaceutically acceptable salts possessing anti-cancer activity.

The design and synthesis of water-soluble analogues of CB30865, a quinazolin-4-one-based antitumor agent

4-[N-[7-Bromo-2-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl] -N-(prop-2-ynyl)amino]-N-(3-pyridylmethyl)benzamide (CB30865) is a quinazolin-4-one antitumor agent whose high growthinhibitory activity (W1L2 IC50 = 2.8 ± 0.50 nM) is believed to have a folate-independent locus of action. In addition, CB30865 represents a class of compounds with unique biochemical characteristics such as a delayed, non-phase specific, cell-cycle arrest. The low aqueous solubility of CB30865 prompted a search for more water-soluble analogues for in vivo evaluation of this class of compounds. It was thought that aqueous solubility could be increased by the introduction of amino functionalities at the 2-position of the quinazolin-4-one ring. A variety of compounds (5a-j, 31a-c, 32, and 33) were synthesized in a linear fashion starting from 3-chloro-4-methylaniline. Most of these compounds (e.g., 5a, 5b, 5g) were significantly more water-soluble than CB30865 (636 μM for 5a at pH 6 and 992 μM for 5g at pH 6). In addition, some of them were up to 6-fold more cytotoxic than CB30865 (e.g., for 5a, W1L2 IC50 = 0.49 ± 0.24 nM) and retained its novel biochemical characteristics.