40398-01-4

Basic information

• Product Name: 2-CHLORO-6-METHYLPHENYL ISOCYANATE
• Synonyms: 6-CHLORO-2-METHYLPHENYLISOCYANATE;2-CHLORO-6-METHYLPHENYL ISOCYANATE;2-Chloro-6-methylphenyl isocyanate 95+%;2-CHLORO-6-METHYLPHENYL ISOCYANATE 97%;2-Chloro-6-methylphenyl isocyanate,97%
• CAS NO: 40398-01-4
• Molecular Formula: C₈H₆ClNO
• Molecular Weight: 167.59
• Product Categories: Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 40398-01-4.mol

Chemical Properties

• Boiling Point: 80 °C2 mm Hg(lit.)
• Flash Point: 225 °F
• Appearance: Clear colorless to slightly yellow liquid
• Density: 1.231 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.107mmHg at 25°C
• Refractive Index: n20/D 1.555(lit.)
• Sensitive: Moisture Sensitive/Lachrymatory
• BRN: 2690768
• CAS DataBase Reference: 2-CHLORO-6-METHYLPHENYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-6-METHYLPHENYL ISOCYANATE(40398-01-4)
• EPA Substance Registry System: 2-CHLORO-6-METHYLPHENYL ISOCYANATE(40398-01-4)

Safety Data

• Hazard Codes: Xn,T,C
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN 2206 6.1/PG 2
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 40398-01-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to slightly yellow liquid

Uses

1-Chloro-2-isocyanato-3-methylbenzene is a building block for organic synthesis. It acts as a reagent in the synthesis of dasatinib, an antitumor drug.

InChI:InChI=1/C8H6ClNO/c1-6-3-2-4-7(9)8(6)10-5-11/h2-4H,1H3

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 87-63-8 2-chloro-6-methylaniline 

Downstream Products

• 124441-49-2 1-(2-Chloro-6-methyl-phenyl)-3-pyridin-4-ylmethyl-urea 

Relevant articles and documents

Design, synthesis and structure-activity relationships of novel diaryl urea derivatives as potential EGFR inhibitors

Two novel series of diaryl urea derivatives 5a-i and 13a-l were synthesized and evaluated for their cytotoxicity against H-460, HT-29, A549, and MDA-MB-231 cancer cell lines in vitro. Therein, 4-aminoquinazolinyl-diaryl urea derivatives 5a-i demonstrated significant activity, and seven of them are more active than sorafenib, with IC50 values ranging from 0.089 to 5.46 μM. Especially, compound 5a exhibited the most active potency both in cellular (IC50 = 0.15, 0.089, 0.36, and 0.75 μM, respectively) and enzymatic assay (IC50 = 56 nM against EGFR), representing a promising lead for further optimization.

Palladium(0)-catalyzed carbon-Hydrogen bond functionalization for the synthesis of indoloquinazolinones

The indoloquinazolinone ring system has attracted considerable attention as a pharmacophore, because it shows various biological activities. The reported synthetic methods for the compound are simple and direct, but are not effective for the direct synthesis of indoloquinazolinone with a methylene group at the C-6 position. A palladium(0)-catalyzed cyclization of chloroquinazolinone via C-H functionalization was developed for a concise synthesis of indoloquinazolinone derivatives. The presence of a substituent at the C-6 position is important for obtaining the product in good yield. The conformation of the reaction intermediate, in particular the N-C-Pd bond angle, is important for the regioselectivity of the reaction.

Synthesis of aryl urea derivatives from aryl amines and aryl isocyanates

The present study describes the synthesis of novel diaryl urea derivatives derived from aryl amine and aryl isocyanates. The synthesized compounds are analogs of sorafenib [4-[4-[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl] amino]phenoxy]-N-methylpyridine-2- carboxamide] having potential antiproliferative activity.