28479-22-3

Basic information

• Product Name: 3-Chloro-4-methylphenyl isocyanate
• Synonyms: 3-Chlore-4-methylphenyl isocyanate;3-CHLORO-4-METHYLPHENYL ISOCYANATE;ISOCYANIC ACID 3-CHLORO-4-METHYLPHENYL ESTER;Isocyanato-3-chloro-4-methyl benzene;3-chloro-p-tolyl isocyanate;3-Chloro-4-MethylPhenylIsocynate;2-CHLORO-4-ISOCYANATO-TOLUENE;3-Chlor-p-tolylisocyanat
• CAS NO: 28479-22-3
• Molecular Formula: C8H6ClNO
• Molecular Weight: 167.59
• EINECS: 249-050-7
• Product Categories: Isocyanates;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 28479-22-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 20-24℃
• Boiling Point: 107 °C3 mm Hg(lit.)
• Flash Point: 229 °F
• Appearance: Colorless to yellow/Liquid or Low Melting Solid
• Density: 1.224 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0279mmHg at 25°C
• Refractive Index: n20/D 1.557(lit.)
• Storage Temp.: 2-8°C
• Sensitive: Moisture Sensitive
• BRN: 2690771
• CAS DataBase Reference: 3-Chloro-4-methylphenyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-4-methylphenyl isocyanate(28479-22-3)
• EPA Substance Registry System: 3-Chloro-4-methylphenyl isocyanate(28479-22-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-42
• Safety Statements: 23-26-36/37-45
• RIDADR: UN 2206 6.1/PG 3
• WGK Germany: 1
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 28479-22-3(Hazardous Substances Data)

Usage

Chemical Properties

Chloromethyl phenyl isocyanate is a colorless to yellow liquid or beige, low-melting solid. Acrid odor.

Uses

3-Chloro-4-methylphenyl isocyanate may be used in the synthesis of the following urea compounds:1-(1-(1-adamantyl)methyl)-3-(3-chloro-4-methylphenyl)urea1-(3-chloro-4-methylphenyl)-3-heptylurea1-(3-chloro-4-methylphenyl)-3-cyclooctylurea1-(3-chloro-4-methylphenyl)-3-(3-fluorobenzyl)urea1-(3-chloro-4-methylphenyl)-3-(4-phenylbutan-2-yl)urea

General Description

A colorless liquid with an acrid odor. Denser than water. Contact may irritate skin, eyes and mucous membranes. Flash point 132°F. Toxic by ingestion, inhalation and skin absorption. Used to make other chemicals.

Air & Water Reactions

Flammable. 3-Chloro-4-methylphenyl isocyanate decomposes in water. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff.

Reactivity Profile

Isocyanates and thioisocyanates, such as 3-Chloro-4-methylphenyl isocyanate, are incompatible with many classes of compounds, reacting exothermically to release toxic gases. Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat. Acids and bases initiate polymerization reactions in these materials. Some isocyanates react with water to form amines and liberate carbon dioxide. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence, [Wischmeyer(1969)].

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Potential Exposure

This material is used in organic synthesis.

Shipping

UN22363-Chloro-4-methylphenyl isocyanate, liquid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Incompatibilities

May form explosive mixture with air. Isocyanates are highly flammable and reactive with many compounds, even with themselves. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Reaction with moist air, water or alcohols may form amines and insoluble polyureas and react exothermically, releasing toxic, corrosive, or flammable gases, including carbon dioxide; and, at the same time, may generate a violent release of heat increasing the concentration of fumes in the air. Incompatible with amines, aldehydes, alkali metals, ammonia, carboxylic acids, caprolactum, alkaline materials, glycols, ketones, mercaptans, hydrides, organotin catalysts, phenols, strong acids, strong bases, strong reducing agents such as hydrides, urethanes, ureas. Elevated temperatures or contact with acids, bases, tertiary amines, and acyl-chlorides may cause explosive polymerization. Attacks some plastics, rubber, and coatings. Contact with metals may evolve flammable hydrogen gas. May accumulate static electrical charges, and may cause ignition of its vapors. Do not store in temperatures above 30C/86F.

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

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 95-74-9 3-chloro-p-toluidine 
• 15545-48-9 N-(3-chloro-4-methylphenyl)-N,N-dimethylurea 

Downstream Products

• 91767-06-5 <3-Chlor-4-methyl-phenylcarbamoylmercapto>-essigsaeure-dimethylamid 
• 91767-05-4 <3-Chlor-4-methyl-phenylcarbamoylmercapto>-essigsaeure-aethylamid 
• 22546-25-4 C₁₀H₁₄ClN₃O 
• 100282-52-8 2-chloro-4-[(N-methoxy-N-methylamino)carbonylamino]phenylmethyl bromide 
• 1450730-04-7 C₁₇H₂₀ClN₃O₃S 
• 1445768-23-9 tert-butyl 2-(3-(3-chloro-4-methylphenyl)ureido)phenylcarbamate 
• 1445768-16-0 tert-butyl 3-(3-(3-chloro-4-methylphenyl)ureido)phenylcarbamate 
• 1445768-11-5 C₁₉H₂₂ClN₃O₃ 
• 1152996-32-1 C₁₄H₁₄ClN₃O 
• 1040328-14-0 C₁₄H₁₄ClN₃O 
• 1153357-90-4 1-(4-aminophenyl)-3-(3-chloro-4-methylphenyl)urea 
• 1437304-90-9 1-(3-chloro-4-methylphenyl)-3-(2-(4-hydroxy-8-nitro-quinazolin-5-ylamino)phenyl)urea 
• 1437304-84-1 1-(3-chloro-4-methylphenyl)-3-{3-[(4-hydroxy-8-nitroquinazolin-5-yl)amino]phenyl}urea 

Relevant articles and documents

Design, synthesis, and biological evaluation of novel substituted thiourea derivatives as potential anticancer agents for NSCLC by blocking K-Ras protein-effectors interactions

Mutation of the proto-oncogene K-Ras is one of the most common molecular mechanisms in non-small cell lung cancer. Many drugs for treating lung cancer have been developed, however, due to clinical observed K-Ras mutations, corresponding chemotherapy and targeted therapy for such mutation are not efficient enough. In this study, on the basis of the crystal structure of K-Ras, 21 analogues (TKR01–TKR21) containing urea or thiourea were rationally designed, which can effectively inhibit the lung cancer cell A549 growth. The designing of these compounds was based on the structure of K-Ras protein, and the related groups were replaced by bioisosteres to improve the affinity and selectivity. Biological testing revealed that compound TKR15 could significantly inhibit the proliferation of A549 cell with IC50 of 0.21 μM. Docking analysis showed that the TKR15 can effectively bind to the hydrophobic cavity and form a hydrogen bond with the Glu37. In addition, through flow apoptosis assay and immunofluorescence staining assay, it confirmed that this compound can inhibit A549 cell proliferation with the mechanism of blocking K-RasG12V protein and effector proteins interactions through the apoptotic pathway. In conclusion, our studies in finding novel potent compound (TKR15) with confirmed mechanism showed great potential for further optimisation and other medicinal chemistry relevant studies.

With anti-tumor effect of a quinazoline-urea derivative and its application (by machine translation)

The present invention relates to a of the general formula (II) anti-tumor function of said quinazoline-urea derivative and its application. The definition of the substituent in the general formula (II) in the specification. This invention, in order to SUO draw non-Buddhist nun and Geftinat compounds as the precursor, retention of SUO draw non-Buddhist nun the pharmocology-carbamido; at the same time, such as in reserved [...] EGFR-TKIs Geftinat, synthesis, and obtain a series of quinazoline-urea derivatives, by the in vitro activity tests, some compounds exhibit excellent anti-tumor activity, such derivatives have high research and utility value. (II). (by machine translation)

A simple and efficient synthesis of diaryl ureas with reduction of the intermediate isocyanate by triethylamine

Thirty symmetrical diaryl urea derivatives were synthesised in moderate to excellent yields from arylamine and triphosgene with triethylamine as a reducing agent for the intermediate, isocyanate. It was significant that part of the products could be collected in almost quantitative yield without column chromatography. The procedure under mild reaction conditions was tolerant of a wide range of functional groups. The structures of the compounds were determined by NMR, MS and X-ray crystallographic analyses.