37408-18-7

Basic information

• Product Name: 4-CHLORO-2-METHYLPHENYL ISOCYANATE
• Synonyms: 4-Chloro-1-isocyanato-2-methylbenzene;4-CHLORO-2-METHYLPHENYL ISOCYANATE;4-CHLORO-2-METHYLPHENYL ISOCYANATE 97%;4-Chloro-o-tolyl isocyanate
• CAS NO: 37408-18-7
• Molecular Formula: C₈H₆ClNO
• Molecular Weight: 167.59
• Mol File: 37408-18-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 36-40 °C(lit.)
• Boiling Point: 103°C 13mm
• Flash Point: >230 °F
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 0.049mmHg at 25°C
• Refractive Index: 1.543
• Sensitive: Moisture Sensitive
• BRN: 2803097
• CAS DataBase Reference: 4-CHLORO-2-METHYLPHENYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-METHYLPHENYL ISOCYANATE(37408-18-7)
• EPA Substance Registry System: 4-CHLORO-2-METHYLPHENYL ISOCYANATE(37408-18-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-26-36
• RIDADR: 2206
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 37408-18-7(Hazardous Substances Data)

Usage

Description

4-Chloro-2-methylphenyl isocyanate, also known as 4-chloro-1-isocyanato-2-methylbenzene, is an organic compound that serves as a crucial intermediate in the synthesis of various chemical products. It is characterized by its isocyanate functional group, which is highly reactive and forms the basis for its diverse applications.

Uses

Used in Chemical Synthesis:
4-Chloro-2-methylphenyl isocyanate is used as a key intermediate in the production of chloromethylphenylcarbamate derivatives. These derivatives are essential in the creation of stationary phases for high-performance liquid chromatography (HPLC), a widely used analytical technique in various fields, including pharmaceuticals, environmental science, and biochemistry.
Used in High-Performance Liquid Chromatography (HPLC) Industry:
In the HPLC industry, 4-chloro-2-methylphenyl isocyanate is used as a precursor for the synthesis of stationary phases. These stationary phases are crucial components in HPLC systems, as they provide the necessary separation and analysis of complex mixtures of compounds. The chloromethylphenylcarbamate derivatives of cellulose, prepared using this intermediate, offer improved separation efficiency and selectivity for a wide range of analytes.

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

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 95-69-2 4-chloro-2-methylbenzeneamine 

Downstream Products

• 40397-77-1 2-Hydroxy-6-oxo-4-phenyl-cyclohex-1-enecarboxylic acid (4-chloro-2-methyl-phenyl)-amide 
• 40397-75-9 2-Hydroxy-6-oxo-3-phenyl-cyclohex-1-enecarboxylic acid (4-chloro-2-methyl-phenyl)-amide 
• 22546-23-2 C₁₀H₁₄ClN₃O 
• 70756-81-9 1-(2'-methyl-4'-chlorophenyl)-3-amidinourea 
• 896746-97-7 4-semicarbazone-3(S)-[2-(2-oxo-5-phenyl-3(R)-(4-chloro-2-methylphenylcarbamoyloxymethyl)-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)acetylamino]butyric acid tert-butyl ester 
• 569345-58-0 N-(4-chloro-2-methylphenyl)-N'-[3-(4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-3-yl)phenyl]urea 
• 52525-28-7 3-(4-chloro-2-methyl-phenyl)-6-methoxy-1H-[1,3,5]triazine-2,4-dione 
• 1201591-75-4 1-(4-chloro-2-methylphenyl)-3-(3-(4-(pyrrolidin-1-yl)piperidin-1-yl)-5-(trifluoromethyl)phenyl)urea 
• 1733-05-7 N'-Methoxy-N'-butyl-N-(4-chlor-2-methyl-phenyl)-harnstoff 
• 1576-16-5 N'-Methoxy-N'-methyl-N-(4-chlor-2-methyl-phenyl)-harnstoff 

Relevant articles and documents

Design, synthesis and structure-activity relationship study of novel urea compounds as FGFR1 inhibitors to treat metastatic triple-negative breast cancer

Triple-negative breast cancer (TNBC) is an aggressive type of cancer characterized by higher metastatic and reoccurrence rates, where approximately one-third of TNBC patients suffer from the metastasis in the brain. At the same time, TNBC shows good responses to chemotherapy, a feature that fuels the search for novel compounds with therapeutic potential in this area. Recently, we have identified novel urea-based compounds with cytotoxicity against selected cell lines and with the ability to cross the blood-brain barrier in vivo. We have synthesized and analyzed a library of more than 40 compounds to elucidate the key features responsible for the observed activity. We have also identified FGFR1 as a molecular target that is affected by the presence of these compounds, confirming our data using in silico model. Overall, we envision that these compounds can be further developed for the potential treatment of metastatic breast cancer.

A new class of inhibitors of secretory phospholipase A2: enolized 1,3-dioxane-4,6-dione-5-carboxamides

Enolized 1,3-dioxane-4,6-dione-5-carboxamides a were identified as a new class of inhibitors of secretory phospholipase A2 from human polymorphonuclear leucocytes (h-PMN PLA2).Among the more than 30 compounds synthesized, the most potent inhibitors (IC50 0.6-10 μM) were found in the series of 2,4-disubstituted phenyl analogues of a.Compound 1a was selected for evaluation of its biological profile.This substance potently inhibited secretory PLA2s from several sources other than human PMNs, with a clear preference for group II over group I PLA2, whereas humancytosolic PLA2 and phospholipase C were not significantly affected.Inhibition of h-PMN PLA2 was calcium-dependent.In intact mammalian cells stimulated in vitro, the release of arachidonic acid and the generation of prostaglandins and leukotrienes were inhibited at concentrations compatible with inhibition of PLA2 as an underlying mechanism.In animal models in vivo (carragheenan oedema, adjuvant arthritis, pertussis pleurisy) 1a showed antiinflammatory activity, although the effect was rather weak compared with standard reference compounds. secretory human PMN phospholipase A2 / enolized 1,3-dioxane-4,6-dione-5-carboxamide inhibitors / cellular eicosanoid synthesis / in vivo antiinflammatory activity / molecular modelling / structure-activity relationship

Triphosgen, ein kristalliner Phosgen-Ersatz

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