19241-37-3

Basic information

• Product Name: 3-CHLORO-4-METHYLPHENYL ISOTHIOCYANATE
• Synonyms: NSC135813;2-Chloro-4-isothiocyanato-1-methylbenzene;3-CHLORO-4-METHYLPHENYL ISOTHIOCYANATE;3-chloro-p-tolyl isothiocyanate;3-Chloro-4-methylphenyl isothiocyate, 99%
• CAS NO: 19241-37-3
• Molecular Formula: C₈H₆ClNS
• Molecular Weight: 183.66
• EINECS: -0
• Mol File: 19241-37-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 127 °C
• Flash Point: 126-127°C/8mm
• Appearance: /
• Density: 1,24 g/cm3
• Vapor Pressure: 0.00385mmHg at 25°C
• Refractive Index: 1.6530
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform, Ethyl Acetate
• Sensitive: Moisture Sensitive
• BRN: 2803098
• CAS DataBase Reference: 3-CHLORO-4-METHYLPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-4-METHYLPHENYL ISOTHIOCYANATE(19241-37-3)
• EPA Substance Registry System: 3-CHLORO-4-METHYLPHENYL ISOTHIOCYANATE(19241-37-3)

Safety Data

• Statements: 23/24/25
• Safety Statements: 26-36/37/39
• RIDADR: 2810
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 19241-37-3(Hazardous Substances Data)

Usage

Description

3-Chloro-4-methylphenyl isothiocyanate is an organic compound that serves as a versatile reagent in the synthesis of various chemical compounds. It is characterized by its ability to form 1,2,4-thiadiazole derivatives and thio analogues of urea herbicides, making it a valuable component in the development of neuroprotectors and agrochemicals.

Uses

Used in Pharmaceutical Industry:
3-Chloro-4-methylphenyl isothiocyanate is used as a reagent for the synthesis of 1,2,4-thiadiazole derivatives, such as 5-Amino-1,2,3-thiadiazole (A630295). These compounds have demonstrated neuroprotective properties, making them valuable in the development of treatments for neurological disorders.
Used in Agrochemical Industry:
3-Chloro-4-methylphenyl isothiocyanate is also used as a reagent to synthesize thio analogues of urea herbicides, such as Fenuron (F279490). These analogues exhibit potent fungicidal activity, making them useful in the development of effective and environmentally friendly pesticides for the control of various plant diseases.

InChI:InChI=1/C8H6ClNS/c1-6-2-3-7(10-5-11)4-8(6)9/h2-4H,1H3

Upstream product

• 75-15-0 carbon disulfide 
• 95-74-9 3-chloro-p-toluidine 
• 302577-03-3 ((3-chloro-4-methylphenyl)amino)phenoxymethane-1-thione 
• 53393-07-0 3,3'-dichloro-4,4'-dimethylthiocarbanilide 
• 463-71-8 thiophosgene 

Downstream Products

• 903503-27-5 1-(3-chloro-4-methylphenyl)-3-(2-(2-(diethylamino)-6-methyl-5-nitropyrimidin-4-ylamino)ethyl)thiourea 
• 1052260-18-0 1-(3-chloro-4-methylphenyl)-3-(3-oxo-1,3-dihydroisobenzofuran-5-yl)thiourea 
• 1158838-99-3 4-(3-(3-chloro-4-methylphenyl)thioureido)-N-(thiazol-2-yl)benzenesulfonamide 
• 894314-32-0 4-(3-(3-chloro-4-methylphenyl)thioureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide 
• 895652-92-3 1-(3-chloro-4-methylphenyl)-3-(4-methyl-3-nitrophenyl)thiourea 

Relevant articles and documents

A catalyst-free method for the synthesis of 1,4,2-dithiazoles from isothiocyanates and hydroxylamine triflic acid salts

A catalyst-free method for the preparation of 1,4,2-dithiazoles is developed by reactions of isothiocyanates with hydroxylamine triflic acid salts. This reaction achieves C-S, C-N, and S-N bond formation, and a range of products are obtained in moderate to good yields. The obvious feature is using shelf-stable hydroxylamine triflic acid salts as a N source to synthesize heterocycles under mild conditions.

Synthesis and biological evaluation of terminal functionalized thiourea-containing dipeptides as antitumor agents

A series of antitumor agents based on terminal functionalized dipeptide derivatives containing the thiourea moiety were synthesized and evaluated for antiproliferative activity using a panel of cancer cell lines, and the effects and mechanism of apoptosis induction were determined. These compounds exhibited significant selectivity to different cancer cell lines with IC50 values at micromolar concentrations. In particular, compound I-11 appeared to be the most potent compound, with an IC50 = 4.85 ± 1.44 μM against the NCI-H460 cell line, at least partly, by the induction of apoptosis. Mechanistically, compound I-11 induced the activation of caspase-12 and CHOP, which triggered apoptotic signalling via the ROS-dependent endoplasmic reticulum pathway and arrested the cell cycle at the S phase. Thus, we concluded that dipeptide derivatives containing the thiourea moiety terminally functionalized by electron-withdrawing substituents may be potential antitumor agents for further investigation.

Design, synthesis, X-ray crystallographic analysis, and biological evaluation of thiazole derivatives as potent and selective inhibitors of human dihydroorotate dehydrogenase

Human dihydroorotate dehydrogenase (HsDHODH) is a flavin-dependent mitochondrial enzyme that has been certified as a potential therapeutic target for the treatment of rheumatoid arthritis and other autoimmune diseases. On the basis of lead compound 4, which was previously identified as potential HsDHODH inhibitor, a novel series of thiazole derivatives were designed and synthesized. The X-ray complex structures of the promising analogues 12 and 33 confirmed that these inhibitors bind at the putative ubiquinone binding tunnel and guided us to explore more potent inhibitors, such as compounds 44, 46, and 47 which showed double digit nanomolar activities of 26, 18, and 29 nM, respectively. Moreover, 44 presented considerable anti-inflammation effect in vivo and significantly alleviated foot swelling in a dose-dependent manner, which disclosed that thiazole-scaffold analogues can be developed into the drug candidates for the treatment of rheumatoid arthritis by suppressing the bioactivity of HsDHODH.