3694-45-9

Basic information

• Product Name: 4-CHLOROBENZYL ISOTHIOCYANATE
• Synonyms: 4-CHLOROBENZYL ISOTHIOCYANATE;1-CHLORO-4-(ISOTHIOCYANATOMETHYL)BENZENE;1-chloro-4-(isothiocyanatomethyl)-benzen;Isothiocyanic acid, p-chlorobenzyl ester;isothiocyanicacid,p-chlorobenzylester;p-chlorobenzylisothiocyanate;4-Chlorobenzylisothiocyanate,95%;4-Chlorobenzyl isothiocyate, 98%
• CAS NO: 3694-45-9
• Molecular Formula: C₈H₆ClNS
• Molecular Weight: 183.66
• EINECS: -0
• Mol File: 3694-45-9.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 170 °C
• Flash Point: 169-170°C/25mm
• Appearance: /
• Density: 1,27 g/cm3
• Vapor Pressure: 0.0071mmHg at 25°C
• Refractive Index: 1.6155
• Water Solubility: 27.18mg/L(25 oC)
• Sensitive: Moisture Sensitive
• BRN: 2085917
• CAS DataBase Reference: 4-CHLOROBENZYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLOROBENZYL ISOTHIOCYANATE(3694-45-9)
• EPA Substance Registry System: 4-CHLOROBENZYL ISOTHIOCYANATE(3694-45-9)

Safety Data

• Hazard Codes: T
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2810
• RTECS: NX8470000
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 3694-45-9(Hazardous Substances Data)

Usage

General Description

4-Chlorobenzyl isothiocyanate is a synthetic, organic chemical compound characterized by the presence of an isothiocyanate group (-N=C=S), a benzyl group attached to the nitrogen atom, and a chlorine atom attached to the benzyl group. Isothiocyanates are known for their anticarcinogenic properties, and 4-Chlorobenzyl isothiocyanate is no exception. It has been studied for its potential applications in cancer research and it may induce cell apoptosis in cancer cells. However, like all isothiocyanates, it can be irritating or corrosive and requires appropriate handling. It commonly appears as colorless to light yellow liquid with a pungent smell and is soluble in most organic solvents.

InChI:InChI=1/C8H6ClNS/c9-8-3-1-7(2-4-8)5-10-6-11/h1-4H,5H2

Upstream product

• 52626-38-7 (4-chloro-benzyl)-dithiocarbamic acid; triethylamine salt 
• 104-86-9 4-chlorobenzylamine 
• 75-15-0 carbon disulfide 
• 873-76-7 para-Chlorobenzyl alcohol 
• 57206-73-2 1,3-bis-(4-chloro-benzyl)-thiourea 
• 65560-92-1 Ammonium-(4-chlorbenzyl)-dithiocarbamat 
• 2082-64-6 4-chlorobenzyl thiocyanate 
• 463-71-8 thiophosgene 

Downstream Products

• 101744-52-9 N-(4-butoxy-phenyl)-N'-(4-chloro-benzyl)-thiourea 
• 24827-37-0 N-(4-chlorobenzyl)thiourea 
• 57206-73-2 1,3-bis-(4-chloro-benzyl)-thiourea 
• 101292-19-7 1-(4-chloro-benzyl)-3-(4-ethoxy-phenyl)-thiourea 
• 68621-05-6 1-benzyl-3-(4-chlorobenzyl)thiourea 
• 103858-94-2 1-(4-chloro-benzyl)-3-(4,5-dihydro-thiazol-2-yl)-thiourea 
• 51623-92-8 1-(4-chloro-benzyl)-3-thiazol-2-yl-thiourea 
• 61290-76-4 3-(4-Chloro-benzyl)-1-(2-hydroxy-ethyl)-1-methyl-thiourea 
• 22908-59-4 N-(4-Chlor-benzyl)-dithiocarbaminsaeure-(2-dimethylamino-ethylester) 
• 107058-42-4 N-<4-Chlor-benzyl>-N'-<4-chlor-benzyloxy>-thioharnstoff 
• 101096-51-9 N-<4-Chlor-benzyl>-N'-<3,4-dichlor-benzyloxy>-thioharnstoff 
• 46460-01-9 1-(p-Chloro-)-benzyl-3-amidino-thiourea 
• 3472-78-4 3-(4-Chlorphenyl)-1,1,3,3-tetrachlor-2-aza-propen-⁽¹⁾ 
• 74787-75-0 1-(4-Chloro-benzyl)-3-(3-hydroxy-propyl)-thiourea 

Relevant articles and documents

HIGH-PURITY ISOTHIOCYANATE COMPOUND PREPARATION METHOD FOR INDUSTRIAL PRODUCTION

The present invention provides a high-purity isothiocyanate compound preparation method for industrial production. Specifically, in the method, organic amine and CS2 are used as raw materials to prepare the thiocarbamate, and then desulfurization is carried out, and the high-purity isothiocyanate compound is obtained by using purification, post-processing and other methods. The method in the present invention is suitable for industrial production, is simple in the post-processing, has a high yield rate, and allows the product to have a high purity, and is suitable for the production of the isothiocyanate compound in the pharmaceutical industry.

Synthesis and anti-endoplasmic reticulum stress activity of N-substituted-2-arylcarbonylhydrazinecarbothioamides

Misfolded or unfolded proteins are accumulated in lumen of endoplasmic reticulum (ER) in ER stress condition. It has been implicated in many pathological conditions such as Alzheimer’s disease, diabetic retinopathy, atherosclerosis, β-cell apoptosis and lung inflammation. We found a series of N-substituted-2-arylcarbonylhydrazinecarbothioamides to potently decrease ER stress signal, showing up to almost 300-fold better activity than 1-hydroxynaphthoic acid and tauro-ursodesoxycholic acid, positive controls, respectively. Structure?activity relationship (SAR) study showed that 2-arylcarbonyl moiety is critical for the activity of the hydrazinecarbothioamide analogues and side chains tethering on thioamide moiety were relatively insensitive to the activity. Some analogues were found to consistently exert the potency under more physiologically relevant condition where ER stress was induced by palmitic acid. ER stress markers such as CHOP and phosphorylated eIF2α and PERK were accordingly decreased in western blotting upon treatment of compound 4h. Potential ER stress inhibitory activity and novel structures could provide a novel platform for new chemical chaperone and therapy for protein misfolding diseases.

Synthesis and cytotoxic evaluation of quinazolin-4(3H)-one derivatives bearing thiocarbamate, thiourea or N-methyldithiocarbamate side Chains

We have previously found that the dithiocarbamate derivatives of quinazolin-4(3H)-one could act as cytotoxic agents against a panel of human tumor cell lines. To investigate the contribution of dithiocarbamate moiety to the cytotoxic activity, three series of novel quinazolin-4(3H)-one derivatives bearing thiocarbamate, thiourea or Nmethyldithiocarbamate side chains were synthesized and tested for their cytotoxic activity against human cancer cell lines A549, MCF-7, HeLa, HT29 and HCT-116 by MTT assay. The results showed that transformation of the dithiocarbamate moiety in lead compound I to thiocarbamate or thiourea led to a decrease or loss of cytotoxic activity. Some N-alkylated analogs of lead compound II preferentially inhibited the proliferation of A549 cells, although their potencies were not improved in comparison with the unalkylated counterparts. The structure-activity relationship obtained in this research will be beneficial for further synthesis and discovery of effective cytotoxic agents.