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

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

Uses

Used in Cancer Research:
4-Chlorobenzyl isothiocyanate is used as a research compound for its potential anticarcinogenic properties. It is being investigated for its ability to induce cell apoptosis in cancer cells, which could contribute to the development of new cancer therapies.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 4-Chlorobenzyl isothiocyanate is used as a starting material or intermediate in the synthesis of various drugs, particularly those targeting cancer treatment. Its potential to induce apoptosis in cancer cells makes it a valuable compound for the development of novel anticancer agents.
Used in Chemical Synthesis:
4-Chlorobenzyl isothiocyanate is used as a reagent in the synthesis of other organic compounds, including those with potential applications in various industries such as agriculture, materials science, and specialty chemicals. Its versatility in chemical reactions makes it a valuable component in the creation of new molecules with specific properties.
Safety Considerations:
Due to its isothiocyanate nature, 4-Chlorobenzyl isothiocyanate can be irritating or corrosive, and it requires appropriate handling to ensure safety during its use in research, pharmaceutical development, and chemical synthesis. Proper protective measures and handling protocols should be followed to minimize risks associated with its use.

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

Upstream product

• 873-76-7 para-Chlorobenzyl alcohol 
• 104-86-9 4-chlorobenzylamine 
• 75-15-0 carbon disulfide 
• 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 
• 52626-38-7 (4-chloro-benzyl)-dithiocarbamic acid; triethylamine salt 

Downstream Products

• 101744-52-9 N-(4-butoxy-phenyl)-N'-(4-chloro-benzyl)-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 
• 1133797-97-3 N-(4-chlorobenzyl)-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-b]isoquinoline-10-carbothioamide 
• 1189740-08-6 C₃₁H₃₇ClN₄O₂S 
• 1384521-74-7 1-(4-chlorobenzyl)-3-((2-methyl-4-oxo-3,4-dihydrodihydroquinazolin-6-yl)methyl)thiourea 
• 1384521-65-6 O-(2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl-4-chlorobenzylcarbamothioate 
• 57206-73-2 1,3-bis-(4-chloro-benzyl)-thiourea 
• 24827-37-0 N-(4-chlorobenzyl)thiourea 
• 6610-36-2 N-(4-chlorobenzyl)hydrazinecarbothioamide 

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.

Application of sulfur-containing isocyanate compounds in growth inhibition of blue-green algae

The invention relates to the application of sulfur-containing isocyanate compounds in the growth inhibition of blue-green algae. The compounds have structures as shown in a general formula I and a general formula II. In the general formula I, R1 represents a methyl group, a phenethyl group, a phenyl group, 4-methylpyridine or 3-methylpyridine. In the general formula II, M represents a carbonyl group, a methylene group and a methylene phenyl group; R3 represents hydrogen or chlorine; R4 represents oxygen, hydrogen, fluorine or chlorine; R5 represents oxygen, hydrogen, chlorine, a methyl group,fluorine, a benzene ring, bromine or a trifluoromethyl group; when R4 and R5 are oxygen, R4 and R5 are cyclized to form 1,3-dioxocyclopentene; R6 represents hydrogen, fluorine, bromine, a trifluoromethyl group, a methyl group and chlorine; and R7 represents hydrogen, a trifluoromethyl group, chlorine and bromine. The sulfur-containing isocyanate compounds with the structures as shown in the general formulas I and II provided by the invention have relatively good inhibition effect on blue-green algae, and can be used as an effective component of a blue-green algae algicide.

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.

Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water

We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.

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.

Design, synthesis, and evaluation of pH-dependent hydrolyzable emetine analogues as treatment for prostate cancer

The N-2′ position of the natural product emetine has been derivatized to thiourea, urea, sulfonamide, dithiocarbamate, carbamate, and pH responsive hydrolyzable amide analogues. In vitro studies of these analogues in PC3 and LNCaP prostate cancer cell lines showed that the analogues are generally less cytotoxic (average IC50 ranging from 0.079 to 10 μM) than emetine (IC50 ranging from 0.0237 to 0.0329 μM). The pH sensitive sodium dithiocarbamate salt 13 and the amide analogues 21, 22, 26 (obtained from maleic and citraconic anhydrides) showed the most promise as acid-activatable prodrugs under mildly acidic conditions found in the cancer microenvironment. These prodrugs released 12-83% of emetine at pH 6.5 and 41-95% emetine at pH 5.5. Compounds 13 and 26 were further shown to exhibit increased cytotoxicity in PC3 cell culture medium that was already below pH 7.0 at the time of treatment.

Selectfluor F-TEDA-BF4 mediated thiocyanation or isothiocyanation of alcohols by in situ generation of [+SCN] under heterogeneous and neutral conditions

A convenient approach for thiocyanation of alcohols has been developed using ammonium thiocyanate as thiocyanating agent in the presence of a catalytic amount of Selectfluor F-TEDA-BF4 in aqueous acetonitrile. In this method various alcohols generally afforded the corresponding thiocyanates or isothiocyanates directly in good to high yield under heterogeneous and neutral conditions.

New potent imidazoisoquinolinone derivatives as anti-Trypanosoma cruzi agents: Biological evaluation and structure-activity relationships

A series of novel benzoimidazo and N-aryl-5-oxo-imidazo[1,2-b]isoquinoline-10-carbothioamides was developed. All the compounds were evaluated for their in vitro action against the epimastigote form of Trypanosoma cruzi. Four of them showed higher activity than Nifurtimox. Their unspecific cytotoxicity was evaluated using HeLa and L6 cells, being non-toxic at concentrations at least 15 and 200 times higher than that of T. cruzi IC50. To gain insight into the mechanism of action, their DNA binding properties and reactivity with glutathione were studied, and QSAR study was performed.

Bronchorelaxing compounds

A compound of the general formula (I) including its pharmaceutically acceptable acid addition salts wherein A is CHR9, wherein R9 is H, C1-C6 alkyl; n is 1-3; B is CHR10, wherein R10 is H, C1-C6 alkyl; m is 1 or 2; D is O or S or optionally NR16, wherein R16 is H, C1-C6 alkyl or C2-C6 acyl; E is CR11R12 or NR13, wherein R11 and R12 are, independent of each other, H or C1-C6 alkyl, R13 is H or C1-C6 alkyl; F is C1-C18 alkyl which may be mono- or di-unsaturated and/or substituted, is useful in treating and preventing pulmonary disease characterized by bronchoconstriction. Also disclosed are pharmaceutical compositions comprising the compound and methods for their manufacture.

A general synthesis of isothiocyanates from dithiocarbamates using claycop

A Convenient and simple synthesis of alkyl, aryl and amino acid isothiocyanates is described by the decomposition of ammonium dithiocarbamates using Claycop in mild conditions.