19241-17-9

Basic information

• Product Name: 3,4-DIMETHYLPHENYL ISOTHIOCYANATE
• Synonyms: 3,4-DIMETHYLPHENYL ISOTHIOCYANATE;4-Isothiocyanato-1,2-dimethylbenzene;3,4-Dimethylisothiocyanatobenzene;3,4-Dimethylphenyl isothiocyate, 99%
• CAS NO: 19241-17-9
• Molecular Formula: C₉H₉NS
• Molecular Weight: 163.24
• Mol File: 19241-17-9.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 132°C/8mm
• Flash Point: 124.9 °C
• Appearance: /
• Density: 1.08
• Vapor Pressure: 0.00704mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: 3,4-DIMETHYLPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHYLPHENYL ISOTHIOCYANATE(19241-17-9)
• EPA Substance Registry System: 3,4-DIMETHYLPHENYL ISOTHIOCYANATE(19241-17-9)

Safety Data

• Hazard Codes: Xi,C
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2810
• HazardClass: IRRITANT, CORROSIVE
• Hazardous Substances Data: 19241-17-9(Hazardous Substances Data)

Usage

Description

3,4-DIMETHYLPHENYL ISOTHIOCYANATE, with the molecular formula C10H9NS, is an isothiocyanate derivative of 3,4-dimethylphenyl. This chemical compound is characterized by its strong and pungent odor and is widely utilized in organic synthesis and chemical research. Its potential biological activities, such as antimicrobial and insecticidal properties, make it a compound of interest in various fields. However, due to its toxic nature and potential to cause irritation to the skin, eyes, and respiratory system, careful handling is essential.

Uses

Used in Organic Synthesis:
3,4-DIMETHYLPHENYL ISOTHIOCYANATE is used as a reagent in organic synthesis for the creation of various organic compounds. Its unique chemical structure allows it to participate in a range of reactions, facilitating the synthesis of complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,4-DIMETHYLPHENYL ISOTHIOCYANATE is used as a key intermediate in the development of new drugs. Its reactivity and versatility make it a valuable component in the synthesis of pharmaceuticals with potential therapeutic applications.
Used in Agrochemical Industry:
3,4-DIMETHYLPHENYL ISOTHIOCYANATE is utilized in the agrochemical industry for the synthesis of compounds with insecticidal and antimicrobial properties. Its potential to control pests and diseases in agriculture makes it a valuable tool in crop protection.
Used in Chemical Research:
In the realm of chemical research, 3,4-DIMETHYLPHENYL ISOTHIOCYANATE serves as a model compound for studying the properties and reactions of isothiocyanates. Its use in research contributes to the understanding of chemical behavior and the development of new synthetic methods and applications.

InChI:InChI=1/C9H9NS/c1-7-3-4-9(10-6-11)5-8(7)2/h3-5H,1-2H3

Upstream product

• 95-64-7 4-amino-o-xylene 
• 58655-30-4 C₆H₁₅N*C₉H₁₁NS₂ 
• 463-71-8 thiophosgene 
• 75-15-0 carbon disulfide 

Downstream Products

• 154640-45-6 C₁₉H₁₉N₅O₂S 

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 bioevaluation of N,4-diaryl-1,3-thiazole-2-amines as tubulin inhibitors with potent antiproliferative activity

A series of N,4-diaryl-1,3-thiazole-2-amines containing three aromatic rings with an amino linker were designed and synthesized as tubulin inhibitors and evaluated for their antiproliferative activity in three human cancer cell lines. Most of the target compounds displayed moderate antiproliferative activity, and N-(2,4-dimethoxyphenyl)-4-(4-methoxyphenyl)-1,3-thiazol-2-amine (10s) was determined to be the most potent compound. Tubulin polymerization and immunostaining experiments revealed that 10s potently inhibited tubulin polymerization and disrupted tubulin microtubule dynamics in a manner similar to CA-4. Moreover, 10s effectively induced SGC-7901 cell cycle arrest at the G2/M phase in both concentrationand time-dependent manners. The molecular docking results revealed that 10s could bind to the colchicine binding site of tubulin.

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.