35967-24-9

Basic information

• Product Name: 3,4,5-TRIMETHOXYPHENYL ISOTHIOCYANATE
• Synonyms: 5-ISOTHIOCYANATO-1,2,3-TRIMETHOXYBENZENE;3,4,5-TRIMETHOXYPHENYL ISOTHIOCYANATE;3,4,5-TRIMETHOXYPHENYL ISOTHIOCYANATE, 9 8%;Benzene, 5-isothiocyanato-1,2,3-trimethoxy-;3,4,5-Trimethoxyphenyl isothiocyate, 99%
• CAS NO: 35967-24-9
• Molecular Formula: C₁₀H₁₁NO₃S
• Molecular Weight: 225.26
• EINECS: 252-820-5
• Product Categories: Thiocyanates/Isothiocyanates;Organic Building Blocks;Sulfur Compounds
• Mol File: 35967-24-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 62-65 °C(lit.)
• Boiling Point: 350.2 °C at 760 mmHg
• Flash Point: 165.6 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 9.02E-05mmHg at 25°C
• Refractive Index: 1.527
• Sensitive: Moisture Sensitive
• BRN: 2736554
• CAS DataBase Reference: 3,4,5-TRIMETHOXYPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-TRIMETHOXYPHENYL ISOTHIOCYANATE(35967-24-9)
• EPA Substance Registry System: 3,4,5-TRIMETHOXYPHENYL ISOTHIOCYANATE(35967-24-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-42
• Safety Statements: 22-26-36
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 35967-24-9(Hazardous Substances Data)

Usage

General Description

3,4,5-TRIMETHOXYPHENYL ISOTHIOCYANATE is a chemical compound with the molecular formula C10H11NO3S. It is a derivative of isothiocyanate, which is known for its biological activities such as anticancer, antimicrobial, and antioxidant properties. 3,4,5-TRIMETHOXYPHENYL ISOTHIOCYANATE is a yellow-colored solid that is soluble in various organic solvents. It is commonly used as a reagent in organic synthesis and as a building block in the development of pharmaceuticals and agrochemicals. Its versatile properties and potential biological activities make it an important target for research in the fields of medicine and agriculture.

InChI:InChI=1/C10H11NO3S/c1-12-8-4-7(11-6-15)5-9(13-2)10(8)14-3/h4-5H,1-3H3

Upstream product

• 24313-88-0 3,4,5-Trimethoxyaniline 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 75-15-0 carbon disulfide 
• 463-71-8 thiophosgene 
• 102439-00-9 3,4,5-trimethoxyaniline hydrochloride 

Downstream Products

• 62829-15-6 (hexahydro-pyrido[1,2-c][1,3]thiazin-1-ylidene)-(3,4,5-trimethoxy-phenyl)-amine 
• 59083-54-4 1-(3,4,5-trimethoxyphenyl)thiourea 
• 767329-29-3 tert-butyl 2-{5-[bis(3-methylbutyl)amino]-2-[(3,4,5-trimethoxyphenyl)amino]-3H-imidazo[4,5-b]pyridin-3-yl}ethylcarbamate 
• 767329-38-4 tert-butyl 2-{5-[(trifluoroacetyl)amino]-2-[(3,4,5-trimethoxyphenyl)amino]-3H-imidazo[4,5-b]pyridin-3-yl}ethylcarbamate 
• 810663-24-2 N-(3,4,5-trimethoxyphenyl)-4-(4-fluorophenyl)-1,3-thiazol-2-amine 

Relevant articles and documents

A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur

Isothiocyanates (ITCs) are typically prepared using amines and highly toxic reagents such as thiophosgene, its derivatives, or CS2. In this work, an investigation of a multicomponent reaction (MCR) using isocyanides, elemental sulfur and amines revealed that isocyanides can be converted to isothiocyanates using sulfur and catalytic amounts of amine bases, especially DBU (down to 2 mol%). This new catalytic reaction was optimized in terms of sustainability, especially considering benign solvents such as Cyrene or γ-butyrolactone (GBL) under moderate heating (40 °C). Purification by column chromatography was further optimized to generate less waste by maintaining high purity of the product. Thus, E-factors as low as 0.989 were achieved and the versatility of this straightforward procedure was shown by converting 20 different isocyanides under catalytic conditions, while obtaining moderate to high yields (34-95%). This journal is

4-Dimethylaminopyridine-catalyzed synthesis of isothiocyanates from amines and carbon disulfide

Isothiocyanates were synthesized by reactions between primary amines and CS2 in the presence of 4-dimethylaminopyridine as a catalyst and tert-butyl hydroperoxide as an oxidant. Various aryl, benzyl, alkyl, and hydroxyl amines were transformed into the corresponding isothiocyanates in 41–82% yields.

N-Trifluoromethyl Hydrazines, Indoles and Their Derivatives

Reported herein is the first efficient strategy to synthesize a broad range of unsymmetrical N-CF3 hydrazines, which served as platform to unlock numerous currently inaccessible derivatives, such as tri- and tetra-substituted N-CF3 hydrazines, hydrazones, sulfonyl hydrazines, and valuable N-CF3 indoles. These compounds proved to be remarkably robust, being compatible with acids, bases, and a wide range of synthetic manipulations. The feasibility of RN(CF3)-NH2 to function as a directing group in C?H functionalization is also showcased.