6095-82-5

Basic information

• Product Name: 2,4,6-TRIMETHYLPHENYL ISOTHIOCYANATE
• Synonyms: 2,4,6-TRIMETHYLPHENYL ISOTHIOCYANATE;MESITYL ISOTHIOCYANATE;2-Isothiocyanato-1,3,5-trimethylbenzene;2,4,6-Trimethylphenyl isothiocyanate 97%;Isothiocyanatomesitylene;2,4,6-Trimethylphenyl isothiocyate, 99%
• CAS NO: 6095-82-5
• Molecular Formula: C₁₀H₁₁NS
• Molecular Weight: 177.27
• Mol File: 6095-82-5.mol

Chemical Properties

• Melting Point: 63-64°C
• Boiling Point: 144-145°C 10mm
• Flash Point: 144-145°C/10mm
• Appearance: Yellow Solid
• Density: 1 g/cm³
• Vapor Pressure: 0.00459mmHg at 25°C
• Refractive Index: 1.549
• Solubility: soluble in Toluene
• Sensitive: Moisture Sensitive
• BRN: 2690815
• CAS DataBase Reference: 2,4,6-TRIMETHYLPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRIMETHYLPHENYL ISOTHIOCYANATE(6095-82-5)
• EPA Substance Registry System: 2,4,6-TRIMETHYLPHENYL ISOTHIOCYANATE(6095-82-5)

Safety Data

• Hazard Codes: T
• Statements: 20/21/22-36/37/38-34
• Safety Statements: 26-36/37/39-45
• RIDADR: 2811
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 6095-82-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 378, 1971 DOI: 10.1055/s-1971-21747

InChI:InChI=1/C10H11NS/c1-7-4-8(2)10(11-6-12)9(3)5-7/h4-5H,1-3H3

Upstream product

• 463-71-8 thiophosgene 
• 88-05-1 2,4,6-trimethylaniline 
• 85451-84-9 N-(2,4,6-Trimethylphenyl)-N'-methyl-thioharnstoff 
• 4669-59-4 bis(diethylamino)dimethylsilane 
• 75-89-8 2,2,2-trifluoroethanol 
• 333-20-0 potassium thioacyanate 
• 113475-82-4 4.5-cis-Bis-methoxycarbonyl-2.2-dimethyl-1.3-dithiolan 
• 2904-57-6 mesitylenecarbonitrile oxide 
• 103721-69-3 (4S,5R)-2-Vinyl-[1,3]dithiolane-4,5-dicarboxylic acid dimethyl ester 
• 113475-90-4 2,2-dimethyl[1,3]dithiolane-1,1-dioxide 
• 113475-83-5 cis-1,4-Dithiaspiro<4.5>decan-2,3-dicarbonsaeure-dimethylester 
• 104084-85-7 6-ethoxy-2-phenyl-1,3-oxazine-4-thione 
• 104084-71-1 6-(N,N-diethylamino)-5-methyl-2-phenyl-1,3-oxazine-4-thione 
• 19172-47-5 Lawessons reagent 

Downstream Products

• 94772-14-2 mesityl-thiocarbamic acid O-ethyl ester 
• 91059-97-1 1-(2,4,6-trimethylphenyl)thiourea 
• 29555-12-2 N,N'-bis(2,4,6-trimethylphenyl)thiourea 
• 117057-03-1 5-Amino-3-morpholin-4-yl-[1,2,4]triazole-1-carbothioic acid (2,4,6-trimethyl-phenyl)-amide 
• 60-29-7 diethyl ether 
• 67-68-5 dimethyl sulfoxide 
• 68-12-2 N,N-dimethyl-formamide 
• 141-78-6 ethyl acetate 
• 100-47-0 benzonitrile 
• 55-21-0 benzamide 
• 2227-79-4 benzenecarbothioamide 
• 512-56-1 trimethyl phosphite 
• 98-95-3 nitrobenzene 
• 680-31-9 N,N,N,N,N,N-hexamethylphosphoric triamide 

Relevant articles and documents

NaOH-promoted one-pot aryl isothiocyanate synthesis under mild benchtop conditions

In this work, we have established a green synthesis of aryl isothiocyanates promoted by the low-cost and readily available NaOH from aryl amines and carbon disulfide in a one-pot procedure. The developed protocol features no extra desulfurating reagents and mild benchtop conditions, in which NaOH serves as both the base and the desulfurating reagent to decompose the dithiocarbamate intermediate. Fourteen examples of aryl amines bearing electronic neutral, rich and poor substituents, as well as benzylamine, have proved to be compatible substrates in the developed method to furnish the corresponding isothiocyanates. The reaction has been performed on a gram scale to further demonstrate its synthetic utility. Compared to the reported base-promoted synthesis of aryl isothiocyanates that requires the use of special equipment, such as the ball mill or the microwave reactor, the simplicity in operation and scalability enables this method to efficiently access a variety of aryl isothiocyanates.

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.

Synthesis of thiocarbamoyl fluorides and isothiocyanates using amines with CF3SO2Cl

A practical and efficient method to synthesize thiocarbamyl fluorides and isothiocyanates from amines with trifluoromethanesulfonyl chloride was developed. In the presence of the reducing agent triphenylphosphine and sodium iodide, thiocarbamyl fluorides and isothiocyanates were synthesized from secondary/primary amine in moderate to excellent yields, respectively. A broad scope of substrates and good functional group compatibility were observed.

Synthesis methods for isothiocyanate derivative

The invention discloses synthesis methods for an isothiocyanate derivative. The first synthesis method includes reacting raw materials, including primary amine, trifluoromethyltrimethylsilane, potassium fluoride and sulfur, with an organic solvent at the room temperature to obtain the isothiocyanate derivative. The synthetic isothiocyanate derivative has the advantages of simple operation, safety,high efficiency, non-toxicity, low raw material price, mild condition, high yield, wide application range of substrates, high compatibility of functional groups and the like. The second synthesis method includes reacting raw materials, including the primary amine, silver trifluoromethane and potassium bromide, with the organic solvent at the room temperature to obtain the isothiocyanate derivative. The isothiocyanate derivative has the advantages of simple operation, safety, high efficiency, easy availability of the raw materials, nearly quantitative yield, wide application range of the substrates, applicability to selective post-modification of drugs or complex compounds, and the like.

Direct, Microwave-Assisted Synthesis of Isothiocyanates

A microwave-assisted desulfuration of readily available dithiocarbamates, formed in situ from primary amines, leading to target isothiocyanates has been developed. This efficient protocol provides a rapid, environmentally benign route to aliphatic and aromatic isothiocyanates.

Synthesis of thiocarbamoyl fluorides and isothiocyanates using CF3SiMe3 and elemental sulfur or AgSCF3 and KBr with amines

Reactions of thiocarbonyl fluoride derived from cheap, readily available, and widely used CF3SiMe3, elemental sulfur, and KF with secondary amines and primary amines at room temperature in THF provided a wide variety of thiocarbamoyl fluorides and isothiocyanates in moderate to excellent yields, respectively. The two reactions show broad substrate scope and good functional group tolerance. Moreover, AgSCF3 reacts with secondary/primary amines under KBr at room temperature, affording quantitative thiocarbamoyl fluorides/isothiocyanates, which feature late-stage application.

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.

Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines

The reaction of thiocarbonyl fluoride, generated from difluorocarbene, with various amines under mild conditions is described. Secondary amines, primary amines, and o-phenylenediamines are converted to thiocarbamoyl fluorides, isothiocyanates, and difluoromethylthiolated heterocycles, respectively. Thiocarbamoyl fluorides were further transformed into trifluoromethylated amines by using a one-pot process. Thiocarbonyl fluoride is generated in situ and is rapidly fully converted in one pot under mild conditions; therefore, no special safety precautions are needed.

Isothiocyanation of amines using the Langlois reagent

The Langlois reagent was found to be effective for the isothiocyanation of primary amines in the presence of copper iodide and diethyl phosphonate.

NOVEL BENZIMIDAZOLE BASED EGFR INHIBITORS

The present invention disclosed a novel EGFR inhibitor compound of formula (I), process for preparation thereof and methods of treating abnormal cell growth in mammals by administering the compounds of formula (I). Wherein, R= -H, 3-CH3, 4-NO2, 4-Cl, 2-CH3, 4-CH3, 4-Br, 4-F R1= -H, -4-OCH3, -4-NO2,-2-NO2, -4-Cl, -2,4,6-CH3, -4-CH3, -2-F,4-Br, -4-CF3, -4-S-CH3, -4-Cl,-3-CF3, -3-S-CH3, -3,5-CF3, -2-S-CH3, -3-CF3,-4-OCF3, -Si-(CH3)3, -Si-(C2H5)3, (CH3)2-Si- C2H5.