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
• Article Data: 29

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 
• 66425-01-2 dimethyl-2,7 thioxo-3 oxo-5 tetrahydro-3,4,5,6 (2H)triazepine-1,2,4 
• 2904-57-6 mesitylenecarbonitrile oxide 
• 119485-60-8 (2-Mercapto-5-ethyl-3-thenyliden)-cyclohexylamin 
• 75-89-8 2,2,2-trifluoroethanol 
• 333-20-0 potassium thioacyanate 
• 2904-63-4 2,4,6-trimethylbenzohydroximoyl chloride 
• 37143-74-1 1-mesityl-3-phenylthiourea 
• 103-72-0 phenyl isothiocyanate 
• 119485-62-0 3-[1-Cyclohexylamino-meth-(Z)-ylidene]-5-methoxy-3H-thiophene-2-thione 
• 113475-82-4 4.5-cis-Bis-methoxycarbonyl-2.2-dimethyl-1.3-dithiolan 

Downstream Products

• 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 
• 98-10-2 benzenesulfonamide 
• 3820-71-1 tetrathiophosphoric acid triphenyl ester 

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.

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.