32324-19-9

Basic information

• Product Name: 2-Toluenesulfonyl isocyanate
• Synonyms: O-TOLUENESULFONYL ISOCYANATE;2-TOLUENESULFONYL ISOCYANATE;2-METHYLBENZENESULFONYL ISOCYANATE;2-Methylbenesulfonylisocyanate;o-Toluenesulfonyl;U-TOLUENESULFONYL ISOCYANATE;o-Toluenesulphonyl isocyanate, tech. 85%;2-Methyl-N-(oxomethylidene)benzenesulfonamide
• CAS NO: 32324-19-9
• Molecular Formula: C₈H₇NO₃S
• Molecular Weight: 197.21
• Product Categories: Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 32324-19-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 129 °C (5 mmHg)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.303 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0033mmHg at 25°C
• Refractive Index: n20/D 1.54(lit.)
• Storage Temp.: 0-6°C
• Solubility: reacts
• Water Solubility: reacts
• CAS DataBase Reference: 2-Toluenesulfonyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Toluenesulfonyl isocyanate(32324-19-9)
• EPA Substance Registry System: 2-Toluenesulfonyl isocyanate(32324-19-9)

Safety Data

• Hazard Codes: Xn
• Statements: 14-20/21/22-42-36/37/38
• Safety Statements: 23-26-27-28-37/39-8-36/37/39
• RIDADR: UN 2206 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 32324-19-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to light yellow liquid

InChI:InChI=1/C8H7NO3S/c1-7-4-2-3-5-8(7)13(11,12)9-6-10/h2-5H,1H3

Upstream product

• 1189-71-5 isocyanate de chlorosulfonyle 
• 68971-87-9 (2-tolyl)tributyltin 
• 17113-82-5 1-methyl-2-(trimethylstannyl)benzene 

Downstream Products

• 119271-21-5 C₁₄H₁₅ClN₄O₃S 
• 138631-18-2 N-<(2-methylphenyl)sulfonyl>-5-<4-(4-phenylbutoxy)phenyl>-2H-tetrazole-2-pentanamide 
• 138631-17-1 N-<<<(2-methylphenyl)sulfonyl>amino>carbonyl>-5-<4-(4-phenylbutoxy)phenyl>-2H-tetrazole-2-pentanamide 
• 88-19-7 methyl 2-(aminosulfonyl)benzoate 
• 64902-61-0 1-(4,6-dimethyl-[1,3,5]triazin-2-yl)-3-(toluene-2-sulfonyl)-urea 
• 1200242-02-9 N-(2,2-dimethylpent-4-enyl)-N'-o-toluenesulfonylurea 
• 128924-57-2 C₁₅H₁₃F₃N₂O₃S 
• 119271-22-6 C₁₄H₁₅BrN₄O₃S 
• 124813-70-3 C₁₄H₁₆N₄O₃S*C₆H₉N₃ 

Relevant articles and documents

Unconventional Regiospecific Syntheses of Aromatic Carbonamides and Thiocarbonamides by Means of Tin-Mediated Friedel-Crafts Reactions

Friedel-Crafts reactions of stannylarenes 1 with tosyl isocyanate (TsNCO, 2) give N-tosylcarbonamides 3 via ipso substitution of the stannyl group.Thus, unconventionally substituted aromatic carbonamides can be obtained.The combination of the reaction of 1 and 2 with that of 1 and chlorosulfonyl isocyanate (14) allows one-pot syntheses of N-(arylsulfonyl)-substituted aromatic carbonamides with optional substitution patterns on both aromatic rings.The known ipso-specific substitutions of stannylarenes with 14 are extended to bi- and tricyclic arenes as well as to thiophenes 6 and 22.One stannyl group can serve as a leaving group for two aromatic systems, as shown with diaryldialkyltins 29.Also, stannylalkanes such as 27 react with 14 to afford alkylsulfonyl isocyanates and products of further reactions, such as 28.From the reactions of 1 with ethoxycarbonyl isocyanate (32), ortho- and meta-substituted aromatic thiocarbonamides 33 which are potential precursors for further syntheses, are accessible.The scope, limitations, and mechanism of these electrophilic substitutions are outlined.