2845-62-7

Basic information

• Product Name: BENZENESULFONYL ISOCYANATE
• Synonyms: BENZENESULPHONYL ISOCYANATE;BENZENESULFONYL ISOCYANATE;phenylsulphonyl isocyanate;Benzenesulfonyl isocyanate, 98+%;Phenylsulfonyl isocyanate.;(Isocyanatosulfonyl)benzene;Isocyanatosulfonylbenzene;Benzenesulfonyl isocyanate,95%
• CAS NO: 2845-62-7
• Molecular Formula: C₇H₅NO₃S
• Molecular Weight: 183.18
• EINECS: 220-640-6
• Product Categories: Pharmaceutical Intermediates;Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 2845-62-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 130 °C9 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear colourless liquid
• Density: 1.369 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0104mmHg at 25°C
• Refractive Index: n20/D 1.536(lit.)
• Storage Temp.: Refrigerator (+4°C)
• Sensitive: Moisture Sensitive
• BRN: 743441
• CAS DataBase Reference: BENZENESULFONYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZENESULFONYL ISOCYANATE(2845-62-7)
• EPA Substance Registry System: BENZENESULFONYL ISOCYANATE(2845-62-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/22-36/38-42
• Safety Statements: 23-26-36
• RIDADR: UN 2922 8/PG 1
• WGK Germany: 3
• F: 10-19-21
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 2845-62-7(Hazardous Substances Data)

Usage

Description

Benzenesulfonyl isocyanate is a clear, colorless liquid that is known for its reactivity with ethanol and phenol, yielding normal urethan products. It is a versatile chemical compound with various applications in different industries due to its unique chemical properties.

Uses

Used in Chemical Synthesis:
Benzenesulfonyl isocyanate is used as a reagent for the synthesis of sterically hindered derivatives of phenols and alcohols. Its ability to react with these compounds makes it a valuable component in the creation of various chemical products.
Used in Polymer Modification:
In the field of polymer science, benzenesulfonyl isocyanate is used in the reaction of semi-crystalline poly(ether ether ketone) films with carbonyl selective reagents. This reaction leads to the production of modified film samples, which can have improved properties or be tailored for specific applications.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, benzenesulfonyl isocyanate can also be used in the pharmaceutical industry for the synthesis of various drugs and drug intermediates. Its reactivity with ethanol and phenol can be exploited to create new compounds with potential therapeutic applications.
Used in Research and Development:
Due to its unique chemical properties and reactivity, benzenesulfonyl isocyanate is also used in research and development settings. Scientists and researchers can utilize this compound to explore new reactions, develop novel materials, and study its potential applications in various fields.

InChI:InChI=1/C7H5NO3S/c9-6-8-12(10,11)7-4-2-1-3-5-7/h1-5H

Upstream product

• 3315-16-0 silver cyanate 
• 98-09-9 benzenesulfonyl chloride 
• 1118-02-1 trimethylsilyl isocyanate 
• 368-43-4 phenylsulfonyl fluoride 
• 1023-95-6 N,N-bis(trimethylsilyl)benzenesulfonamide 
• 98-10-2 benzenesulfonamide 
• 198778-00-6 9-Benzenesulfonyl-3,3-dimethyl-4,6-dioxa-1,2,9-triaza-spiro[4.4]non-1-ene 
• 201230-82-2 carbon monoxide 
• 17338-33-9 C₆H₅ClNO₂S^(1-)*K⁽¹⁺⁾ 
• 127-52-6 chloramine-B 
• 87301-29-9 N-(phenylsulfonylimino)-phenyl-λ³-iodane 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 6452-61-5 di-n-butyldiphenyltin 
• 960-16-7 tributylphenylstannane 

Downstream Products

• 3559-04-4 N-benzoyl-benzenesulfonamide 
• 124813-66-7 C₁₃H₁₄N₄O₃S*C₆H₉N₃ 
• 72647-81-5 N-phenylsulfonyl-N'-(2,6-dimethylpyrimidin-4-yl)urea 
• 142503-54-6 N-(1,2-benzisothiazol-3-yl)-N'-benzenesulfonylurea 
• 142141-29-5 4-methyl-3-methylimino-5-phenylsulfonylimino-1,2,4-dithiazolidine 
• 142141-30-8 2,4-dimethyl-3-phenylsulfonylimino-1,2,4-thiadiazolidine-5-thione 
• 119271-20-4 N-phenylsulfonyl-N'-(5-chloro-2,6-dimethylpyrimidin-4-yl)urea 
• 100374-93-4 N-([(4-bromophenyl)amino]carbonyl)benzenesulfonamide 
• 2880-08-2 4-chlorophenyl N-(phenylsulfonyl)carbamate 
• 98-10-2 benzenesulfonamide 
• 124-38-9 carbon dioxide 
• 98-11-3 benzenesulfonic acid 
• 127-63-9 diphenyl sulphone 
• 351527-46-3 C₁₇H₁₇N₃O₇S 

Relevant articles and documents

Spiro-fysed 2-alkoxy-2-amino-Δ3-1,3,4-oxadiazolines. Synthesis and thermolysis to corresponding aminooxycarbenes

Δ3-1,3,4-Oxadiazolines spiro-fused at C2 to C2 to oxazolidines (12) or to C2 of tetrahydro-1,3-oxazines (13) were synthesized. The oxadiazolines undergo thermolysis in benzene at 90°C with first-order rate constants of (1.6-50) × 10-5 s-1. The dependence of these rate constants on the nature of the substituents present on the oxadiazoline ring is consistent with a mechanism involving a carbonyl ylide intermediate. Substituents on N of the oxazolidine or tetrahydro-1,3-oxazine moieties play a major role in determining the fragmentation pathways. Oxadiazolines with N-carbonyl groups (12c-j, 13d,e) afford essentially quantitative yields of the corresponding aminooxycarbenes, while other fragmentation reactions compete with carbene generation in the case of oxadiazolines with N-methyl (12b, 13c) or N-sulfonyl (12k) groups.

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.

Eine neue Palladium-katalysierte Carbonylierung von aromatischen N-Chlorsulfonamidaten zu Arylsulfonylisocyanaten

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