18303-04-3

Basic information

• Product Name: N-(TERT-BUTOXYCARBONYL)-P-TOLUENESULFONAMIDE
• Synonyms: LABOTEST-BB LT00453242;N-(TERT-BUTOXYCARBONYL)-P-TOLUENESULFONAMIDE;N-BOC-P-TOLUENESULFONAMIDE;N-(tert-Butoxycarbonyl-p-tolunesulfonamide;(tert-Butoxycarbonyl)tosylamine;N-(p-Tolylsulfonyl)carbamic acid tert-butyl ester;N-Tosylcarbamic acid tert-butyl ester;Tosylcarbamic acid tert-butyl ester
• CAS NO: 18303-04-3
• Molecular Formula: C₁₂H₁₇NO₄S
• Molecular Weight: 271.33
• Product Categories: Amination;Synthetic Organic Chemistry;Nitrogen Compounds;Organic Building Blocks;Protected Amines
• Mol File: 18303-04-3.mol

Chemical Properties

• Melting Point: 121-123 °C(lit.)
• Appearance: /
• Density: 1.201g/cm³
• Refractive Index: 1.521
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: chloroform: soluble25mg/mL, clear, colorless
• PKA: 4.84±0.10(Predicted)
• CAS DataBase Reference: N-(TERT-BUTOXYCARBONYL)-P-TOLUENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(TERT-BUTOXYCARBONYL)-P-TOLUENESULFONAMIDE(18303-04-3)
• EPA Substance Registry System: N-(TERT-BUTOXYCARBONYL)-P-TOLUENESULFONAMIDE(18303-04-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 18303-04-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
N-(TERT-BUTOXYCARBONYL)-P-TOLUENESULFONAMIDE is used as a key intermediate in the preparation of enyne amide, which serves as a precursor for the Pauson-Khand reaction. This reaction is an important method for the synthesis of cyclopentenones, a class of compounds with significant applications in the pharmaceutical and chemical industries.
Used in Organic Chemistry:
In the field of organic chemistry, N-(TERT-BUTOXYCARBONYL)-P-TOLUENESULFONAMIDE is used as a reagent for the formation of sulfonyl-protected amines. This application is crucial for the protection of amine groups during various chemical reactions, allowing for selective functionalization of other groups in the molecule.
Used in Pharmaceutical Industry:
N-(TERT-BUTOXYCARBONYL)-P-TOLUENESULFONAMIDE is also utilized in the pharmaceutical industry for the synthesis of various drug candidates. Its ability to form sulfonyl-protected amines makes it a valuable building block in the development of new medications with potential therapeutic applications.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 379, 1994 DOI: 10.1016/0040-4039(94)85058-5

InChI:InChI=1/C12H17NO4S/c1-9-5-7-10(8-6-9)18(15,16)13-11(14)17-12(2,3)4/h5-8H,1-4H3,(H,13,14)

Upstream product

• 4083-64-1 Tosyl isocyanate 
• 75-65-0 tert-butyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 70-55-3 toluene-4-sulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 14437-03-7 methyl tosylcarbamate 
• 941-55-9 4-toluenesulfonyl azide 
• 13939-06-5 molybdenum hexacarbonyl 
• 34619-03-9 tert-butyldicarbonate 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 108-88-3 toluene 
• 147357-85-5 N-benzyl-N-(benzyloxycarbonyl) toluenesulfonamide 
• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 170948-10-4 N-benzyl N-(tert-butoxycarbonyl) toluenesulfonamide 

Downstream Products

• 139928-91-9 C₁₇H₂₅NO₆S 
• 143944-89-2 N-(tert-butyloxycarbonyl)-N-[(4-methylphenyl)sulfonyl]-4-chlorobutylamine 
• 126745-57-1 C₁₇H₂₃NO₄S 
• 3712-40-1 tert-butyl cyclohexylcarbamate 
• 126745-56-0 N-(2-phenylethyl)-N-tert-butoxycarbonyl-p-toluenesulfonamide 
• 134078-66-3 tert-butyl N-<(2Z,4E)-8-(pivaloyloxy)-2,4-octadienyl>-N-(p-toluenesulfonyl)carbamate 
• 3422-01-3 tert-butyl phenylcarbamate 
• 151654-96-5 C₂₀H₂₇NO₄S 
• 151654-92-1 C₂₁H₂₉NO₄S 
• 151655-10-6 C₂₂H₃₁NO₄S 
• 151655-01-5 C₂₂H₃₁NO₄S 
• 151679-27-5 C₂₅H₃₉NO₄SSi 
• 151130-66-4 C₂₅H₃₃NO₆S 
• 433732-83-3 1,1-dimethylethyl (E)-3-hexenyl[(4-methylphenyl)sulfonyl]carbamate 

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