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
• Article Data: 48

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

Description

N-(TERT-BUTOXYCARBONYL)-P-TOLUENESULFONAMIDE, also known as a N-substituted sulphonamide, is a chemical compound that plays a significant role in various chemical reactions and synthesis processes. It is characterized by its ability to react with N-trityl L-serine esters under Mitsunobu reaction conditions and can be directly coupled with primary, secondary, and allylic alcohols under the same conditions to produce various sulfonyl-protected amines.

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

Downstream Products

• 143944-89-2 N-(tert-butyloxycarbonyl)-N-[(4-methylphenyl)sulfonyl]-4-chlorobutylamine 
• 126745-57-1 C₁₇H₂₃NO₄S 
• 433732-83-3 1,1-dimethylethyl (E)-3-hexenyl[(4-methylphenyl)sulfonyl]carbamate 
• 866036-95-5 tert-butyl 1-methyl-3-butenyl[(4-methylphenyl)sulfonyl]carbamate 
• 178908-92-4 C₁₉H₂₇NO₆S 
• 338463-00-6 N-(tert-butoxycarbonyl)-N-but-3-ynyl-4-methylbenzenesulfonamide 
• 286376-22-5 N-tert-butoxycarbonyl-N-(but-2-yn-1-yl)-(4-methylphenyl)sulfonamide 
• 349471-98-3 (+/-)-N-(6-chloro-3-methyl-5-triisopropylsiloxyhex-3-ene)-N-t-butoxycarbonyl-N-tosylamide 
• 1026926-01-1 C₂₃H₃₇NO₄S 
• 756821-37-1 (1R,6R)-N-(tert-butoxycarbonyl)-N-[(6-tert-butyldimethylsilanyloxy)cyclohept-3-enyl]toluensulfonamide 
• 944546-58-1 C₂₅H₃₂O₄BrNS 

Relevant articles and documents

Synthesis, catalytic activity and redox properties of palladium(0) complexes with 15-membered triolefinic macrocyclic ligands containing one, two or three ferrocenyl groups

A series of 15-membered triolefinic macrocycles containing ferrocenyl groups and their palladium(0) complexes have been synthesized and characterized. Their catalytic activity has been demonstrated in Suzuki-type cross-coupling and in the Heck reaction. Their redox properties have been investigated by means of cyclic voltammetry.

Nickel-Catalyzed C(sp3)-H Functionalization of Benzyl Nitriles: Direct Michael Addition to Terminal Vinyl Ketones

An efficient nickel(0)-catalyzed addition of benzyl nitriles to terminal vinyl ketones via C(sp3)-H functionalization has been developed. The reaction provides a novel and efficient protocol for the synthesis of α-functionalized benzyl nitriles with a wide range of structural diversity under mild reaction conditions while obviating the use of a strong base. The work might be potentially useful toward the development of an enantioselective variant using chiral nitrogen ligands.

A Radical-Initiated Fragmentary Rearrangement Cascade of Ene-Ynamides to [1,2]-Annulated Indoles via Site-Selective Cyclization

Straightforward access to [1,2]-annulated indoles, key substructures in natural products, is highly desirable yet challenging. Herein, a radical triggered fragmentary cyclization cascade reaction of ene-ynamides is presented, providing a rapid access into [1,2]-annulated indoles by an intermolecular radical addition, intramolecular cyclization, desulfonylative aryl migration, and site-selective C(sp2)-N cyclization sequence. DFT calculations support oxidation of N-centered radical species to cations prior to the C-N bond formation, followed by an unusual aza-Nazarov cyclization.