CAS 18303-04-3 N-Boc-p-toluenesulfonamide (HCID 688170)

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Basic information

CAS: 18303-04-3
Standard SMILES: Cc1ccc(S(=O)(=O)NC(=O)OC(C)(C)C)cc1
InChIKey: DUTLOVSBVBGNDM-UHFFFAOYSA-N
Molecular formula: C12H17NO4S
Average molar mass: 271.33 g/mol
Monoisotopic mass: 271.0878292

Names & identifiers

Preferred name: N-Boc-p-toluenesulfonamide
IUPAC: tert-butyl N-(4-methylphenyl)sulfonylcarbamate
English name: N-(TERT-BUTOXYCARBONYL)-P-TOLUENESULFONAMIDE
Molecular formula: C12H17NO4S
Molecular weight: 271.33

Names & synonyms

18303-04-3N-Boc-p-toluenesulfonamideDTXSID90350809RefChem:363502DTXCID90301876N-(tert-Butoxycarbonyl)-p-toluenesulfonamidetert-Butyl tosylcarbamateMFCD00134267tert-butyl N-(4-methylphenyl)sulfonylcarbamateN-Boc-4-tolylsulfonamidetert-butyl N-(4-methylbenzenesulfonyl)carbamateN-Boc-4-toluenesulfonamide

Show more names

TsNBocLABOTEST-BB LT00453242N-Boc-toluenesulfonamidetert-Butyl N-tosylcarbamate(tert-Butoxycarbonyl)tosylamine

SCHEMBL497667tert-Butyl N-(p-tosyl)carbamateFS-3882CS-0037692N-(p-tolylsulfonyl)-carbamic acid tert-butyl ester(tert-butoxy)-N-[(4-methylphenyl)sulfonyl]carboxamideN-Boc-4-methylbenzenesulfonamideCarbamic acid, [(4-methylphenyl)sulfonyl]-, 1,1-dimethylethyl ester

Database identifiers

CAS: 18303-04-3
PubChem CID: 688170
DTXSID: DTXSID90350809
Nikkaji: J145.915E

Properties

Computed structural properties

XLogP: 2.5
Topological polar surface area: 80.9 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 4
Heavy atoms: 18
Formal charge: 0
Complexity: 383

Physicochemical properties

Melting point: 121 · 121-123 °C(lit.)
Density: 1.201 · 1.201±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: 25 mg/mL, · chloroform: soluble25mg/mL, clear, colorless
form: powder to crystal
pka: 4.84 · 4.84±0.10(Predicted)
color: White to Almost white
InChI: InChI=1S/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)
InChIKey: DUTLOVSBVBGNDM-UHFFFAOYSA-N
SMILES: C(OC(C)(C)C)(=O)NS(C1=CC=C(C)C=C1)(=O)=O
CAS DataBase Reference: 18303 · 18303-04-3
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements

Safety & regulation

Safety data

wgk: 3
hs_code: 29350090
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 24/25
Storage Class: 10 - Combustible liquids
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Chemistry & industry

Applications · 3 items

DescriptionN-(TERT-BUTOXYCARBONYL)-P-TOLUENESULFONAMIDE is an useful component in Mitsunobu reactions for the direct preparation of protected amines from alcohols.

UsesN-(tert-Butoxycarbonyl)-p-toluenesulfonamide may be used in the preparation of enyne amide, precursor for Pauson-Khand reaction.

General DescriptionN-(tert-Butoxycarbonyl)-p-toluenesulfonamide is a N-substituted sulphonamide and its reaction with N-trityl L-serine esters under Mitsunobu reaction conditions is reported. It can be directly coupled with primary, secondary and allylic alcohols under Mitsunobu conditions to afford various sulfonyl-protected amines.