N-(tert-Butoxycarbonyl)-p-toluenesulfonamide

Base Information

• Chemical Name: N-(tert-Butoxycarbonyl)-p-toluenesulfonamide
• CAS No.: 18303-04-3
• Molecular Formula: C12H17 N O4 S
• Molecular Weight: 271.337
• Hs Code.: 29350090
• DSSTox Substance ID: DTXSID90350809
• Nikkaji Number: J145.915E
• Wikidata: Q82126913
• Mol file: 18303-04-3.mol

Synonyms:18303-04-3;N-(tert-Butoxycarbonyl)-p-toluenesulfonamide;tert-Butyl tosylcarbamate;N-Boc-p-toluenesulfonamide;tert-butyl N-(4-methylphenyl)sulfonylcarbamate;Carbamic acid, [(4-methylphenyl)sulfonyl]-, 1,1-dimethylethyl ester;MFCD00134267;N-Boc-4-tolylsulfonamide;N-Boc-4-toluenesulfonamide;tert-butyl N-(4-methylbenzenesulfonyl)carbamate;SCHEMBL497667;(tert-butoxy)-N-[(4-methylphenyl)sulfonyl]carboxamide;N-Boc-4-methylbenzenesulfonamide;tert-Butyl N-(p-tosyl)carbamate;DTXSID90350809;DUTLOVSBVBGNDM-UHFFFAOYSA-N;AKOS015838172;FS-3882;N-(t-butoxycarbonyl)-p-toluenesulfonamide;SY052568;n-(tert-butoxycarbonyl)p-toluenesulfonamide;B1648;CS-0037692;tert-Butyl N-[(4-methylphenyl)sulfonyl]carbamate;N-(p-tolylsulfonyl)-carbamic acid tert-butyl ester;N-(tert-Butoxycarbonyl)-4-methylbenzenesulfonamide;J-011716;TSNBOC;N-(TERT-BUTOXYCARBONYL)-P-TOLUENESULFONAMIDE

Chemical Property of N-(tert-Butoxycarbonyl)-p-toluenesulfonamide

Chemical Property:

• Melting Point: 121-123 °C(lit.)
• PKA: 4.84±0.10(Predicted)
• PSA: 80.85000
• Density: 1.201g/cm³
• LogP: 3.68010
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: chloroform: soluble25mg/mL, clear, colorless
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 271.08782920
• Heavy Atom Count: 18
• Complexity: 383

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-(tert-Butoxycarbonyl)-p-toluenesulfonamide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(=O)OC(C)(C)C
• Uses: N-(tert-Butoxycarbonyl)-p-toluenesulfonamide may be used in the preparation of enyne amide, precursor for Pauson-Khand reaction.

Technology Process of N-(tert-Butoxycarbonyl)-p-toluenesulfonamide

There total 12 articles about N-(tert-Butoxycarbonyl)-p-toluenesulfonamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + toluene-4-sulfonamide (70-55-3) → N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide (18303-04-3)

Guidance literature:

With dmap; triethylamine; In 1,2-dichloro-ethane; at 20 ℃;

DOI:10.3762/bjoc.14.250

Reference yield: 98.0%

Tosyl isocyanate (4083-64-1) + tert-butyl alcohol (75-65-0) → N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide (18303-04-3)

Guidance literature:

Tosyl isocyanate; tert-butyl alcohol; In dichloromethane; at 0 - 20 ℃;

With 5-hydroxymethyl-2-norbornene; In dichloromethane; at 0 - 20 ℃;

With [{1,3-bis(mesyl)imidazolidin-2-yl}RuCl₂(PCy₃)(=CHPh)]; In dichloromethane; Further stages.; Heating;

DOI:10.1021/ol0257880

Reference yield: 96.0%

N-benzyl N-(tert-butoxycarbonyl) toluenesulfonamide (170948-10-4) → N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide (18303-04-3)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; under 760.051 Torr;

DOI:10.1016/j.tetlet.2004.09.118

upstream raw materials:

Tosyl isocyanate

tert-butyl alcohol

di-tert-butyl dicarbonate

toluene-4-sulfonamide

Downstream raw materials:

C₁₇H₂₅NO₆S

C₂₂H₂₉NO₄S

C₄₈H₆₃N₃O₁₂S₃

(E)-5-[(N-tert-Butoxycarbonyl)p-tolylsulfonylamino]tridec-7-ene

Refernces

• 1、 Khanam, Ariza,Mandal, Pintu Kumar. "DirectN-glycosylation of tosyl and nosyl carbamates with trichloroacetimidate donors". supporting information. p. 15386 - 15391. Retrieved 2021/09/07.
• 2、 -. "Synthesis method of azetidine silicon precursor compound and method for synthesizing six-membered silicon-nitrogen heterocyclic compound by using azetidine silicon precursor compound". Paragraph 0091-0095. . Retrieved 2021/06/26.