1271301-08-6

Basic information

• Product Name: tert-butyl 2-(benzo[d]thiazol-2-ylsulfonyl)-2-phenylacetate
• Synonyms: tert-butyl 2-(benzo[d]thiazol-2-ylsulfonyl)-2-phenylacetate
• CAS NO: 1271301-08-6
• Molecular Weight: 389.496
• Mol File: 1271301-08-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: tert-butyl 2-(benzo[d]thiazol-2-ylsulfonyl)-2-phenylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 2-(benzo[d]thiazol-2-ylsulfonyl)-2-phenylacetate(1271301-08-6)
• EPA Substance Registry System: tert-butyl 2-(benzo[d]thiazol-2-ylsulfonyl)-2-phenylacetate(1271301-08-6)

Safety Data

• Hazardous Substances Data: 1271301-08-6(Hazardous Substances Data)

Upstream product

• 100-51-6 benzyl alcohol 
• 149-30-4 2-Mercaptobenzothiazole 
• 100-39-0 benzyl bromide 
• 67219-33-4 2-phenylmethanesulfonyl-benzothiazole 
• 49761-82-2 tert-butyl 1H-imidazole-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 19654-17-2 2-benzylthiobenzothiazole 

Downstream Products

• 16537-09-0 t-butyl phenylacetate 

Relevant articles and documents

One and Two-Carbon Homologation of Primary and Secondary Alcohols to Corresponding Carboxylic Esters Using β-Carbonyl BT Sulfones as a Common Intermediate

Herein we report the efficient one- and two-carbon homologation of 1° and 2° alcohols to their corresponding homologated esters via the Mitsunobu reaction using β-carbonyl benzothiazole (BT) sulfone intermediates. The one-carbon homologation approach uses standard Mitsunobu C-S bond formation, oxidation and subsequent alkylation, while the two-carbon homologation uses a less common C-C bond forming Mitsunobu reaction. In this latter case, the use of β-BT sulfone bearing esters lowers the pKa sufficiently enough for the substrate to be used as a carbon-based nucleophile and deliver the homologated β-BT sulfone ester, and this superfluous sulfone group can then be cleaved. In this paper we describe several methods for the effective desulfonylation of BT sulfones and have developed methodology for one-pot alkylation-desulfonylation sequences. As such, overall, a one-carbon homologation sequence can be achieved in a two-pot (four step) procedure and the two-carbon homologation in a two-pot (three step) procedure (three-pot; four step when C-acid synthesis is included). This methodology has been applied to a wide variety of functionality (esters, silyl ethers, benzyls, heteroaryls, ketones, olefins and alkynes) and are all tolerated well providing good to very good overall yields. The power of our method was demonstrated in site-selective ingenol C20 allylic alcohol two-carbon homologation.

Practical synthesis of β-acyl and β-alkoxycarbonyl heterocyclic sulfones

A short and efficient synthesis for β-acyl and β-alkoxycarbonyl heterocyclic sulfones containing benzothiazol (BT) and phenyltetrazol (PT) heterocyclic core is presented here. The method seems to be general and provides the desired C-nucleophiles in very good to excellent yields from readily available starting materials.