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1-[(1-Phenylthio)benzyl]-1H-benzotriazole is a benzotriazole-derived compound that serves as a versatile synthetic intermediate, particularly in thioalkylation reactions with reactive aromatic compounds. It can be prepared from benzotriazole, an aldehyde, and thiophenol, and it reacts under mild conditions to yield thioalkylation products in moderate to good yields. While its oxidation behavior has been studied with reagents like m-chloroperbenzoic acid (m-CPBA), leading to sulfoxides or sulfones, no heterolytic cleavage products between the α-carbon and N-1 of the benzotriazole moiety have been isolated. 1-[(1-phenylthio)benzyl]-1H-benzotriazole is primarily valued for its utility in organic synthesis as a thioalkylating agent.

138904-87-7

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138904-87-7 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 138904-87-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,8,9,0 and 4 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 138904-87:
(8*1)+(7*3)+(6*8)+(5*9)+(4*0)+(3*4)+(2*8)+(1*7)=157
157 % 10 = 7
So 138904-87-7 is a valid CAS Registry Number.

138904-87-7Relevant academic research and scientific papers

Oxidation of 1-[(Aryl)(phenylseleno)methyl]-, 1-[(Aryl)(arylthio)-(phenylseleno)methyl]-, and 1-[(Aryl)(diphenylseleno)-methyl]benzotriazoles with m-Chloroperbenzoic Acid

Kang, Yoon Ho,Kim, Kyongtae

, p. 1741 - 1752 (1997)

During the last decade, benzotriazole (1) has received much attention as an excellent synthetic auxiliary [1]. Recently Katritzky, et al. [2] studied the oxidation of 1-(phenylthiomethyl)benzotriazole (2a) and 1-(2-phenyl-1-phenylthioethyl)benzotriazole (2b) and obtained their sulfones and sulfoxides by treatment with m-chloroperbenzoic acid (m-CPBA) and sodium periodate, respectively. No compounds derived from a heterolytic cleavage between the α-carbon and the N-1 atoms of the foregoing compounds were isolated.

Thioalkylation of reactive aromatic compounds with α-(benzotriazol-1-yl)benzyl phenyl sulfide

Katritzky,Xie,Afridi,Fan,Kuzmierkiewicz

, p. 47 - 50 (1993)

1-[α-(Phenylthio)benzyl]- and 1[(4-methylphenyl)(phenylthio)methyl]benzotriazole, readily available from benzotriazole, an aldehyde and thiophenol, react with a variety of active aromatic compounds under mild conditions to give the thioalkylation products in moderate to good yields.

Efficient syntheses of thiochromans via cationic cycloadditions

Katritzky,Button

, p. 5595 - 5600 (2007/10/03)

α-(Benzotriazolyl)methyl thioethers 1a-e reacted with styrenes under Lewis acid catalysis to give novel polysubstituted thiochromans (3,4-dihydro-2H-1 -benzothiopyrans) 3-14 and 16-20 in generally high yields. Most thiochromans were isolated as one diastereomer following recrystallization. The configuration and conformation of the products are predicted on the basis of their NMR data. A stepwise reaction, proceeding via a [4+ + 2] cationic polar cycloaddition mechanism, is proposed.

A convenient route to β-phenylthioalkyl ketones

Katritzky, Alan R.,Fang, Yunfeng,Feng, Daming,Silina, Alina,Prakash, Indra

, p. 331 - 337 (2007/10/03)

The preparation of β-phenylthioalkyl ketones via the reactions of α- benzotriazolylalkyl phenyl sulfides (1a-e) with enamines (5a-d) is described.

182. A Convenient Synthesis of Vinyl Sulfides

Katritzky, Alan R.,Afridi, Amir S.,Kuzmierkiewicz, Wojciech

, p. 1931 - 1935 (2007/10/02)

tert-Alkyl sulfides, with an α-(1H-benzotriazol-1-yl) group 6 and 13, are readily prepared from N--1H-benzotriazoles 3 and N-(11), respectively, by reaction with BuLi and then with the appropriate electrophile.The tert-alkyl sulfides 6 a

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