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Ethyl 4-methylbenzenesulfinate, also known as ethyl tosyl or p-toluenesulfonic acid ethyl ester, is an organic compound with the chemical formula C9H12O3S. It is a colorless to pale yellow liquid that is soluble in organic solvents and has a pungent odor. ethyl 4-methylbenzenesulfinate is derived from the reaction of p-toluenesulfonic acid with ethanol and serves as a valuable intermediate in the synthesis of various organic compounds, particularly in the pharmaceutical and agrochemical industries. Ethyl 4-methylbenzenesulfinate is known for its reactivity as a sulfonylating agent, which allows it to be used in the preparation of sulfonamides and other sulfur-containing compounds. Its stability and ease of handling make it a preferred choice in many chemical reactions.

1858-86-2

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1858-86-2 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 1858-86-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,5 and 8 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1858-86:
(6*1)+(5*8)+(4*5)+(3*8)+(2*8)+(1*6)=112
112 % 10 = 2
So 1858-86-2 is a valid CAS Registry Number.

1858-86-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl 4-methylbenzenesulfinate

1.2 Other means of identification

Product number -
Other names ethyl p-methylbenzenesulphinate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1858-86-2 SDS

1858-86-2Relevant academic research and scientific papers

Isocyanide-Induced Esterification of Sulfinic Acids to Access Sulfinates

Yang, Jianjing,Dong, Haozhe,Yan, Kelu,Song, Xiaodan,Yu, Jie,Wen, Jiangwei

supporting information, p. 5417 - 5421 (2021/09/29)

The isocyanide-induced esterification of sulfinic acids with alcohols or thiophenols access to sulfinates has been developed. Various primary, secondary, and tertiary alcohols could be compatible with the established protocols. Notably, such an isocyanide-induced synthetic strategy presented the advantages of simple operation, good functional group tolerance, and more than 40 examples up to 99% yields. (Figure presented.).

Dual Roles of Rongalite: Reductive Coupling Reaction to Construct Thiosulfonates Using Sulfonyl Hydrazides

Zhang, Guofu,Fan, Qiankun,Zhao, Yiyong,Wang, Huimin,Ding, Chengrong

, p. 81 - 85 (2020/11/03)

A tunable and practical transformation of structurally diverse sulfonyl hydrazides into thiosulfonates in the presence of Rongalite (NaHSO 2·CH 2O) was developed. Transition-metal-free conditions, operational simplicity, and readily available reagents are the striking features of this protocol. It is the first example for the synthesis of thiosulfonates using sulfonyl hydrazides with the assistance of reductant. Additionally, the mechanistic studies revealed that this transformation probably undergoes via a reducing-coupling pathway.

NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions

Zhang, Guofu,Fan, Qiankun,Wang, Huimin,Zhao, Yiyong,Ding, Chengrong

, p. 833 - 837 (2020/12/07)

We have developed a protocol for the NaHSO3-promoted esterification of sulfonyl hydrazides with alcohols for the synthesis of sulfinic esters. Various sulfonyl hydrazides could be converted to the corresponding sulfinic esters in good to high yields. The merits of this protocol include mild transition-metal-free reaction conditions, an inexpensive and available reagent, and operational simplicity. Controlled experiments reveal that this transformation probably undergoes via a radical pathway. (Figure presented.).

Preparation method of sulfinate compound

-

Paragraph 0055-0058, (2021/02/13)

The invention relates to a preparation method of a sulfinate compound shown as a formula (III), which comprises the following steps: by using a sulfonyl hydrazine compound shown as a formula (I) and alcohol shown as a formula (II) as raw materials, adding

Iodine-catalyzed sulfuration of isoquinolin-1(2H)-ones applying ethyl sulfinates

Mu, Yangxiu,Yang, Minghua,Li, Fengxia,Iqbal, Zafar,Jiang, Rui,Hou, Jing,Guo, Xin,Yang, Zhixiang,Tang, Dong

supporting information, p. 4934 - 4937 (2021/03/26)

An efficient sulfuration of isoquinolin-1(2H)-ones at the C-4 position is reported by employing ethyl sulfinates, and the corresponding products are obtained in moderate to excellent yields in the presence of iodine. This synthetic strategy provides a range of thioether-isoquinolin-1(2H)-ones while tolerating a number of functional groups on the isoquinoline nitrogen atom and benzene ring. In addition, pyridin-2(1H)-one is also reacted smoothly and afforded the corresponding thioether product in moderate yield. A plausible mechanism is suggested based on the preliminary mechanistic studies.

Direct synthesis of sulfinic esters via ultrasound accelerated tandem reaction of thiols and alcohols with N-bromosuccinimide

Nguyen, Lan-Anh Thi,Le, Tri-Nghia,Duong, Cong-Thang,Vo, Chi-Tam,Duus, Fritz,Luu, Thi Xuan Thi

, p. 519 - 528 (2021/05/27)

The direct transformation of various thiols and simple alcohols with N-bromosuccinimide into sulfinic esters has been investigated by using different categories of base/acidic catalysts as well as co-solvents under varied reaction conditions. The reaction was found out to afford the sulfinic esters with high yields in the absence of catalysts, especially within the shorter time under the acceleration of ultrasonic irradiation than under the longer-lasting conventional stirring conditions.

Metal-Free C-C Coupling of an Allenyl Sulfone with Picolyl Amides to Access Vinyl Sulfones via Pyridine-Initiated in Situ Generation of Sulfinate Anion

Omer, Humair M.,Liu, Peng,Brummond, Kay M.

, p. 7959 - 7975 (2020/07/15)

Vinyl sulfones are privileged motifs known for their biological activity and synthetic utility. Synthetic transformations to efficiently access high-value compounds with these motifs are desired and sought after. Herein, a new procedure is described to fo

Electrochemical Synthesis of Sulfinic Esters via Aerobic Oxidative Esterification of Thiophenols with Alcohols

Zhou, Hongyan,Duan, Jiaokui,Xie, Dongtai,Yang, Jingya,Ma, Ben,Wang, Ganggang,Wu, Chengqi,Wang, Xi-Cun

, p. 2705 - 2712 (2020/09/15)

A method for the electrochemical synthesis of sulfinic esters by aerobic oxidative coupling of thiophenols and alcohols has been developed. Using electrons as the redox reagent and O 2in air as the oxygen source, the reactions proceeded smoothly at room temperature, even for a gram-scale preparation. No use of catalyst, clean redox reagent, green and abundant oxygen source, and mild reaction conditions make this strategy eco-friendl.

Efficient electrosynthesis of sulfinic esters via oxidative cross-coupling between alcohols and thiophenols

Gong, Fengping,Lu, Fangling,Zuo, Lin,Wang, Qi,Li, Ru,Hu, Jiaxin,Li, Zhen,Takfaoui, Abdelilah,Lei, Aiwen

, p. 192 - 196 (2019/09/13)

A new protocol for S O bond formation was developed by electrochemical oxidative cross-coupling between alcohols and thiophenols. With this strategy, a series of valuable sulfinic ester derivatives were synthesized up to 96% yield from basic starting materials. A preliminary mechanistic investigation reveals that this reaction involves oxygen reduction reaction (ORR).

Electrochemical synthesis of sulfinic esters from alcohols and thiophenols

He, Yang,Zhang, Jinli,Xu, Liang,Wei, Yu

supporting information, (2020/01/31)

Electrochemical oxidative couplings between S[sbnd]H and O[sbnd]H bonds are achieved herein directly from readily-available alcohols and thiophenols, affording a series of diverse sulfinic esters. This strategy can take advantage of 6 equivalents of alcohol, relative to thiophenol, to achieve moderate to good yields, without the assistance of any metallic catalysts, bases, and additional oxidants.

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