[[디플루오로(트리메틸실릴)메틸]티오]-벤젠

[[디플루오로(트리메틸실릴)메틸]티오]-벤젠 C화학적 특성, 용도, 생산

개요

An effective reagent to introduce difluoromethyl groups into carbonyls, imines, enamines, and alkyl halides. Not only various simple aldehydes and ketones, but also functionalized carbonyls such as α- and γ-ketoesters and cyclic imides can be difluoro(phenylthio)methylated in high yields under the activation of a catalytic amount of Lewis bases. The substitution reaction proceeds well with primary alkyl bromides and iodides as the limiting reactant when cesium fluorode/15-crown-5 is used as the fluoride source/additive. Under radical conditions, the difluoro(phenylthio)methyl compounds containing vinyl functional groups can form 5- or 6-membered rings via intramolecular cyclization.

물리적 성질

colorless liquid; bp 86–87?C/4 mmHg.

용도

Organofluorine compounds have received remarkable interest in recent years due to their wide-ranging biological effects. The development of general synthetic routes to such compounds and the use of new fluorinated compounds as building blocks are of great importance. Of particular interest is the selective incorporation of the gem-difluoromethylene group ‘CF2’ into organic molecules. The report on the synthesis of PhSCF2SiMe3 was published in 2003 by Prakash et al., and the reagent has become one of the most versatile and efficient nucleophilic (phenylthio)difluoromethylating reagents.
When excess potassium t-butoxide was used as a promoter, PhSCF2SiMe3 reacted with diphenyl disulfide to give the corresponding dithioacetal in 85% yield (eq 8).

제조 방법

[difluoro(phenylthio)methyl]trimethylsilane (PhSCF2SiMe3) was prepared for the first time by Prakash et al.,1 using the Barbier coupling reaction of bromodifluoromethylphenyl sulfide,2 prepared from dibromodifluoromethane and sodium benzenethiolate,3 magnesium metal, and chlorotrimethylsilane (TMSCl) in DMF (eq 1).

화학 반응

(1) Difluoromethylation of aldehydes and ketones.

(2) Difluoromethylation of imines and enamines.

(3) (Phenylthio)difluoromethylation of imines for further cyclizations.

(4) Difluoromethylation of alkyl halides.

[[디플루오로(트리메틸실릴)메틸]티오]-벤젠 준비 용품 및 원자재

원자재

준비 용품

[[디플루오로(트리메틸실릴)메틸]티오]-벤젠 공급 업체

공급자	전화	이메일	국가	제품 수	이점
Zibo Hangyu Biotechnology Development Co., Ltd	+86-0533-2185556 +8617865335152	Mandy@hangyubiotech.com	China	10978	58
J & K SCIENTIFIC LTD.	010-82848833 400-666-7788	jkinfo@jkchemical.com	China	94717	76
Daicel Chiral Technologies (China)CO.,LTD	021-50460086-9 15921403865	han_yajun@dctc.daicel.com	China	7176	65
Greenherbs Science and Technology Development Co., Ltd.	010-61136123	pub02@greenherbs.com.cn	China	4049	58
JinJin Le Chemical Co., Ltd	10106090	jjlchem2@163.com	China	9986	58
Shenzhen Polymeri Biochemical Technology Co., Ltd.	+86-400-002-6226 13028896684	sales@rrkchem.com	China	56068	58
Jiangsu aikang biomedical research and development co., LTD	025-66110311 13155353615	qzhang@aikonchem.com	China	15527	58
Shanghai Ruipu Medical Technology Co., Ltd	15895968936	1018762393@qq.com	China	9993	58
TCI (Shanghai) Chemical Trading Co., Ltd.	021-021-61109150	sales@tcisct.com	China	31163	58
Ningbo Chemrio Chemtech Co,.Ltd.	0574-27891269 18667892864	frank.xiaodong@chemriotech.com	China	3595	58