58479-61-1 Usage
Description
tert-Butylchlorodiphenylsilane, also known as TBDPS-Cl, is an organosilicon compound that serves as a silylating reagent in various chemical reactions. It is characterized by its bulky tert-butyl group and two phenyl groups attached to a silicon atom, with one of the phenyl groups bearing a chlorine substituent. This unique structure provides steric hindrance and reactivity that make it useful in protecting alcohols and preparing silyl ethers.
Uses
Used in Organic Synthesis:
tert-Butylchlorodiphenylsilane is used as a silylating reagent for protecting primary and secondary alcohols as their TBDPS ethers. This protection is crucial in organic synthesis to prevent unwanted reactions from occurring at the alcohol functional group. The reagent is effective in the presence of ammonium nitrate or ammonium perchlorate, providing excellent yields of the corresponding silyl ethers in a short reaction time.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, tert-Butylchlorodiphenylsilane plays a significant role as a raw material and precursor in the synthesis of various compounds. It is used in the preparation of 1-benzyloxy-3-(tert-butyldiphenylsilyloxy)propan-2-ol, a key intermediate for the synthesis of mono-O-protected pyrimidine acyclic nucleosides, which are important in the development of antiviral and anticancer drugs.
Used in the Synthesis of Interphenylene Phenyloxazoles:
tert-Butylchlorodiphenylsilane is also used in the synthesis of interphenylene phenyloxazoles, a class of compounds with potential therapeutic applications. These compounds can be used for the treatment of circulatory disorders, angina, and stroke, offering new avenues for medical intervention in cardiovascular health.
Used in the Conversion of Hemiacetals:
tert-Butylchlorodiphenylsilane can react with hemiacetals, converting them into ring-opened silyl ether carbonyl compounds instead of mixed acetals. This unique reactivity is attributed to the sizable TBDPS group, which presents too much steric hindrance for the formation of the corresponding mixed silyl acetals. This property can be exploited in organic synthesis to selectively obtain desired products.
Preparation
a dry 1 L, three-necked round bottomed
flask is equipped with a magnetic stirring bar, a 500mL equalizing
dropping funnel fitted with a rubber septum, a reflux condenser,
and nitrogen inlet tube. The flask is flushed with nitrogen,
then charged with 127 g (0.5 mol) of diphenyldichlorosilane
in 300mL of redistilled pentane. A solution of tbutyllithium
in pentane (500 mL, 0.55 mol), is transferred under
nitrogen pressure to the dropping funnel using a stainless steel,
double-tip transfer needle. This solution is slowly added to the
contents of the flask and when the addition is complete, the
mixture is refluxed 30 h under nitrogen with stirring. The suspension
is allowed to cool to rt, the precipitated lithium chloride
is rapidly filtered through a pad of Celite, and the latter
is washed with 200mL of pentane. The solvent is removed by
evaporation, and the colorless residue is distilled through a short
(10 cm), Vigreux column, to give 125–132 g of the colorless title
compound.
Purification Methods
Purify it by repeated fractional distillaton. It is soluble in DMF and pentane [Hanessian & Lavalee Can J Chem 53 2975 1975, Robl et al. J Med Chem 34 2804 1991]. [Beilstein 4 IV 4076 for tert-butylchlorodimethylsilane.]
Check Digit Verification of cas no
The CAS Registry Mumber 58479-61-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,4,7 and 9 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 58479-61:
(7*5)+(6*8)+(5*4)+(4*7)+(3*9)+(2*6)+(1*1)=171
171 % 10 = 1
So 58479-61-1 is a valid CAS Registry Number.
InChI:InChI=1/C16H19ClSi/c1-16(2,3)18(17,14-10-6-4-7-11-14)15-12-8-5-9-13-15/h4-13H,1-3H3
58479-61-1Relevant articles and documents
Synthesis of (±)-diplodialide B and A
Shenvi,Gerlach
, p. 2426 - 2433 (1980)
-
Neutral-Eosin-Y-Photocatalyzed Silane Chlorination Using Dichloromethane
Fan, Xuanzi,Xiao, Pin,Jiao, Zeqing,Yang, Tingting,Dai, Xiaojuan,Xu, Wengang,Tan, Jin Da,Cui, Ganglong,Su, Hongmei,Fang, Weihai,Wu, Jie
supporting information, p. 12580 - 12584 (2019/08/16)
Chlorosilanes are versatile reagents in organic synthesis and material science. A mild pathway is now reported for the quantitative conversion of hydrosilanes to silyl chlorides under visible-light irradiation using neutral eosin Y as a hydrogen-atom-transfer photocatalyst and dichloromethane as a chlorinating agent. Stepwise chlorination of di- and trihydrosilanes was achieved in a highly selective fashion assisted by continuous-flow micro-tubing reactors. The ability to access silyl radicals using photocatalytic Si?H activation promoted by eosin Y offers new perspectives for the synthesis of valuable silicon reagents in a convenient and green manner.
Iron-catalyzed chlorination of silanes
Savela, Risto,Zawartka, Wojciech,Leino, Reko
experimental part, p. 3199 - 3206 (2012/06/04)
A simple and highly efficient iron-catalyzed method for the chlorination of silanes has been developed. By use of 0.5-2% of the Fe(III)-based catalyst FeCl3 or Fe(acac)3 in the presence of 1-1.5 equiv of acetyl chloride as the chlorine donor, a large number of silanes, alkoxysilanes, and silanols were converted to the corresponding chlorosilanes in 50-93% yields. In contrast to earlier reported methods often suffering from expensive catalysts or use of stoichiometric metal salts, hazardous reagents, and reaction conditions, the presently described methodology allows benign reaction conditions and simple workup while using only catalytic amounts of a readily available and economically viable iron catalyst.