58479-61-1 Usage
Chemical Properties
Tert-Butylchlorodiphenylsilane is a colorless to pale brown oily liquid with pungent odor, may be used as silylating agent for derivatization of alcohols, ketones, carboxylic acids, amines, amides and mercaptanes selectively into functional groups in different sterical environments.
Physical properties
colorless liquid, bp 93–95°C/0.015 mmHg;
n20
D 1.5680; d 1.057 g cm?3.
Uses
Different sources of media describe the Uses of 58479-61-1 differently. You can refer to the following data:
1. Several newmethods have been developed
for using the reagent to protect primary and secondary alcohols
as their TBDPS ethers. In the presence of ammonium nitrate or
ammonium perchlorate, reaction between TBDPS-Cl and a primary
alcohol, such as benzyl alcohol, in DMF provided excellent
yields of the corresponding silyl ethers in just 15 min (eq 1).19
When silver nitrate was used as promoter, the reactions gave
inferior yields under otherwise identical conditions.When TBDPS-Cl is used to react with hemiacetals, it converts
hemiacetals into ring-opened silyl ether carbonyl compounds, instead
of mixed acetals.Presumably, the sizable TBDPS group
presents too much steric hindrance for the formation of the corresponding
mixed silyl acetals.
2. tert-Butyldiphenylchlorosilane acts as a silylating reagent used to protect alcohols and in the preparation of silyl ethers. It plays a major role as a raw material and a precursor in organic synthesis and pharmaceuticals. It is also used for the synthesis of interphenylene phenyloxazoles which can be used for the treatment of circulatory disorders, angina and stroke.
3. tert-Butylchlorodiphenylsilane can be used to prepare 1-benzyloxy-3-(tert-butyldiphenylsilyloxy)propan-2-ol, a key intermediate for the synthesis of mono-O-protected pyrimidine acyclic nucleosides.
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.
