tert-Butylchlorodiphenylsilane, CAS No. 58479-61-1

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58479-61-1

Catalog No. EBD29910

CAS 58479-61-1

Name tert-Butylchlorodiphenylsilane

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Basic Information

Synonyms: tert-Butylsiphenylchlorosilane t-Butyldiphenylchlorosilane Tert-Butylchloridediphenylsilane Tert-Butyl(chloro)diphenylsilane Tert-butyl-diphenylchlorosilance Chloro(2-methyl-2-propanyl)diphenylsilane tert-Butylchlorodiphenylsilane

Molecular Formula: C16H19ClSi

Molecular Weight: 274.86

MDL Number: MFCD00000497

Categories: Synthetic Chemistry > Basic Synthetic Reagents > Protecting and Deprotecting Reagents Synthetic Chemistry > Organic Building Blocks > Other Organic Building Blocks

Product Description:

Tert-Butyldiphenylsilyl chloride (TBDPS-Cl, CAS 58479-61-1) is a versatile organosilicon reagent widely used in organic synthesis. It is a colorless to pale yellow liquid that serves as a precursor for the corresponding silyl ethers. Its primary function is as a protecting group reagent for alcohols and phenols, forming tert-butyldiphenylsilyl (TBDPS) ethers. The TBDPS group is a bulky silyl protecting group known for its high stability under a wide range of reaction conditions, including basic media and various oxidizing or reducing environments. It is particularly valued for its orthogonal deprotection profile compared to other common silyl groups like TMS, TBDMS, and TIPS. TBDPS ethers are typically cleaved using fluoride sources such as tetra-n-butylammonium fluoride (TBAF) or hydrogen fluoride, allowing for selective deprotection in complex multi-step syntheses. Due to its robustness and selectivity, TBDPS-Cl is an indispensable tool in the synthesis of complex natural products, pharmaceuticals, and fine chemicals, where the protection of hydroxyl groups is a critical strategic step.

Physical Properties

Boiling Point: 90 °C/0.01 mmHg(lit.)

Flash Point: 112 °C

Density: 1.057 g/mL at 25 °C(lit.)

Solubility: reacts

Refractivity: n20/D 1.568(lit.)

Storage: Store at 5°C

Safety Information

Packing Level: II

Hazard Category: 8

Transport Codes: 2987

Analytical Data

Appearance: Colorless-light yellow to brown liquid