Description

(3S)-4-Chloro-3-[(trimethylsilyl)oxy]butanenitrile (CAS No. 727382-14-1) is a high-purity organosilicon compound with the molecular formula C₇H₁₄ClNOSi. This chiral nitrile derivative features a reactive chloro group and a trimethylsilyloxy (TMS) protecting group, making it a valuable intermediate in asymmetric synthesis and pharmaceutical manufacturing. The compound is supplied as a clear, colorless to pale yellow liquid with ≥95% purity (GC), rigorously tested for consistency in quality and performance. Ideal for use in nucleophilic substitution reactions, chiral auxiliaries, and as a precursor for β-amino alcohols. Store under inert atmosphere at 2-8°C to maintain stability.

Properties

• CAS Number: 727382-14-1
• Complexity: 158
• IUPAC Name: 4-chloro-3-trimethylsilyloxy-butanenitrile
• InChI: InChI=1S/C7H14ClNOSi/c1-11(2,3)10-7(6-8)4-5-9/h7H,4,6H2,1-3H3
• InChI Key: FLYSOKSACGLOAO-UHFFFAOYSA-N
• Exact Mass: 191.0533183
• Molecular Formula: C7H14ClNOSi
• Molecular Weight: 191.73
• SMILES: C[Si](C)(C)OC(CC#N)CCl
• Topological: 33
• Monoisotopic Mass: 191.0533183
• Synonyms: (3S)-4-Chloro-3-[(trimethylsilyl)oxy]butanenitrile, 727382-14-1, 4-chloro-3-[(trimethylsilyl)oxy]butanenitrile, 4-Chloro-3-((trimethylsilyl)oxy)butanenitrile, (S)-4-Chloro-3-(trimethylsilanyloxy)butyronitrile, MFCD30537510, SCHEMBL2226034, FLYSOKSACGLOAO-UHFFFAOYSA-N, 4-chloro-3-trimethylsiloxybutyr-onitrile, 4-chloro-3-trimethylsilyloxybutanenitrile, 81091-27-2, SY326597, Butanenitrile, 4-chloro-3-[(trimethylsilyl)oxy]-

Application

This compound serves as a key chiral building block in the synthesis of β-amino acids and other pharmacologically active molecules. The TMS-protected hydroxy group enhances stereoselectivity in nucleophilic reactions, while the chloro and nitrile functionalities allow for further derivatization. Researchers utilize it in asymmetric catalysis and as an intermediate for angiotensin-converting enzyme (ACE) inhibitors. Its reactivity is particularly valuable in peptide mimetics and small-molecule drug discovery.

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