128302-78-3

Basic information

• Product Name: 2-(tert-Butyldimethylsilyloxy)malononitrile
• Synonyms: (tert-Butyldimethylsiloxy)malononitrile;(tert-Butyldimethylsilyloxy)malononitrile;2-(tert-Butyldimethylsiloxy)malononitrile;2-(tert-Butyldimethylsilyloxy)malononitrile;2-[(tert-Butyldimethylsilyl)oxy]malononitrile;{[tert-butyl(dimethyl)silyl]oxy}propanedinitrile
• CAS NO: 128302-78-3
• Molecular Formula: C₉H₁₆N₂OSi
• Molecular Weight: 196.32
• Mol File: 128302-78-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 220.4±30.0 °C(Predicted)
• Appearance: /
• Density: 0.951±0.06 g/cm3(Predicted)
• Refractive Index: 1.4290 to 1.4330
• CAS DataBase Reference: 2-(tert-Butyldimethylsilyloxy)malononitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(tert-Butyldimethylsilyloxy)malononitrile(128302-78-3)
• EPA Substance Registry System: 2-(tert-Butyldimethylsilyloxy)malononitrile(128302-78-3)

Safety Data

• RIDADR: UN 3276 6.1/PG III
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 128302-78-3(Hazardous Substances Data)

Usage

Uses

(tert-Butyldimethylsilyloxy)malononitrile is a useful reagent used in the preparation of peptides and Boc-amino acids.

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 20342-65-8 2-hydroxypropanedinitrile 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 128302-76-1 2-(tert-Butyl-dimethyl-silanyloxy)-malonamide 

Downstream Products

• 121054-03-3 2-hydroxy-4-phenylbutanenitrile 

Relevant articles and documents

A case study of the MAC (masked acyl cyanide) oxyhomologation of N, N -dibenzyl-l-phenylalaninal with anti diastereoselectivity: Preparation of (2 S,3 S)-allophenylnorstatin esters

The three-component reaction between a protected α-amino aldehyde, an alcohol and an α-silyloxymalononitrile provides an expedient access to protected α-hydroxy-β-amino acid derivatives. The prototypical process, performed on N-Cbz-phenylalaninal, is known to proceed with syn diastereoselectivity. The present study demonstrates that the diastereoselectivity of the reaction can be inverted, using the rationale of a Felkin-Anh interaction model. Reactions performed on N,N-dibenzyl-l-phenylalaninal proceed with a high anti diastereoselectivity, providing a panel of synthetically useful ester derivatives of (2S,3S)-allophenylnorstatin. The procedure is exploited to accomplish one of the most efficient syntheses of the title compound to date, in 3 steps (66% yield) from N,N-dibenzyl-l-phenylalaninal.

Squaramide-catalyzed enantioselective Michael addition of masked acyl cyanides to substituted enones

Masked acyl cyanide (MAC) reagents are shown to be effective umpolung synthons for enantioselective Michael addition to substituted enones. The reactions are catalyzed by chiral squaramides and afford adducts in high yields (90-99%) and with excellent enantioselectivities (85-98%). The addition products are unmasked to produce dicyanohydrins that, upon treatment with a variety of nucleophiles, provide γ-keto acids, esters, and amides. The use of this umpolung synthon has enabled, in enantiomerically enriched form, the first total synthesis of the prenylated phenol (+)-fornicin C.

Development of a new acyl anion equivalent for the preparation of masked activated esters and their use to prepare a dipeptide

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