2567-01-3

Usage

General Description

Colorless liquid with a mild odor. Used in organic synthesis.

Air & Water Reactions

Flammable. Soluble in water.

Reactivity Profile

A hydroxylated nitrile. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Fire Hazard

Flash point data for 3-hydroxy-2-methylpropiononitrile are not available. 3-hydroxy-2-methylpropiononitrile is probably combustible.

InChI:InChI=1/C4H7NO/c1-4(2-5)3-6/h4,6H,3H2,1H3

Upstream product

• 598-18-5 2-bromopropanol 
• 143-33-9 sodium cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 75-56-9 methyloxirane 
• 151-50-8 potassium cyanide 
• 28539-02-8 1-Hydroxymethyl-1H-benzotriazole 
• 107-12-0 propiononitrile 

Relevant academic research and scientific papers

Anionic, in situ generation of formaldehyde: A very useful and versatile tool in synthesis

(Chemical Equation Presented) A very simple, safe and powerful method for the in situ generation of formaldehyde at low temperature in anhydrous conditions is described. This new tool avoids the use of gaseous formaldehyde and is suitable for basic carbon nucleophiles which cannot be generated in aqueous reaction media. Various substrates, including organolithium reagents and enolates, underwent smooth hydroxymethylation showing the versatility of this process. A Wittig reaction was also carried out in high yield.

Deamination Reactions, 54. - Decomposition of 1-Cyano-1-propanediazonium Ions

The nitrous acid decomposition of 2-aminobutanenitrile (9) was studied with regard to product distribution and stereochemistry.The formation of 2-(hydroxyimino)butanenitriles (21, 22; 8-28percent) indicates the intervention of 1-cyanopropyl radicals (24) that are captured by NO.The polar reactions lead mainly to elimination (10-13) and nucleophilic substitution (14-16), rearrangement playing a minor role. (R)-9 was prepared from (R)-2-aminobutanoic acid.The nitrous acid deamination of (R)-9 afforded the cyanohydrin 16 with 81percent net inversion.Owing to destabilization of the carbocation 26 by CN, the SN2 route of nucleophilic displacement is preferred over SN1.The influence of CN is shown to be smaller than that of CF3. Key Words: α-Cyanodiazonium ions / α-Cyanoalkyl radicals / Carbocations, destabilized / Substitution, nucleophilic / Deamination reactions / Diazonium ions / Radicals

Highly Regioselective and Stereospecific Functionalization of 1,2-Proanediol with Trimethyl(X)silanes Employing the 1,3,2λ5-Dioxaphospholane Methodology

The regioselective ring opening of (S)-4-methyl-2,2,2-triphenyl-1,3,2λ5-dioxaphospholanes (2) was initiated with several trimethylsilyl reagents (Me3SiX: X = PhS, I, Br; Cl, CN, and N3) to afford the regioisomeric (silyloxy)phosphonium salts.A stereospecific extrusion of triphenylphosphine oxide from these oxyphosphonium salts gave predominatly the thermodynamically less stable C-2-X-substituted derivatives with nearly complete inversion of stereochemistry at the C-2 stereogenic center (i.e., X = PhS).

Easy Direct Stereo- and Regioselective Formation of β-Hydroxy Nitriles by Reaction of 1,2-Epoxides with Potassium Cyanide in the Presence of Metal Salts

A simple efficient, anti stereoselective, and highly regioselective method for the synthesis of β-hydroxy nitriles by the direct opening of 1,2-epoxides with KCN in acetonitrile, in the presence of metal salts, is described.This new method appears to be competitive with the other methods previously reported. Key words: β-hydroxy nitriles; epoxide opening reactions; regioselectivity; catalysts.