5699-72-9

Basic information

• Product Name: 2-hydroxyvaleronitrile
• Synonyms: 2-hydroxyvaleronitrile;beta-hydroxyvaleronitrile;2-Hydroxypentane nitrile, 98 %;Butanal cyanhydrin;Butyraldehyde cyanohydrin;2-hydroxypentanenitrile
• CAS NO: 5699-72-9
• Molecular Formula: C₅H₉NO
• Molecular Weight: 99.13106
• EINECS: 227-182-6
• Mol File: 5699-72-9.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 207.3°Cat760mmHg
• Flash Point: 79.2°C
• Appearance: /
• Density: 0.968g/cm³
• Vapor Pressure: 0.0529mmHg at 25°C
• Refractive Index: 1.433
• CAS DataBase Reference: 2-hydroxyvaleronitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxyvaleronitrile(5699-72-9)
• EPA Substance Registry System: 2-hydroxyvaleronitrile(5699-72-9)

Safety Data

• Hazardous Substances Data: 5699-72-9(Hazardous Substances Data)

Usage

General Description

2-Hydroxyvaleronitrile is a chemical compound with the formula C5H9NO. It is a colorless liquid with a faint almond-like odor. It is used as a building block in the synthesis of a variety of organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. It can be produced by the hydrolysis of valeronitrile, which is an intermediate in the production of adiponitrile. 2-Hydroxyvaleronitrile has been found to be a precursor to the production of the cancer-fighting drug tamoxifen, and it has also been investigated as a potential precursor to the production of a variety of other pharmaceuticals and agrochemicals. However, it is important to handle 2-hydroxyvaleronitrile with care, as it is toxic and can cause irritation to the skin, eyes, and respiratory tract.

InChI:InChI=1/C5H9NO/c1-2-3-5(7)4-6/h5,7H,2-3H2,1H3

Upstream product

• 74-90-8 hydrogen cyanide 
• 123-72-8 butyraldehyde 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 151-50-8 potassium cyanide 
• 78485-85-5 2-Trimethylsilanyloxy-pentanenitrile 
• 74-90-8 hydrogen isocyanide 
• 773837-37-9 sodium cyanide 
• 4435-33-0 sodium 1-hydroxy-1-butanesulfonate 
• 143-33-9 sodium cyanide 

Downstream Products

• 10021-63-3 (R)-(+)-2-hydroxypentanenitrile 
• 39201-33-7 4-cyanobutyric acid 
• 107-92-6 butyric acid 
• 129265-90-3 2-(Phenylacetoxy)pentannitril 
• 13284-42-9 2-pentenenitrile 
• 5343-92-0 1,2-pentanediol 
• 102008-41-3 N,N-dibenzyl-norvaline amide 
• 618-57-5 propyl-succinic acid 
• 13706-89-3 heptane-3,4-dione 
• 88945-70-4 ethyl 2-hydroxy-n-valerate 
• 129265-91-4 2-(Phenylpropionyloxy)pentannitril 
• 127894-07-9 2-(o-hydroxyanilido)butyronitril 
• 617-31-2 2-hydroxyvaleric acid 
• 27395-11-5 N-Formylamid v. Homovalin 

Relevant articles and documents

Oxygen-to-Oxygen Silyl Migration of α-Siloxy Sulfoxides and Oxidation-Triggered Allicin Formation

Oxidation of α-siloxy thioethers leads to the formation of the corresponding sulfoxides as unstable intermediates, which undergo an intramolecular oxygen-to-oxygen silyl migration to break the C-S linkage. This process produces silyl protected sulfenic acids and subsequently thiosulfinates. It was used to develop oxidation-triggered allicin donors.

Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles

The enantioselective synthesis of α-thiocarboxylic acids by biocatalytic dynamic kinetic resolution (DKR) of nitrile precursors exploiting nitrilase enzymes is described. A panel of 35 nitrilase biocatalysts were screened and enzymes Nit27 and Nit34 were found to catalyse the DKR of racemic α-thionitriles under mild conditions, affording the corresponding carboxylic acids with high conversions and good-to-excellent ee. The ammonia produced in situ during the biocatalytic transformation favours the racemization of the nitrile enantiomers and, in turn, the DKR without the need of any external additive base.

A method for synthesis of 1, 2 - pentanediol (by machine translation)

The invention relates to the field of organic synthetic technology, in particular to a 1, 2 - pentanediol synthetic method, comprises the following steps: (1) heating the raw material-butyraldehyde, adjusting the pH after adding the hydrocyanic acid, obtained by the reaction of 2 - hydroxy pentanonitrile; (2) taking step (1) in 2 - hydroxy pentanonitrile, adding an alcohol as a solvent to stir and mix, add water to stir and mix, hydrogen chloride gas, in 5 °C the following reaction under the condition for a period of time, to continue the reaction temperature, after the reaction product after the neutralization reaction, centrifugal separation, obtained after the distillation is 2 - hydroxy valeric acid ester compound; (3) heating the step (2) in 2 - hydroxy valeric acid ester compound, under the effects of catalyst after hydrogenation reaction to obtain the 1, 2 - pentanediol. Using the synthesis method of the invention, the 1, 2 - pentanediol yield, and reduces the production cost. (by machine translation)