4111-12-0

Basic information

• Product Name: 2-hydroxy-2-methylhexanenitrile
• Synonyms: 2-Hydroxy-2-methylhexanenitrile; hexanenitrile, 2-hydroxy-2-methyl-
• CAS NO: 4111-12-0
• Molecular Formula: C₇H₁₃NO
• Molecular Weight: 127.1842
• Mol File: 4111-12-0.mol

Chemical Properties

• Boiling Point: 231.903°C at 760 mmHg
• Flash Point: 94.052°C
• Density: 0.942g/cm³
• Vapor Pressure: 0.011mmHg at 25°C
• Refractive Index: 1.444
• CAS DataBase Reference: 2-hydroxy-2-methylhexanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-2-methylhexanenitrile(4111-12-0)
• EPA Substance Registry System: 2-hydroxy-2-methylhexanenitrile(4111-12-0)

Safety Data

• Hazardous Substances Data: 4111-12-0(Hazardous Substances Data)

Upstream product

• 591-78-6 n-hexan-2-one 
• 143-33-9 sodium cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 91409-34-6 2-Methyl-2-((trimethylsilyl)oxy)hexanenitrile 
• 151-50-8 potassium cyanide 
• 74-90-8 hydrogen cyanide 
• 64-17-5 ethanol 

Downstream Products

• 591-78-6 n-hexan-2-one 
• 10021-63-3 (R)-(+)-2-hydroxypentanenitrile 
• 107537-99-5 (S)-2-Hydroxypentanenitrile 
• 1092080-89-1 (S)-1-cyano-1-methylpentyl (S)-2-methoxy-2-phenylacetate 
• 1092080-87-9 (S)-1-cyano-1-methylpentyl (R)-2-methoxy-2-phenylacetate 
• 61408-68-2 (16R)-16-methoxy-16-methyl-PGE₂ methyl ester 
• 76817-56-6 (16S)-16-methoxy-16-methyl-PGE₁ methyl ester 
• 76817-54-4 (15S,16R)-16-methoxy-16-methyl-epi-PGE₁ methyl ester 
• 76817-55-5 (8R,11R,12R,15S,16S)-11,15-diydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid methyl ester 
• 76822-56-5 mexiprostil 
• 74-90-8 hydrogen cyanide 
• 253782-12-6 (R)-(+)-8-bromo-2-hydroxyoctanenitrile 
• 52358-06-2 (S)-hexanal cyanohydrin 
• 52358-06-2 (R)-2-hydroxyheptanenitrile 

Relevant articles and documents

A new (R)-hydroxynitrile lyase from Prunus mume: Asymmetric synthesis of cyanohydrins

A new hydroxynitrile lyase (HNL) was isolated from the seed of Japanese apricot (Prunus mume). The enzyme has similar properties with HNL isolated from other Prunus species and is FAD containing enzyme. It accepts a large number of unnatural substrates (benzaldehyde and its variant) for the addition of HCN to produce the corresponding cyanohydrins in excellent optical and chemical yields. A new HPLC based enantioselective assay technique was developed for the enzyme, which promotes the addition of KCN to benzaldehyde in a buffered solution (pH=4.5).

LANTHANIDES AS LEWIS-ACID CATALYSTS IN ALDOL ADDITION, CYANOHYDRIN-FORMING AND OXIRANE RING OPENING REACTIONS

Lanthanide trichlorides (Ln = La,Ce,Sm) and Eu(fod)3 catalyze the aldol addition of silyl enol ethers to aldehydes, the addition of trimethylsilyl cyanide to aldehydes and ketones as well as the synthesis of β-cyanosilyl ethers.

Structure-Activity Studies of 16-Methoxy-16-methyl Prostaglandins

The synthesis of the pure diastereoisomer of 16-methoxy-16-methyl-PGF2α, -PGE2, and PGE1 is described.The absolute configuration of C-16 was established by chemical methods, while the absolute C-15 configurations of the diastereoisomers were assigned tentatively on the basis of their chromatographic behavior and NMR spectra.The synthetic prostaglandin analogues were evaluated for antisecretory, antifertility, and diarrheogenic effects.Both the C-15 and C-16 configurations were found to be critical for the biological activities.These studies indicate that the introduction of the methyl and methoxy groups at C-16 into the prostaglandin analogues markedly increases the ratio of antisecretory to diarrheogenic action.One of the PGE1 derivatives, 9f(15α,16R) (MDL 646, mexiprostil), was selected for further pharmacological evaluation and is currently under clinical investigation.