2-Hydroxy-3-methylbutanenitrile

Base Information

• Chemical Name: 2-Hydroxy-3-methylbutanenitrile
• CAS No.: 15344-34-0
• Molecular Formula: C5H9NO
• Molecular Weight: 99.1326
• Hs Code.: 2926909090
• European Community (EC) Number: 857-526-6
• DSSTox Substance ID: DTXSID101320985
• Nikkaji Number: J27.735E
• Mol file: 15344-34-0.mol

Synonyms:2-hydroxy-3-methylbutanenitrile;15344-34-0;Isobutanal cyanhydrin;ISOBUTYRALDEHYDE CYANOHYDRIN;DTXSID101320985;MFCD00798446;AKOS008146495;AB07208;LS-06940;CS-0208256;EN300-62480;Z802900598

Chemical Property of 2-Hydroxy-3-methylbutanenitrile

Chemical Property:

• Vapor Pressure: 0.098mmHg at 25°C
• Refractive Index: 1.431
• Boiling Point: 197.265°C at 760 mmHg
• Flash Point: 73.103°C
• PSA: 44.02000
• Density: 0.965g/cm³
• LogP: 0.52688
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 99.068413911
• Heavy Atom Count: 7
• Complexity: 89.5

Purity/Quality:

98%Min ^*data from raw suppliers

2-Hydroxy-3-methylbutanenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C#N)O

Technology Process of 2-Hydroxy-3-methylbutanenitrile

There total 16 articles about 2-Hydroxy-3-methylbutanenitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

trimethylsilyl cyanide (7677-24-9) + isobutyraldehyde (78-84-2) → 2-hydroxy-3-methylbutanenitrile (15344-34-0)

Guidance literature:

trimethylsilyl cyanide; isobutyraldehyde; With titanium(IV) isopropylate; C₃₇H₅₇N₃O₂; In dichloromethane; at 20 ℃; for 0.5h;

With hydrogenchloride; In dichloromethane; water; ethyl acetate; for 5h;

DOI:10.1039/c1ob05695f

Reference yield: 97.0%

sodium cyanide (773837-37-9) + isovaleraldehyde (590-86-3) → 2-hydroxy-3-methylbutanenitrile (15344-34-0)

Guidance literature:

With sodium hydrogensulfite; In water; at 0 - 50 ℃; for 3h; Temperature;

Reference yield: 95.0%

potassium cyanide + isobutyraldehyde (78-84-2) → 2-hydroxy-3-methylbutanenitrile (15344-34-0)

Guidance literature:

isobutyraldehyde; With sodium hydrogensulfite; In water; at 0 ℃; for 0.5h;

potassium cyanide; In water; at 20 ℃; for 2.16667h;

DOI:10.1016/j.tet.2009.01.117

upstream raw materials:

hydrogen cyanide

isobutyraldehyde

carbonyl cyanide

isopropylmagnesium bromide

Downstream raw materials:

3,5-Dichloro-6-isopropyl-[1,4]oxazin-2-one

2-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylamino)-3-methyl-butyronitrile

Heterodendrin

Epiheterodendrin

Refernces

• 1、 Davis,J.W.. "-". . p. 3980 - 3982. Retrieved 1978.
• 2、 Lauder, Kate,Anselmi, Silvia,Finnigan, James D.,Qi, Yuyin,Charnock, Simon J.,Castagnolo, Daniele. "Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles". supporting information. p. 10422 - 10426. Retrieved 2020/07/24.
• 3、 Choi, Junwon,Fu, Gregory C.. "Catalytic asymmetric synthesis of secondary nitriles via stereoconvergent negishi arylations and alkenylations of racemic α-bromonitriles". supporting information; experimental part. p. 9102 - 9105. Retrieved 2012/07/13.