3-Hydroxybutyronitrile

Base Information

• Chemical Name: 3-Hydroxybutyronitrile
• CAS No.: 4368-06-3
• Molecular Formula: C4H7NO
• Molecular Weight: 85.1057
• Hs Code.: 29269095
• European Community (EC) Number: 224-457-2
• DSSTox Substance ID: DTXSID70963097
• Nikkaji Number: J205.747F
• Mol file: 4368-06-3.mol

Synonyms:3-Hydroxybutyronitrile;3-hydroxybutanenitrile;4368-06-3;beta-Hydroxybutyronitrile;beta-hydroxybutanenitrile;3-Hydroxybutyronitrile, 97%;DTXSID70963097;CHEBI:142961;BCP28827;EINECS 224-457-2;MFCD03427120;AKOS010136331;SB44677;SB44678;CS-0261013;FT-0690408;FT-0771397;EN300-76665;E83965;Z847151284

Chemical Property of 3-Hydroxybutyronitrile

Chemical Property:

• Appearance/Colour: clear slightly yellow to amber liquid
• Vapor Pressure: 0.0286mmHg at 25°C
• Refractive Index: n20/D 1.429(lit.)
• Boiling Point: 217.3 °C at 760 mmHg
• PKA: 13.89±0.20(Predicted)
• Flash Point: 85.2 °C
• PSA: 44.02000
• Density: 0.991 g/cm³
• LogP: 0.28088
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 85.052763847
• Heavy Atom Count: 6
• Complexity: 70.9

Purity/Quality:

98%,99%, ^*data from raw suppliers

β-Hydroxybutyronitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC#N)O
• Uses: β-Hydroxybutyronitrile is an intermediate used to prepare 2-Methylazetidine which is a derivative of Azetidine (A813000), a useful building block in the synthesis of polypeptides and other nitrogen containing compounds with potential biological properties.

Technology Process of 3-Hydroxybutyronitrile

There total 30 articles about 3-Hydroxybutyronitrile 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: 90.0%

ethyl acetate (141-78-6) + acetonitrile (75-05-8,26809-02-9) → 3-hydroxybutanenitrile (4368-06-3)

Guidance literature:

ethyl acetate; acetonitrile; With lithium diisopropyl amide; In tetrahydrofuran; at -60 ℃; for 3h;

With sodium tetrahydroborate; In tetrahydrofuran; at -60 - 20 ℃; for 2h;

DOI:10.1002/1099-0690(200207)2002:13<2094::AID-EJOC2094>3.0.CO;2-E

Reference yield: 85.0%

acetaldehyde (75-07-0,9002-91-9) + acetonitrile (75-05-8,26809-02-9) → 3-hydroxybutanenitrile (4368-06-3)

Guidance literature:

acetonitrile; With sodium hydride; In toluene; for 2h; Inert atmosphere; Reflux;

acetaldehyde; In toluene; for 3h; Solvent; Reagent/catalyst; Inert atmosphere; Reflux;

Reference yield: 82.0%

potassium cyanide (151-50-8) + methyloxirane (75-56-9,16033-71-9) → 3-hydroxybutanenitrile (4368-06-3)

Guidance literature:

salcomine; In ethylene glycol; at 20 ℃; for 2.2h;

DOI:10.1139/V06-158

upstream raw materials:

1-bromo-2-propanol

potassium cyanide

(R)-1-bromo-2-propanol

1-iodopropan-2-ol

Downstream raw materials:

acetaldehyde

acetonitrile

but-2-enenitrile

(Z)-2-butenenitrile

Refernces

• 1、 -. "Preparation method 3 -amino -5 -alkyl isoxazole". Paragraph 0024-0027; 0029-0032. . Retrieved 2020/06/05.
• 2、 Ren, Shishuai,Xie, Shangqing,Zheng, Tingting,Wang, Yangyang,Xu, Shilu,Xue, Benjing,Li, Xiaoyan,Sun, Hongjian,Fuhr, Olaf,Fenske, Dieter. "Synthesis of silyl iron hydride: Via Si-H activation and its dual catalytic application in the hydrosilylation of carbonyl compounds and dehydration of benzamides". . p. 4352 - 4359. Retrieved 2018/03/26.