Lactonitrile

Base Information

• Chemical Name: Lactonitrile
• CAS No.: 78-97-7
• Deprecated CAS: 42492-95-5
• Molecular Formula: C3H5 N O
• Molecular Weight: 71.0788
• European Community (EC) Number: 201-163-2
• NSC Number: 7764
• UN Number: 3276,2810
• UNII: SJ38QDA188
• DSSTox Substance ID: DTXSID6025432
• Nikkaji Number: J1.488E
• Wikipedia: Lactonitrile
• Wikidata: Q6469032
• Metabolomics Workbench ID: 132007
• ChEMBL ID: CHEMBL3559764
• Mol file: 78-97-7.mol

Synonyms:acetaldehyde cyanohydrin;lactonitrile

Chemical Property of Lactonitrile

Chemical Property:

• Appearance/Colour: Straw colored liquid.
• Vapor Pressure: 0.222mmHg at 25°C
• Melting Point: -40.15°C
• Refractive Index: n20/D 1.404
• Boiling Point: 90 ºC (17 mmHg)
• PKA: 11.38±0.20(Predicted)
• Flash Point: 77 °C
• PSA: 44.02000
• Density: 0.991
• LogP: -0.10922
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 71.037113783
• Heavy Atom Count: 5
• Complexity: 60.5
• Transport DOT Label: Poison

Purity/Quality:

DL-Lactonitrile ≥97.0% (T) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+,T
• Statements: 23/25-27-25-20
• Safety Statements: 13-36/37/39-45-23-36/37-28

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CC(C#N)O
• Uses: It is used primarily as a solvent, and as an intermediate in production of ethyl acetate and lactic acid. 2-Hydroxypropanenitrile is a useful compound for efficient lactamide synthesis by fed batch method using nitrile hydratase of Rhodococcus pyridinivorans NIT-36.

Technology Process of Lactonitrile

There total 40 articles about Lactonitrile 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: 99.54%

hydrogen cyanide (74-90-8) + acetaldehyde (75-07-0,9002-91-9) → 2-hydroxy-propionitrile (78-97-7)

Guidance literature:

With triethylamine; at 5 - 10 ℃; Product distribution / selectivity;

Reference yield: 80.0%

2-[(tert-butyldimethylsilyl)oxy]propanenitrile (114711-04-5) → 2-hydroxy-propionitrile (78-97-7)

Guidance literature:

With P(MeNCH₂CH₂)3N; In dimethyl sulfoxide; at 80 ℃; for 19h;

DOI:10.1021/jo991591i

Reference yield: 80.0%

potassium cyanide (151-50-8) + acetaldehyde (75-07-0,9002-91-9) → 2-hydroxy-propionitrile (78-97-7)

Guidance literature:

With sodium hydrogensulfite; In water; at 0 ℃; for 2h;

upstream raw materials:

hydrogen cyanide

potassium cyanide

acetaldehyde

chloroform

Downstream raw materials:

N-(1,1,3,3-tetramethyl-butyl)-lactamide

3-hydroxy-6-hydroxymethyl-2-D,L-lactoyl-pyran-4-one

3-hydroxy-2-butanon

Pentaerythritol

Refernces

• 1、 Xu, Jianfeng,Ritson, Dougal J.,Ranjan, Sukrit,Todd, Zoe R.,Sasselov, Dimitar D.,Sutherland, John D.. "Photochemical reductive homologation of hydrogen cyanide using sulfite and ferrocyanide". supporting information. p. 5566 - 5569. Retrieved 2018/06/04.
• 2、 -. "Preparation method of 2-hydroxy acid ester". Paragraph 0034-0035. . Retrieved 2017/04/11.