Acetone cyanohydrin

Base Information

• Chemical Name: Acetone cyanohydrin
• CAS No.: 75-86-5
• Deprecated CAS: 59182-86-4
• Molecular Formula: C4H7NO
• Molecular Weight: 85.1057
• Hs Code.: 2926.90
• European Community (EC) Number: 200-909-4
• ICSC Number: 0611
• NSC Number: 131093,7080,977
• UN Number: 1541
• UNII: CO1YOV1KFI
• DSSTox Substance ID: DTXSID7025427
• Nikkaji Number: J1.468K
• Wikipedia: Acetone_cyanohydrin
• Wikidata: Q222936
• Metabolomics Workbench ID: 50041
• ChEMBL ID: CHEMBL1231861
• Mol file: 75-86-5.mol

Synonyms:acetoncyanhydrine;acetone cyanohydrin;acetone cyanohydrin, 14C-labeled

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Chemical Property of Acetone cyanohydrin

Chemical Property:

• Appearance/Colour: yellowish liquid
• Vapor Pressure: 0.566mmHg at 25°C
• Melting Point: -19ºC
• Refractive Index: n20/D 1.399(lit.)
• Boiling Point: 82ºC
• PKA: 11.45±0.29(Predicted)
• Flash Point: 73 ºC
• PSA: 44.02000
• Density: 0.932
• LogP: 0.28088
• Water Solubility.: miscible
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 85.052763847
• Heavy Atom Count: 6
• Complexity: 87
• Transport DOT Label: Poison Inhalation Hazard

Purity/Quality:

Safty Information:

• Hazard Codes: T+:Very toxic
• Statements: R26/27/28:; R50:
• Safety Statements: S27:; S45:; S60:; S61:; S7/9:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CC(C)(C#N)O
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the cardiovascular system and central nervous system. This may result in asphyxia, cardiac disorders, convulsions, cyanosis and respiratory failure. Exposure could cause death. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the central nervous system and thyroid. This may result in impaired functions.

Technology Process of Acetone cyanohydrin

There total 26 articles about Acetone cyanohydrin 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%

potassium cyanide + acetone (67-64-1) → 2-hydroxy-2-methylpropanenitrile (75-86-5)

Guidance literature:

With acetic acid; In water; at 30 ℃; Microreactor technology; Continuous flow system;

DOI:10.1016/j.tetlet.2010.06.004

Reference yield: 95.0%

hydrogen cyanide (74-90-8) + acetone (67-64-1) → 2-hydroxy-2-methylpropanenitrile (75-86-5)

Guidance literature:

With sodium hydroxide; sulfuric acid; sodium cyanide; In water; at 10 ℃; for 1.5h; pH=7.3;

Reference yield: 37.3%

2-amino-2-cyanopropane (19355-69-2) → 2-cyano-2-nitropropane (18992-13-7) + 1-cyano-1-methylethylnitrate (40561-27-1) + tris-(1-cyano-1-methyl-ethyl)-hydroxylamine (58102-56-0) + 2-hydroxy-2-methylpropanenitrile (75-86-5)

Guidance literature:

With perchloric acid; sodium nitrite; at 25 ℃; Product distribution; var. α-aminonitriles; other conditions, also radical scavengers;

DOI:10.1039/c39920000047

upstream raw materials:

hydrogen cyanide

potassium cyanide

acetone sodium bisulfite

methanol

Downstream raw materials:

2-methyl-2-pyrrolidin-1-ylpropionitrile

hydrogen cyanide

acetone

3-chloro-2-methylpropanenitrile

Refernces

• 1、 Svirbely,Roth. "-". . p. 3106,3109. Retrieved 1953.
• 2、 Yerabolu, Jayasudhan Reddy,Liotta, Charles L,Krishnamurthy, Ramanarayanan. "Anchimeric-Assisted Spontaneous Hydrolysis of Cyanohydrins Under Ambient Conditions: Implications for Cyanide-Initiated Selective Transformations". supporting information. p. 8756 - 8765. Retrieved 2017/06/30.
• 3、 Xie, Yinjun,Guo, Shengmei,Wu, Longmin,Xia, Chungu,Huang, Hanmin. "Metal bridging for directing and accelerating electron transfer as exemplified by harnessing the reactivity of AIBN". supporting information. p. 5900 - 5904. Retrieved 2015/05/13.