Glycolonitrile

Base Information

• Chemical Name: Glycolonitrile
• CAS No.: 107-16-4
• Molecular Formula: C2H3NO
• Molecular Weight: 57.0519
• Hs Code.: 2926.90
• European Community (EC) Number: 203-469-1
• ICSC Number: 1427
• NSC Number: 1790
• UN Number: 2810,3276
• UNII: ZCI474BE63
• DSSTox Substance ID: DTXSID3025417
• Nikkaji Number: J4.058D
• Wikipedia: Glycolonitrile
• Wikidata: Q25807
• Mol file: 107-16-4.mol

Synonyms:cyanohydrin formaldehyde;glycolonitrile;hydroxyacetonitrile

Chemical Property of Glycolonitrile

Chemical Property:

• Appearance/Colour: clear to pale yellow liquid
• Vapor Pressure: 0.0593mmHg at 25°C
• Melting Point: -72 °C
• Refractive Index: n20/D 1.389
• Boiling Point: 183 ºC
• PKA: 11.31±0.10(Predicted)
• Flash Point: 133 ºF
• PSA: 44.02000
• Density: 1.087 g/cm³
• LogP: -0.49772
• Water Solubility.: >=10 g/100 mL at 20 ºC
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 57.021463719
• Heavy Atom Count: 4
• Complexity: 41.2
• Transport DOT Label: Poison

Purity/Quality:

Glycolic acid nitrile solution ~70% in H2O ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 36/37/39-45-36/37-28

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C(C#N)O
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes. The substance may cause effects on the cellular respiration. This may result in convulsions and respiratory failure. Exposure could cause death. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the nervous system and thyroid.
• Uses: Solvent and organic intermediate.

Technology Process of Glycolonitrile

There total 31 articles about Glycolonitrile 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: 97.0%

betaine (107-43-7) + cyanomethyl bromide (590-17-0) → Trimethylammoniumessigsaeurebetain-ethylester-bromid (60379-56-8) + glycolonitrile (107-16-4)

Guidance literature:

In ethanol; at 40 ℃; for 72h; Yields of byproduct given;

DOI:10.1007/BF00811130

Reference yield: 95.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + hydrogen cyanide (74-90-8) → glycolonitrile (107-16-4)

Guidance literature:

With sodium hydroxide; In methanol; at 20 - 25 ℃; for 2h;

DOI:10.1002/adsc.200700061

Reference yield: 89.0%

cyanomethyl bromide (590-17-0) → Trimethylammoniumessigsaeurebetain-ethylester-bromid (60379-56-8) + glycolonitrile (107-16-4)

Guidance literature:

With betaine; In ethanol; at 40 ℃; for 72h; Yields of byproduct given;

DOI:10.1007/BF00811130

upstream raw materials:

methanol

formaldehyd

hydrogen cyanide

2-hydroxy-2-methyl-butyronitrile

Downstream raw materials:

piperidin-1-yl-acetonitrile

4-morpholinoacetonitrile

N-(cyanomethyl)ethylamine

(N,N-dipropylamino)acetonitrile

Refernces

• 1、 Panova, Anna,Mersinger, Lawrence J.,Liu, Qiang,Foo, Thomas,Roe, D. Christopher,Spillan, William L.,Sigmund, Amy E.,Ben-Bassat, Arie,Winona Wagner,O'Keefe, Daniel P.,Wu, Shijun,Perrillo, Kelly L.,Payne, Mark S.,Breske, Stephen T.,Gallagher, F. Glenn,Dicosimo, Robert. "Chemoenzymatic synthesis of glycolic acid". . p. 1462 - 1474. Retrieved 2007.
• 2、 Schlesinger,Miller. "-". . p. 3729,3731, 3734. Retrieved 1973.
• 3、 Gowda, Basavalinganadoddy Thimme,Mahadevappa, Darndinasivara S.. "Chloraminometric Reactions: Kinetics and Mechanisms of Oxidations of Amino-acids by Sodium N-Chlorotoluene-p-sulphonamide in Acid and Alkaline Media". . p. 323 - 334. Retrieved 1983.
• 4、 Claes, Laurens,Matthessen, Roman,Rombouts, Ine,Stassen, Ivo,De Baerdemaeker, Trees,Depla, Diederik,Delcour, Jan A.,Lagrain, Bert,De Vos, Dirk E.. "Bio-based nitriles from the heterogeneously catalyzed oxidative decarboxylation of amino acids". . p. 345 - 352. Retrieved 2015.
• 5、 -. "INHIBITORS OF HUMAN HERPESVIRUSES". Page/Page column 86; 130-132. . Retrieved 2021/09/11.
• 6、 -. "Preparation and pre-use treatment method for glycolonitrile with cyanide-containing tail gas as raw material". Paragraph 0009; 0020; 0021. . Retrieved 2017/03/17.