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50640

Sigma-Aldrich

Glycolic acid nitrile solution

~70% in H2O

Synonym(s):

Formaldehyde cyanohydrin, Hydroxyacetonitrile

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About This Item

Linear Formula:
HOCH2CN
CAS Number:
107-16-4
Molecular Weight:
57.05
Beilstein:
605328
MDL number:
MFCD00042731
UNSPSC Code:
12352100
PubChem Substance ID:
57651261
NACRES:
NA.22

contains

~0.5% phosphoric acid as stabilizer

Quality Level

100

concentration

~70% in H2O

refractive index

n20/D 1.389

density

1.076 g/mL at 20 °C

SMILES string

OCC#N

InChI

1S/C2H3NO/c3-1-2-4/h4H,2H2

InChI key

LTYRAPJYLUPLCI-UHFFFAOYSA-N

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General description

The product is a 70% solution of glycolic acid nitrile in water. Glycolic acid nitrile, also known as hydroxyacetonitrile is the simplest cyanohydrin. The microwave spectra of hydroxyacetonitrile have been recorded in gas-phase and its rotational constants have been calculated. Ice containing formaldehyde and hydrogen cyanide react under astrophysical-like conditions to form hydroxyacetonitrile.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Rotational isomerism and barriers to internal rotation in hydroxyacetonitrile from microwave spectroscopy.
Cazzoli G, et al.
J. Chem. Soc., Faraday II, 69, 569-578 (1973)
Hydroxyacetonitrile (HOCH2CN) formation in astrophysical conditions. competition with the aminomethanol, a glycine precursor.
Danger G, et al.
The Astrophysical Journal, 756(1), 11-11 (2012)
Microwave and Quantum-Chemical Study of Conformational Properties and Intramolecular Hydrogen Bonding of 2-Hydroxy-3-Butynenitrile (HC=CCH(OH)C=N).
M?llendal H, et al.
The Journal of Physical Chemistry A, 119(4), 634-640 (2015)
Formation of hydroxyacetonitrile (HOCH2CN) and polyoxymethylene (POM)-derivatives in comets from formaldehyde (CH2O) and hydrogen cyanide (HCN) activated by water.
Danger G, et al.
Physical Chemistry Chemical Physics, 16(8), 3360-3370 (2014)
Shijun Wu et al.
Biotechnology and bioengineering, 99(3), 717-720 (2007-09-06)
A key step in a chemoenzymatic process for the production of high-purity glycolic acid (GLA) is the enzymatic conversion of glycolonitrile (GLN) to ammonium glycolate using a nitrilase derived from Acidovorax facilis 72W. Protein engineering and over-expression of this nitrilase
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