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A10000

Sigma-Aldrich

Acetone cyanohydrin

99%

Synonym(s):

α-Hydroxyisobutyronitrile, 2-Hydroxyisobutyronitrile

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About This Item

Linear Formula:
(CH3)2C(OH)CN
CAS Number:
75-86-5
Molecular Weight:
85.10
Beilstein:
605391
EC Number:
200-909-4
MDL number:
MFCD00004455
UNSPSC Code:
12352100
PubChem Substance ID:
24890489
NACRES:
NA.02

vapor pressure

0.3 psi ( 20 °C)

Quality Level

200

Assay

99%

form

liquid

contains

H3PO4 as stabilizer (Europe)
 sulfuric acid as stabilizer (US)

expl. lim.

11 %

refractive index

n20/D 1.399 (lit.)

bp

82 °C/23 mmHg (lit.)

mp

−19 °C (lit.)

density

0.932 g/mL at 25 °C (lit.)

SMILES string

CC(C)(O)C#N

InChI

1S/C4H7NO/c1-4(2,6)3-5/h6H,1-2H3

InChI key

MWFMGBPGAXYFAR-UHFFFAOYSA-N

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General description

Acetone cyanohydrin serves as a source of hydrogen cyanide in the Mitsunobu reaction. Also an intermediate for methacrylamide synthesis.

Application

Acetone cyanohydrin can be used as a cyanide source for:
  • Cyanation reactions of aryl halides, aldehydes and alcohols.
  • Stereospecific epoxide ring opening.
  • Strecker reaction of α-amido sulfones to synthesize α-amino nitriles.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H300 + H310 + H330,H410

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

167.0 °F - closed cup

Flash Point(C)

75 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK9563
STBK9562
STBK5401
STBK5402
STBK5536

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Rondon Tosta Ramalho et al.
Acta cirurgica brasileira, 25(1), 111-116 (2010-02-04)
To evaluate the antitumor effect of acetone cyanohydrin in Ehrlich ascites tumor cells in vitro. The Ehrlich ascites tumor cells and lymphocytes were incubated with different concentrations of acetone cyanohydrin (0, 0.5, 1.0, 2.0, 10.0, 20.0 and 30.0 microg x
Z I Zholdakova et al.
Gigiena i sanitariia, (8)(8), 16-18 (1994-09-01)
The study of acetone cyanohydrin (ACH) showed that it is an unstable substance. Its stability in water depends on pH of water and less so on its initial concentration; water temperature and biota are insignificant. Acetone and cyanid-ion, forming from
H Lauble et al.
Protein science : a publication of the Protein Society, 10(5), 1015-1022 (2001-04-24)
The structure and function of hydroxynitrile lyase from Manihot esculenta (MeHNL) have been analyzed by X-ray crystallography and site-directed mutagenesis. The crystal structure of the MeHNL-S80A mutant enzyme has been refined to an R-factor of 18.0% against diffraction data to
Regiospecific opening of 1, 2-expoxides with acetone cyanohydrin under mildly basic conditions.
Mitchell D and Koenig TM
Tetrahedron Letters, 33(23), 3281-3284 (1992)
Phase transfer catalyzed enantioselective Strecker reactions of ?-amido sulfones with cyanohydrins.
Herrera RP, et al.
The Journal of Organic Chemistry, 71(26), 9869-9872 (2006)
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