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Key Documents

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:
Molecular Weight:
85.10
Beilstein:
605391
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.02

vapor pressure

0.3 psi ( 20 °C)

Quality Level

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

Signal Word

Danger

Hazard Statements

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

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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A Convenient Procedure for the Palladium-Catalyzed Cyanation of Aryl Halides.
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Angewandte Chemie (International ed. in English), 42(14), 1661-1664 (2003)
Cyanohydrins in nature and the laboratory: biology, preparations, and synthetic applications.
Gregory RJH
Chemical Reviews, 99(12), 3649-3682 (1999)
[Method of determining the level of rodanides in biological matter].
O V Shekhter et al.
Gigiena i sanitariia, (2)(2), 54-55 (1994-02-01)
D Selmar et al.
Analytical biochemistry, 166(1), 208-211 (1987-10-01)
A colorimetric assay for alpha-hydroxynitrile lyase which utilizes acetone cyanohydrin as a substrate is described. The assay is based on measurement of the HCN formed when the lyase catalyzes the dissociation of acetone cyanohydrin. The procedure was devised for use
Ting-Zhou Zhang et al.
Journal of Zhejiang University. Science. B, 6(3), 175-181 (2005-02-01)
Optically active form of alpha-cyano-3-phenoxybenzyl (CPB) alcohol, building block of pyrethroid insecticides, was synthesized as its acetate by the combination of anion-exchange resin (D301)-catalyzed transcyanation between m-phenoxybenzaldehyde (m-PBA) and acetone cyanohydrin (AC), and lipase (from Alcaligenes sp.)-catalyzed enantioselective transesterification of

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