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Merck
CN

A10000

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
UNSPSC Code:
12352100
NACRES:
NA.02
PubChem Substance ID:
24890489
EC Number:
200-909-4
Beilstein/REAXYS Number:
605391
MDL number:
MFCD00004455
Assay:
99%
Form:
liquid

Key Documents

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InChI

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

InChI key

MWFMGBPGAXYFAR-UHFFFAOYSA-N

SMILES string

CC(C)(O)C#N

vapor pressure

0.3 psi ( 20 °C)

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.)

Quality Level

200

Related Categories

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

signalword

Danger

Hazard Classifications

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

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

监管及禁止进口产品
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Certificates of Analysis (COA)

Lot/Batch Number
SDBB6388
SDBB6759
SDBB4353
STBL4812
STBL4811

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[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
A Convenient Procedure for the Palladium-Catalyzed Cyanation of Aryl Halides.
Sundermeier M, et al.
Angewandte Chemie (International ed. in English), 42(14), 1661-1664 (2003)
Zr (OBut)4 As an effective promoter for the Meerwein-Ponndorf-Verley alkynylation and cyanation of aldehydes: development of new asymmetric cyanohydrin synthesis.
Ooi T, et al.
Tetrahedron, 57(5), 867-873 (2001)
Cyanohydrins in nature and the laboratory: biology, preparations, and synthetic applications.
Gregory RJH
Chemical Reviews, 99(12), 3649-3682 (1999)
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