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Acetone cyanohydrin information


Acetone cyanohydrin
Skeletal formula of acetone cyanohydrin
Ball and stick model of acetone cyanohydrin
Ball and stick model of acetone cyanohydrin
Spacefill model of acetone cyanohydrin
Spacefill model of acetone cyanohydrin
Names
Preferred IUPAC name
2-Hydroxy-2-methylpropanenitrile[2]
Other names
  • Cyanohydrin-2-propanone[1]
  • α-Hydroxyisobutyronitrile[1]
  • 2-Hydroxy-2-methyl-propionitrile[1]
Identifiers
CAS Number
  • 75-86-5 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B00479
Beilstein Reference
605391
ChEBI
  • CHEBI:15348 checkY
ChemSpider
  • 6166 checkY
DrugBank
  • DB02203 checkY
ECHA InfoCard 100.000.828 Edit this at Wikidata
EC Number
  • 200-909-4
KEGG
  • C02659 checkY
MeSH acetone+cyanohydrin
PubChem CID
  • 6406
RTECS number
  • OD9275000
UNII
  • CO1YOV1KFI checkY
UN number 1541
CompTox Dashboard (EPA)
  • DTXSID7025427 Edit this at Wikidata
InChI
  • InChI=1S/C4H7NO/c1-4(2,6)3-5/h6H,1-2H3 checkY
    Key: MWFMGBPGAXYFAR-UHFFFAOYSA-N checkY
SMILES
  • CC(C)(O)C#N
Properties
Chemical formula
C4H7NO
Molar mass 85.106 g·mol−1
Appearance Colourless liquid
Density 932 mg·mL−1
Melting point −21.2 °C; −6.3 °F; 251.9 K
Boiling point 95 °C; 203 °F; 368 K
Vapor pressure 2 kPa (at 20 °C)
Refractive index (nD)
1.399
Thermochemistry
Std enthalpy of
formation fH298)
−121.7 to −120.1 kJ·mol−1
Std enthalpy of
combustion cH298)
−2.4514 to −2.4498 MJ·mol−1
Hazards
GHS labelling:
Pictograms
GHS06: Toxic GHS09: Environmental hazard
Signal word
Danger
Hazard statements
H300, H310, H330, H410
Precautionary statements
P260, P273, P280, P284, P301+P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
4
1
2
Flash point 75 °C (167 °F; 348 K)
Explosive limits 2.25–11%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
  • 15.8 mg·kg−1 (dermal, rabbit)
  • 18.65 mg·kg−1 (oral, rat)
NIOSH (US health exposure limits):
PEL (Permissible)
None[1]
REL (Recommended)
C 1 ppm (4 mg·m−3) [15-minute][1]
IDLH (Immediate danger)
N.D.[1]
Safety data sheet (SDS) fishersci.com
Related compounds
Related alkanenitriles
  • Acetonitrile
  • Aminoacetonitrile
  • Glycolonitrile
  • Cyanogen
  • Propanenitrile
  • Aminopropionitrile
  • Malononitrile
  • Pivalonitrile
  • Butyronitrile
  • Succinonitrile
  • Tetramethylsuccinonitrile
Related compounds
DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Acetone cyanohydrin (ACH) is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic. It liberates hydrogen cyanide easily, so it is used as a source of such. For this reason, this cyanohydrin is also highly toxic.

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0005". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ "acetone cyanohydrin - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 8 June 2012.

and 28 Related for: Acetone cyanohydrin information

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Acetone cyanohydrin

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Acetone cyanohydrin (ACH) is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate...

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Cyanohydrin

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they are hydrolyzed to the α-hydroxy acid. Acetone cyanohydrin, (CH3)2C(OH)CN is the cyanohydrin of acetone. It is generated as an intermediate in the...

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Acetone

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the world's acetone is used as a solvent, and a quarter is consumed as acetone cyanohydrin, a precursor to methyl methacrylate. Acetone is a good solvent...

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Methyl methacrylate

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the condensation of acetone and hydrogen cyanide: (CH3)2CO + HCN → (CH3)2C(OH)CN Sulfuric acid then hydrolyzes acetone cyanohydrin (ACH) to a sulfate ester-adduct...

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Hydroxynitrilase

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reaction acetone cyanohydrin ⇌ {\displaystyle \rightleftharpoons } cyanide + acetone Hence, this enzyme has one substrate, acetone cyanohydrin, and two...

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Cyanohydrin reaction

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Cyanohydrin reaction of acetone with potassium cyanide Organic Syntheses Coll. Vol. 2, p. 7; Vol. 15, p. 1 Article Cyanohydrin reaction of benzoquinone...

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Acetone imine

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academic interest. Acetone imine is prepared by dehydrocyanation of the cyanoamine of acetone, which is prepared from acetone cyanohydrin. Dicyclohexylcarbodiimide...

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Nitrile

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prepared by transcyanohydrin reactions starting, for example, with acetone cyanohydrin as a source of HCN. Nitriles can be prepared by the dehydration of...

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Cassava

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juice of the bitter cassava root, which is poisonous (it contains acetone cyanohydrin, a compound which decomposes to the highly toxic hydrogen cyanide...

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Linamarase

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substance. The enzyme converts the cyanide containing compounds into acetone cyanohydrin, which spontaneously decomposes to hydrogen cyanide (HCN). The HCN...

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Methacrylic acid

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(PMMA). In the most common route, methacrylic acid is prepared from acetone cyanohydrin, which is converted to methacrylamide sulfate using sulfuric acid...

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Linamarin

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plants such as cassava, lima beans, and flax. It is a glucoside of acetone cyanohydrin. Upon exposure to enzymes and gut flora in the human intestine, linamarin...

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EPA list of extremely hazardous substances

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Top 0–9 A B C D E F G H I J K L M N O P Q R S T U V W X Y Z Acetone cyanohydrin Acetone thiosemicarbazide Acrolein Acrylamide Acrylonitrile Acryloyl...

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Lotaustralin

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the glucoside of methyl ethyl ketone cyanohydrin and is structurally related to linamarin, the acetone cyanohydrin glucoside also found in these plants...

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Hydrocyanation

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transhydrocyanation, an equivalent of HCN is transferred from a cyanohydrin, e.g. acetone cyanohydrin, to another HCN acceptor. The transfer is an equilibrium...

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Acetonitrile

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children by acetonitrile-based nail polish remover, one of which was fatal. Acetone and ethyl acetate are often preferred as safer for domestic use, and acetonitrile...

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Azobisisobutyronitrile

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anti-Markovnikov selectivity. AIBN is produced in two steps from acetone cyanohydrin. Reaction with hydrazine gives the substituted dialkylhydrazine....

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ACH

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the Lech, Bavaria, Germany Ach, Iran, a village in Qazvin Province Acetone cyanohydrin, an organic compound Acetylcholine (ACh), a neurotransmitter Aluminium...

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Hydantoin

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5-dimethyl compound can also be obtained from acetone cyanohydrin (also discovered by Urech: see cyanohydrin reaction) and ammonium carbonate. This reaction...

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Methyl vinyl ketone

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of acetone and formaldehyde, followed by dehydration. Similarly it is prepared by the Mannich reaction involving diethylammonium chloride and acetone, which...

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Glycolonitrile

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hydroxyacetonitrile or formaldehyde cyanohydrin, is the organic compound with the formula HOCH2CN. It is the simplest cyanohydrin and it is derived from formaldehyde...

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Azo compound

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compounds pose the risk of explosion. AIBN is produced by converting acetone cyanohydrin to the hydrazine derivative followed by oxidation: 2 (CH3)2C(CN)OH...

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Ammonium bisulfate

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acid by ammonia. It is commonly collected as a byproduct of the "acetone cyanohydrin route" to the commodity chemical methyl methacrylate. It can also...

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Sadamichi Hirasawa

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contemporary investigation claimed that the true poison may have been acetone cyanohydrin, a military poison deliberately designed to be slow-acting, which...

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Mesotrione

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mesotrione using a catalytic amount of cyanide ion derived from acetone cyanohydrin. Mesotrione inhibits the enzyme 4-hydroxyphenylpyruvate dioxygenase...

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Trimethylsilyl cyanide

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and regioselectivity of the addition of the cyano group are lower. Acetone cyanohydrin can be used to reversibly generate the cyanide anion. (4) Trimethylsilyl...

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Cyanogen

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Glycolonitrile Propionitrile Aminopropionitrile Malononitrile Pivalonitrile Acetone cyanohydrin Related compounds DBNPA Except where otherwise noted, data are given...

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Malononitrile

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Glycolonitrile Cyanogen Propanenitrile Aminopropionitrile Pivalonitrile Acetone cyanohydrin Butyronitrile Succinonitrile Tetramethylsuccinonitrile Related compounds...

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