Acetone cyanohydrin
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Names | |||
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Preferred IUPAC name
2-Hydroxy-2-methylpropanenitrile[2] | |||
Other names | |||
Identifiers | |||
3D model (
JSmol ) |
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3DMet | |||
605391 | |||
ChEBI | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard
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100.000.828 | ||
EC Number |
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KEGG | |||
MeSH | acetone+cyanohydrin | ||
PubChem CID
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RTECS number
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UNII | |||
UN number | 1541 | ||
CompTox Dashboard (EPA)
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Properties | |||
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)
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1.399 | ||
Thermochemistry | |||
Std enthalpy of (ΔfH⦵298)formation |
−121.7 to −120.1 kJ·mol−1 | ||
Std enthalpy of (ΔcH⦵298)combustion |
−2.4514 to −2.4498 MJ·mol−1 | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H300, H310, H330, H410 | |||
P260, P273, P280, P284, P301+P310 | |||
NFPA 704 (fire diamond) | |||
Flash point | 75 °C (167 °F; 348 K) | ||
Explosive limits
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2.25–11% | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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NIOSH (US health exposure limits): | |||
PEL (Permissible)
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None[1] | ||
REL (Recommended)
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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
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Related compounds
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DBNPA | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Acetone cyanohydrin (ACH) is an
Preparation
In the laboratory, this compound may be prepared by treating sodium cyanide with acetone, followed by acidification:[3]
Considering the high toxicity of acetone cyanohydrin, a lab scale production has been developed using a
Reactions
Acetone cyanohydrin is an intermediate en route to
It is used as a surrogate in place of HCN, as illustrated by its use as a precursor to lithium cyanide:[8]
- (CH3)2C(OH)CN + LiH → (CH3)2CO + LiCN + H2
In transhydrocyanation, an equivalent of HCN is transferred from acetone cyanohydrin to another acceptor, with acetone as byproduct. The transfer is an equilibrium process, initiated by base. The reaction can be driven by trapping reactions or by the use of a superior HCN acceptor, such as an aldehyde.[9] In the hydrocyanation reaction of butadiene, the transfer is irreversible.[10]
Natural occurrence
Cassava tubers contain linamarin, a glucoside of acetohydrin, and the enzyme linamarase for hydrolysing the glucoside. Crushing the tubers releases these compounds and produces acetone cyanohydrin.
Safety
Acetone cyanohydrin is classified as an
References
- ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0005". National Institute for Occupational Safety and Health (NIOSH).
- ^ "acetone cyanohydrin - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 8 June 2012.
- ^ Cox, R. F. B.; Stormont, R. T. "Acetone Cyanohydrin". Organic Syntheses; Collected Volumes, vol. 2, p. 7.
- .
- ^ Wagner, E. C.; Baizer, Manuel. "5,5-Dimethylhydantoin". Organic Syntheses; Collected Volumes, vol. 3, p. 323.
- .
- ISBN 978-3527306732..
- .
- ISBN 0471936235.
- PMID 17902667.
External links
- SIDS Initial Assessment Report for Acetone cyanohydrin from the Organisation for Economic Co-operation and Development(OECD)
- CDC - NIOSH Pocket Guide to Chemical Hazards - Acetone Cyanohydrin