acetone cyanohydrin acetone cyanohydrin 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. acetone cyanohydrin ball and stick model of acetone cyanohydrin spacefill model of acetone cyanohydrin names preferred iupac name 2-hydroxy-2-methylpropanenitrile other names cyanohydrin-2-propanoneα-hydroxyisobutyronitrile2-hydroxy-2-methyl-propionitrile identifiers cas number 75-86-5 y 3d model (jsmol) interactive image 3dmet b00479 beilstein reference 605391 chebi chebi:15348 y chemspider 6166 y drugbank db02203 y echa infocard 100.000.828 ec number 200-909-4 kegg c02659 y mesh acetone+cyanohydrin pubchem cid 6406 rtecs number od9275000 unii co1yov1kfi y un number 1541 comptox dashboard (epa) dtxsid7025427 inchi inchi=1s/c4h7no/c1-4(2,6)3-5/h6h,1-2h3 ykey: mwfmgbpgaxyfar-uhfffaoysa-n y 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 offormation (δfh⦵298) −121.7 to −120.1 kj·mol−1 std enthalpy ofcombustion (δch⦵298) −2.4514 to −2.4498 mj·mol−1 hazards ghs labelling: pictograms signal word danger hazard statements h300, h310, h330, h410 precautionary statements p260, p273, p280, p284, p301+p310 nfpa 704 (fire diamond) 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 rel (recommended) c 1 ppm (4 mg·m−3) idlh (immediate danger) n.d. safety data sheet (sds) fishersci.com related compounds related alkanenitriles acetonitrileaminoacetonitrileglycolonitrilecyanogenpropanenitrileaminopropionitrilemalononitrilepivalonitrilebutyronitrilesuccinonitriletetramethylsuccinonitrile related compounds dbnpa except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). y verify (what is yn ?) infobox references preparation in the laboratory, this compound may be prepared by treating sodium cyanide with acetone, followed by acidification: considering the high toxicity of acetone cyanohydrin, a lab scale production has been developed using a microreactor-scale flow chemistry to avoid needing to manufacture and store large quantities of the reagent. alternatively, a simplified procedure involves the action of sodium or potassium cyanide on the sodium bisulfite adduct of acetone prepared in situ. this gives a less pure product, one that is nonetheless suitable for most syntheses. reactions acetone cyanohydrin is an intermediate en route to methyl methacrylate. treatment with sulfuric acid gives the sulfate ester of the methacrylamide, methanolysis of which gives ammonium bisulfate and methyl methacrylate. it is used as a surrogate in place of hcn, as illustrated by its use as a precursor to lithium cyanide: (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. in the hydrocyanation reaction of butadiene, the transfer is irreversible. 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