| Revision as of 10:41, 8 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|error |
Latest revision as of 20:30, 19 May 2021 edit LegionMammal978 (talk | contribs)Extended confirmed users7,894 edits correct IUPAC name |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
| verifiedrevid = 443656980 |
|
| verifiedrevid = 443658192 |
|
| ImageFile = Acetone cyanohydrin.svg |
|
| ImageFile = Endothion.svg |
|
|
| PIN = ''S''- ''O'',''O''-dimethyl phosphorothioate |
|
| ImageFile2 = Acetone cyanohydrin 3D.png |
|
|
⚫ |
|Section1={{Chembox Identifiers |
|
| IUPACName = 2-hydroxy-2-methylpropanenitrile |
|
|
|
| InChI = InChI=1S/C9H13O6PS/c1-12-9-5-15-7(4-8(9)10)6-17-16(11,13-2)14-3/h4-5H,6H2,1-3H3 |
|
| OtherNames = |
|
|
|
| InChIKey = YCAGGFXSFQFVQL-UHFFFAOYSA-N |
| ⚫ |
| Section1 = {{Chembox Identifiers |
|
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
|
| KEGG = C02659 |
|
|
| InChI = 1/C4H7NO/c1-4(2,6)3-5/h6H,1-2H3 |
|
|
| InChIKey = MWFMGBPGAXYFAR-UHFFFAOYAL |
|
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI = 1S/C4H7NO/c1-4(2,6)3-5/h6H,1-2H3 |
|
| StdInChI = 1S/C9H10NO3PS/c1-11-14(15,12-2)13-9-5-3-8(7-10)4-6-9/h3-6H,1-2H3 |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey = MWFMGBPGAXYFAR-UHFFFAOYSA-N |
|
| StdInChIKey = SCKHCCSZFPSHGR-UHFFFAOYSA-N |
|
| CASNo = 75-86-5 |
|
| CASNo = 2778-04-3 |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = V047DQ6B7X |
|
| EC-number = 200-909-4 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| ChemSpiderID = 6166 |
|
| PubChem = 17717 |
|
|
| SMILES = COC1=COC(=CC1=O)CSP(=O)(OC)OC |
|
| PubChem = 6406 |
|
|
|
| ChemSpiderID = 16569 |
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
|
| ChEBI = 15348 |
|
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
|
| DrugBank = DB02203 |
|
|
| SMILES = N#CC(O)(C)C |
|
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
|
| C=9|H=13|O=6|P=1|S=1 |
|
| Formula = C<sub>4</sub>H<sub>7</sub>NO |
|
|
|
| Appearance = White Crystals |
|
| MolarMass = 85.105 g/mol |
|
|
⚫ |
| Density = 0.932 g/cm<sup>3</sup> |
|
| Appearance = |
|
|
|
| MeltingPtF = 19 to 205 |
| ⚫ |
| Density = 0.932 g/cm<sup>3</sup> |
|
|
|
| BoilingPtF = |
|
| MeltingPt = −19 °C |
|
|
⚫ |
| Solubility = 150 g/100 ml |
|
| BoilingPt = 95 °C |
|
| ⚫ |
| Solubility = |
|
|
}} |
|
}} |
|
| Section7 = {{Chembox Hazards |
|
|Section7={{Chembox Hazards |
|
|
| ExternalSDS = <ref name="cpcb-msds">{{cite web|url=http://www.cpcb.nic.in/divisionsofheadoffice/pci-ssi/MATERIAL_SAFETY-DATABASE/MSDS2008/237.pdf|title=Material Safety Data Sheets: Endothion|publisher=Central Pollution Control Board, Ministry of Environment & Forests, Government of India|access-date=2011-12-09|archive-url=https://web.archive.org/web/20101215041823/http://cpcb.nic.in/divisionsofheadoffice/pci-ssi/MATERIAL_SAFETY-DATABASE/MSDS2008/237.pdf|archive-date=2010-12-15|url-status=dead}}</ref> |
|
| ExternalMSDS = |
|
|
|
| NFPA-H = 3 |
|
| EUIndex = 608-004-00-X |
|
|
| NFPA-H = 4 |
|
| NFPA-F = 0 |
|
| NFPA-F = 1 |
|
| NFPA-R = 0 |
|
| NFPA-R = 2 |
|
| FlashPt = |
|
| FlashPt = |
|
| AutoignitionPt = |
|
| Autoignition = |
|
|
}} |
|
}} |
|
}} |
|
}} |
|
'''Acetone cyanohydrin''' is an ] used in the production of ], the ] of the transparent plastic ] (PMMA), also known as acrylic. |
|
|
|
|
|
|
|
'''Endothion''' is an ] used as an ] and ]. It is part of the chemical class of ] compounds. It is generally described as white crystals with a slight odor. It is used as an ], but not sold in the ] or ].<ref name="NOAA">{{cite web|url=http://cameochemicals.noaa.gov/chemical/4980|title=Endothion|publisher=CAMEO Chemicals|access-date=2011-11-09}} </ref> |
|
==Preparation== |
|
|
The compound is generated as part of the acetone cyanohydrin (ACH) route to methyl methacrylate. It is treated with sulfuric acid to give the sulfate ester of the methacrylamide, methanolysis of which gives ] and MMA.<ref>{{citation | first = William | last = Bauer, Jr. | title = Methacrylic Acid and Derivatives | work = Ullmann's Encyclopedia of Industrial Chemistry | year = 2002 | publisher = Wiley-VCH | location = Weinheim | doi = 10.1002/14356007.a16_441}}.</ref> In the laboratory, this compound may be prepared by reacting ] with ], followed by acidification:<ref>{{OrgSynth | first1 = R. F. B. | last1 = Cox | first2 = R. T. | last2 = Stormont | title = Acetone Cyanohydrin | prep = cv2p0007 | collvol = 2 | collvolpages = 7}}</ref> |
|
|
|
|
|
:] |
|
|
|
|
|
A simplified procedure involving the action of sodium or potassium cyanide on the sodium bisulfite adduct of acetone prepared ''in situ'' is possible, though the quality of the product is inferior.<ref>{{OrgSynth | first1 = E. C. | last1 = Wagner | first2 = Manuel | last2 = Baizer | title = 5,5-Dimethylhydantoin | prep = cv3p0323 | collvol = 3 | collvolpages = 323}}</ref> |
|
|
|
|
|
== Natural occurrence == |
|
|
] tubers contain ], a ] of acetohydrin, and the enzyme linamarinase for hydrolysing the glucoside. Crushing the tubers releases these compounds and produces acetone cyanohydrin, which is potentially lethally toxic. |
|
|
|
|
|
|
|
==Synonyms== |
|
|
* *2-(S-DIMETHYLPHOSPHOROTHIO- METHYL)-5-METHOXY-4-PYRONE |
|
|
* 5-METHOXY-2-(DIMETHOXYPHOSPHINYLTHIOMETHYL) PYRONE-4 |
|
|
* AC-18737 |
|
|
* ENDOCID |
|
|
* ENDOCIDE |
|
|
* ENT 24653 |
|
|
* EXOTHION |
|
|
* FMC 5767 |
|
|
* NIA 5767 |
|
|
* NIAGARA 5767 |
|
|
* O,O-DIMETHYL PHOSPHOROTHIOATE, S-ESTER WITH 2-(MERCAPTOMETHYL)-5-METHOXY-4H-PYRAN-4-ONE |
|
|
* O,O-DIMETHYL S-(5-METHOXY- 4-OXO-4H-PYRAN-2-YL) PHOSPHOROTHIOATE |
|
|
* O,O-DIMETHYL S-(5-METHOXYPYRONYL- 2-METHYL) THIOPHOSPHATE |
|
|
* PHOSPHATE 100 |
|
|
* PHOSPHOPYRON |
|
|
* PHOSPHOPYRONE |
|
|
* PHOSPHOROTHIOIC ACID, O,O-DIMETHYL ESTER, S-ESTER WITH 2-(MERCAPTOMETHYL)-5-METHOXY-4H-PYRAN-4-ONE |
|
|
* PHOSPHOROTHIOIC ACID, S-((5-METHOXY-4-OXO-4H-PYRAN-2-YL)METHYL) O,O-DIMETHYL ESTER |
|
|
* S-(5-METHOXY-4-PYRON-2-YLMETHYL) DIMETHYL PHOSPHOROTHIOATE |
|
|
* S-5-METHOXY-4-OXOPYRAN-2-YLMETHYL DIMETHYL PHOSPHOROTHIOATE |
|
|
* S-5-METHOXY-4-PYRON-2-YLMETHYL O,O-DIMETHYL PHOSPHOROTHIOATE |
|
|
* S- O,O-DIMETHYL PHOSPHOROTHIOATE |
|
==Safety== |
|
==Safety== |
|
|
Endothion can enter the body via inhalation, ingestion, and contact with the skin and eyes. Symptoms of endothion poisoning include ], ], ], ], ], ], and ], Noncardiacogenic ], ].<ref name="cpcb-msds"/> |
|
Acetone cyanohydrin is classified as an ] in the US ]. The principal hazards of acetone cyanohydrin arise from its ready decomposition on contact with water, which releases highly toxic ]. |
|
|
|
|
|
|
== References == |
|
==References== |
|
{{reflist}} |
|
{{reflist}} |
|
|
|
|
|
==External links== |
|
==External links== |
|
*{{SIDS|name=Acetone cyanohydrin|id=75865}} |
|
|
|
|
|
|
|
{{Insecticides}} |
| ⚫ |
] |
|
|
|
{{Acetylcholine metabolism and transport modulators}} |
|
|
|
|
|
|
] |
|
] |
|
|
|
] |
|
] |
|
|
⚫ |
] |
|
] |
|
|
|
] |
|
] |
|
|
] |
|
|
] |
|
|
] |
|