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词条 2,2,2-Trichloroethanol
释义

  1. Use in organic synthesis

  2. See also

  3. References

{{chembox
| verifiedrevid = 477209540
| Name = 2,2,2-Trichloroethanol
| ImageFileL1 = 2,2,2-trichloroethanol.svg
| ImageNameL1 = 2,2,2-Trichloroethanol
| ImageFileR1 = 2,2,2-trichloroethanol-3D-vdW.png
| ImageNameR1 = 2,2,2-Trichloroethanol
| IUPACName = 2,2,2-Trichloroethanol
| Section1 = {{Chembox Identifiers
| IUPHAR_ligand = 2293
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28094
| ChemSpiderID = 7961
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = AW835AJ62N
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C07490
| InChI = 1/C2H3Cl3O/c3-2(4,5)1-6/h6H,1H2
| InChIKey = KPWDGTGXUYRARH-UHFFFAOYAW
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1171
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2H3Cl3O/c3-2(4,5)1-6/h6H,1H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KPWDGTGXUYRARH-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 115-20-8
| SMILES = ClC(Cl)(Cl)CO
| Section2 = {{Chembox Properties
| Formula = C2H3Cl3O
| MolarMass = 149.40 g/mol
| Density = 1.55 g/cm3
| MeltingPtC = 17.8
| BoilingPtC = 151
}}2,2,2-Trichloroethanol is an organic compound related to ethanol, except the hydrogen atoms at position 2 are replaced with chlorine atoms. In humans, its pharmacological effects are similar to those of its prodrugs, chloral hydrate and chlorobutanol. It has, historically, been used as a sedative hypnotic.[1] The hypnotic drug triclofos (2,2,2-trichloroethyl phosphate) is metabolized in vivo to 2,2,2-trichloroethanol. Chronic exposure may result in kidney and liver damage.[2]2,2,2-Trichloroethanol can be added to SDS-PAGE gels in order to enable fluorescent detection of proteins without a staining step. This imaging step is compatible with later analysis by, e.g., immunoblotting.[3]

Use in organic synthesis

2,2,2-trichloroethanol is an effective protecting group for carboxylic acids due to its ease in addition and removal.[4]

See also

  • 1,1,1-Trichloroethane
  • Tribromoethanol
  • Triclofos

References

1. ^The Merck Index, 13th Edition.
2. ^{{cite book |author1=S. Budavari|author2=M. O'Neil|author3=Ann Smith |author4=P. Heckelman |author5=J. Obenchain |title=The Merck Index |title-link=Merck Index |edition=12th print |date=15 March 1996 |publisher=Taylor & Francis |isbn=978-0-911910-12-4}}
3. ^{{cite journal|last1=Ladner|first1=Carol|title=Visible fluorescent detection of proteins in polyacrylamide gels without staining|journal=Analytical Biochemistry|date=March 2004|volume=326|issue=1|pages=13–20|doi=10.1016/j.ab.2003.10.047|pmid=14769330|url=http://www.sciencedirect.com/science/article/pii/S0003269703008017}}
4. ^{{Citation|last=Lowder|first=Patrick D.|date=2001-04-15|publisher=John Wiley & Sons, Ltd|language=en|doi=10.1002/047084289x.rt203|isbn=978-0471936237|title=Encyclopedia of Reagents for Organic Synthesis|chapter=2,2,2-Trichloroethanol}}
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8 : Organochlorides|Alcohols|Sedatives|GABAA receptor positive allosteric modulators|Glycine receptor agonists|NMDA receptor antagonists|Halohydrins|Trichloromethyl compounds

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