Chloral hydrate

Chloral hydrate
  Carbon, C
  Chlorine, Cl
  Oxygen, O
  Hydrogen, H
Names
Preferred IUPAC name
2,2,2-Trichloroethane-1,1-diol
Other names
  • Trichloroacetaldehyde monohydrate
  • Chlorali hydras
  • Tradenames:
  • Aquachloral
  • Chloradorm
  • Chloratol[1]
  • Noctec
  • Novo-Chlorhydrate
  • Somnos
  • Somnote
Identifiers
3D model (JSmol)
1698497
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.562 Edit this at Wikidata
EC Number
  • 206-117-5
101369
KEGG
RTECS number
  • FM875000
UNII
UN number 2811
  • InChI=1S/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H checkY
    Key: RNFNDJAIBTYOQL-UHFFFAOYSA-N checkY
  • InChI=1/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H
    Key: RNFNDJAIBTYOQL-UHFFFAOYAY
  • ClC(Cl)(Cl)C(O)O
Properties[3]
CCl3CH(OH)2
Molar mass 165.39 g·mol−1
Appearance Colorless solid
Odor Aromatic, slightly acrid
Density 1.9081 g/cm3
Melting point 57 °C (135 °F; 330 K)
Boiling point 98 °C (208 °F; 371 K) (decomposes)
660 g/(100 ml)
Solubility Very soluble in benzene, ethyl ether, ethanol
log P 0.99
Acidity (pKa) 9.66, 11.0[2]
Structure
Monoclinic
Pharmacology
N05CC01 (WHO)
Oral syrup, rectal suppository
Pharmacokinetics:
Well absorbed
Hepatic and renal (converted to trichloroethanol)
8–10 hours
Bile, feces, urine (various metabolites not unchanged)
Legal status
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation mark
Danger
H301, H315, H319
P264, P270, P280, P301+P310, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P405, P501
Lethal dose or concentration (LD, LC):
1100 mg/kg (oral)
Safety data sheet (SDS) External MSDS[dead link]
Related compounds
Related compounds
 Chloral, chlorobutanol, Triclofos
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chloral hydrate is a geminal diol with the formula Cl3C−CH(OH)2. It was first used as a sedative and hypnotic in Germany in the 1870s. Over time it was replaced by safer and more effective alternatives but it remained in usage in the United States until at least the 1970s.[4] It sometimes finds usage as a laboratory chemical reagent and precursor. It is derived from chloral (trichloroacetaldehyde) by the addition of one equivalent of water.

  1. ^ Vardanyan, R.S.; Hruby, V.J. (2006). "Soporific Agents (Hypnotics and Sedative Drugs)". Synthesis of Essential Drugs. pp. 57–68. doi:10.1016/B978-044452166-8/50004-2. ISBN 978-0-444-52166-8.
  2. ^ Gawron, O.; Draus, F. (1958). "Kinetic Evidence for Reaction of Chloralate Ion with p-Nitrophenyl Acetate in Aqueous Solution". Journal of the American Chemical Society. 80 (20): 5392–5394. doi:10.1021/ja01553a018.
  3. ^ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (85th ed.). CRC Press. pp. 3–98. ISBN 978-0-8493-0484-2.
  4. ^ Kales, Anthony (1 September 1970). "Hypnotic Drugs and Their Effectiveness: All-night EEG Studies of Insomniac Subjects". Archives of General Psychiatry. 23 (3): 226–232. doi:10.1001/archpsyc.1970.01750030034006. PMID 4318151.