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; Noctec; Novo-Chlorhydrate; Somnos; Somnote;
Identifiers
CAS Number	302-17-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1698497
ChEBI	CHEBI:28142 ;
ChEMBL	ChEMBL455917 ;
ChemSpider	2606 ;
DrugBank	DB01563 ;
ECHA InfoCard	100.005.562
EC Number	206-117-5;
Gmelin Reference	101369
KEGG	D00265 ;
PubChem CID	2707;
RTECS number	FM875000;
UNII	418M5916WG ;
UN number	2811
CompTox Dashboard (EPA)	DTXSID7020261 ;
	InChI InChI=1S/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H Key: RNFNDJAIBTYOQL-UHFFFAOYSA-N ; InChI=1/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H Key: RNFNDJAIBTYOQL-UHFFFAOYAY;
	SMILES ClC(Cl)(Cl)C(O)O;
Properties
Chemical formula	CCl3CH(OH)2
Molar mass	165.39 g·mol−1
Appearance	Colourless 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)
Solubility in water	660 g/(100 ml)
Solubility	Very soluble in benzene, ethyl ether, ethanol
log P	0.99
Acidity (pKa)	9.66, 11.0
Structure
Crystal structure	Monoclinic
Pharmacology
ATC code	N05CC01 (WHO)
Routes of; administration	Oral syrup, rectal suppository
	Pharmacokinetics:
Bioavailability	Well absorbed
Metabolism	Hepatic and renal (converted to trichloroethanol)
Biological half-life	8–10 hours
Excretion	Bile, feces, urine (various metabolites not unchanged)
Legal status	BR: Class C1 (Other controlled substances); CA: Unscheduled; US: Schedule IV;
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H319
Precautionary statements	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):
LD50 (median dose)	1100 mg/kg (oral)
Safety data sheet (SDS)	External MSDS
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). Infobox references

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 use 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.

^ 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.
^ 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. Bibcode:1958JAChS..80.5392G. doi:10.1021/ja01553a018.
^ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (85th ed.). CRC Press. pp. 3–98. ISBN 978-0-8493-0484-2.
^ 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.

[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. Bibcode:1958JAChS..80.5392G. 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.

[1970EEGstudy-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.

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