2,2,2-trichloroethane-1,1-diol

• ChemBase ID: 1347
• Molecular Formular: C2H3Cl3O2
• Molecular Mass: 165.40302
• Monoisotopic Mass: 163.91986238
• SMILES: ClC(Cl)(Cl)C(O)O
• Canonical SMILES: OC(C(Cl)(Cl)Cl)O
• InChI: InChI=1S/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H
• InChIKey: RNFNDJAIBTYOQL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2,2-trichloroethane-1,1-diol
• IUPAC Traditional name: tosyl
• Brand Name: Somnote; Aquachloral Supprettes
• Synonyms: Trichloroacetaldehyde hydrate; Chloral hydrate solution; Chloral hydrate solution; ‘Ground joint separation aid’ Fluka; Chloral hydrate; Chloral hydrate; Trichloroacetaldehyde monohydrate; Tradenames: Aquachloral, Novo-Chlorhydrate, Somnos, Noctec, Somnote; 水合氯醛 溶液; 水合氯醛 溶液; `磨口连接头分离助剂' Fluka; 三氯乙醛 水合物; 氯醛 水合物

Database IDs

• CAS Number: 302-17-0
• EC Number: 206-117-5
• MDL Number: MFCD00044479
• Beilstein Number: 1698497
• PubChem SID: 46507155; 160964807; 24853847; 24893053; 24849282
• PubChem CID: 2707
• CHEBI ID: 28142
• ATC CODE: N05CC01
• CHEMBL: 455917
• Chemspider ID: 2606
• DrugBank ID: DB01563
• KEGG ID: D00265
• Unique Ingredient Identifier: 418M5916WG
• Wikipedia Title: Chloral_hydrate

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.509397
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.69231254
• LogD (pH = 7.4): 0.6889953
• Log P: 0.69235504
• Molar Refractivity: 29.2457 cm^3
• Polarizability: 11.635822 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.88
• LOG S: -0.58
• Solubility (Water): 4.34e+01 g/l

PROPERTIES

Physical Property

• Solubility: 793 mg/mL at 25 oC [YALKOWSKY,SH & HE,Y (2003)]
• Apperance: Colorless solid
• Melting Point: 57 °C(lit.); 57°C
• Boiling Point: 98°C
• Flash Point: 16 °C; 60.8 °F
• Density: 1.20 g/mL at 20 °C; 1.43 g/mL at 20 °C; 1.91 g/cm^3
• Hydrophobicity(logP): 0.99 [HANSCH,C ET AL. (1995)]
• pKa: 9.66, 11.0
• pH: 3.5-5.5 (20 °C, 10%)

Safety Information

• RTECS: FM8750000
• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 3286
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-36/38-39/23/24/25; 25-36/38; R22 R36 R37 R38
• Safety Statements: 16-26-36/37-45; 25-45; 26-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301-H312-H315-H319-H332-H370; H301-H315-H319
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P305 + P351 + P338-P307 + P311; P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3286 3/PG 2
• Drug Control: USDEA Schedule IV

Pharmacology Properties

• Admin Routes: Oral codeine/syrup, rectal suppository
• Bioavailability: well absorbed
• Excretion: bile, feces, urine (various metabolites not unchanged)
• Half Life: 8–10 hours in plasma
• Metabolism: converted to trichloroethanol, hepatic and renal
• Legal Status: Schedule IV (US)
• Pregnancy Category: C (US)

Product Information

• Purity: ≥98.0% (T); ≥99.5%; ≥99.7%; 99.5-101%
• Concentration: 1 g/mL
• Grade: p.a.; SAJ first grade; SAJ special grade
• Compostion: chloral hydrate, 32%; methanol, 26%
• Suitability: complies for appearance of solution; complies for reaction against H2SO4
• Ignition Residue: ≤0.1% (as SO4)
• Impurities: ≤0.002% heavy metals (as Pb); ≤0.1% non-volatile matter; chlor alcoholate, complies; organic volatile impurities, complies (GC); residual solvents, complies
• Antion Traces: chloride (Cl-): ≤50 mg/kg
• Quality: crystallized; meets analytical specification of Ph. Eur., BP, USP
• Linear Formula: Cl3CCH(OH)2

DETAILS

DrugBank - DB01563

• Drug Groups: illicit; experimental
• Description: A hypnotic and sedative used in the treatment of insomnia. The safety margin is too narrow for chloral hydrate to be used as a general anesthetic in humans, but it is commonly used for that purpose in animal experiments. It is no longer considered useful as an anti-anxiety medication. [PubChem]
• Indication: Mainly used as a hyponotic in the treatment of insomnia; however, it is only effective as a hypnotic for short-term use. May be used as a routine sedative preoperatively to decrease anxiety and cause sedation and/or sleep with respiration depression or cough reflex.
• Biotransformation: Metabolized by the liver and erythrocytes to form trichloroethanol, an active metabolite. This reaction is catalyzed by alcohol dehydrogenase and other enzymes. Oxidation of chloral hydrate and trichloroethanol to trichloroacetic acid in the liver and kidneys also occurs to a lesser extent. Trichloroethanol also undergoes glucuronidation to produce an inactive metabolism.
• Absorption: Rapidly absorbed in the GI tract following oral or rectal administration. Chloral hydrate and its active metabolite, trichloroethanol, have been detected in CSF, umbilical cord blood, fetal blood, and amniotic fluid.
• Elimination: Trichloroethanol, trichloroethanol glucuronide, and trichloroacetic acid are excreted in the urine. Some trichloroethanol glucuronide may be secreted into bile and excreted in the feces.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - C8383

Application
Sedative/hypnotic that is used as an anesthetic for laboratory and farm animals.

Sigma Aldrich - 23100

Other Notes
Sales restrictions may apply

Sigma Aldrich - 84670

Application
medium for the separation of ground joints sticking together
Other Notes
Sales restrictions may apply