Difference between revisions of "Chloral hydrate"
(Created page with "{{Chembox | Name = Chloral hydrate | Reference = | IUPACName = 2,2,2-Trichloroethane-1,1-diol | PIN = | SystematicName = | OtherNames = Aquachloral<br>Chloradorm<br>Chloratol<...") |
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| pKa = 9.66, 11.0 | | pKa = 9.66, 11.0 | ||
| pKb = | | pKb = | ||
| − | | Solubility = | + | | Solubility = 239 g/100 ml (0 °C)<br>292 g/100 ml (5 °C)<br>470 g/100 ml (17 °C)<br>793 g/100 ml (25 °C)<br>1005 g/100 ml (30 °C)<br>1430 g/100 ml (40 °C)<ref>Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941</ref> |
| − | | SolubleOther = Very soluble in [[acetone | + | | SolubleOther = Very soluble in [[acetone]], [[diethyl ether]], [[ethanol]], [[Methyl ethyl ketone|MEK]], [[methanol]], [[pyridine]]<br>Sparingly soluble in [[benzene]], [[carbon disulfide]] |
| − | | Solubility1 = | + | | Solubility1 = 1.47 g/100 ml (20 °C) |
| − | | Solvent1 = | + | | Solvent1 = carbon disulfide |
| − | | Solubility2 = | + | | Solubility2 = 3.8 g/100 ml (0 °C)<br>5.2 g/100 ml (10 °C)<br>15.5 g/100 ml (20 °C)<br>65 g/100 ml (27.7 °C) |
| − | | Solvent2 = | + | | Solvent2 = chloroform |
| − | | Solubility3 = | + | | Solubility3 = 200 g/100 ml (25 °C) |
| − | | Solvent3 = ethanol | + | | Solvent3 = diethyl ether |
| + | | Solubility4 = 188 g/100 ml (0 °C)<br>200 g/100 ml (5 °C)<br>425 g/100 ml (20 °C)<br>950 g/100 ml (30 °C)<br>5600 g/100 ml (45 °C) | ||
| + | | Solvent4 = ethanol | ||
| VaporPressure = 15 mmHg at 25 °C | | VaporPressure = 15 mmHg at 25 °C | ||
}} | }} | ||
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| ExternalMSDS = [https://jmp.sh/D0ZGJYdS Sigma-Aldrich] | | ExternalMSDS = [https://jmp.sh/D0ZGJYdS Sigma-Aldrich] | ||
| FlashPt = | | FlashPt = | ||
| − | | LD50 = 1100 mg/kg ( | + | | LD50 = 479 (rat, oral)<br>1100 mg/kg (mouse, oral) |
| LC50 = | | LC50 = | ||
| MainHazards = Irritant | | MainHazards = Irritant | ||
| Line 125: | Line 127: | ||
===Physical=== | ===Physical=== | ||
Chloral hydrate is a colorless crystalline solid, with a characteristic odor. It is highly soluble in water and many other solvents. | Chloral hydrate is a colorless crystalline solid, with a characteristic odor. It is highly soluble in water and many other solvents. | ||
| + | |||
| + | Other solubility data: | ||
| + | *[[pyridine]]: 80.9 g/100 g (20 °C) | ||
| + | *[[quinoline]]: 12.56 g/100 g (20 °C) | ||
| + | *[[toluene]]: 3.25 g/100 g (0 °C); 8 g/100 g (10 °C); 21 g/100 g (20 °C); 77 g/100 g (35 °C); 200 g/100 g (45 °C) | ||
==Availability== | ==Availability== | ||
| Line 142: | Line 149: | ||
==Projects== | ==Projects== | ||
*Sedative | *Sedative | ||
| − | *Make isatin | + | *Make [[isatin]] |
*Make Hoyer's solution | *Make Hoyer's solution | ||
*Make Melzer's reagent | *Make Melzer's reagent | ||
Latest revision as of 12:57, 1 January 2024
| Names | |
|---|---|
| IUPAC name
2,2,2-Trichloroethane-1,1-diol
| |
| Other names
Aquachloral
Chloradorm Chloratol Noctec Novo-Chlorhydrate Somnos Somnote Trichloroacetaldehyde monohydrate | |
| Properties | |
| C2H3Cl3O2 Cl3CCH(OH)2 | |
| Molar mass | 165.39 g/mol |
| Appearance | Colorless crystalline solid |
| Odor | Aromatic, slightly acrid |
| Density | 1.9081 g/cm3 (20 °C) |
| Melting point | 57 °C (135 °F; 330 K) |
| Boiling point | 98 °C (208 °F; 371 K) |
| 239 g/100 ml (0 °C) 292 g/100 ml (5 °C) 470 g/100 ml (17 °C) 793 g/100 ml (25 °C) 1005 g/100 ml (30 °C) 1430 g/100 ml (40 °C)[1] | |
| Solubility | Very soluble in acetone, diethyl ether, ethanol, MEK, methanol, pyridine Sparingly soluble in benzene, carbon disulfide |
| Solubility in carbon disulfide | 1.47 g/100 ml (20 °C) |
| Solubility in chloroform | 3.8 g/100 ml (0 °C) 5.2 g/100 ml (10 °C) 15.5 g/100 ml (20 °C) 65 g/100 ml (27.7 °C) |
| Solubility in diethyl ether | 200 g/100 ml (25 °C) |
| Solubility in ethanol | 188 g/100 ml (0 °C) 200 g/100 ml (5 °C) 425 g/100 ml (20 °C) 950 g/100 ml (30 °C) 5600 g/100 ml (45 °C) |
| Vapor pressure | 15 mmHg at 25 °C |
| Acidity (pKa) | 9.66, 11.0 |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
479 (rat, oral) 1100 mg/kg (mouse, oral) |
| Related compounds | |
| Related compounds
|
Chlorobutanol |
| 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 an organic compound, a geminal diol with the formula C2H3Cl3O2.It has limited use as a sedative and hypnotic pharmaceutical drug.
Contents
Properties
Chemical
Heating a mixture of chloral hydrate and sulfuric acid will yield chloral, which distills over.
Chloral hydrate reacts with aniline and hydroxylamine to give a condensation product which cyclicizes in sulfuric acid to give isatin
Aqueous solutions of chloral hydrate decomposed rapidly when exposed to ultraviolet light, with the formation of hydrochloric acid, trichloroacetic acid and formic acid.
Physical
Chloral hydrate is a colorless crystalline solid, with a characteristic odor. It is highly soluble in water and many other solvents.
Other solubility data:
- pyridine: 80.9 g/100 g (20 °C)
- quinoline: 12.56 g/100 g (20 °C)
- toluene: 3.25 g/100 g (0 °C); 8 g/100 g (10 °C); 21 g/100 g (20 °C); 77 g/100 g (35 °C); 200 g/100 g (45 °C)
Availability
Chloral hydrate is sold by chemical suppliers.
In the United States, chloral hydrate is a schedule IV controlled substance and requires a physician's prescription. In most other countries, the sale of this compound is regulated and thus it cannot be acquired this way.
Preparation
Chloral hydrate is produced from the addition of chlorine to ethanol, in acidic solution:
- 4 Cl2 + C2H5OH + H2O → Cl3CCH(OH)2 + 5 HCl
In basic conditions the haloform reaction takes place and chloral hydrate is decomposed by hydrolysis to form chloroform.
Pure chloral hydrate can be obtained by adding chloral to one equivalent of water.
Projects
- Sedative
- Make isatin
- Make Hoyer's solution
- Make Melzer's reagent
Handling
Safety
Chloral hydrate is a sedative, with all the side effects that come. Long-term use of chloral hydrate is associated with a rapid development of tolerance to its effects and possible addiction as well as adverse effects including rashes, gastric discomfort and severe kidney, heart, and even liver failure.
Storage
In closed airtight bottles. Ampouling may be an option.
Disposal
Sodium hydroxide breaks down this compound into chloroform. Excess NaOH in turn, will further break down chloroform. Strong UV light has also been shown to break down this compound.
References
- ↑ Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941
