Difference between revisions of "Chloral hydrate"

From Sciencemadness Wiki
Jump to: navigation, search
(Created page with "{{Chembox | Name = Chloral hydrate | Reference = | IUPACName = 2,2,2-Trichloroethane-1,1-diol | PIN = | SystematicName = | OtherNames = Aquachloral<br>Chloradorm<br>Chloratol<...")
 
 
Line 64: Line 64:
 
| pKa = 9.66, 11.0
 
| pKa = 9.66, 11.0
 
| pKb =  
 
| pKb =  
| Solubility = 79.3 g/100 ml (at 25 °C)
+
| 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]], [[benzene]], [[diethyl ether]], [[ethanol]], [[Methyl ethyl ketone|MEK]]
+
| SolubleOther = Very soluble in [[acetone]], [[diethyl ether]], [[ethanol]], [[Methyl ethyl ketone|MEK]], [[methanol]], [[pyridine]]<br>Sparingly soluble in [[benzene]], [[carbon disulfide]]
| Solubility1 = 50 g/100 ml
+
| Solubility1 = 1.47 g/100 ml (20 °C)
| Solvent1 = chloroform
+
| Solvent1 = carbon disulfide
| Solubility2 = 66 g/100 ml
+
| 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 = diethyl ether
+
| Solvent2 = chloroform
| Solubility3 = 77 g/100 ml
+
| 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
 
   }}
 
   }}
Line 97: Line 99:
 
| ExternalMSDS = [https://jmp.sh/D0ZGJYdS Sigma-Aldrich]
 
| ExternalMSDS = [https://jmp.sh/D0ZGJYdS Sigma-Aldrich]
 
| FlashPt =  
 
| FlashPt =  
| LD50 = 1100 mg/kg (rat, oral)
+
| 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

Chloral hydrate
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):
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.

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

  1. Seidell A. Solubilities of organic compounds. - 3ed., vol.2. - New York: D. Van Nostrand Company, 1941

Relevant Sciencemadness threads