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Basic Information
CAS No.: 123-63-7
Name: Paracetaldehyde
Molecular Structure:
Molecular Structure of 123-63-7 (Paracetaldehyde)
Formula: C6H12O3
Molecular Weight: 132.159
Synonyms: 1,3,5-trioxane, 2,4,6-trimethyl-;Acetaldehyde, trimer;1,3,5-Trioxane,2,4,6-trimethyl-;Tiracetaldehyde;Paral (TN);Acetaldehyde trimer;Elaldehyde;2,4,6-Trimethyl-1,3, 5-trioxacyclohexane;2,4,6-Trimethyl-s-trioxane;s-Trimethyltrioxymethylene;Triacetaldehyde;PCHO;Paral;s-Trioxane, 2,4,6-trimethyl-;1,3,5-Trimethyl-2,4,6-trioxane;2,4,6-Trimethyl-1,3,5-trioxane;
EINECS: 204-639-8
Density: 0.946 g/cm3
Melting Point: 12 °C
Boiling Point: 124 °C at 760 mmHg
Flash Point: 39.2 °C
Solubility: 0.994 g/mL at 20 °C(lit.) in water
Appearance: Colourless to yellowish clear liquid
Hazard Symbols: FlammableF
Risk Codes: 11
Safety: 9-16-29-33
Transport Information: UN 1993 3/PG 2
PSA: 27.69000
LogP: 1.08780
Synthetic route
75-07-0

acetaldehyde

123-63-7

paracetaldehyde

Conditions
ConditionsYield
With [P(2-pyridyl)3W(CO)(NO)2](2+)(BF4(1-))2 at 20℃; for 24h;96%
With indium(III) chloride at 20℃; for 0.0666667h;78%
chloro-trimethyl-silane at 20℃;70%
1115-15-7

divinyl sulfoxide

A

188290-36-0

thiophene

B

123-63-7

paracetaldehyde

Conditions
ConditionsYield
at 350℃; for 0.0666667h; Mechanism; Product distribution; other temperature, other time;A 26.1%
B 19.5%
at 530 - 550℃; Product distribution;
108-62-3

metaldehyde

123-63-7

paracetaldehyde

Conditions
ConditionsYield
Uebergang des erhaltenen Acetaldehyds;
624-85-1

ethyl hypochlorite

64-17-5

ethanol

A

105-57-7

diethyl acetal

B

75-07-0

acetaldehyde

C

123-63-7

paracetaldehyde

624-85-1

ethyl hypochlorite

123-63-7

paracetaldehyde

Conditions
ConditionsYield
With ethanol
75-03-6

ethyl iodide

75-07-0

acetaldehyde

123-63-7

paracetaldehyde

75-44-5

phosgene

75-07-0

acetaldehyde

123-63-7

paracetaldehyde

2074-87-5

carbon nitride

75-07-0

acetaldehyde

123-63-7

paracetaldehyde

64-17-5

ethanol

75-07-0

acetaldehyde

A

431-03-8

dimethylglyoxal

B

123-63-7

paracetaldehyde

C

513-85-9

2.3-butanediol

Conditions
ConditionsYield
bei der Belichtung;
64-17-5

ethanol

75-07-0

acetaldehyde

A

123-63-7

paracetaldehyde

B

513-85-9

2.3-butanediol

Conditions
ConditionsYield
bei der Belichtung;
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History

In 1829, paraldehyde  was first synthesized by Wildenbusch.
In 1882, paraldehyde was introduced into clinical practice in the UK by the Italian physician Vincenzo Cervello.
Paraldehyde (123-63-7) was the last injection given to Edith Alice Morrell in 1950 by the suspected serial killer John Bodkin Adams. He was tried for her murder but acquitted.
It is one of the safest hypnotics and was regularly given at bedtime in psychiatric hospitals and geriatric wards up to the 1960s.

Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

Specification

The Paraldehyde, with the CAS registry number 123-63-7 and EINECS registry number 204-639-8, has the systematic name of 2,4,6-trimethyl-1,3,5-trioxane. It is a kind of colourless to yellowish clear liquid with a pleasant odor, and belongs to the following product categories: Intermediates; Organics; Aldehyde; Organoborons; Pyridine; Organohalides; Quinoline; Benzothiophene. The molecular formula of the chemical is C6H12O3. What's more, it should be stored at 2-8°C.  

The Paraldehyde is the cyclic trimer of acetaldehyde molecules,and it is used in resin manufacture, as a preservative, and in other processes as a solvent. It is also used in the generation of aldehyde fuchsin.

The physical properties of Paraldehyde are as followings: (1)ACD/LogP: 0.86; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.86; (4)ACD/LogD (pH 7.4): 0.86; (5)#H bond acceptors: 3; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 0; (8)Polar Surface Area: 27.69 Å2; (9)Index of Refraction: 1.385; (10)Molar Refractivity: 32.77 cm3; (11)Molar Volume: 139.5 cm3; (12)Polarizability: 12.99×10-24cm3; (13)Surface Tension: 24.9 dyne/cm; (14)Density: 0.946 g/cm3; (15)Flash Point: 39.2 °C; (16)Enthalpy of Vaporization: 34.7 kJ/mol; (17)Boiling Point: 124 °C at 760 mmHg; (18)Vapour Pressure: 15.7 mmHg at 25°C.  

Preparation and uses: This chemical can be prepared by acetaldehyde. The reaction will need catalyst inorganic acid. And it is a kind of polyreaction. And it is always used in the agricultural chemical.

You should be cautious while dealing with this chemical. It is a kind of highly flammable chemical. Therefore, you had better take the following instructions: Keep container in a well-ventilated place; Keep away from sources of ignition - No smoking; Do not empty into drains; Take precautionary measures against static discharges.

You can still convert the following datas into molecular structure:
(1)SMILES: CC1OC(C)OC(C)O1
(2)InChI: InChI=1/C6H12O3/c1-4-7-5(2)9-6(3)8-4/h4-6H,1-3H3
(3)InChIKey: SQYNKIJPMDEDEG-UHFFFAOYAO

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 3300mg/kg (3300mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
man LDLo rectal 333mg/kg (333mg/kg) GASTROINTESTINAL: NECROTIC GHANGES South African Medical Journal. Vol. 29, Pg. 1021, 1955.
man LDLo unreported 1462mg/kg (1462mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TDLo intramuscular 568mg/kg (568mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
British Journal of Psychiatry. Vol. 149, Pg. 650, 1986.
mouse LD50 intraperitoneal 1257mg/kg (1257mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 119, Pg. 19, 1957.
mouse LD50 oral 2750mg/kg (2750mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 119, Pg. 19, 1957.
rabbit LD50 oral 3304mg/kg (3304mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 29, Pg. 730, 1932.
rabbit LD50 skin 14100uL/kg (14.1mL/kg)   Union Carbide Data Sheet. Vol. 3/24/1970,
rat LCLo inhalation 4000ppm/4H (4000ppm)   Union Carbide Data Sheet. Vol. 3/24/1970,
rat LD50 oral 1530mg/kg (1530mg/kg)   Union Carbide Data Sheet. Vol. 3/24/1970,
rat LDLo intraperitoneal 2100mg/kg (2100mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 156, 1959.
rat LDLo subcutaneous 1650mg/kg (1650mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 182, Pg. 348, 1936.