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Basic Information
CAS No.: 646-06-0
Name: 1,3-Dioxolane
Article Data: 54
Molecular Structure:
Molecular Structure of 646-06-0 (1,3-Dioxolane)
Formula: C3H6O2
Molecular Weight: 74.0794
Synonyms: 1,3-Dioxolan;1,3-Dioxole, dihydro-;Ethylene glycol formal;5-Crown-2;Glycol methylene ether;Formal glycol;Dioxolan [Czech];Dioxolane;Glycol formal;1,3-Dioxacyclopentane;
EINECS: 211-463-5
Density: 1.046 g/cm3
Melting Point: -95 °C(lit.)
Boiling Point: 75.6 °C at 760 mmHg
Flash Point: 1.7 °C
Solubility: Soluble in water
Appearance: Colourless liquid
Hazard Symbols: FlammableF
Risk Codes: 11
Safety: 16
Transport Information: UN 1166 3/PG 2
PSA: 18.46000
LogP: -0.00930
Synthetic route
50-00-0

formaldehyd

64-17-5

ethanol

646-06-0

1,3-DIOXOLANE

Conditions
ConditionsYield
With C13H22N4O6S2(2+)*2CF3O3S(1-) In water at 130℃; for 2h; Reagent/catalyst;95.4%
50-00-0

formaldehyd

107-21-1

ethylene glycol

646-06-0

1,3-DIOXOLANE

Conditions
ConditionsYield
at 60 - 95℃; for 3h; Concentration; Temperature;94.3%
With phosphoric acid
With phosphoric acid; water
107-21-1

ethylene glycol

paraformaldehyde

paraformaldehyde

646-06-0

1,3-DIOXOLANE

Conditions
ConditionsYield
With sulfur dioxide at 105 - 164℃; for 4h;85%
50-00-0

formaldehyd

1124-68-1

(CH2CH2O2)B(O-n-C4H9)

646-06-0

1,3-DIOXOLANE

Conditions
ConditionsYield
With zinc(II) chloride at 130 - 150℃;77%
67-56-1

methanol

107-21-1

ethylene glycol

646-06-0

1,3-DIOXOLANE

Conditions
ConditionsYield
With iron(III) chloride hexahydrate; sodium nitrite at 50℃; for 24h; UV-irradiation;71%
75-07-0

acetaldehyde

646-06-0

1,3-DIOXOLANE

Conditions
ConditionsYield
In toluene69%
107-21-1

ethylene glycol

polyoxymethylene

polyoxymethylene

646-06-0

1,3-DIOXOLANE

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In 1,4-dioxane at 100℃; for 3h; Sealed tube;66%
With iron(III) chloride
With phosphoric acid at 100℃; im Rohr;
With hydrogenchloride at 100℃;
4544-20-1

2-ethoxy-1,3-dioxolane

A

646-06-0

1,3-DIOXOLANE

B

64-17-5

ethanol

C

4468-92-2

2-ethoxymethoxy-ethanol

Conditions
ConditionsYield
With diisobutylaluminium hydride In hexane at 35 - 40℃;A 45%
B n/a
C 45%
50-00-0

formaldehyd

1309123-32-7

C9H19BO3

646-06-0

1,3-DIOXOLANE

Conditions
ConditionsYield
With zinc(II) chloride at 130 - 150℃;31%

Fe(CO)4(COCH2CH2O)

A

646-06-0

1,3-DIOXOLANE

Conditions
ConditionsYield
With H2 In decalin High Pressure; 71.5 atm H2 at room temp., heated to 200°C and stirred for 24 h; pressure realesed, detn. by GC and GC-MS;A 27%
B n/a
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Specification

The 1,3-Dioxolane, with the cas registry number 646-06-0, is a kind of clear colourless liquid. This is completely soluble in water and soluble in alcohol, ether, and benzene. And it could be easily ignited by heat, sparks or flames, and the vapor may form explosive mixtures with air. In addition, its product categories are various, including Dioxanes & Dioxolanes; Dioxolanes; Intermediates & Fine Chemicals; Pharmaceuticals.It is highly flammable. When exposed to air 1,3-Dioxolane undergoes autooxidation with formation of peroxides. In the distillation process peroxides will concentrate causing violent explosion. Soluble in water.

Properties of 1,3-Dioxolane:
The characteristics of this chemical are as follows: (1)ACD/LogP: -0.73; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.73; (4)ACD/LogD (pH 7.4): -0.73; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 9.61; (8)ACD/KOC (pH 7.4): 9.61; (9)#H bond acceptors: 2; (10)Polar Surface Area: 18.46; (11)Index of Refraction: 1.396; (12)Molar Refractivity: 17.04 cm3; (13)Molar Volume: 70.8 cm3; (14)Polarizability: 6.75 ×10-24 cm3; (15)Surface Tension: 32.7 dyne/cm; (16)Density: 1.046 g/cm3; (17)Flash Point: 1.7 °C; (18)Enthalpy of Vaporization: 30.36 kJ/mol; (19)Boiling Point: 75.6 °C at 760 mmHg; (20)Vapour Pressure: 115 mmHg at 25°C; (21)Exact Mass: 74.036779; (22)MonoIsotopic Mass: 74.036779; (23)Topological Polar Surface Area: 18.5; (24)Heavy Atom Count: 5; (25)Formal Charge: 0; (26)Complexity: 24.1.

Structure Descriptors of 1,3-Dioxolane:
(1)Canonical SMILES: C1COCO1
(2)InChI: InChI=1S/C3H6O2/c1-2-5-3-4-1/h1-3H2
(3)InChIKey: WNXJIVFYUVYPPR-UHFFFAOYSA-N 

Toxicity of 1,3-Dioxolane is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LC50 inhalation 10500mg/m3/2H (10500mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 70, 1982.
mouse LD50 oral 3200mg/kg (3200mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 70, 1982.
rabbit LCLo inhalation 32000ppm/4H (32000ppm)   Union Carbide Data Sheet. Vol. 12/17/1971,
rabbit LD50 oral 5200mg/kg (5200mg/kg)   National Technical Information Service. Vol. OTS0537791,
rabbit LD50 skin 8480uL/kg (8.48mL/kg)   Union Carbide Data Sheet. Vol. 12/17/1971,
rat LC50 inhalation 20650mg/m3/4H (20650mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 70, 1982.
rat LD50 oral 3gm/kg (3000mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 60, 1949.
rat LD50 skin 15gm/kg (15000mg/kg)   National Technical Information Service. Vol. OTS0537791,
rat LDLo intraperitoneal 500mg/kg (500mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

KIDNEY, URETER, AND BLADDER: RENAL FUNCTION TESTS DEPRESSED
Journal of Pharmacy and Pharmacology. Vol. 11, Pg. 150, 1959.
 

Preparation of 1,3-Dioxolane
The first way: have the reaction of paraformaldehyde and ethylene glycol. The second way: paraformaldehyde could react with ethylene glycol with the existence of concentrated sulfuric acid, and then go through salting out with sodium chloride, soild sodium hydroxide and drying, and then rectifying to get this chemical.

Use of 1,3-Dioxolane
The production methods of 1,3-Dioxolane are as below: As to its usage, it is widely applied in many ways. It could be used as the solvent and extractant for oil and axunge, and as the silk finishing agent or sealing rubber; It could also be used as the galvanolysis solvent of lithium battery, stabilizing agent, and the intermediate for Acyclovir-d4.