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1,3-Butadiene diepoxide
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Name

1,3-Butadiene diepoxide

 EINECS 215-979-1
CAS No. 1464-53-5 Density 1.751g/cm3
PSA 25.06000 LogP -0.21600
Solubility Soluble in water (1000 g/L). Melting Point 2-4 °C(lit.)
Formula  C4H6 O2 Boiling Point 56-58 °C25 mm Hg(lit.)
Molecular Weight 86.0904 Flash Point 40°C
Transport Information UN 3384 6.1/PG 1 Appearance clear colorless to very slightly yellow liquid
Safety Confirmed carcinogen with experimental tumorigenic data. Poison by ingestion, inhalation, skin contact, and intraperitoneal routes. Human mutation data reported. A severe skin and eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes. Risk Codes 45-46-24/25-26-34
Molecular Structure Molecular Structure of 1464-53-5 (1,3-BUTADIENE DIEPOXIDE) Hazard Symbols
Synonyms

Butane,1,2:3,4-diepoxy- (6CI,8CI);1,1'-Bi[ethylene oxide];1,2:3,4-Diepoxybutane;1,3-Butadiene diepoxide;Bioxirane;Butadiene diepoxide;Butadiene dioxide;Butane diepoxide;Diepoxybutane;Dioxybutadiene;NSC 629;

Article Data 28

1,3-Butadiene diepoxide Synthetic route

1,4-di-O-tosyl-L-threitol

1464-53-5

rac-1,2,3,4-diepoxybutane

Conditions
ConditionsYield
With potassium hydroxide In diethyl ether; water at 20℃; for 1h;97%
909878-64-4

meso-erythritol

A

564-00-1

meso-1,2,3,4-diepoxybutane

1464-53-5

rac-1,2,3,4-diepoxybutane

Conditions
ConditionsYield
Stage #1: meso-erythritol With pyridine; p-toluenesulfonyl chloride at 3 - 7℃; for 16h;
Stage #2: With potassium hydroxide In dichloromethane for 2.5h;		A 37%
B n/a
930-22-3

epoxybutene

A

564-00-1

meso-1,2,3,4-diepoxybutane

1464-53-5

rac-1,2,3,4-diepoxybutane

Conditions
ConditionsYield
With Perbenzoic acid; chloroform
With manganese(II) sulfate; dihydrogen peroxide; sodium oxalate; oxalic acid; N,N',N''-trimethyl-1,4,7-triazacyclononane In acetonitrile at 4.9℃; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With 3,3-dimethyldioxirane In acetone at -15℃; for 2.5h; Title compound not separated from byproducts;
299-70-7

threo-1,4-dibromo-2,3-butanediol

1464-53-5

rac-1,2,3,4-diepoxybutane

Conditions
ConditionsYield
With potassium hydroxide; diethyl ether dianhydride of inactive cleavable erythritol;
1947-58-6

dl-2,3-dibromo-1,4-butanediol

1464-53-5

rac-1,2,3,4-diepoxybutane

Conditions
ConditionsYield
With potassium hydroxide
racem.-2,3-dichloro-butane-1,4-diol

racem.-2,3-dichloro-butane-1,4-diol

1464-53-5

rac-1,2,3,4-diepoxybutane

Conditions
ConditionsYield
With potassium hydroxide
882-33-7

diphenyldisulfane

1464-53-5

rac-1,2,3,4-diepoxybutane

(2RS,3RS)-1,4-bis(phenylsulfanyl)butane-2,3-diol

Conditions
ConditionsYield
With rongalite; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; regioselective reaction;94%
1826-67-1

vinyl magnesium bromide

1464-53-5

rac-1,2,3,4-diepoxybutane

(4R*,5R*)-octa-1,7-diene-4,5-diol

Conditions
ConditionsYield
With copper(l) iodide In tetrahydrofuran at -30℃; for 1h;93%
With copper(I) bromide In tetrahydrofuran at -30 - 0℃; for 2h;72%
1666-13-3

diphenyl diselenide

1464-53-5

rac-1,2,3,4-diepoxybutane

(2RS,3RS)-1,4-bis(phenylselanyl)butane-2,3-diol

Conditions
ConditionsYield
With rongalite; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; regioselective reaction;93%
1464-53-5

rac-1,2,3,4-diepoxybutane

1730-25-2

allylmagnesium bromide

(5RS,6RS)-deca-1,9-diene-5,6-diol

Conditions
ConditionsYield
With copper(l) iodide In diethyl ether at -30℃; for 1h;86%

1,3-Butadiene diepoxide Consensus Reports

NTP 10th Report on Carcinogens. EPA Extremely Hazardous Substances List. EPA Genetic Toxicology Program. Community Right-To-Know List. Reported in EPA TSCA Inventory.

1,3-Butadiene diepoxide Specification

The 1,1'-Bi(ethylene oxide), with the cas registry number 1464-53-5, has its systematic name of 2-(oxiran-2-yl)oxirane. This is a kind of light yellow liquid. When store, it should be kept in the dry, cool, well-ventilated room with the temperature of 0-6°C, away from the food material. This chemical is mainly used in curing polymers ; crosslinking textile fibers and to prevent spoilage.

The characteristics of this chemical are as followings: (1)#H bond acceptors: 2 ; (2)#Freely Rotating Bonds: 1; (3)Polar Surface Area: 25.06; (4)Index of Refraction: 1.546; (5)Molar Refractivity: 19.7 cm3; (6)Molar Volume: 62.2 cm3; (7)Polarizability: 7.81× 10-24 cm3; (8)Surface Tension: 63.3 dyne/cm; (9)Density: 1.383 g/cm3; (10)Flash Point: 45.6 °C; (11)Enthalpy of Vaporization: 35.98 kJ/mol; (12)Boiling Point: 138 °C at 760 mmHg; (13)Vapour Pressure: 8.53 mmHg at 25°C.

You should be cautious while dealing with this chemical. For being a kind of toxic chemical, it is harmful if swallowed or by inhalation. Then it may at very low levels cause damage to health, and may even cause cancer and heritable genetic damage. Besides, it may cause burns. Therefore, you should take the following instructions. Avoid exposure - obtain special instructions before use, and if in case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).
 
Addtionally, the following datas could be converted inte the molecular structure:
(1)SMILES:C1OC1C2CO2
(2)InChI:InChI=1/C4H6O2/c1-3(5-1)4-2-6-4/h3-4H,1-2H2
(3)InChIKey:ZFIVKAOQEXOYFY-UHFFFAOYAG

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 31mg/kg (31mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 230, Pg. 559, 1957.
 
mouse LD50 oral 72mg/kg (72mg/kg)   Shell Chemical Company. Unpublished Report. Vol. -, Pg. 2, 1961.
rabbit LD50 skin 89uL/kg (0.089mL/kg)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 10, Pg. 61, 1954.
rat LC50 inhalation 90ppm/4H (90ppm)   Shell Chemical Company. Unpublished Report. Vol. -, Pg. 2, 1961.
rat LD50 oral 78mg/kg (78mg/kg)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 10, Pg. 61, 1954.

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