Product Name

  • Name

    1,3-BUTADIENE DIEPOXIDE

  • EINECS 215-979-1
  • CAS No. 1464-53-5
  • Article Data28
  • CAS DataBase
  • Density 1.751g/cm3
  • 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;
  • PSA 25.06000
  • LogP -0.21600

Synthetic route

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

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

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

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

meso-erythritol

A

meso-1,2,3,4-diepoxybutane
564-00-1

meso-1,2,3,4-diepoxybutane

rac-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
epoxybutene
930-22-3

epoxybutene

A

meso-1,2,3,4-diepoxybutane
564-00-1

meso-1,2,3,4-diepoxybutane

rac-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;
threo-1,4-dibromo-2,3-butanediol
299-70-7

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

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

Conditions
ConditionsYield
With potassium hydroxide; diethyl ether dianhydride of inactive cleavable erythritol;
dl-2,3-dibromo-1,4-butanediol
1947-58-6

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

rac-1,2,3,4-diepoxybutane
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

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

Conditions
ConditionsYield
With potassium hydroxide
diphenyldisulfane
882-33-7

diphenyldisulfane

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

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

(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%
vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

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

(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%
diphenyl diselenide
1666-13-3

diphenyl diselenide

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

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

(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%
rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

allylmagnesium bromide
1730-25-2

allylmagnesium bromide

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

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

Conditions
ConditionsYield
With copper(l) iodide In diethyl ether at -30℃; for 1h;86%
4-(tert-butyldimethylsilyloxy)-1-butyne
78592-82-2

4-(tert-butyldimethylsilyloxy)-1-butyne

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

(E)-8-(tert-butyldimethylsilyloxy)-1,2-epoxyoct-5-ene

(E)-8-(tert-butyldimethylsilyloxy)-1,2-epoxyoct-5-ene

Conditions
ConditionsYield
Stage #1: 4-(tert-butyldimethylsilyloxy)-1-butyne With Schwartz's reagent at 20℃; for 0.25h;
Stage #2: With methyllithium; thien-2-yl(cyano)copper lithium In tetrahydrofuran; diethyl ether at -78℃; for 0.25h;
Stage #3: rac-1,2,3,4-diepoxybutane In tetrahydrofuran; diethyl ether at 0℃; for 3h;		85%
methyllithium
917-54-4

methyllithium

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

1,2-epoxypentan-3-ol

1,2-epoxypentan-3-ol

Conditions
ConditionsYield
Stage #1: methyllithium With thien-2-yl(cyano)copper lithium In tetrahydrofuran at -78 - 0℃;
Stage #2: rac-1,2,3,4-diepoxybutane In tetrahydrofuran at 0℃; for 3h;		82%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

(+/-)-(2S,3S)-1,2-epoxy-3-octanol

(+/-)-(2S,3S)-1,2-epoxy-3-octanol

Conditions
ConditionsYield
Stage #1: n-butyllithium With thien-2-yl(cyano)copper lithium In tetrahydrofuran at -78 - 0℃;
Stage #2: rac-1,2,3,4-diepoxybutane In tetrahydrofuran at 0℃; for 3h;		79%
phosgene
75-44-5

phosgene

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

(4R,5R)-4,5-Bis-chloromethyl-[1,3]dioxolan-2-one

(4R,5R)-4,5-Bis-chloromethyl-[1,3]dioxolan-2-one

Conditions
ConditionsYield
With pyridine In diethyl ether; dichloromethane a) RT, 16 h, 2.) 50 deg C, 3 h;75%
rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1,2-epoxy-6-trimethylsilylhex-5-yn-3-ol

1,2-epoxy-6-trimethylsilylhex-5-yn-3-ol

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 1h;
Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 0.25h;
Stage #3: rac-1,2,3,4-diepoxybutane In tetrahydrofuran; hexane at -78℃; for 5h;		71%
n-octyne
629-05-0

n-octyne

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

(E)-1,2-epoxydodec-5-en-3-ol

(E)-1,2-epoxydodec-5-en-3-ol

Conditions
ConditionsYield
Stage #1: n-octyne With Schwartz's reagent at 20℃; for 0.25h;
Stage #2: With methyllithium; thien-2-yl(cyano)copper lithium In tetrahydrofuran; diethyl ether at -78℃; for 0.25h;
Stage #3: rac-1,2,3,4-diepoxybutane In tetrahydrofuran; diethyl ether at 0℃; for 3h;		70%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

trans-hexane-1,2-diol
22520-19-0

trans-hexane-1,2-diol

Conditions
ConditionsYield
With copper(l) iodide In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2h;59%
rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

(±)-trans-selenolane-3,4-diol

(±)-trans-selenolane-3,4-diol

Conditions
ConditionsYield
With sodium hydrogen selenide at 20℃; for 0.166667h;55%
rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

(TMS-CH=CH)(2-thienyl)Cu(CN)Li

(TMS-CH=CH)(2-thienyl)Cu(CN)Li

(S)-1-(S)-Oxiranyl-2-thiophen-2-yl-ethanol

(S)-1-(S)-Oxiranyl-2-thiophen-2-yl-ethanol

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 0℃;50%
rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

A

(S,S)-diepoxybutane
298-18-0, 564-00-1, 1464-53-5, 30419-67-1, 34897-03-5, 30031-64-2

(S,S)-diepoxybutane

B

(R,R)-butane-1,2:3,4-bisoxide
564-00-1, 1464-53-5, 30031-64-2, 34897-03-5, 298-18-0, 30419-67-1

(R,R)-butane-1,2:3,4-bisoxide

C

(S,S)-3,4-epoxy-1,2-butanediol

(S,S)-3,4-epoxy-1,2-butanediol

Conditions
ConditionsYield
With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; water at 0 - 20℃;A n/a
B n/a
C 36%
...Expand
rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

A

(S,S)-diepoxybutane
298-18-0, 564-00-1, 1464-53-5, 30419-67-1, 34897-03-5, 30031-64-2

(S,S)-diepoxybutane

B

(R,R)-butane-1,2:3,4-bisoxide
564-00-1, 1464-53-5, 30031-64-2, 34897-03-5, 298-18-0, 30419-67-1

(R,R)-butane-1,2:3,4-bisoxide

C

(R,R)-3,4-epoxy-1,2-butanediol

(R,R)-3,4-epoxy-1,2-butanediol

Conditions
ConditionsYield
With [(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(III) acetate; water In tetrahydrofuran at 0 - 20℃;A n/a
B n/a
C 36%
...Expand
rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

A

(S,S)-diepoxybutane
298-18-0, 564-00-1, 1464-53-5, 30419-67-1, 34897-03-5, 30031-64-2

(S,S)-diepoxybutane

B

(S,S)-3,4-epoxy-1,2-butanediol

(S,S)-3,4-epoxy-1,2-butanediol

C

(R,R)-3,4-epoxy-1,2-butanediol

(R,R)-3,4-epoxy-1,2-butanediol

Conditions
ConditionsYield
With [(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(III) acetate; water at 0 - 20℃;A 36%
B n/a
C n/a
...Expand
rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

A

(R,R)-butane-1,2:3,4-bisoxide
564-00-1, 1464-53-5, 30031-64-2, 34897-03-5, 298-18-0, 30419-67-1

(R,R)-butane-1,2:3,4-bisoxide

B

(S,S)-3,4-epoxy-1,2-butanediol

(S,S)-3,4-epoxy-1,2-butanediol

C

(R,R)-3,4-epoxy-1,2-butanediol

(R,R)-3,4-epoxy-1,2-butanediol

Conditions
ConditionsYield
With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; water at 0 - 20℃;A 36%
B n/a
C n/a
...Expand
rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

A

(S,S)-diepoxybutane
298-18-0, 564-00-1, 1464-53-5, 30419-67-1, 34897-03-5, 30031-64-2

(S,S)-diepoxybutane

B

(R,R)-3,4-epoxy-1,2-butanediol

(R,R)-3,4-epoxy-1,2-butanediol

Conditions
ConditionsYield
With [(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(III) acetate; water at 0 - 20℃;A 36%
B n/a
With [(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(III) acetate; water In tetrahydrofuran at 0 - 20℃;A n/a
B 36%
rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

A

(R,R)-butane-1,2:3,4-bisoxide
564-00-1, 1464-53-5, 30031-64-2, 34897-03-5, 298-18-0, 30419-67-1

(R,R)-butane-1,2:3,4-bisoxide

B

(S,S)-3,4-epoxy-1,2-butanediol

(S,S)-3,4-epoxy-1,2-butanediol

Conditions
ConditionsYield
With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; water In tetrahydrofuran at 0 - 20℃; for 16h;A 36%
B n/a
With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; water In tetrahydrofuran at 0 - 20℃; for 12h;A n/a
B 36%
piperidine
110-89-4

piperidine

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

racem.-1,4-dipiperidino-butane-2,3-diol
74653-97-7

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

Conditions
ConditionsYield
With diethyl ether
4-chloro-aniline
106-47-8

4-chloro-aniline

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

1-(4-chloro-phenyl)-pyrrolidine-3r,4t-diol

1-(4-chloro-phenyl)-pyrrolidine-3r,4t-diol

Conditions
ConditionsYield
With benzene Erhitzen des Reaktionsprodukts bis auf 260grad/15 Torr;
4-methoxy-aniline
104-94-9

4-methoxy-aniline

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

(+/-)-1-(4-methoxy-phenyl)-pyrrolidine-3r,4t-diol
31908-14-2

(+/-)-1-(4-methoxy-phenyl)-pyrrolidine-3r,4t-diol

Conditions
ConditionsYield
With benzene Erhitzen des Reaktionsprodukts unter vermindertem Druck bis auf 240grad;
aniline
62-53-3

aniline

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

1-phenyl-pyrrolidine-3r,4t-diol

1-phenyl-pyrrolidine-3r,4t-diol

Conditions
ConditionsYield
at 210℃; under 20 Torr;
3-chloro-aniline
108-42-9

3-chloro-aniline

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

(+/-)-1-(3-chloro-phenyl)-pyrrolidine-3r,4t-diol

(+/-)-1-(3-chloro-phenyl)-pyrrolidine-3r,4t-diol

Conditions
ConditionsYield
With benzene Erhitzen des Reaktiosprodukts bis auf 260grad/15 Torr;
4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

rac-1,2,3,4-diepoxybutane
1464-53-5

rac-1,2,3,4-diepoxybutane

(+/-)-1-(4-ethoxy-phenyl)-pyrrolidine-3r,4t-diol

(+/-)-1-(4-ethoxy-phenyl)-pyrrolidine-3r,4t-diol

Conditions
ConditionsYield
With benzene Erhitzen des Reaktionsprodukts unter vermindertem Druck bis auf 240grad;

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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