1464-53-5

Basic information

• Product Name: 1,3-BUTADIENE DIEPOXIDE
• Synonyms: 1,1’-bi(ethyleneoxide);1,1'-Bi[ethylene oxide];1,2:3,4-diepoxy-butan;2,4-diepoxybutane;3,4-Diepoxybutane;alkylepoxides;Bioxiran;Bioxirane
• CAS NO: 1464-53-5
• Molecular Formula: C₄H₆O₂
• Molecular Weight: 86.09
• EINECS: 215-979-1
• Mol File: 1464-53-5.mol
• Article Data: 20

Chemical Properties

• Melting Point: 2-4 °C(lit.)
• Boiling Point: 56-58 °C25 mm Hg(lit.)
• Flash Point: 114 °F
• Appearance: /
• Density: 1.113 g/mL at 25 °C(lit.)
• Vapor Pressure: 25 mm Hg ( 56 °C)
• Refractive Index: n20/D 1.434(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: Soluble in water (1000 g/L).
• Merck: 14,3676
• BRN: 79831
• CAS DataBase Reference: 1,3-BUTADIENE DIEPOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BUTADIENE DIEPOXIDE(1464-53-5)
• EPA Substance Registry System: 1,3-BUTADIENE DIEPOXIDE(1464-53-5)

Safety Data

• Hazard Codes: T+
• Statements: 45-46-24/25-26-34-10
• Safety Statements: 53-45-36/37/39-28-26
• RIDADR: UN 3384 6.1/PG 1
• WGK Germany: 1
• RTECS: EJ8225000
• F: 8-10-18
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 1464-53-5(Hazardous Substances Data)

Usage

Description

1,3-Butadiene Diepoxide, also known as Diepoxybutane, is a colorless liquid with clear to very slightly yellow appearance. It is a chemical compound that possesses cross-linking properties, making it useful in various applications across different industries.

Uses

1. Used in Research and Chemical Synthesis:
1,3-Butadiene Diepoxide is used as a research chemical and a chemical intermediate, playing a crucial role in the development and production of various compounds and materials.
2. Used in the Polymer Industry:
In the polymer industry, 1,3-Butadiene Diepoxide is used as a curing agent for polymers. Its cross-linking properties help in enhancing the strength and stability of the polymers.
3. Used in the Textile Industry:
1,3-Butadiene Diepoxide is used as a cross-linking agent for textile fabrics. This application improves the durability and strength of the fabrics, making them more resistant to wear and tear.
4. Used in the Pharmaceutical Industry:
1,3-Butadiene Diepoxide is used in the synthesis of erythritol and pharmaceuticals, contributing to the development of new drugs and medications.
5. Used in the Food Industry:
1,3-Butadiene Diepoxide is used to prevent microbial spoilage in the food industry, ensuring the preservation of food products and extending their shelf life.
6. Used in the Evaluation of Anti-Diabetic and Anti-Ulcer Potential:
1,3-Butadiene Diepoxide is used as a substance in the evaluation of the anti-diabetic and anti-ulcer potential of selected fresh fruit samples and their GC/MS analysis.
7. Used in the Inhibition of CYD2E1 Activity:
1,3-Butadiene Diepoxide is used in determining the inhibitory potency of 4-carbon alkanes and alkenes towards CYD2E1 activity, which is essential in understanding their impact on various biological processes.
8. Used in the Diagnosis of Fanconi Anemia:
Due to its cross-linking properties, 1,3-Butadiene Diepoxide is used as a test agent in the diagnosis of Fanconi anemia, a genetic disorder characterized by chromosomal instability.

Production Methods

Diepoxybutane is prepared by chlorination of butadiene followed by epoxidation with peracetic acid, with subsequent hydrolysis of the epoxide group and final reepoxidation with caustic.

Reactivity Profile

Epoxides, such as 1,3-BUTADIENE DIEPOXIDE, are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

Hazard

Probable carcinogen; neoplastigen; tumorigenic; poison; mutagen.

Health Hazard

Severe skin and eye irritant. Accidental minor exposure caused swelling of the eyelids, upper respiratory tract irritation and painful eye irritation 6 hours after exposure.NOTE: The dl- and meso-forms (CAS Registry Numbers 298-18-0 and 564-00-1, respectively) as well as the L(-) form (CAS Registry Number 30031-64-2) have all been determined to be positive animal carcinogens.

Fire Hazard

When heated to decomposition 1,3-BUTADIENE DIEPOXIDE emits acrid smoke and irritating fumes.

Safety Profile

Confirmed carcinogen withexperimental tumorigenic data. Poison by ingestion,inhalation, skin contact, and intraperitoneal routes.Human mutation data reported. A severe skin and eyeirritant. When heated to decomposition it emits acridsmoke and irritat

Carcinogenicity

Diepoxybutane is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

InChI:InChI=1/C4H6O2/c1-3(5-1)4-2-6-4/h3-4H,1-2H2

Synthetic route

1,4-di-O-tosyl-L-threitol → rac-1,2,3,4-diepoxybutane (1464-53-5)

Conditions	Yield
With potassium hydroxide In diethyl ether; water at 20℃; for 1h;	97%

meso-erythritol (909878-64-4) → meso-1,2,3,4-diepoxybutane (564-00-1) + rac-1,2,3,4-diepoxybutane (1464-53-5)

Conditions	Yield
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) → meso-1,2,3,4-diepoxybutane (564-00-1) + rac-1,2,3,4-diepoxybutane (1464-53-5)

Conditions	Yield
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) → rac-1,2,3,4-diepoxybutane (1464-53-5)

Conditions	Yield
With potassium hydroxide; diethyl ether dianhydride of inactive cleavable erythritol;

dl-2,3-dibromo-1,4-butanediol (1947-58-6) → rac-1,2,3,4-diepoxybutane (1464-53-5)

Conditions	Yield
With potassium hydroxide

racem.-2,3-dichloro-butane-1,4-diol → rac-1,2,3,4-diepoxybutane (1464-53-5)

Conditions	Yield
With potassium hydroxide

diphenyldisulfane (882-33-7) + rac-1,2,3,4-diepoxybutane (1464-53-5) → (2RS,3RS)-1,4-bis(phenylsulfanyl)butane-2,3-diol

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

vinyl magnesium bromide (1826-67-1) + rac-1,2,3,4-diepoxybutane (1464-53-5) → (4R*,5R*)-octa-1,7-diene-4,5-diol

Conditions	Yield
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) + rac-1,2,3,4-diepoxybutane (1464-53-5) → (2RS,3RS)-1,4-bis(phenylselanyl)butane-2,3-diol

Conditions	Yield
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) + allylmagnesium bromide (1730-25-2) → (5RS,6RS)-deca-1,9-diene-5,6-diol

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

4-(tert-butyldimethylsilyloxy)-1-butyne (78592-82-2) + rac-1,2,3,4-diepoxybutane (1464-53-5) → (E)-8-(tert-butyldimethylsilyloxy)-1,2-epoxyoct-5-ene

Conditions	Yield
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) + rac-1,2,3,4-diepoxybutane (1464-53-5) → 1,2-epoxypentan-3-ol

Conditions	Yield
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) + rac-1,2,3,4-diepoxybutane (1464-53-5) → (+/-)-(2S,3S)-1,2-epoxy-3-octanol

Conditions	Yield
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) + rac-1,2,3,4-diepoxybutane (1464-53-5) → (4R,5R)-4,5-Bis-chloromethyl-[1,3]dioxolan-2-one

Conditions	Yield
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) + trimethylsilylacetylene (1066-54-2) → 1,2-epoxy-6-trimethylsilylhex-5-yn-3-ol

Conditions	Yield
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) + rac-1,2,3,4-diepoxybutane (1464-53-5) → (E)-1,2-epoxydodec-5-en-3-ol

Conditions	Yield
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) + rac-1,2,3,4-diepoxybutane (1464-53-5) → trans-hexane-1,2-diol (22520-19-0)

Conditions	Yield
With copper(l) iodide In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2h;	59%

rac-1,2,3,4-diepoxybutane (1464-53-5) → (±)-trans-selenolane-3,4-diol

Conditions	Yield
With sodium hydrogen selenide at 20℃; for 0.166667h;	55%

rac-1,2,3,4-diepoxybutane (1464-53-5) + (TMS-CH=CH)(2-thienyl)Cu(CN)Li → (S)-1-(S)-Oxiranyl-2-thiophen-2-yl-ethanol

Conditions	Yield
In tetrahydrofuran at -78 - 0℃;	50%

rac-1,2,3,4-diepoxybutane (1464-53-5) → (S,S)-diepoxybutane (298-18-0, 564-00-1, 1464-53-5, 30419-67-1, 34897-03-5, 30031-64-2) + (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) + (S,S)-3,4-epoxy-1,2-butanediol

Conditions	Yield
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%

rac-1,2,3,4-diepoxybutane (1464-53-5) → (S,S)-diepoxybutane (298-18-0, 564-00-1, 1464-53-5, 30419-67-1, 34897-03-5, 30031-64-2) + (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)-3,4-epoxy-1,2-butanediol

Conditions	Yield
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%

rac-1,2,3,4-diepoxybutane (1464-53-5) → (S,S)-diepoxybutane (298-18-0, 564-00-1, 1464-53-5, 30419-67-1, 34897-03-5, 30031-64-2) + (S,S)-3,4-epoxy-1,2-butanediol + (R,R)-3,4-epoxy-1,2-butanediol

Conditions	Yield
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

rac-1,2,3,4-diepoxybutane (1464-53-5) → (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) + (S,S)-3,4-epoxy-1,2-butanediol + (R,R)-3,4-epoxy-1,2-butanediol

Conditions	Yield
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

rac-1,2,3,4-diepoxybutane (1464-53-5) → (S,S)-diepoxybutane (298-18-0, 564-00-1, 1464-53-5, 30419-67-1, 34897-03-5, 30031-64-2) + (R,R)-3,4-epoxy-1,2-butanediol

Conditions	Yield
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) → (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) + (S,S)-3,4-epoxy-1,2-butanediol

Conditions	Yield
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) + rac-1,2,3,4-diepoxybutane (1464-53-5) → racem.-1,4-dipiperidino-butane-2,3-diol (74653-97-7)

Conditions	Yield
With diethyl ether

4-chloro-aniline (106-47-8) + rac-1,2,3,4-diepoxybutane (1464-53-5) → 1-(4-chloro-phenyl)-pyrrolidine-3r,4t-diol

Conditions	Yield
With benzene Erhitzen des Reaktionsprodukts bis auf 260grad/15 Torr;

4-methoxy-aniline (104-94-9) + rac-1,2,3,4-diepoxybutane (1464-53-5) → (+/-)-1-(4-methoxy-phenyl)-pyrrolidine-3r,4t-diol (31908-14-2)

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

aniline (62-53-3) + rac-1,2,3,4-diepoxybutane (1464-53-5) → 1-phenyl-pyrrolidine-3r,4t-diol

Conditions	Yield
at 210℃; under 20 Torr;

3-chloro-aniline (108-42-9) + rac-1,2,3,4-diepoxybutane (1464-53-5) → (+/-)-1-(3-chloro-phenyl)-pyrrolidine-3r,4t-diol

Conditions	Yield
With benzene Erhitzen des Reaktiosprodukts bis auf 260grad/15 Torr;

4-Ethoxyaniline (156-43-4) + rac-1,2,3,4-diepoxybutane (1464-53-5) → (+/-)-1-(4-ethoxy-phenyl)-pyrrolidine-3r,4t-diol

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

Upstream product

• 930-22-3 epoxybutene 
• 106-99-0 buta-1,3-diene 
• 299-70-7 threo-1,4-dibromo-2,3-butanediol 
• 1947-58-6 dl-2,3-dibromo-1,4-butanediol 
• 172821-20-4 (2R,3R)-1,4-diiodobutane-2,3-diol 
• 1947-62-2 treosulfan 
• 139165-54-1 (2S,3S)-1,4-dichlorobutan-2,3-diol 
• 299-74-1 treosulfan 
• 57495-46-2 (2S,3S)-butane-1,4-diol bis[4-methylbenzenesulfonate] 
• 68138-99-8 1,4-di-O-tosyl-L-threitol 
• 909878-64-4 meso-erythritol 
• 20163-90-0 2,3-dibromo-1,4-dihydroxy-2-butane 
• 75-21-8 oxirane 

Downstream Products

• 69010-01-1 (2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol 
• 50622-10-1 (-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol 
• 239090-01-8 (2S,3S)-1,4-bis(2-methoxyphenyl)-2,3-butanediol 
• 239090-00-7 (2S,3S)-1,4-bis(4-methoxyphenyl)-2,3-butanediol 
• 17177-50-3 (+/-)-(1,2-Dihydroxyethyl)oxirane 
• 298-18-0 (S,S)-diepoxybutane 
• 564-00-1 (R,R)-butane-1,2:3,4-bisoxide 
• 6892-68-8 1,4-dithio-erythritol 
• 27565-41-9 1,4-dithio-D,L-threitol 
• 92339-12-3 1,4-Bis(acetylamino)-N,N'-bis[3,5-bis(1,3-dihydroxy-2-propylaminocarbonyl)-2,4,6-triiodophenyl]-2,3-dihydroxybutane 
• 1014976-40-9 5-oxiran-2-yl-1,3-oxathiolane-2-thione 
• 28368-55-0 erythtritol 1,4-dinitrate 
• 12505-77-0 boron monoxide 

Relevant articles and documents

Multigram-scale stereoselective synthesis of meso-1,3-butadiene bisepoxide

meso-1,3-Butadiene bisepoxide, a potential building block for natural product synthesis and of interest as a toxic metabolite of butadiene, was synthesized in multi-gram scale in two steps from meso-erythritol in good overall yield.

Raman, infrared, and microwave spectra and conformational preferences of meso-Bisoxirane

Vibrational infrared and Raman spectra of liquid and solid meso-bisoxirane and infrared spectra of the gaseous phase were recorded. Additionally, microwave rotational spectra from 40 to 18 GHz were recorded. The vibrational spectra demonstrate the presence of two conformations in the fluid phases but only one in the solid state. Infrared and Raman activities and gas-phase band contours indicate that the trans conformer with C(i) molecular symmetry is more stable than the gauche conformer (C1 symmetry). Variable temperature studies of two pairs of Raman lines are consistent with a ΔH value of 0.31 ± 0.10 kcal/mol in the liquid state. Rotational constants (A = 9187.45 ± 0.04, B = 2651.80 ± 0.01, C = 2608.92 ± 0.01 MHz) and the dipole moment (μ(total) = 3.03 D) were determined for the gauche conformer. Model calculations give an acceptable match to the observed rotational constants for an H-C-C'-H' dihedral angle of 60°. The relationship of meso-bisoxirane to other similar three-membered ring compounds is discussed. Published by Elsevier Science B.V.

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts

An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).

METHOD FOR REPROCESSING MIXTURES CONTAINING BIS-EPOXIDE

The invention relates to a method for reprocessing mixtures containing (a) one or several bis-epoxides of general formula (I), wherein R1 and R2 are identical or different and are selected among hydrogen and C1-C3 alkyl, (b) one or several organic solvents, (c) water, and (d) other optional compounds. The inventive method is characterized in that the mixture is subjected to an at least two-stage distillation process, at least one bis-epoxide (a) being converted into the gas phase in at least one stage.