2,2'-Bioxirane

Base Information

• Chemical Name: 2,2'-Bioxirane
• CAS No.: 1464-53-5
• Molecular Formula: C4H6 O2
• Molecular Weight: 86.0904
• Hs Code.: 29109000
• European Community (EC) Number: 215-979-1,206-060-6,677-189-7
• NSC Number: 629
• UN Number: 2929,3384,3082
• DSSTox Substance ID: DTXSID0041307
• Nikkaji Number: J3.668D
• Wikipedia: Diepoxybutane
• Wikidata: Q5274970
• NCI Thesaurus Code: C44373
• ChEMBL ID: CHEMBL1964283
• Mol file: 1464-53-5.mol

Synonyms:1,2,3,4-diepoxybutane;1,2-3,4-diepoxybutane;2,2'-bioxirane;butadiene bisoxide;butadiene diepoxide;butadiene dioxide;diepoxybutane;diepoxybutane, meso-;erythritol anhydride;erythritol anhydride, ((R*,R*)-(+-))-isomer;erythritol anhydride, (R*,S*)-isomer;erythritol anhydride, (R-(R*,R*))-isomer;erythritol anhydride, (S-(R*,R*))-isomer;meso-diepoxybutane

Chemical Property of 2,2'-Bioxirane

Chemical Property:

• Appearance/Colour: clear colorless to very slightly yellow liquid
• Vapor Pressure: 25 mm Hg ( 56 °C)
• Melting Point: 2-4 °C(lit.)
• Refractive Index: n20/D 1.434(lit.)
• Boiling Point: 56-58 °C25 mm Hg(lit.)
• Flash Point: 40°C
• PSA: 25.06000
• Density: 1.751g/cm³
• LogP: -0.21600
• Storage Temp.: 0-6°C
• Water Solubility.: Soluble in water (1000 g/L).
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 86.036779430
• Heavy Atom Count: 6
• Complexity: 61.9
• Transport DOT Label: Poison Flammable Liquid,Poison Inhalation Hazard Flammable Liquid

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,3-Butadiene diepoxide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+
• Statements: 45-46-24/25-26-34-10
• Safety Statements: 53-45-36/37/39-28-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Epoxides
• Canonical SMILES: C1C(O1)C2CO2
• Uses: Diepoxybutane has been used as a research chemical, as a chemical intermediate, as a curing agent for polymers, as a cross-linking agent for textile fabrics, and to prevent microbial spoilage (IARC 1976, HSDB 2009). It has also been used to synthesize erythritol and pharmaceuticals (HSDB 2009). Because of its cross-linking properties, diepoxybutane is used as a test agent in the diagnosis of Fanconi anemia, which is characterized by chromosomal instability (Auerbach et al. 1989). Curing of polymers; cross-linking of textile fibers; prevention of microbial spoilage Butadiene diepoxide is used as a research chemical, as a chemical intermediate, as a curing agent for polymers, as a cross-linking agent for textile fabrics, and to prevent microbial spoilage. It is also been used to synthesize erythritol and pharmaceuticals. 1,3-Butadiene Diepoxide is used as a substance in the evaluation of anti-diabetic and anti-ulcer potential of selected fresh fruits samples and their GC/MS analysis. Also in the inhibitory potency of 4-carbon alkanes and alkenes towards CYD2E1 activity.

Technology Process of 2,2'-Bioxirane

There total 29 articles about 2,2'-Bioxirane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(2R,3R)-1,4-diiodobutane-2,3-diol (172821-20-4) → (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)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 1h;

DOI:10.1016/0040-4039(95)01658-9

Reference yield: 95.5%

buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → epoxybutene (930-22-3,62249-81-4) + 1,2:3,4-Diepoxybutane (564-00-1,1464-53-5,30031-64-2,30419-67-1,34897-03-5,298-18-0)

Guidance literature:

With sodium oxalate; oxalic acid; manganese(II) acetate; N,N',N''-trimethyl-1,4,7-triazacyclononane; In water;

buta-1,3-diene; With dihydrogen peroxide; In water; at -40 - 25 ℃; for 8.5h; under 2400.24 - 3900.39 Torr; Cooling with acetone-dry ice;

Reference yield: 81.0%

treosulfan (299-74-1,1947-62-2,13308-13-9,17088-46-9,21106-06-9,299-75-2,5380-21-2) → (S,S)-diepoxybutane (298-18-0,564-00-1,1464-53-5,30419-67-1,34897-03-5,30031-64-2)

Guidance literature:

With potassium hydroxide; In diethyl ether; water; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.15227/orgsyn.076.0101

upstream raw materials:

epoxybutene

oxirane

2,3-dibromo-1,4-dihydroxy-2-butane

buta-1,3-diene

Downstream raw materials:

(S,S)-diepoxybutane

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

Refernces

• 1、 Quayle,Rahman,Herbert. "Transition metal promoted acetylene isomerisation reactions in organic synthesis: A synthesis of (+)-(4S,5S) - Muricatacin". . p. 8087 - 8088. Retrieved 1995.
• 2、 Daugey,De Rycke,Brotin,Buffeteau. "Chiroptical properties of 2,2’-bioxirane". . p. 342 - 350. Retrieved 2018/01/15.
• 3、 Darko, Ampofo K.,Curran, F. Chris,Copin, Chloé,McElwee-White, Lisa. "Carbonylation of functionalized diamine diols to cyclic ureas: Application to derivatives of DMP 450". experimental part. p. 3976 - 3983. Retrieved 2011/06/25.