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:

97% ^*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
• General Description: 1,3-Butadiene diepoxide (also known as meso-bisoxirane) is a compound of interest as a potential building block for natural product synthesis and as a toxic metabolite of butadiene. It exists in two conformations (trans and gauche) in fluid phases, with the trans conformer (C_i symmetry) being more stable than the gauche conformer (C₁ symmetry). Spectroscopic studies reveal a ΔH value of 0.31 ± 0.10 kcal/mol between these conformers in the liquid state, and only the trans form persists in the solid state. The gauche conformer has a dipole moment of 3.03 D and a dihedral angle of approximately 60° between the H-C-C'-H' atoms.

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:

1,4-dithio-erythritol

1,4-dithio-D,L-threitol

5-oxiran-2-yl-1,3-oxathiolane-2-thione

erythtritol 1,4-dinitrate