Vinylene carbonate

Base Information

• Chemical Name: Vinylene carbonate
• CAS No.: 872-36-6
• Molecular Formula: C3H2O3
• Molecular Weight: 86.0471
• Hs Code.: 29209090
• European Community (EC) Number: 212-825-5
• NSC Number: 47201,20980
• UNII: 1X0ZZF9WFV
• DSSTox Substance ID: DTXSID1074888
• Nikkaji Number: J55.532K
• Wikipedia: Vinylene_carbonate
• Wikidata: Q2802973
• Mol file: 872-36-6.mol

Synonyms:1,3-dioxol-2-one;vinylene carbonate

Chemical Property of Vinylene carbonate

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 89.9mmHg at 25°C
• Melting Point: 19-22 °C(lit.)
• Refractive Index: n20/D 1.421(lit.)
• Boiling Point: 79.2 °C at 760 mmHg
• Flash Point: 53.1 °C
• PSA: 43.35000
• Density: 1.42 g/cm³
• LogP: 0.23280
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: 11.5 g/100 mL
• Water Solubility.: 11.5 g/100 mL
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 86.000393922
• Heavy Atom Count: 6
• Complexity: 84.2

Purity/Quality:

99% ^*data from raw suppliers

VinyleneCarbonate(ContainsUpto2%BHT) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N,T
• Statements: 43-36-51/53-48/22-41-38-24-22
• Safety Statements: 37/39-26-24-61-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=COC(=O)O1
• Uses: Vinylene carbonate is used as an additive to electrolyte solutions for anode side Lithiumion batteries. It also acts as a sealant to seal at least a portion of the silicon-polyvinyl acid interface. It is further used for great improvement of high temperature performance of the battery.

Technology Process of Vinylene carbonate

There total 13 articles about Vinylene carbonate 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: 96.5%

4-chloro-1,3-dioxolan-2-one (3967-54-2) → vinylene carbonate (872-36-6)

Guidance literature:

With 4-tert-Butylcatechol; triethylamine; In ethyl acetate; at 25 - 30 ℃; for 1.66667h; Solvent; Reagent/catalyst; Temperature; Flow reactor; Large scale;

Reference yield: 95.6%

Vinyl chloroformate (5130-24-5) → vinylene carbonate (872-36-6)

Guidance literature:

With triethylamine; at 34 - 49 ℃; for 0.0555556h; Temperature; Flow reactor; Sonication; Inert atmosphere;

Reference yield: 70.0%

α-(2-oxo-1,3-dioxolan-4-yl)cobalamin → vinylene carbonate (872-36-6) + {Co(C20H6N4(CH3)8(CH2CH2CONH2)3(CH2CONH2)3(CH2CH2CONHCH2CH(CH3)OPO2OC4H8O3C9H9N2))(H2O)}(1+) (27085-12-7)

Guidance literature:

In water; Irradiation (UV/VIS); in pH 7 phosphate buffer, aerobic irrdn. with a 275-W sunlamp, not stirred;

upstream raw materials:

4-chloro-1,3-dioxolan-2-one

diethyl ether

triethylamine

[1,3]-dioxolan-2-one

Downstream raw materials:

exo-/endo-3,5,10-Trioxatricyclo<5.2.1.0^2.6>dec-8-en-4-on

cis-9,10-dihydro-9,10-ethanoanthracene-11,12-diol cyclic carbonate

(3ar,7ac)-3a,4,7,7a-tetrahydro-4c,7c-methano-benzo[1,3]dioxol-2-one

(3aRS,7aSR)-5,6-dimethyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxol-2-one

Refernces

Total synthesis of (±)-trichodermamide B and of a putative biosynthetic precursor to aspergillazine A using an oxaza-cope rearrangement

10.1002/anie.200801652

The study reports the first total synthesis of (±)-trichodermamide B and a putative biosynthetic precursor to aspergillazine A using an oxaza-Cope rearrangement. Trichodermamides A and B are modified dipeptides isolated from a marine-derived fungus, with trichodermamide B showing significant in vitro activity against HCT-116 human colon carcinoma and moderate antimicrobial activity. The key chemical transformations involve the use of 3-benzyloxy-2,2-dimethoxy-3,5-cyclohexadienone (5) and vinylene carbonate in a Diels–Alder reaction to form the substrate for the oxaza-Cope rearrangement. Methyl ester 11 is obtained from the resultant compound 9 through several steps and serves as the substrate for the crucial nitrosation/oxaza-Cope rearrangement, yielding the desired oxazine 13. Further transformations, including allylic transposition and amide formation, lead to the synthesis of trichodermamide B. Additionally, the study explores the synthesis of the C5 thiol analogue of trichodermamides (21), proposed as a biosynthetic precursor to aspergillazine A, but finds that its cyclization to aspergillazine A is not spontaneous under various reaction conditions.