Vinyl benzoate

Base Information

• Chemical Name: Vinyl benzoate
• CAS No.: 769-78-8
• Molecular Formula: C9H8 O2
• Molecular Weight: 148.161
• European Community (EC) Number: 212-214-3
• NSC Number: 2296
• UNII: F1E7C1GGKU
• DSSTox Substance ID: DTXSID50227700
• Nikkaji Number: J36.031G
• Wikidata: Q27157643
• ChEMBL ID: CHEMBL2260720
• Mol file: 769-78-8.mol

Synonyms:Vinyl benzoate;769-78-8;ethenyl benzoate;Benzoic acid, ethenyl ester;Benzoic acid vinyl ester;BENZOIC ACID, VINYL ESTER;Vinylester kyseliny benzoove;NSC 2296;EINECS 212-214-3;UNII-F1E7C1GGKU;Vinylester kyseliny benzoove [Czech];F1E7C1GGKU;BRN 2041125;AI3-24554;CHEBI:84279;NSC-2296;4-09-00-00295 (Beilstein Handbook Reference);benzoic acid vinyl;Benzoic Acid Ethenyl ester;WLN: 1U1OVR;SCHEMBL14903;CHEMBL2260720;KOZCZZVUFDCZGG-UHFFFAOYSA-;DTXSID50227700;NSC2296;MFCD00048141;STL280432;AKOS015889572;Vinyl Benzoate (stabilized with MEHQ);LS-38553;B1032;FT-0632925;BENZOIC ACID VINYL ESTER;VINYL BENZOATE;F71333;A855147;Q27157643;2-BENZYL-4,4,4-TRIFLUORO-3-OXOBUTYRICACIDETHYLESTER;Vinyl benzoate, >=99%, contains <=20 ppm Hydroquinone and/or <=50 ppm MEHQ as stabilizer

Chemical Property of Vinyl benzoate

Chemical Property:

• Vapor Pressure: 0.4 mm Hg ( 25 °C)
• Melting Point: -32 °C
• Refractive Index: n20/D 1.529(lit.)
• Boiling Point: 95-96°C20mm Hg(lit.)
• Flash Point: 180°F
• PSA: 26.30000
• Density: 1.07g/mLat 25°C(lit.)
• LogP: 1.98690
• Storage Temp.: 2-8°C
• Solubility.: Soluble in methanol
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 148.052429494
• Heavy Atom Count: 11
• Complexity: 146

Purity/Quality:

98% ^*data from raw suppliers

Vinyl benzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=COC(=O)C1=CC=CC=C1
• Uses: It is used as chemical reagent and pharmaceutical intermediates.

Technology Process of Vinyl benzoate

There total 33 articles about Vinyl benzoate 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%

benzoic acid (65-85-0,8013-63-6) + 2,4,6-trivinylcyclotriboroxane*pyridine complex → vinyl benzoate (769-78-8,24991-32-0)

Guidance literature:

With N,N'-diethylurea; copper(II) bis(trifluoromethanesulfonate); triethylamine; In tetrahydrofuran; at 50 ℃; for 16h;

DOI:10.1002/adsc.201800914

Reference yield: 89.6%

(R/S)-benzoic acid 1-chloroethyl ester (5819-19-2) → vinyl benzoate (769-78-8,24991-32-0)

Guidance literature:

With oxirane; lithium chloride; at 0 - 10 ℃; for 4h; under 750.075 Torr; Reagent/catalyst; Temperature; Autoclave; Inert atmosphere;

Reference yield: 88.0%

1,2-dibromoethyl benzoate → vinyl benzoate (769-78-8,24991-32-0)

Guidance literature:

With 1,1'-bis(trimethylsilyl)-1,1',4,4'-tetrahydro-4,4'-bipyridylidene; In acetonitrile; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c7cc07377a

upstream raw materials:

1,2-ethanediol, dibenzoate

benzoyl chloride

acetaldehyde

vinyl acetate

Downstream raw materials:

2-benzoyloxy-1-butyronitrile

(R/S)-benzoic acid 1-chloroethyl ester

2-Benzoyloxy-vinylphosphinsaeure-dichlorid

α-Benzoyl-β,β-dichlorethyl-phosphonsaeure-dichlorid

Refernces

• 1、 -. "Normal Alpha Olefin Synthesis Using Dehydroformylation or Dehydroxymethylation". Paragraph 0127; 0128; 0129. . Retrieved 2019/09/06.
• 2、 Jia, Xiaofan,Foley, Aisling M.,Liu, Chang,Vaughan, Benjamin A.,McKeown, Bradley A.,Zhang, Sen,Gunnoe, T. Brent. "Styrene Production from Benzene and Ethylene Catalyzed by Palladium(II): Enhancement of Selectivity toward Styrene via Temperature-dependent Vinyl Ester Consumption". supporting information. p. 3532 - 3541. Retrieved 2019/09/12.