3-Vinylbenzoic acid

Base Information

• Chemical Name: 3-Vinylbenzoic acid
• CAS No.: 28447-20-3
• Molecular Formula: C9H8O2
• Molecular Weight: 148.161
• Hs Code.: 2916399090
• European Community (EC) Number: 627-463-7
• DSSTox Substance ID: DTXSID10403301
• Nikkaji Number: J473.774A
• Wikidata: Q82206933
• Mol file: 28447-20-3.mol

Synonyms:3-Vinylbenzoic acid;28447-20-3;3-ethenylbenzoic Acid;3-Ethenyl-benzoic acid;3-VINYLBENZOICACID;Benzoic acid, 3-ethenyl-;3-vinyl benzoic acid;3-Vinylbenzoic acid, 96%;SCHEMBL15036;DTXSID10403301;VWXZFDWVWMQRQR-UHFFFAOYSA-N;MFCD00157038;AKOS006223966;AS-47796;AM20040091;CS-0204842;FT-0692281;F16168;A853641

Chemical Property of 3-Vinylbenzoic acid

Chemical Property:

• Melting Point: 91-95 °C(lit.)
• Boiling Point: 298.7 °C at 760 mmHg
• PKA: 4.14±0.10(Predicted)
• Flash Point: 135.7 °C
• PSA: 37.30000
• Density: 1.158 g/cm³
• LogP: 2.02780
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 148.052429494
• Heavy Atom Count: 11
• Complexity: 163

Purity/Quality:

97% ^*data from raw suppliers

3-Vinylbenzoic acid 96% ^*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=CC1=CC(=CC=C1)C(=O)O
• Uses: Polymers were created by the imprinting of tri-O-acetyladenosine in acrylic polymer matrix with the use of methacrylic acid (MAA) or 3-vinylbenzoic acid (VBA) as a functional monomer and ethylene glycol dimethacrylate as a cross-linking agent. Nine active ester monomers based on 4-vinylbenzoic acid have been synthesized. Under free radical polymerization conditions these monomers could successfully be polymerized yielding reactive polymers

Technology Process of 3-Vinylbenzoic acid

There total 10 articles about 3-Vinylbenzoic acid 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: 70.0%

vinyl magnesium bromide (1826-67-1) + 3-Iodobenzoic acid (618-51-9) → 3-vinylbenzoic acid (28447-20-3)

Guidance literature:

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; -78 deg C, 10 min, 20 deg C, 1 h;

DOI:10.1016/S0022-328X(96)06794-0

Reference yield:

trifluoromethyl vinyl sulfoxide (18370-91-7) + 3-Iodobenzoic acid (618-51-9) → 3-vinylbenzoic acid (28447-20-3) + (E)-1-(3-hydroxycarbonylphenyl)-2-trifluoromethylsulfinylethylene

Guidance literature:

With palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 110 - 115 ℃; for 15h; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.01.136

Reference yield:

tri-n-butyl(vinyl)tin (7486-35-3) + 3-Iodobenzoic acid (618-51-9) → 3-vinylbenzoic acid (28447-20-3)

Guidance literature:

With lithium hydroxide; caesium carbonate; potassium iodide; Merrifield resin; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Yield given. Multistep reaction; 1.) DMF, 80 deg C, 16 h; 2.) DMF, 60 degC, 24 h; 3.) THF, MeOH, H₂O, reflux, 18 h;

DOI:10.1016/S0040-4039(98)00778-3

upstream raw materials:

3-cyanostyrene

3-ethenylbenzaldehyde

vinyl magnesium bromide

3-Iodobenzoic acid

Downstream raw materials:

7,10,13-tri(triethylsilyl)-2-debenzoyl-2-(3-ethenylbenzoyl)-10-deacetylbaccatin III

C₆₁H₈₀INO₁₄Si₂

3-vinylbenzoyl chloride

(1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-15-(ethenyl)-1-quinquecyclopropanemethyl 3-ethenylbenzoate