2-Vinylbenzoic acid

Base Information

• Chemical Name: 2-Vinylbenzoic acid
• CAS No.: 27326-43-8
• Molecular Formula: C9H8O2
• Molecular Weight: 148.161
• Hs Code.: 2916399090
• European Community (EC) Number: 250-234-4,681-725-5
• DSSTox Substance ID: DTXSID50184642
• Nikkaji Number: J558.404C
• Wikidata: Q83055551
• Mol file: 27326-43-8.mol

Synonyms:2-vinylbenzoic acid;27326-43-8;Vinylbenzoic acid;2-ethenylbenzoic acid;Benzoic acid, ethenyl-;30551-66-7;EINECS 250-234-4;2-vinylbenzoicacid;Benzoic acid, 2-ethenyl- (9CI);Benzoic acid,2-ethenyl-;SCHEMBL31100;2-Vinylbenzoic acid, AldrichCPR;DTXSID50184642;XUDBVJCTLZTSDC-UHFFFAOYSA-N;MFCD02066273;AKOS006377004;AS-50089;AM20040070;CS-0313033;O10854;A819018

Chemical Property of 2-Vinylbenzoic acid

Chemical Property:

• Melting Point: 94℃
• Boiling Point: 282.688 °C at 760 mmHg
• PKA: 3.87±0.36(Predicted)
• Flash Point: 129.386 °C
• PSA: 37.30000
• Density: 1.158 g/cm³
• LogP: 2.02780
• XLogP3: 2.9
• 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:

99% ^*data from raw suppliers

2-Vinylbenzoic acid Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC1=CC=CC=C1C(=O)O
• Uses: As intermediate in orgaic syntheses. Phthalides were obtained in low yields by palladium-assisted cyclization of 2-vinylbenzoic acid and 2-(2-methyl-2-propenyl)- benzoic acid.

Technology Process of 2-Vinylbenzoic acid

There total 21 articles about 2-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: 98.0%

o-carboxybenzaldehyde (119-67-5) → 2-vinylbenzoic acid (27326-43-8)

Guidance literature:

o-carboxybenzaldehyde; With potassium tert-butylate; Methyltriphenylphosphonium bromide; In tetrahydrofuran; at 0 ℃; for 1.5h;

In tetrahydrofuran; at 60 ℃;

DOI:10.1002/ejoc.202101070

Reference yield: 97.0%

Methyltriphenylphosphonium bromide (1779-49-3) + o-carboxybenzaldehyde (119-67-5) → 2-vinylbenzoic acid (27326-43-8)

Guidance literature:

Methyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

o-carboxybenzaldehyde; In tetrahydrofuran; Inert atmosphere; Reflux;

DOI:10.1002/adsc.202000260

Reference yield: 95.0%

2-ethenylbenzoic acid ethyl ester (32082-32-9) → 2-vinylbenzoic acid (27326-43-8)

Guidance literature:

With lithium hydroxide; In methanol; water; at 60 ℃; for 21h;

DOI:10.1021/jo062159l

upstream raw materials:

3-methylphthalide

potassium acetate

methylmagnesium bromide

o-carboxybenzaldehyde

Downstream raw materials:

2-(4-benzylphenyl)-3,4-dihydroisoquinolin-1(2H)-one

N-benzyloxycarbonyl-2-ethenylaniline

(E)-4'-chlorostilbene-1-carboxylic acid

methyl o-vinylbenzoate

Refernces

• 1、 Brückner, Reinhard,Koblischek, Philip. "Syntheses of 6,7-Benzotropolone by Using Ring-Closing Metathesis Variants Obviating a Strongly Acidic Hydrolysis Thereafter". . . Retrieved 2022/03/02.
• 2、 Deng, Xiaojun,He, Wei,Huang, Xie,Ji, Nan,Liu, Huixia. "Study on the ArI-catalyzed intramolecularoxy-cyclization of 2-alkenylbenzamides to benzoiminolactones". . p. 3654 - 3658. Retrieved 2020/06/03.