2-Ethynylbenzoic acid

Base Information

• Chemical Name: 2-Ethynylbenzoic acid
• CAS No.: 33578-00-6
• Molecular Formula: C9H6O2
• Molecular Weight: 146.145
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID60506937
• Nikkaji Number: J1.071.211D
• Wikidata: Q82362917
• Mol file: 33578-00-6.mol

Synonyms:2-Ethynylbenzoic acid;33578-00-6;2-ETHYNYL-BENZOIC ACID;2-ethynylbenzoicacid;MFCD06203346;Benzoic acid, 2-ethynyl-;(2-ethynyl)benzoic acid;ethynylbenzoic acid;SCHEMBL688471;DTXSID60506937;WLZ3443;AKOS005259788;AM85731;DS-6195;11,15-Dihydroxy-16-kauren-19-oicacid;SY101655;CS-0059275;FT-0695105;A821855;W-202376;F2147-2793

Chemical Property of 2-Ethynylbenzoic acid

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 121-123℃
• Refractive Index: 1.592
• Boiling Point: 282.086 °C at 760 mmHg
• PKA: 3.45±0.36(Predicted)
• Flash Point: 128.393 °C
• PSA: 37.30000
• Density: 1.23 g/cm³
• LogP: 1.36610
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 146.036779430
• Heavy Atom Count: 11
• Complexity: 199

Purity/Quality:

99%, ^*data from raw suppliers

2-EthynylbenzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=CC=CC=C1C(=O)O

Technology Process of 2-Ethynylbenzoic acid

There total 5 articles about 2-Ethynylbenzoic 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: 100.0%

methyl 2-(2-trimethylsilyl-1-ethynyl)benzoate (107793-07-7) → (2-ethynyl)benzoic acid (33578-00-6)

Guidance literature:

With water; sodium hydroxide; In methanol; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/anie.202014511

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + phenylacetylene (536-74-3) → (2-ethynyl)benzoic acid (33578-00-6) + phenylpropyolic acid (637-44-5)

Guidance literature:

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Multistep reaction; 1) hexane, reflux, 3 h;

Reference yield:

o-iodo-methyl-benzoic acid (610-97-9) → (2-ethynyl)benzoic acid (33578-00-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / PPh₃; triethylamine / CuI; PdCl₂(PPh₃)2 / tetrahydrofuran / 20 °C

2: 97 percent / potasssium carbonate / methanol; ethanol

3: 99 percent / aq. NaOH / methanol; ethanol / 75 °C

With sodium hydroxide; potassium carbonate; triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; methanol; ethanol; 1: Sonogashira coupling reaction;

DOI:10.1016/j.tet.2007.07.066

upstream raw materials:

carbon dioxide

phenylacetylene

o-iodo-methyl-benzoic acid

methyl 2-(2-trimethylsilyl-1-ethynyl)benzoate

Downstream raw materials:

(S)-1-(2-(4-methylphenylsulfonamido)phenyl)-2-propanyl 2-ethynylbenzoate

3-(2-(4-methylphenylsulfonamido)phenyl)propyl 2-ethynylbenzoate

(+/-)-4-(2-(4-methylphenylsulfonamido)phenyl)-2-butyl 2-ethynylbenzoate

4-(2-(4-methylphenylsulfonamido)phenyl)butyl 2-ethynylbenzoate

Refernces

• 1、 Okamura, Toshitaka,Fujiki, Shogo,Iwabuchi, Yoshiharu,Kanoh, Naoki. "Gold(i)-catalyzed Nicholas reaction with aromatic molecules utilizing a bifunctional propargyl dicobalt hexacarbonyl complex". . p. 8522 - 8526. Retrieved 2019/10/02.
• 2、 Mancuso, Raffaella,Pomelli, Christian C.,Malafronte, Francesco,Maner, Asif,Marino, Nadia,Chiappe, Cinzia,Gabriele, Bartolo. "Divergent syntheses of iodinated isobenzofuranones and isochromenones by iodolactonization of 2-alkynylbenzoic acids in ionic liquids". . p. 4831 - 4841. Retrieved 2017/07/10.