4-Phenylbut-3-ynoic acid

Base Information

• Chemical Name: 4-Phenylbut-3-ynoic acid
• CAS No.: 7218-49-7
• Molecular Formula: C10H8O2
• Molecular Weight: 160.172
• European Community (EC) Number: 868-831-9
• DSSTox Substance ID: DTXSID10222514
• Nikkaji Number: J730.586I
• Wikidata: Q83100772
• Mol file: 7218-49-7.mol

Synonyms:4-phenylbut-3-ynoic acid;7218-49-7;4-Phenyl-3-butynoic acid;3-Butynoic acid, 4-phenyl-;4-phenylbut-3-ynoicacid;SCHEMBL5383548;DTXSID10222514;AKOS011624890;AT25408;EN300-108144;Z976639296

Chemical Property of 4-Phenylbut-3-ynoic acid

Chemical Property:

• Vapor Pressure: 0.000102mmHg at 25°C
• Boiling Point: 324.2°Cat760mmHg
• Flash Point: 147.4°C
• Density: 1.19g/cm³
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 160.052429494
• Heavy Atom Count: 12
• Complexity: 213

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C#CCC(=O)O

Technology Process of 4-Phenylbut-3-ynoic acid

There total 8 articles about 4-Phenylbut-3-ynoic 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: 63.0%

2-(methoxymethoxy)-2-(3-phenylprop-2-yn-1-yl)malononitrile → 4-phenyl-3-butynoic acid (7218-49-7)

Guidance literature:

With (R)-10-camphorsulfonic acid; acetic acid; In water; at 60 ℃; for 15h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.6b00790

Reference yield: 29.0%

carbon dioxide (124-38-9,18923-20-1) + 1-chloro-3-phenyl-2-propyne (3355-31-5) → 4-phenyl-3-butynoic acid (7218-49-7)

Guidance literature:

With (1,2-dimethoxyethane)dichloronickel(II); C₁₅H₂₇P*(x)BF₄*H⁽¹⁺⁾; magnesium chloride; zinc; In N,N-dimethyl-formamide; at 20 ℃; under 760.051 Torr; Schlenk technique;

DOI:10.1021/ja311045f

Reference yield:

3-Phenyl-2-propyn-1-ol (1504-58-1) → 4-phenyl-3-butynoic acid (7218-49-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 23 °C / Inert atmosphere

2: (R)-10-camphorsulfonic acid; acetic acid / water / 15 h / 60 °C / Sealed tube; Inert atmosphere

With di-isopropyl azodicarboxylate; (R)-10-camphorsulfonic acid; acetic acid; triphenylphosphine; In tetrahydrofuran; water; 1: |Mitsunobu Displacement / 2: |Mitsunobu Displacement;

DOI:10.1021/acs.orglett.6b00790

upstream raw materials:

4-Phenyl-but-1-en-3-yn-1-one

1-chloro-4-phenyl-1-(phenylsulfinyl)but-3-yn-2-one

ethyl 3-oxo-4-phenylbutyrate

carbon dioxide

Downstream raw materials:

5-phenyl-3H-furan-2-one

4-phenyl-2,3-allenoic acid

4-phenyl-3-butynoic acid chloride

5,5-Dimethyl-4-phenyl-3-phenylethynyl-1,5-dihydro-pyrrol-2-one