Ethyl 3-ethynylbenzoate

Base Information

• Chemical Name: Ethyl 3-ethynylbenzoate
• CAS No.: 178742-95-5
• Molecular Formula: C11H10O2
• Molecular Weight: 174.199
• Hs Code.: 2916399090
• European Community (EC) Number: 860-468-4
• DSSTox Substance ID: DTXSID40573864
• Wikidata: Q82462712
• Mol file: 178742-95-5.mol

Synonyms:Ethyl 3-ethynylbenzoate;178742-95-5;Benzoic acid, 3-ethynyl-, ethyl ester;3-Ethynyl-benzoic Acid Ethyl Ester;3-Ethynylbenzoic acid ethyl ester;Ethyl3-ethynylbenzoate;SCHEMBL1505304;DTXSID40573864;DIZFWJVCPSJKGW-UHFFFAOYSA-N;MFCD13195274;AKOS015951034;CS-0216070;A50670;EN300-331731;Z1255436549

Chemical Property of Ethyl 3-ethynylbenzoate

Chemical Property:

• Boiling Point: 268.0±23.0 °C(Predicted)
• PSA: 26.30000
• Density: 1.08±0.1 g/cm3(Predicted)
• LogP: 1.84460
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 174.068079557
• Heavy Atom Count: 13
• Complexity: 224

Purity/Quality:

98%, ^*data from raw suppliers

3-Ethynyl-benzoicacidethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Ethyl 3-ethynylbenzoate

There total 7 articles about Ethyl 3-ethynylbenzoate 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: 96.0%

ethyl 3-<(trimethylsilyl)ethynyl>benzoate (150969-58-7) → ethyl 3-(ethynyl)benzoate (178742-95-5)

Guidance literature:

With potassium carbonate; In ethanol; for 2h; Ambient temperature;

DOI:10.1248/cpb.47.398

Reference yield: 66.0%

→ 3-ethynylbenzoyl chloride (143587-37-5) + ethyl 3-(ethynyl)benzoate (178742-95-5)

Guidance literature:

Reference yield:

ethyl 3-bromobenzoate (24398-88-7) → ethyl 3-(ethynyl)benzoate (178742-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / diisopropylamine, copper(I) iodide, bis(triphenylphosphine)palladium(II) chloride / tetrahydrofuran / 5 h / 45 °C

2: 96 percent / K₂CO₃ / ethanol / 2 h / Ambient temperature

With copper(l) iodide; bis(triphenylphosphine)palladium(II)-chloride; potassium carbonate; diisopropylamine; In tetrahydrofuran; ethanol;

DOI:10.1248/cpb.47.398

upstream raw materials:

2-ethynyl-1,3-butadiene

propynoic acid ethyl ester

ethyl 3-<(trimethylsilyl)ethynyl>benzoate

ethyl 3-bromobenzoate

Downstream raw materials:

1,4-bis(3-hydroxycarbonylphenyl)-butadiyne

1,2-bis(3-ethoxycarbonylphenyl)acetylene

cis-3,3'-bis(diphenylhydroxymethyl)stilbene

3,3'-bis(hydroxydiphenylmethyl)diphenylacetylene