Ethyl 4-Ethynylbenzoate

Base Information

• Chemical Name: Ethyl 4-Ethynylbenzoate
• CAS No.: 10602-03-6
• Molecular Formula: C11H10O2
• Molecular Weight: 174.199
• Hs Code.: 2916399090
• European Community (EC) Number: 870-624-3
• DSSTox Substance ID: DTXSID80573863
• Nikkaji Number: J1.656.146K
• Wikidata: Q82462711
• Mol file: 10602-03-6.mol

Synonyms:Ethyl 4-Ethynylbenzoate;10602-03-6;MFCD00168821;Benzoic acid, 4-ethynyl-, ethyl ester;Ethyl4-Ethynylbenzoate;4-Ethynyl-benzoic acid ethyl ester;ethyl p-ethynylbenzoate;Ethyl-4-ethynylbenzoate;ethyl 4-ethynyl-benzoate;SCHEMBL1007303;CKAGLAFXBLZHAS-UHFFFAOYSA-;DTXSID80573863;CKAGLAFXBLZHAS-UHFFFAOYSA-N;CS-D0535;AKOS015888301;AM802882;CS-11272;SY013309;EN300-7383802;A895907;2-Cyclopropyl- 4-oxazolecarboxylic acid ethyl ester;InChI=1/C11H10O2/c1-3-9-5-7-10(8-6-9)11(12)13-4-2/h1,5-8H,4H2,2H3

Chemical Property of Ethyl 4-Ethynylbenzoate

Chemical Property:

• Melting Point: 28 °C
• Boiling Point: 257.092 °C at 760 mmHg
• Flash Point: 100.987 °C
• PSA: 26.30000
• Density: 1.088 g/cm³
• LogP: 1.84460
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 174.068079557
• Heavy Atom Count: 13
• Complexity: 216

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl 4-ethynylbenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Ethyl 4-Ethynylbenzoate

There total 19 articles about Ethyl 4-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: 98.0%

ethyl 4-(trimethylsilylethynyl)benzoate (150969-54-3) → ethyl 4-ethynylbenzoate (10602-03-6)

Guidance literature:

With potassium fluoride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h;

DOI:10.1021/acs.joc.1c00333

Reference yield: 97.0%

→ ethyl 4-ethynylbenzoate (10602-03-6)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 1h;

Reference yield: 69.0%

ethanol (64-17-5) + 4-Ethynyl-benzoic acid (10602-00-3) → ethyl 4-ethynylbenzoate (10602-03-6)

Guidance literature:

With toluene-4-sulfonic acid; at 60 ℃; for 48h;

DOI:10.1039/c9tc01301f

upstream raw materials:

2-ethynyl-1,3-butadiene

propynoic acid ethyl ester

ethyl 4-(trimethylsilylethynyl)benzoate

4-iodobenzoic acid ethyl ester

Downstream raw materials:

2-(4-ethoxycarbonylphenyl)-1,4-dihydro-4-oxoquinoline

4-[(E)-4-(3,3-Dimethyl-6-oxo-cyclohex-1-enyl)-but-3-en-1-ynyl]-benzoic acid ethyl ester

(E)-4-(2-trimethylsilanylvinyl)benzoic acid ethyl ester

(E)-ethyl 4-(2-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)vinyl)benzoate

Refernces

• 1、 Pauly, Anja C.,Theato, Patrick. "Synthesis and characterization of poly(phenylacetylenes) featuring activated ester side groups". . p. 211 - 224. Retrieved 2011.
• 2、 Sekine, Keisuke,Ushiyama, Aina,Endo, Yu,Mikami, Koichi. "Enantioselective Functionalization of Difluorocyclopropenes Catalyzed by Chiral Copper Complexes: Proposal for Chiral gem-Dimethyl and tert-Butyl Analogues". . p. 7916 - 7924. Retrieved 2020.
• 3、 Miura, Tomoya,Tanaka, Takamasa,Yada, Akira,Murakami, Masahiro. "Doyle-kirmse reaction using triazoles leading to one-pot multifunctionalization of terminal alkynes". . p. 1308 - 1310. Retrieved 2013.
• 4、 Iijima, Toru,Endo, Yasuyuki,Tsuji, Motonori,Kawachi, Emiko,Kagechika, Hiroyuki,Shudo, Koichi. "Dicarba-closo-dodecaboranes as a pharmacophore. Retinoidal antagonists and potential agonists". . p. 398 - 404. Retrieved 1999.
• 5、 Chakraborty, Biswajit,Dutta, Debasmita,Mukherjee, Sanjukta,Das, Supriya,Maiti, Nakul C.,Das, Padma,Chowdhury, Chinmay. "Synthesis and biological evaluation of a novel betulinic acid derivative as an inducer of apoptosis in human colon carcinoma cells (HT-29)". . p. 93 - 105. Retrieved 2015.
• 6、 Huang, Huan-Ming,Bellotti, Peter,Daniliuc, Constantin G.,Glorius, Frank. "Radical Carbonyl Propargylation by Dual Catalysis". supporting information. p. 2464 - 2471. Retrieved 2020/12/07.