Methyl 2-((trimethylsilyl)ethynyl)benzoate

Base Information

• Chemical Name: Methyl 2-((trimethylsilyl)ethynyl)benzoate
• CAS No.: 107793-07-7
• Molecular Formula: C13H16O2Si
• Molecular Weight: 232.354
• DSSTox Substance ID: DTXSID80453499
• Nikkaji Number: J1.067.537E
• Wikidata: Q82274647
• Mol file: 107793-07-7.mol

Synonyms:methyl 2-((trimethylsilyl)ethynyl)benzoate;107793-07-7;Methyl 2-(2-trimethylsilylethynyl)benzoate;SCHEMBL497720;METHYL 2-[2-(TRIMETHYLSILYL)ETHYNYL]BENZOATE;DTXSID80453499;KJKMOADDOGZYQC-UHFFFAOYSA-N;methyl2-((trimethylsilyl)ethynyl)benzoate;CS-0416089;FT-0734340;trimethylsilylethynylbenzoic acid methyl ester;F78979;2-(Trimethylsilylethynyl)benzoic acid methyl ester;2-Trimethylsilanylethynyl-benzoic Acid Methyl Ester;J-521795

Chemical Property of Methyl 2-((trimethylsilyl)ethynyl)benzoate

Chemical Property:

• PSA: 26.30000
• LogP: 2.70210
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 232.091956283
• Heavy Atom Count: 16
• Complexity: 316

Purity/Quality:

98%min ^*data from raw suppliers

Methyl2-((trimethylsilyl)ethynyl)benzoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1=CC=CC=C1C#C[Si](C)(C)C

Technology Process of Methyl 2-((trimethylsilyl)ethynyl)benzoate

There total 10 articles about Methyl 2-((trimethylsilyl)ethynyl)benzoate 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%

o-iodo-methyl-benzoic acid (610-97-9) + trimethylsilylacetylene (1066-54-2) → methyl 2-(2-trimethylsilyl-1-ethynyl)benzoate (107793-07-7)

Guidance literature:

With triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tet.2007.07.066

Reference yield: 96.0%

2-bromobenzoic acid methyl ester (610-94-6) + trimethylsilylacetylene (1066-54-2) → methyl 2-(2-trimethylsilyl-1-ethynyl)benzoate (107793-07-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 80 ℃; Cooling with liquid nitrogen; Sealed tube;

DOI:10.1016/j.tet.2020.131437

Reference yield: 76.0%

trimethylsilylacetylene (1066-54-2) → methyl 2-(2-trimethylsilyl-1-ethynyl)benzoate (107793-07-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20 ℃; Inert atmosphere;

DOI:10.1002/adsc.201600492

upstream raw materials:

o-iodo-methyl-benzoic acid

trimethylsilylacetylene

2-bromobenzoic acid methyl ester

piperidine

Downstream raw materials:

2-(2'-aminophenylethynyl)benzoic acid methyl ester

2-(3-aminophenylethynyl)benzoic acid methyl ester

2-{2-[(S)-3-tert-butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionylamino]phenylethynyl}benzoic acid methyl ester

2-{3-[(S)-3-tert-butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionylamino]phenylethynyl}benzoic acid methyl ester

Refernces

• 1、 Wilkins, Lewis C.,Günther, Benjamin A. R.,Walther, Melanie,Lawson, James R.,Wirth, Thomas,Melen, Rebecca L.. "Contrasting Frustrated Lewis Pair Reactivity with Selenium- and Boron-Based Lewis Acids". . p. 11292 - 11295. Retrieved 2016.
• 2、 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.
• 3、 Lhermet, Rudy,Fürstner, Alois. "Cross-Metathesis of Terminal Alkynes". . p. 13188 - 13193. Retrieved 2014.
• 4、 Ming, Xiao-Xia,Wu, Shuai,Tian, Ze-Yu,Song, Jia-Wei,Zhang, Cheng-Pan. "Pd/Cu-Catalyzed Vinylation of Terminal Alkynes with (2-Bromoethyl)diphenylsulfonium Triflate". supporting information. p. 6795 - 6800. Retrieved 2021/09/08.
• 5、 Lin, Xinxin,Fang, Zheng,Zeng, Cuilian,Zhu, Chenlong,Pang, Xinyan,Liu, Chengkou,He, Wei,Duan, Jindian,Qin, Ning,Guo, Kai. "Continuous Electrochemical Synthesis of Iso-Coumarin Derivatives from o-(1-Alkynyl) Benzoates under Metal- and Oxidant-Free". supporting information. p. 13738 - 13742. Retrieved 2020/10/02.