Tert-butyl 4-ethynylbenzoate

Base Information

• Chemical Name: Tert-butyl 4-ethynylbenzoate
• CAS No.: 111291-97-5
• Molecular Formula: C13H14O2
• Molecular Weight: 202.253
• DSSTox Substance ID: DTXSID40553404
• Nikkaji Number: J3.594.496F
• Wikidata: Q82433983
• Mol file: 111291-97-5.mol

Synonyms:TERT-BUTYL 4-ETHYNYLBENZOATE;111291-97-5;tert.-butyl 4-ethynylbenzoate;AMY331;SCHEMBL6258711;DTXSID40553404;FWAUARVBLKIMRS-UHFFFAOYSA-N;AB2737;MFCD09037869;AKOS015911092;DS-4794;4-Ethinyl benzoic acid tert.-butyl ester;4-ethinyl-benzoic acid tert.-butyl ester;CS-0028342;A802336

Chemical Property of Tert-butyl 4-ethynylbenzoate

Chemical Property:

• Vapor Pressure: 0.004mmHg at 25°C
• Melting Point: 71.5-72 °C
• Refractive Index: 1.52
• Boiling Point: 279.525 °C at 760 mmHg
• Flash Point: 112.148 °C
• PSA: 26.30000
• Density: 1.046 g/cm³
• LogP: 2.62320
• Storage Temp.: 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 202.099379685
• Heavy Atom Count: 15
• Complexity: 269

Purity/Quality:

98%min ^*data from raw suppliers

tert-Butyl4-Ethynylbenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Tert-butyl 4-ethynylbenzoate

There total 9 articles about Tert-butyl 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: 99.0%

tert-butyl 4-<(trimethylsilyl)ethynyl>benzoate (111291-96-4) → 4-ethynylbenzoic acid tert-butyl ester (111291-97-5)

Guidance literature:

With caesium carbonate; In tert-butyl alcohol; at 40 ℃; for 8h;

DOI:10.1021/jacs.9b02544

Reference yield: 70.0%

potassium tert-butylate (865-47-4) + 4-ethynylbenzoyl chloride (62480-31-3) → 4-ethynylbenzoic acid tert-butyl ester (111291-97-5)

Guidance literature:

In tert-butyl alcohol; Heating;

DOI:10.1021/ja035212l

Reference yield:

tert-butyl-4-bromobenzoate (59247-47-1) + trimethylsilylacetylene (1066-54-2) → 4-ethynylbenzoic acid tert-butyl ester (111291-97-5)

Guidance literature:

With triphenylphosphine; palladium diacetate; In triethylamine;

upstream raw materials:

tert-butyl 4-<(trimethylsilyl)ethynyl>benzoate

potassium tert-butylate

4-ethynylbenzoyl chloride

4-chlorobenzoyl chloride

Downstream raw materials:

2-(pivaloylamino)-4-hydroxy-6-<<4-(tert-butoxycarbonyl)phenyl>ethynyl>pyrido<2,3-d>pyrimidine

diethyl N-(4-ethynylbenzoyl)-L-glutamate

C₃₇H₃₄BrNO₄

4-[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-pentafluoroethyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenylethynyl]benzoic acid tert-butyl ester

Refernces

• 1、 Galanti, Agostino,Santoro, Jasmin,Mannancherry, Rajesh,Duez, Quentin,Diez-Cabanes, Valentin,Valá?ek, Michal,De Winter, Julien,Cornil, Jér?me,Gerbaux, Pascal,Mayor, Marcel,Samorì, Paolo. "A New Class of Rigid Multi(azobenzene) Switches Featuring Electronic Decoupling: Unravelling the Isomerization in Individual Photochromes". supporting information. p. 9273 - 9283. Retrieved 2019/06/07.
• 2、 Molt,Ruebeling,Schrader. "A selective biomimetic tweezer for noradrenaline". . p. 12086 - 12087. Retrieved 2007/10/03.