Methyl 3-(4-bromophenyl)prop-2-ynoate

Base Information

• Chemical Name: Methyl 3-(4-bromophenyl)prop-2-ynoate
• CAS No.: 42122-27-0
• Molecular Formula: C10H7BrO2
• Molecular Weight: 239.068
• European Community (EC) Number: 839-082-5
• DSSTox Substance ID: DTXSID60356530
• Nikkaji Number: J1.059.722F
• Wikidata: Q82135913
• Mol file: 42122-27-0.mol

Synonyms:42122-27-0;methyl 3-(4-bromophenyl)prop-2-ynoate;methyl 3-(4-bromophenyl)propiolate;2-Propynoic acid, 3-(4-bromophenyl)-, methyl ester;SCHEMBL406741;DTXSID60356530;WNFQGEHRFXJKKS-UHFFFAOYSA-N;AKOS013859040;AT20430;methyl 3-(4-bromophenyl)-2-propynoate;CS-0310595;FT-0704139;M2893;EN300-743541;2-Propynoicacid,3-(4-bromophenyl)-,methylester

Chemical Property of Methyl 3-(4-bromophenyl)prop-2-ynoate

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 237.96294
• Heavy Atom Count: 13
• Complexity: 240

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C#CC1=CC=C(C=C1)Br

Technology Process of Methyl 3-(4-bromophenyl)prop-2-ynoate

There total 19 articles about Methyl 3-(4-bromophenyl)prop-2-ynoate 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%

methanol (67-56-1) + 2-bromo-1-(4-bromophenyl)-3,3-difluorocyclopropene → (4-bromophenyl)-propynoic acid methyl ester (42122-27-0)

Guidance literature:

Heating;

Reference yield: 90.0%

carbon dioxide (124-38-9,18923-20-1) + (4-bromophenyl)(trimethylsilyl)acetylene (16116-78-2) + methyl iodide (74-88-4) → (4-bromophenyl)-propynoic acid methyl ester (42122-27-0)

Guidance literature:

carbon dioxide; With cesium fluoride; In N,N-dimethyl-formamide; at 120 ℃; Inert atmosphere;

(4-bromophenyl)(trimethylsilyl)acetylene; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

methyl iodide; In N,N-dimethyl-formamide; at 20 ℃; for 13h; Inert atmosphere;

DOI:10.1021/acs.orglett.1c01171

Reference yield: 80.0%

methyl 3-(4-bromophenyl)-3-oxopropanoate (126629-81-0) → (4-bromophenyl)-propynoic acid methyl ester (42122-27-0)

Guidance literature:

methyl 3-(4-bromophenyl)-3-oxopropanoate; With lithium hexamethyldisilazane; In tetrahydrofuran; ethylbenzene; at -70 ℃; for 0.5h; Inert atmosphere;

With diethyl chlorophosphate; In tetrahydrofuran; ethylbenzene; at -78 - 20 ℃; for 0.5h; Inert atmosphere;

With lithium hexamethyldisilazane; In tetrahydrofuran; ethylbenzene; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1139/cjc-2016-0181

upstream raw materials:

diazomethane

3-(4-bromophenyl)-2-propynoic acid

methanol

4-bromo-1-ethynylbenzene

Downstream raw materials:

E-methyl β-piperidino-p-bromocinnamate

E-methyl β-(N,N-diethylamino)-p-bromocinnamate

3-(4-bromophenyl)-1-methylpyrrolidine