Diethyl 4-bromophenylmalonate

Base Information

• Chemical Name: Diethyl 4-bromophenylmalonate
• CAS No.: 93139-85-6
• Molecular Formula: C13H15 Br O4
• Molecular Weight: 315.164
• Hs Code.: 2917399090
• DSSTox Substance ID: DTXSID40441216
• Mol file: 93139-85-6.mol

Synonyms:DIETHYL 4-BROMOPHENYLMALONATE;93139-85-6;Diethyl 2-(4-bromophenyl)propanedioate;Diethyl (4-bromophenyl)malonate;MFCD06205062;diethyl 2-(4-bromophenyl)malonate;SCHEMBL536847;Propanedioic acid, (4-bromophenyl)-, diethyl ester;diethyl (4-bromphenyl)malonate;DTXSID40441216;NEEVEYWBDFTMKS-UHFFFAOYSA-N;diethyl (4-bromophenyl)propanedioate;BBL101989;STL555786;AKOS005259927;AS-9792;Diethyl 4-bromophenylmalonate, AldrichCPR;FT-0711409;2-(4-bromo-phenyl)malonic acid diethyl ester;J-520297

Chemical Property of Diethyl 4-bromophenylmalonate

Chemical Property:

• Boiling Point: 190-192 °C(Press: 16 Torr)
• PKA: 11.07±0.46(Predicted)
• PSA: 52.60000
• Density: 1.378±0.06 g/cm3(Predicted)
• LogP: 2.65890
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 314.01537
• Heavy Atom Count: 18
• Complexity: 267

Purity/Quality:

97% ^*data from raw suppliers

Diethyl 4-bromophenylmalonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Diethyl 4-bromophenylmalonate

There total 6 articles about Diethyl 4-bromophenylmalonate 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: 90.0%

Ethyl 4-bromophenylacetate (14062-25-0) + Diethyl carbonate (105-58-8,76619-83-5) → 2-(4-bromophenyl)malonic acid diethyl ester (93139-85-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; Inert atmosphere; Reflux;

DOI:10.1021/acs.joc.6b02428

Reference yield: 79.0%

2,4,6-tris(4-bromophenyl)boroxin (7519-94-0) + diethyl malonate (105-53-3) → 2-(4-bromophenyl)malonic acid diethyl ester (93139-85-6)

Guidance literature:

With cesium acetate; copper(II) bis(trifluoromethanesulfonate); triethylamine; In 1,2-dichloro-ethane; at 30 ℃; for 33h; Glovebox; Inert atmosphere;

DOI:10.1002/anie.201510558

Reference yield: 76.0%

Ethyl 4-bromophenylacetate (14062-25-0) + ethyl cyanoformate (623-49-4) → 2-(4-bromophenyl)malonic acid diethyl ester (93139-85-6)

Guidance literature:

Ethyl 4-bromophenylacetate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

ethyl cyanoformate; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/ja0382361

upstream raw materials:

Ethyl 4-bromophenylacetate

ethyl cyanoformate

2-(4-bromophenyl)-acetic acid

Diethyl carbonate

Downstream raw materials:

p-phenylene-bis-(diethyl malonate)

5-(p-bromophenyl)-4,6(1H,5H)-pyrimidinedione

Allyl-<4-brom-phenyl->-malonsaeure-diaethylester

(4-bromo-phenyl)-malonyl dichloride

Refernces

• 1、 Li, Zexian,Shi, Zhuangzhi,Wang, Minyan. "Radical Addition Enables 1,2-Aryl Migration from a Vinyl-Substituted All-Carbon Quaternary Center". supporting information. p. 186 - 190. Retrieved 2020/11/02.
• 2、 -. "MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS". Paragraph 00661. . Retrieved 2018/09/12.