Diethyl bromomalonate

Base Information

• Chemical Name: Diethyl bromomalonate
• CAS No.: 685-87-0
• Deprecated CAS: 201742-85-0
• Molecular Formula: C7H11BrO4
• Molecular Weight: 239.066
• Hs Code.: 29171900
• European Community (EC) Number: 211-683-1
• NSC Number: 1985
• UNII: UN4643QTM3
• DSSTox Substance ID: DTXSID9060992
• Nikkaji Number: J134.655E
• Wikidata: Q72469210
• Mol file: 685-87-0.mol

Synonyms:Diethyl bromomalonate;685-87-0;Diethyl 2-bromomalonate;Bromomalonic acid diethyl ester;Ethyl bromomalonate;Propanedioic acid, bromo-, diethyl ester;diethyl 2-bromopropanedioate;Diethylbromomalonate;1,3-diethyl 2-bromopropanedioate;C7H11BrO4;Propanedioic acid, 2-bromo-, 1,3-diethyl ester;alpha-Bromomalonic ester;diethyl bromopropanedioate;Malonic acid, bromo-, diethyl ester;.alpha.-Bromomalonic ester;Diethyl .alpha.-bromomalonate;UN4643QTM3;NSC 1985;NSC-1985;EINECS 211-683-1;2-bromo-propanedioic acid diethyl ester;AI3-01376;Diethyl2-bromomalonate;diethyl bromo-malonate;diethyl-2-bromomalonate;diethyl 2-bromo-malonate;Diethyl bromomalonate, 92%;UNII-UN4643QTM3;SCHEMBL166529;C7-H11-Br-O4;DTXSID9060992;AMY4081;NSC1985;2-bromo-malonic acid diethyl ester;CS-B0964;BBL027739;BR1275;MFCD00009138;STL299667;AKOS000121112;AS-15784;A9123;B1205;FT-0624777;EN300-26547;A930345;F2190-0286

Chemical Property of Diethyl bromomalonate

Chemical Property:

• Appearance/Colour: Clear colourless to slightly yellow liquid
• Vapor Pressure: 0.0542mmHg at 25°C
• Melting Point: -54°C
• Refractive Index: n20/D 1.451(lit.)
• Boiling Point: 233.999 °C at 760 mmHg
• PKA: 9.29±0.46(Predicted)
• Flash Point: 89.603 °C
• PSA: 52.60000
• Density: 1.452 g/cm³
• LogP: 0.87610
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Lachrymatory
• Solubility.: Chloroform, Hexanes
• Water Solubility.: Does not mix well with water.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 237.98407
• Heavy Atom Count: 12
• Complexity: 151

Purity/Quality:

99% ^*data from raw suppliers

Diethyl Bromomalonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Esters
• Canonical SMILES: CCOC(=O)C(C(=O)OCC)Br
• Uses: Diethyl Bromomalonate is a chemical constituent of the asymmetric cyclopropanation of chalcones. Also used in the preparation of nanaplatforms for NIR imaging-guided photodynamic therapy of cancer cel ls. Diethyl bromomalonate is used in perfumes. It is also used to synthesize other compounds such as barbiturates, artificial flavorings, vitamin B1, and vitamin B6.

Technology Process of Diethyl bromomalonate

There total 16 articles about Diethyl bromomalonate 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%

diethyl malonate (105-53-3) → Diethyl 2-bromomalonate (685-87-0)

Guidance literature:

With bromine; In tetrachloromethane; for 1h; Heating; Irradiation;

DOI:10.1016/S0040-4020(01)88659-2

Reference yield: 95.0%

diethyl dibromomalonate (631-22-1) + EtTe(CH2)3OH (189247-71-0) → Diethyl 2-bromomalonate (685-87-0) + 2-Bromo-2-ethyl-2λ4-[1,2]oxatellurolane

Guidance literature:

In dichloromethane; for 2h; Ambient temperature;

Reference yield: 91.0%

diethyl dibromomalonate (631-22-1) → Diethyl 2-bromomalonate (685-87-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 28 ℃; for 18h; Irradiation; Inert atmosphere;

DOI:10.1021/acs.orglett.9b03848

upstream raw materials:

bromocyane

diethyl malonate

diethyl dibromomalonate

ethyl methyl malonate

Downstream raw materials:

diethyl 2-phthalimidomalonate

m-phenylenediamino-di-malonic acid tetraethyl ester

Benzofuran-2-carboxylic acid

4-((1,3-diethoxy-1,3-dioxopropan-2-yl)amino)benzoic acid

Refernces

• 1、 -. "2-methoxyphenoxy pyrimidine antitumor compound as well as preparation method and application thereof". Paragraph 0045-0047. . Retrieved 2021/05/12.
• 2、 Li, Xing,Zheng, Leijie,Gong, Xiaolei,Chang, Honghong,Gao, Wenchao,Wei, Wenlong. "NBS/DBU-Promoted One-Pot Three-Component Cycloaddition of Malonic Acid Derivatives, Nitrosoarenes, and Alkenes: Synthesis of Isoxazolidines". . p. 1096 - 1107. Retrieved 2021/01/14.