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CAS

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29263-94-3

Diethyl 2-bromo-2-methylmalonate is a clear, colorless liquid that serves as an initiator in the atom transfer radical polymerization of methyl methacrylate. It is also utilized in the synthesis of polystyrene macroinitiator and has been investigated for its role in the radical chain conversion of primary bromoesters to corresponding esters using 1,2,2,6,6-pentamethylpiperidine as a reducing agent.

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  • 29263-94-3 Structure

  • Basic information

    1. Product Name: Diethyl 2-bromo-2-methylmalonate
    2. Synonyms: 2-BROMO-2-METHYLMALONIC ACID DIETHYL ESTER;DIETHYL BROMOMETHYLMALONATE;DIETHYL 2-BROMO-2-METHYLMALONATE;2-Brom-2-methylmalonic acid diethylester;2-BROMO-2-METHYLPROPANDIOIC ACID DIETHYL ESTER;2-(bromomethyl)-propanedioic acid diethyl ester;Diethyl 2-bromo-2-methylmalonate, 98+%;Diethyl 2-bromo-2-methylpropanedioate
    3. CAS NO:29263-94-3
    4. Molecular Formula: C8H13BrO4
    5. Molecular Weight: 253.09
    6. EINECS: 249-541-6
    7. Product Categories: Pharmaceutical Intermediates;TheMalonateRamificationProducts;C8 to C9;Carbonyl Compounds;Esters
    8. Mol File: 29263-94-3.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 105-106 °C (5 mmHg)
    3. Flash Point: >230 °F
    4. Appearance: clear, colorless liquid
    5. Density: 1.325 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.0433mmHg at 25°C
    7. Refractive Index: n20/D 1.449(lit.)
    8. Storage Temp.: Inert atmosphere,Room Temperature
    9. Solubility: N/A
    10. BRN: 1779673
    11. CAS DataBase Reference: Diethyl 2-bromo-2-methylmalonate(CAS DataBase Reference)
    12. NIST Chemistry Reference: Diethyl 2-bromo-2-methylmalonate(29263-94-3)
    13. EPA Substance Registry System: Diethyl 2-bromo-2-methylmalonate(29263-94-3)

  • Safety Data

    1. Hazard Codes: C
    2. Statements: 34-20/21/22
    3. Safety Statements: 26-36/37/39-45
    4. RIDADR: UN 3265 8/PG 2
    5. WGK Germany: 3
    6. RTECS:
    7. HazardClass: 8
    8. PackingGroup: III
    9. Hazardous Substances Data: 29263-94-3(Hazardous Substances Data)

29263-94-3 Usage

Uses

Used in Polymer Synthesis:
Diethyl 2-bromo-2-methylmalonate is used as an initiator for atom transfer radical polymerization, specifically in the synthesis of methyl methacrylate. This application is crucial for creating polymers with controlled molecular weights and architectures, which are essential in various industries.
Used in Chemical Research:
In the field of chemical research, Diethyl 2-bromo-2-methylmalonate is used as a key compound in investigating the effectiveness of reducing agents, such as 1,2,2,6,6-pentamethylpiperidine, for the radical chain conversion of primary bromoesters to esters. This research contributes to the understanding of reaction mechanisms and the development of new synthetic methods.
Used in the Production of Polystyrene Macroinitiators:
Diethyl 2-bromo-2-methylmalonate is utilized in the synthesis of polystyrene macroinitiators via atom transfer radical polymerization. These macroinitiators are essential in the production of block copolymers and other advanced polymer materials with tailored properties for various applications.

Check Digit Verification of cas no

The CAS Registry Mumber 29263-94-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,2,6 and 3 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 29263-94:
(7*2)+(6*9)+(5*2)+(4*6)+(3*3)+(2*9)+(1*4)=133
133 % 10 = 3
So 29263-94-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H13BrO4/c1-4-12-6(10)8(3,9)7(11)13-5-2/h4-5H2,1-3H3

29263-94-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Detail

  • Alfa Aesar

  • (L00575)  Diethyl 2-bromo-2-methylmalonate, 98%   

  • 29263-94-3

  • 25g

  • 443.0CNY

  • Detail

  • Alfa Aesar

  • (L00575)  Diethyl 2-bromo-2-methylmalonate, 98%   

  • 29263-94-3

  • 100g

  • 1652.0CNY

  • Detail

29263-94-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name diethyl 2-bromo-2-methylpropanedioate

1.2 Other means of identification

Product number -
Other names 2-bromo-2-methylmalonic acid diethyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:29263-94-3 SDS

29263-94-3Upstream product

29263-94-3Relevant articles and documents

N,N-Dibromobenzenesulfonamide: A useful regenrable reagent for bromination of various carbanionic substrates

Tajbakhsh, Mahmood,Khazaei, Ardeshir,Mahalli, Majid Shabani,Vaghi, Ramin Ghorbani

, p. 1159 - 1163 (2007/10/03)

N,N-Dibromobenzenesulfonamide(dibromoamine-B), which is prepared easily in high yield, has been employed as effective brominating agent for carbanionic substrates under mild conditions. β-Diketones and β-ketoesters were brominated by this reagent without using any bases. The reagent can be recovered, rebrominated, and reused several times.

One-pot synthesis using supported reagents system: Conversion of β-dicarbonyl compounds to α-thiocyano-β-dicarbonyl compounds using CuBr2/Al2O3-KSCN/SiO2

Suzuki, Yoshitada,Kodomari, Mitsuo

, p. 1091 - 1092 (2007/10/03)

Transformation of β-dicarbonyl compound 1 to α-thiocyano-α-dicarbonyl compounds 3 in one-pot was achieved by using supported reagents system CuBr2/Al2O3 - KSCN/SiO2, in which 1 reacts first with CuBr2/Al2O3 and the product, α-bromo-β-dicarbonyl compound 2 reacts with KSCN/SiO2 to give the final product 3 in good yield.

Rate Constants for Halogen Atom Transfer from Representative α-Halocarbonyl Compounds to Primary Alkyl Radicals

Curran, Dennis P.,Bosch, Eric,Kaplan, Jere,Newcomb, Martin

, p. 1826 - 1831 (2007/10/02)

Rate constants for halogen atom transfer from diethyl methyliodomalonate (7a), iodoacetonitrile (7b), ethyl 2-methyl-2-iodopropanoate (7c), ethyl iodoacetate (7d), diethyl methylbromomalonate (7e), and ethyl bromoacetate (7f) to simple primary alkyl radicals have been studied by a variety of competition reactions.The Arrhenius functions for halogen atom transfer to the undecyl radical from halides 7d and 7f are log (kI, M-1 s-1) = 10.4 - 4.4/θ and log (kBr, M-1 s-1) = 10.4 - 8.2/θ, respectively.The rate constants for halogen atom transfer to a primaryradical from the series of compounds 7a-7f at 50 deg C are 1.8 x 109, 1.7 x 109, ca. 6 x 108, 2.6 x 107, 1.0 x 106, and 7.0 x 104 M-1 s-1, respectively.The kinetic values are useful for the planning of synthetic methods that incorporate an atom transfer-cyclization process.

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