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419214

Sigma-Aldrich

Dimethyl 2,6-dibromoheptanedioate

greener alternative

97%

Synonym(s):

2,6-Dibromoheptanedioic acid dimethyl ester

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About This Item

Linear Formula:
CH2[CH2CH(Br)CO2CH3]2
CAS Number:
Molecular Weight:
346.01
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

form

liquid

greener alternative product score

old score: 2
new score: 1
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greener alternative product characteristics

Waste Prevention
Safer Solvents and Auxiliaries
Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

refractive index

n20/D 1.501 (lit.)

bp

130-140 °C/0.01 mmHg (lit.)

density

1.59 g/mL at 25 °C (lit.)

greener alternative category

SMILES string

COC(=O)C(Br)CCCC(Br)C(=O)OC

InChI

1S/C9H14Br2O4/c1-14-8(12)6(10)4-3-5-7(11)9(13)15-2/h6-7H,3-5H2,1-2H3

InChI key

AWWJYEJSCIDADZ-UHFFFAOYSA-N

General description

Dimethyl 2,6-dibromoheptanedioate acts as a bifunctional initiator in various polymerization reactions. Its electrochemical cyclization affords high yields of three- to six-membered dimethyl 1,2-cycloalkanedicarboxylates.
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Application

Dimethyl 2,6-dibromoheptanedioate may be used in the following studies:
  • Preparation of difunctional poly(n-butyl acrylate) (pBA) macroinitiator.
  • As initiator for the synthesis of dibromo-terminated polystyrene, via atom transfer radical polymerization (ATRP).
  • Preparation of polytrithiocarbonate, which serves as Reversible Addition-Fragmentation chain Transfer (RAFT) agent for radical polymerization reactions.

Pictograms

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Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of Dimethyl 1, 2-Cycloalkanedicarboxylates by Electrochemical Cyclization of Dimethyl a, a'-Dibromoalkanedioates Using a Copper Anode.
Tokuda M, et al.
Bulletin of the Chemical Society of Japan, 64(8), 2590-2592 (1991)
Reversible redox cleavage/coupling of polystyrene with disulfide or thiol groups prepared by atom transfer radical polymerization.
Tsarevsky NV and Matyjaszewski K.
Macromolecules, 35(24), 9009-9014 (2002)
ABA triblock copolymers containing polyhedral oligomeric silsesquioxane pendant groups: synthesis and unique properties.
Pyun J, et al.
Polymer, 44(9), 2739-2750 (2003)
Multiblock Copolymers of Styrene and Butyl Acrylate via Polytrithiocarbonate-Mediated RAFT Polymerization.
Ebeling B and Vana P.
Polymers (Basel, Switzerland), 3(2), 719-739 (2011)

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