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419214

Sigma-Aldrich

Dimethyl 2,6-dibromoheptanedioate

greener alternative

97%

Sinónimos:

2,6-Dibromoheptanedioic acid dimethyl ester

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About This Item

Fórmula lineal:
CH2[CH2CH(Br)CO2CH3]2
Número de CAS:
868-73-5
Peso molecular:
346.01
MDL number:
MFCD00192080
UNSPSC Code:
12352100
PubChem Substance ID:
24866099
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.

sustainability

Greener Alternative Product

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

Re-engineered,

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

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

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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