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347191

Sigma-Aldrich

Diethyl meso-2,5-dibromoadipate

98%

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About This Item

Linear Formula:
[-CH2CH(Br)CO2C2H5]2
CAS Number:
869-10-3
Molecular Weight:
360.04
MDL number:
MFCD00075379
UNSPSC Code:
12352100
PubChem Substance ID:
24861319
NACRES:
NA.22

Quality Level

100

Assay

98%

mp

65-67 °C (lit.)

functional group

bromo
ester

SMILES string

CCOC(=O)[C@@H](Br)CC[C@@H](Br)C(=O)OCC

InChI

1S/C10H16Br2O4/c1-3-15-9(13)7(11)5-6-8(12)10(14)16-4-2/h7-8H,3-6H2,1-2H3/t7-,8+

InChI key

UBCNJHBDCUBIPB-OCAPTIKFSA-N

General description

Diethyl meso-2,5-dibromoadipate reacts with N-methylallylamine in the presence of potassium carbonate to yield two diastereomers of diethyl 2-allyl-N-methylpyrrolidine-2,5-dicarboxylate.

Application

Diethyl meso-2,5-dibromoadipate may be employed as difunctional initiator during n-butyl acrylate (n-BuA) polymerization, leading to α,ω-bromo-poly(n-BuA) having narrow molecular weight distribution. It was also used:
  • as bifunctional atom transfer radical polymerization (ATRP) initiator
  • as initiator during the solution polymerization of octadecyl ester ether dimer by ATRP
  • in the synthesis of diethyl 2,5-diazidoadipate

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H335

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000271598
0000271597
0000251279
MKBW6595V
MKBG4591V

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Tandem cyclisation and [2, 3]-Stevens rearrangement to 2-substituted pyrrolidines.
Smith SC and Bentley PD.
Tetrahedron Letters, 43(5), 899-902 (2002)
Effect of Block Order of ABA-and BAB-Type NIPAAm/HEMA Triblock Copolymers on Thermoresponsive Behavior of Solutions.
Zhao X, et al.
Macromolecular Chemistry and Physics, 208(16), 1773-1781 (2007)
GRAFTING CARBOXYLIC ACIDS AND TERTIARY AMINES ONTO AZIDE-CONTAINING ALIPHATIC POLYESTERS.
Brown AH and Sheares VV.
Polymer Preprints (American Chemical Society, Division of Polymer Chemistry), 49(1), 181-181 (2008)
ATOM TRANSFER RADICAL POLYMERIZATION OF OCTADECYL a-(HYDROXYMETHYL) ACRYLATE ESTER ETHER DIMER AND THEIR CORRESPONDING BLOCK COPOLYMERS.
Ozkal E, et al.
Polymer Preprints (American Chemical Society, Division of Polymer Chemistry), 49(1), 416-416 (2008)
Controlled radical polymerization of (meth) acrylates by ATRP with NiBr2 (PPh3) 2 as catalyst.
Moineau G, et al.
Macromolecules, 32(1), 27-35 (1999)

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