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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.)

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

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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Tandem cyclisation and [2, 3]-Stevens rearrangement to 2-substituted pyrrolidines.
Smith SC and Bentley PD.
Tetrahedron Letters, 43(5), 899-902 (2002)
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)
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)
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)
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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