Diethyl 2,5-dibromohexanedioate Chemical Properties

Melting point:

65-67 °C (lit.)

Boiling point:

134°C/0.5mmHg(lit.)

Density 

1.7082 (rough estimate)

refractive index 

1.5010 (estimate)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DCM

form 

Solid

color 

Brown

Sensitive 

Light Sensitive

InChI

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

InChIKey

UBCNJHBDCUBIPB-UHFFFAOYSA-N

SMILES

C(OCC)(=O)C(Br)CCC(Br)C(OCC)=O

CAS DataBase Reference

869-10-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34-36/37

Safety Statements 

26-27-28-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

HazardClass 

8

PackingGroup 

III

HS Code 

29171900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Diethyl 2,5-dibromohexanedioate Usage And Synthesis

Uses

Diethyl α,α'-Dibromoadipate is an intermediate in the synthesis of Muconic Acid, a metabolite found in urine found in workers with prolonged exposure to Benzene.

Uses

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

Uses

Diethyl 2,5-dibromohexanedioate can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development processes and chemical production processes.

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.

Synthesis

meso-2,5-Dibromo-hexanedioic acid diethyl ester JS-053: Adipic acid (795 g, 3.93 mol) was added in small portions to thionylchloride (980 mL, 5.44 mol) for 2 hours at 65 degC. This suspension was mechanically stirred and heated on an oil bath for an additional 3.5 hours at 70 degC, until the gas evolution was finished. To the UV lamp irradiated (2x 120W) solution was added dropwise bromine (664 mL, 12.48 mol) for 7 hours at 85-95 degC. After finishing of absorption of bromine, the reaction mixture was cooled down, poured into ethanol (4000 mL, 96 %) at -5 degC and mechanically stirred for an additional 1 week at rt. Crystals were filtered off and washed with ethanol (2x 300 mL, 96 %) to afford meso-2,5-dibromo-hexanedioic acid diethyl ester (JS-053, 1343 g, 3.73 mol, yield 95 %, GC 98 %, mp 66 degC/lit.

Diethyl 2,5-dibromohexanedioate(869-10-3)Related Product Information

• Diethyl adipate
• Ethyl dibromofluoroacetate
• Diethyl phthalate
• Diethyl malonate
• Adipic dihydrazide
• 2,5-Dibromopyrazine
• Diethyl pimelate
• Diethyl carbonate
• Diethyl oxalate
• Mefenpyr-diethyl
• Adipic acid
• Diethyl oxalacetate
• Dioctyl adipate
• Diethyl ether
• Ethyl 2-bromopropionate
• Monoethyl Adipate
• (S)-(-)-2-BROMOPROPIONIC ACID
• 1,4-Dibromopentane