• Dimethyl trans-2,3-Dibromobutenedioate (CAS 116631-94-8) - TCI D4073 - AMI Scientific
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TCI

CAS 116631-94-8

Dimethyl trans-2,3-Dibromobutenedioate TCI D4073

Dimethyl trans-2,3-Dibromobutenedioate TCI D4073
Rp 8.470.350,00
Rp 8.470.350,00
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TCI D4073 Dimethyl trans-2,3-Dibromobutenedioate is the dimethyl ester of butenedioic acid carrying two bromine atoms on the carbon–carbon double bond in a defined trans configuration. The structure combines three elements of reactivity in a single small molecule: an electron-poor carbon–carbon double bond, two electron-withdrawing ester groups, and two vinylic bromine atoms. In the organic synthesis laboratory, this compound serves as a versatile building block used to construct heterocyclic rings, conjugated systems, and a range of substituted alkene derivatives that are difficult to obtain through other synthetic routes.

The characteristic that makes this reagent a preferred choice is its behaviour as a strongly activated Michael acceptor and dienophile. The presence of two ester groups lowers the electron density at the double bond, so the compound is readily attacked by nucleophiles such as amines, thiols, and enolates, and also reacts with dienes through Diels–Alder cycloaddition. The vinylic bromine atoms add a second dimension: once addition has taken place, bromine can be removed by elimination to restore unsaturation, or exploited in cross-coupling reactions. The defined trans configuration further helps control product stereochemistry in many transformations.

In Indonesian laboratories, this material is typically used in university and institutional organic synthesis groups, in medicinal chemistry and heterocyclic chemistry research, and in method development work where a compact, highly functionalised electrophile is required. It is usually handled at bench scale for exploratory reactions and route scouting, where a single building block that can be elaborated through several different bond-forming steps reduces the number of separate reagents that a laboratory needs to keep on hand.

  • Michael addition chemistry — the two electron-withdrawing ester groups strongly activate the double bond, allowing clean conjugate addition of amines, thiols, and enolate nucleophiles.
  • Diels–Alder cycloaddition — the electron-poor alkene functions as an activated dienophile, reacting with dienes to build cyclic frameworks bearing two ester handles for further elaboration.
  • Heterocyclic ring construction — combined nucleophilic addition and bromide displacement or elimination allows the compound to be closed into heterocyclic ring systems in synthesis programmes.
  • Cross-coupling substrate preparation — the two vinylic bromine atoms provide reactive sites that can be carried forward into palladium-mediated cross-coupling reactions to install new carbon substituents.
  • Stereocontrolled alkene synthesis — the defined trans configuration of the starting material helps direct the stereochemical outcome of addition and elimination sequences leading to substituted alkene derivatives.

Brand TCI
CAS number 116631-94-8
Molecular formula —
Purity —
Category Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes available in standard TCI research-scale catalogue pack sizes; please confirm the size required when ordering
Physical form —
Storage keep in the tightly closed original container under the conditions stated on the manufacturer's label and safety data sheet
  • Chemical name: Dimethyl trans-2,3-Dibromobutenedioate

Store the material in its tightly closed original container, in a cool, dry, and well-ventilated area away from direct sunlight, heat sources, and incompatible materials such as strong bases, strong oxidising agents, and nucleophilic reagents. Amber glass or the supplied manufacturer packaging is suitable for keeping the compound protected from light and moisture. As a reactive brominated ester, it should be handled in a fume hood using nitrile gloves, safety goggles, and a laboratory coat, avoiding contact with skin and eyes and inhalation of vapours. Transfer with clean, dry glassware, close containers immediately after use, and record opening dates for inventory control. Always consult the manufacturer's safety data sheet before use, and dispose of residues and contaminated materials as halogenated organic chemical waste according to applicable institutional and local regulations.

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