Vinyl bromoacetate

• CAS: 5309-70-6
• Catalog Number: ACM5309706
• Category: Main Products
• Molecular Weight: 164.99
• Molecular Formula: C₄H₅BrO₂
• Synonyms: bromoacetic acid allyl ester; Brom-essigsaeure-p-tolylester; p-Tolyl-bromacetat; Brom-essigsaeure-vinylester; vinylbromoacetate; bromo-acetic acid vinyl ester; bromo-acetic acid p-tolyl ester; Acetic acid,bromo-,4-methylphenyl ester
• IUPAC Name: ethenyl2-bromoacetate
• InChI Key: DFEHSFZILGOAJK-UHFFFAOYSA-N
• Boiling Point: 467ºC at 760 mmHg
• Flash Point: 236.2ºC
• Density: 1.1 g/cm³
• Exact Mass: 163.94700
• Safety Description: 26-36/37/39

Case Study

Vinyl Bromoacetate as a Key Material for the Enzymatic Synthesis of Glutathione-Everolimus

Wang, Haibo, et al. Medicinal Chemistry Research 27 (2018): 583-591.

In this work, an enzymatic synthesis method for glutathione-everolimus was developed, in which intermediate 2 was synthesized using vinyl bromoacetate as a raw material. The stability of the glutathione-everolimus conjugate showed that the prodrug could be made into a lyophilized solid and reconstituted with 0.9% sodium chloride injection for intravenous infusion. In addition, according to in vivo testing, the conjugate was proved to be an effective, safe and well-tolerated prodrug for injection, which can be used to treat renal cell carcinoma.
Synthesis Strategy
· Compared with vinyl chloroacetate, the use of vinyl bromoacetate as a raw material achieved a stable enzymatic synthesis:
· Intermediate Synthesis: Vinyl bromoacetate reacted with everolimus via immobilized lipase catalysis to form Intermediate 2.
· Process Efficiency: This step achieved quantitative conversion with minimal workup-only filtration (to remove lipase) and evaporation of excess vinyl bromoacetate/byproducts. No chromatographic purification was needed.
· Conjugation Advantage: The bromine atom in Intermediate 2 exhibited superior reactivity versus chlorine, enabling efficient nucleophilic substitution with glutathione's thiol group.
· Yield: Final conjugation with glutathione achieved 83% yield after RP-HPLC purification-nearly doubling the prior chemical synthesis yield (42%).
· Scalability: Successfully scaled to hundreds of grams per batch with high reproducibility.

Custom Q&A

What is the molecular formula of vinyl bromoacetate?

The molecular formula of vinyl bromoacetate is C4H5BrO2.

What are some synonyms for vinyl bromoacetate?

Some synonyms for vinyl bromoacetate are vinyl 2-bromoacetate, vinyl-2-bromoacetate, and ethenyl 2-bromoacetate.

What is the molecular weight of vinyl bromoacetate?

The molecular weight of vinyl bromoacetate is 164.99 g/mol.

When was vinyl bromoacetate created?

Vinyl bromoacetate was created on February 9, 2007.

What is the IUPAC name of vinyl bromoacetate?

The IUPAC name of vinyl bromoacetate is ethenyl 2-bromoacetate.

What is the InChI key of vinyl bromoacetate?

The InChI key of vinyl bromoacetate is DFEHSFZILGOAJK-UHFFFAOYSA-N.

What is the canonical SMILES representation of vinyl bromoacetate?

The canonical SMILES representation of vinyl bromoacetate is C=COC(=O)CBr.

What is the XLogP3-AA value of vinyl bromoacetate?

The XLogP3-AA value of vinyl bromoacetate is 1.4.

How many hydrogen bond acceptor counts does vinyl bromoacetate have?

Vinyl bromoacetate has 2 hydrogen bond acceptor counts.

Is vinyl bromoacetate a canonicalized compound?

Yes, vinyl bromoacetate is a canonicalized compound.