Production Method 1

79762-78-0

Reaction Conditions

1.1 Reagents: Bromine Solvents: Dichloromethane ;  0 - 5 °C; 18 h, 5 °C → rt
1.2 Reagents: Sodium thiosulfate Solvents: Water ;  rt
2.1 Reagents: Triethylamine Solvents: Dichloromethane ;  rt; 16 h, rt

Reference

How Reaction Conditions May Influence the Regioselectivity in the Synthesis of 2,3-Dihydro-1,4-benzoxathiine Derivatives

Casiraghi, Andrea; et al, Journal of Organic Chemistry, 2018, 83(21), 13217-13227

Production Method 2

79762-78-0

Reaction Conditions

1.1 Reagents: Bromine Solvents: Dichloromethane ;  20 min, < 10 °C; 120 min, 5 °C
2.1 Reagents: Triethylamine Solvents: Diethyl ether ;  rt; rt → 0 °C; overnight, rt

Reference

Mechanism-based inactivation of coenzyme B12-dependent 2-methyleneglutarate mutase by (Z)-glutaconate and buta-1,3-diene-2,3-dicarboxylate

Buckel, Wolfgang; et al, European Journal of Inorganic Chemistry, 2006, (18), 3622-3626

Production Method 3

49855-41-6

79762-78-0

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dichloromethane ;  rt; 16 h, rt

Reference

How Reaction Conditions May Influence the Regioselectivity in the Synthesis of 2,3-Dihydro-1,4-benzoxathiine Derivatives

Casiraghi, Andrea; et al, Journal of Organic Chemistry, 2018, 83(21), 13217-13227

Production Method 4

49855-41-6

79762-78-0

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Diethyl ether

Reference

Dienophilic captodative olefins. VI. Synthesis and Diels-Alder cycloadditions of alkyl α-(alkylthio)acrylates with cyclopentadiene: steric effect on reactivity and on stereoselectivity

Boucher, Jean Luc; et al, Tetrahedron, 1988, 44(12), 3595-605

Production Method 5

49855-41-6

79762-78-0

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Diethyl ether ;  rt; rt → 0 °C; overnight, rt

Reference

Mechanism-based inactivation of coenzyme B12-dependent 2-methyleneglutarate mutase by (Z)-glutaconate and buta-1,3-diene-2,3-dicarboxylate

Buckel, Wolfgang; et al, European Journal of Inorganic Chemistry, 2006, (18), 3622-3626

Production Method 6

79762-78-0

Reaction Conditions

1.1 Reagents: Bromine Solvents: Carbon tetrachloride
2.1 Reagents: Triethylamine Solvents: Diethyl ether

Reference

Dienophilic captodative olefins. VI. Synthesis and Diels-Alder cycloadditions of alkyl α-(alkylthio)acrylates with cyclopentadiene: steric effect on reactivity and on stereoselectivity

Boucher, Jean Luc; et al, Tetrahedron, 1988, 44(12), 3595-605

2-Propenoic acid,2-bromo-, 1,1-dimethylethyl ester Raw materials

• tert-butyl 2,3-dibromopropanoate

2-Propenoic acid,2-bromo-, 1,1-dimethylethyl ester Preparation Products

• 2-Propenoic acid,2-bromo-, 1,1-dimethylethyl ester (79762-78-0)

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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Carboxylic acid esters
• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Carboxylic acid derivatives Carboxylic acid esters

Introduction to 2-Propenoic acid, 2-bromo-, 1,1-dimethylethyl ester (CAS No. 79762-78-0) and Its Emerging Applications in Chemical Biology

The compound 2-Propenoic acid, 2-bromo-, 1,1-dimethylethyl ester, identified by the CAS number 79762-78-0, is a specialized organic ester that has garnered significant attention in the field of chemical biology due to its unique structural and functional properties. This compound belongs to the class of α,β-unsaturated carboxylic acid esters, characterized by a conjugated system of a double bond and a carboxylate ester group. The presence of a bromine substituent at the α-position and a tert-butyl ester group at the carboxyl position imparts distinct reactivity and utility in synthetic chemistry and biological applications.

Recent advancements in the field of medicinal chemistry have highlighted the importance of such functionalized esters in drug discovery and development. The bromo-substituted propenoic acid ester serves as an excellent intermediate in the synthesis of more complex molecules, particularly in the construction of heterocyclic scaffolds that are prevalent in biologically active compounds. The tert-butyl group not only enhances the stability of the molecule during synthetic transformations but also influences its solubility and metabolic behavior, making it a valuable building block for pharmacological investigations.

One of the most compelling aspects of CAS No. 79762-78-0 is its role in the development of novel bioactive molecules. Researchers have leveraged its reactivity to introduce diverse functional groups into target structures, facilitating the creation of libraries for high-throughput screening. The bromine atom, in particular, serves as a versatile handle for further modifications via cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings, enabling the rapid assembly of complex organic architectures.

In the realm of natural product synthesis, this compound has been employed to mimic key structural motifs found in bioactive natural products. For instance, its incorporation into thiazole or pyrazole derivatives has led to the discovery of compounds with promising biological activities. The conjugated unsaturated system enhances electronic delocalization, which can be critical for interactions with biological targets such as enzymes or receptors. This property has been exploited in designing molecules with enhanced binding affinity and selectivity.

The pharmaceutical industry has also shown interest in 2-Propenoic acid, 2-bromo-, 1,1-dimethylethyl ester due to its potential as a precursor for drug candidates targeting various diseases. Its structural features make it amenable to modifications that can fine-tune pharmacokinetic properties such as bioavailability and metabolic stability. Additionally, computational studies have suggested that derivatives of this compound may exhibit desirable pharmacological profiles when incorporated into specific therapeutic scaffolds.

From a synthetic chemistry perspective, the reactivity of CAS No 79762-78-0 is well-suited for modern methodologies that emphasize efficiency and sustainability. Transition-metal-catalyzed reactions have been particularly useful in elaborating its structure, allowing for rapid diversification without excessive waste generation. This aligns with broader trends in green chemistry, where minimizing hazardous byproducts and maximizing atom economy are paramount.

The versatility of this compound extends to material science applications as well. Researchers have explored its use in polymer chemistry, where it can serve as a monomer or cross-linking agent to generate materials with tailored properties. The presence of both reactive double bonds and functional ester groups allows for controlled polymerization techniques such as radical or cationic polymerization, leading to materials with potential uses ranging from coatings to biodegradable polymers.

Recent studies have also begun to investigate the potential applications of this compound in agrochemicals. Its structural framework is reminiscent of certain herbicides and fungicides that have demonstrated efficacy in crop protection. By modifying its side chains or introducing additional functional groups, chemists aim to develop next-generation agrochemicals that are more effective against pests while being environmentally benign.

The synthesis of CAS No 79762-78-0 itself presents an interesting challenge due to its sensitivity to hydrolysis and oxidation under certain conditions. However, advances in synthetic techniques have made it more accessible than ever before. Modern protocols often involve careful control over reaction conditions—such as temperature gradients or inert atmospheres—to ensure high yields and purity levels suitable for downstream applications.

In conclusion,2-Propenoic acid, 2-bromo-, 1,1-dimethylethyl ester (CAS No. 79762-78-0) represents a multifaceted compound with broad utility across multiple disciplines within chemical science. Its unique combination of structural features makes it an invaluable tool for synthetic chemists seeking novel molecular architectures while offering researchers in pharmaceuticals and materials science opportunities for innovation-driven discovery.

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