26735-82-0

Usage

Classification

Aromatic compound

Uses

Synthesis of pharmaceutical and agrochemical compounds, production of polymers and resins

Contains a bromoMethyl group

Versatile building block for further chemical reactions

Potential role

Intermediate in the manufacturing of various organic compounds and materials

Upstream product

• 4167-06-0 2-bromo-2-(bromomethyl)succinic acid 
• 97-65-4 2-methylenesuccinic acid 
• 2170-03-8 itaconic acid anhydride 
• 32793-59-2 3-bromo-3-(bromomethyl)dibromofuran-2,5-dione 
• 616-02-4 citraconic acid anhydride 

Downstream Products

• 2212-99-9 (+/-)-marasmic acid 
• 150240-39-4 chaetomellic anhydride A 
• 493-46-9 tetrahydro-4-methylene-5-oxo-2-tridecyl-3-furancarboxylic acid 
• 493-46-9 dl-Alloprotolichesterinsaeure 

Relevant academic research and scientific papers

A synthesis of (±)-sparteine

In a synthesis of racemic sparteine, Diels Alder reaction between dimethyl bromomesaconate 14 and dicyclopentenyl 4, followed by cyclopropane formation, set up the stereochemistry at C-1 and C-5 as S and R, respectively, in a meso intermediate 8. The ster

Synthesis of spherical polyols from itaconic acid

The Diels-Alder reaction of some bromo derivatives of the itaconic acid with cyclopenta-1,3-diene gave a simple access to precursors of spherical polyols of synthetic interest. Georg Thieme Verlag Stuttgart - New York.

A facile synthesis of natural products chaetomellic acid A and 1,7(Z)-nonadecadiene-2,3-dicarboxylic acid

Synthesis of recently isolated bioactive natural products chaetomellic acid A anhydride (1) and a novel 1,7- (Z)-nonadecadiene-2,3-dicarboxylic acid (2) have been described. Chemoselective carbon-carbon SN2′ coupling reactions of appropriate Grignard reagents with dimethyl bromomethylfumarate (7) in diethyl ether in the presence of HMPA at room temperature furnished the corresponding diesters 8 and 15 in 60-62% yields. The formed diesters 8 and 15 on hydrolysis gave respectively the corresponding desired diacids 9 and 2 in quantitative yields. Acetic anhydride induced ring closure of diacids 9 and 2 respectively gave the chaetomellic acid A anhydride (1) and isochaetomellic acid B anhydride (16) with 38-39% overall yields in five steps.

FACILE SYNTHESIS OF 2-METHYLENE-4-BUTYROLACTONES

2-Methylene-4-butyrolactones were conveniently synthesized by treatment of an aldehyde with 2-carboethoxyallyl(-ic) bromide and metallic tin (and aluminium) in good yields.Protolichesterinic acid was synthesized by employing the method.