203176-36-7

Basic information

• Product Name: (E)-1-(2-Bromovinyl)-2-methoxybenzene
• Synonyms: 1-[(E)-2-Bromovinyl]-2-methoxy-benzene
• CAS NO: 203176-36-7
• Molecular Formula: C₉H₉BrO
• Molecular Weight: 213.074
• Mol File: 203176-36-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 267.4 °C at 760 mmHg
• Flash Point: 105.9 °C
• Density: 1.41 g/cm³
• CAS DataBase Reference: (E)-1-(2-Bromovinyl)-2-methoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(2-Bromovinyl)-2-methoxybenzene(203176-36-7)
• EPA Substance Registry System: (E)-1-(2-Bromovinyl)-2-methoxybenzene(203176-36-7)

Safety Data

• Hazardous Substances Data: 203176-36-7(Hazardous Substances Data)

Usage

Description

(E)-1-(2-Bromovinyl)-2-methoxybenzene, also known as o-Bromoeugenol, is a chemical compound with the formula C9H9BrO2. It is a derivative of eugenol, a phenolic compound found in various essential oils. (E)-1-(2-Bromovinyl)-2-methoxybenzene is a colorless to pale yellow liquid with a strong, sweet, spicy odor and is widely recognized for its applications in the synthesis of pharmaceuticals, organic compounds, and as a flavoring agent in the food and beverage industry.

Uses

Used in Flavor and Fragrance Industry:
(E)-1-(2-Bromovinyl)-2-methoxybenzene is used as a flavoring agent for its strong, sweet, spicy odor, adding unique taste and aroma to food and beverages.
Used in Pharmaceutical Synthesis:
(E)-1-(2-Bromovinyl)-2-methoxybenzene is used as an intermediate in the production of various pharmaceuticals, contributing to the development of new drugs and medicinal compounds.
Used in Organic Compounds Synthesis:
(E)-1-(2-Bromovinyl)-2-methoxybenzene serves as an intermediate in the synthesis of organic compounds, playing a crucial role in the creation of a diverse range of chemical products.
Used in Pesticide Production:
(E)-1-(2-Bromovinyl)-2-methoxybenzene is utilized in the production of pesticides, highlighting its versatility in different chemical applications.
Investigated for Biological Activities:
(E)-1-(2-Bromovinyl)-2-methoxybenzene has been explored for its potential antimicrobial and antioxidant properties, indicating its possible use in the development of new treatments and products in the healthcare and pharmaceutical sectors.

Upstream product

• 90585-32-3 1,1-dibromo-2-(2-methoxyphenyl)ethene 
• 135-02-4 ortho-anisaldehyde 
• 6099-03-2 3-(2'-methoxyphenyl)propenoic acid 
• 1011-54-7 2-methoxycinnamic acid 

Downstream Products

• 49550-23-4 9-(2-methoxybenzylidene)-9H-fluorene 
• 834-99-1 1-methoxyphenanthrene 
• 1136238-66-8 C₁₆H₁₆O 
• 1221429-39-5 5-(2-methoxyphenyl)-2-phenyl-1H-imidazole 
• 1612145-76-2 C₁₄H₁₆O₂ 
• 1612145-41-1 (R,E)-6-(2-methoxyphenyl)-2-phenylhex-5-en-3-yn-2-ol 
• 23517-08-0 (E)-1-(but-1-en-3-yn-1-yl)-2-methoxybenzene 
• 1206103-17-4 (1E,3E)-1-(4-hydroxy-3-methoxyphenyl)-4-(2-methoxyphenyl)-1,3-butadiene 
• 682356-47-4 tributyl(o-methoxystyryl)stannane 

Relevant articles and documents

Nickel-Catalyzed, Regio- and Enantioselective Benzylic Alkenylation of Olefins with Alkenyl Bromide

A NiH-catalyzed migratory hydroalkenylation reaction of olefins with alkenyl bromides has been developed, affording benzylic alkenylation products with high yields and excellent chemoselectivity. The mild conditions of the reaction preclude olefinic products from undergoing further isomerization or subsequent alkenylation. Catalytic enantioselective hydroalkenylation of styrenes was achieved by using a chiral bisoxazoline ligand.

Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization

A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.

Ultrasonically Assisted Decarboxylative Bromination of α,β-Unsaturated Carboxylic Acids under Vilsmeier-Haack Conditions

An efficient method for decarboxylative bromination of cinnamic acids (α,β-unsaturated carboxylic acids or 3-arylpropenoic acids) was achieved under relatively mild conditions using Vilsmeier-Haack reagent and KBr in acetonitrile media. Vilsmeier-Haack reagent is prepared by using 1:1 ratio of oxychloride (SOCl2 or POCl3) and DMF under chilled condition. Ultrasonically assisted reactions underwent smoothly with highly significant rate enhancements and afforded bromostyrenes as products in very good yields even though the reactions were too sluggish.