7166-19-0

Basic information

• Product Name: (2-bromo-2-nitrovinyl)benzene
• Synonyms: (2-bromo-2-nitrovinyl)benzene;beta-bromo-beta-nitrostyrene;β-Bromo-β-nitrostyrene;Benzene, (2-bromo-2-nitroethenyl)-;b-Bromo-b-nitrostyrene.;BETA-BROMO-BETA-NITROSOSTYRENE;Slimitrole;1-Bromo-1-nitro-2-phenylethylene
• CAS NO: 7166-19-0
• Molecular Formula: C₈H₆BrNO₂
• Molecular Weight: 228.04274
• EINECS: 230-515-8
• Mol File: 7166-19-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 153℃ (ethyl acetate )
• Boiling Point: 285.1°Cat760mmHg
• Flash Point: 126.2°C
• Appearance: /
• Density: 1.6857 (rough estimate)
• Vapor Pressure: 0.00493mmHg at 25°C
• Refractive Index: 1.6120 (estimate)
• CAS DataBase Reference: (2-bromo-2-nitrovinyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (2-bromo-2-nitrovinyl)benzene(7166-19-0)
• EPA Substance Registry System: (2-bromo-2-nitrovinyl)benzene(7166-19-0)

Safety Data

• RIDADR: 2811
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 7166-19-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 4664, 1951 DOI: 10.1021/ja01154a051

Air & Water Reactions

(2-bromo-2-nitrovinyl)benzene is sensitive to moisture and prolonged exposure to light. (2-bromo-2-nitrovinyl)benzene is rapidly hydrolyzed in water. . Insoluble in water.

Reactivity Profile

A halogenated and nitrated aliphatic hydrocarbon. The unsaturated aliphatic hydrocarbons are generally much more reactive than the alkanes, which are saturated aliphatic hydrocarbons. Strong oxidizers may react vigorously with them. Reducing agents can react exothermically to release gaseous hydrogen.

Fire Hazard

(2-bromo-2-nitrovinyl)benzene is combustible.

InChI:InChI=1/C8H6BrNO2/c9-8(10(11)12)6-7-4-2-1-3-5-7/h1-6H

Upstream product

• 67-66-3 chloroform 
• 344319-06-8 N-(2-bromo-2-nitro-1-phenyl-ethyl)-p-toluidine 
• 7726-95-6 bromine 
• 7732-18-5 water 
• 18315-81-6 (Z)-2-bromo-2-nitro-1-phenylethene 
• 100-52-7 benzaldehyde 
• 102-96-5 (2-nitroethenyl)benzene 
• 563-70-2 bromonitromethane 
• 1077-18-5 N-benzylidenebutan-1-amine 
• 3425-99-8 (1,2-dibromo-2-nitroethyl)benzene 
• 103-64-0 bromostyrene 

Downstream Products

• 14645-81-9 1-Brom-1,3-dinitro-2-phenyl-pentan 
• 65899-65-2 1-Brom-1,1-dinitro-2-methoxy-2-phenylaethan 
• 28387-29-3 α-(N-benzoylamino)methyltriphenylphosphonium bromide 
• 27250-14-2 (1-Methoxy-2-nitro-1-propoxy-ethyl)-benzene 
• 112616-91-8 (Z)‐2‐(2‐nitro‐1‐phenylvinyl)‐1H‐pyrrole 
• 112616-86-1 1-methyl-2-(2-nitro-1-phenylethen-1-yl)pyrrole 
• 879-45-8 α,β-Dibromo-β-nitrostyrene 
• 875-73-0 α,β,β-tribromostyrene 

Relevant articles and documents

Organocatalytic Asymmetric Synthesis of Aza-Spirooxindoles via Michael/Friedel-Crafts Cascade Reaction of 1,3-Nitroenynes and 3-Pyrrolyloxindoles

An asymmetric [3+3] cyclization of nitroenynes and 3-pyrrolyloxindoles has been realized with a chiral bifunctional squaramide catalyst. This Michael/Friedel-Crafts cascade strategy provides a facile and efficient access to enantioenriched polycyclic aza-spirooxindoles with 32-95% isolated yields and excellent stereocontrol under mild reaction conditions.

A novel tandem sequence to pyrrole syntheses by 5-endo-dig cyclization of 1,3-enynes with amines

The synthesis of pentasubstituted pyrroles has been described using molecular iodine from 1,3-enynes and amines via a sequential tandem aza-Michael addition, iodocyclization, and oxidative aromatization. The protocol is simple and efficient to afford the target products at ambient conditions.

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