695-02-3

Basic information

• Product Name: NortricyclylBromide
• Synonyms: Tricyclo(2.2.1.0(2,6))heptane, 3-bromo-
• CAS NO: 695-02-3
• Molecular Formula: C₇H₉Br
• Molecular Weight: 173.052
• Mol File: 695-02-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 175.46°C (estimate)
• Flash Point: 57.2°C
• Appearance: /
• Density: 1.4658 (rough estimate)
• Vapor Pressure: 1mmHg at 25°C
• Refractive Index: 1.4878 (estimate)
• CAS DataBase Reference: NortricyclylBromide(CAS DataBase Reference)
• NIST Chemistry Reference: NortricyclylBromide(695-02-3)
• EPA Substance Registry System: NortricyclylBromide(695-02-3)

Safety Data

• Hazardous Substances Data: 695-02-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H9Br/c8-7-3-1-4-5(2-3)6(4)7/h3-7H,1-2H2

Upstream product

• 498-66-8 norborn-2-ene 
• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 7726-95-6 bromine 
• 593-60-2 Vinyl bromide 
• 542-92-7 cyclopenta-1,3-diene 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 87968-91-0 Toluene-4-sulfonic acid (1R,2R,4S,7S)-7-bromo-bicyclo[2.2.1]hept-2-yl ester 
• 87968-91-0 Toluene-4-sulfonic acid (1S,2R,4R,7R)-7-bromo-bicyclo[2.2.1]hept-2-yl ester 
• 17985-13-6 (bicyclo<2.2.1>hept-5-en-2-yl)trimethylsilane 

Downstream Products

• 136879-33-9 2,6-cyclo-norbornane-3-carbanilide 
• 10389-63-6 anti-7-bromo-exo-2-norbornyl acetate 
• 498-66-8 norborn-2-ene 
• 279-19-6 nortricyclane 
• 21942-28-9 3-nortricyclyltrimethyltin 
• 21957-51-7 endo-2-norbornene-5-yl-trimethyl tin 

Relevant articles and documents

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Regio- and stereochemical aspects of bromochlorination of norbornene

Bromochlorination of norbornene whose chemo- and regio-selectivity is determined by the type of the halogenating reagent used was studied. Three isomeric bromochloronorbornanes (2-endo-bromo-3-exo-chloro-, 2-exo-bromo-3-endo-chloro-, and 2-exo-bromo-7-syn-chlorobicyclo[2.2.1.]heptanes), 2-exo-7-syn- and 2-exo-7-anti-dibromo- and -dichloro-norbornanes, and 2-bromonortricyclane were isolated and characterized by 1H and 13C NMR spectra. The spectral and structural characteristics of the resulting compounds are discussed.

Efficient Utilization of Tetrabutylammonium Bifluoride in Halofluorination Reactions

The halofluorination reaction of a variety of alkenes by using tetrabutylammonium bifluoride (TBABF) in the presence of N-halosuccinimide is described.This process occurs stereospecifically to afford anti addition products, and with unsymmetrical olefins a marked Markovnikov-type regioselectivity is observed.In some cases, formation of a remarkable amount of the corresponding dihalo derivatives was found, but this undesirable side reaction can be avoided by using N-iodosucciniumide (NIS) as halogenating agent.If N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS) is utilized, these dihalo compounds can be easily removed from the halofluorinated compounds by simple column chromatography on silica gel.A mechanism for this side reaction is postulated.

Cross-linked Poly-(4-vinylpyridine-styrene)-Bromine Complexes as Stereoselective Brominating Agents

Cross-linked poly(styrene-4-vinylpyridine) beads, containing 40-43percent of pyridine rings, were transformed with bromine to provide three types of brominating agents (1), (2), and (3).Reactions of cis- and trans-1-phenylpropene with (1), (2), and (3) resulted in a high degree of anti-stereoselectivity.The reactivity increases from (1) to (3); solvent polarity had no significant effect on stereoselectivity, but affects the reactivity, being significantly greater in acetonitrile and chloroform than in cyclohexane and dioxan.Bromination of 1-phenylcyclohexene with (1) and (3) resulted in the formation of trans-1,2-dibromo-1-phenylcyclohexane (9) and 3-bromo-2-phenylcyclohexene (10), the temperature affecting only the ratio of the products.Bromonation of norbornene with the reagents (1), (2) and (3) resulted in the formation of seven products: 2-exo-bromonorbornane (12), 7-bromonortricyclane (13), 2-exo,3-endo-dibromonorbornane (14), 2-exo-7-anti-dibromonorbornane (15), 2-exo,5-endo-dibromonorbornane (16), 2-exo,5-exo-dibromonorbornane (17), and 2-exo,7-syn-dibromonorbornane (18).