5889-54-3

Basic information

• Product Name: Bicyclo(2.2.1)hept-2-ene, 5-bromo-, exo-
• Synonyms: Bicyclo(2.2.1)hept-2-ene, 5-bromo-, exo-
• CAS NO: 5889-54-3
• Molecular Formula: C₇H₉Br
• Molecular Weight: 173.05036
• Mol File: 5889-54-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 187.7°Cat760mmHg
• Flash Point: 61.8°C
• Appearance: /
• Density: 1.533g/cm³
• Vapor Pressure: 0.858mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: Bicyclo(2.2.1)hept-2-ene, 5-bromo-, exo-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo(2.2.1)hept-2-ene, 5-bromo-, exo-(5889-54-3)
• EPA Substance Registry System: Bicyclo(2.2.1)hept-2-ene, 5-bromo-, exo-(5889-54-3)

Safety Data

• Hazardous Substances Data: 5889-54-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H9Br/c8-7-4-5-1-2-6(7)3-5/h1-2,5-7H,3-4H2

Upstream product

• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 593-60-2 Vinyl bromide 
• 542-92-7 cyclopenta-1,3-diene 
• 71338-98-2 p-Toluolsulfonsaeure-(6exo-brom-2exo-norbornyl)ester 
• 71338-98-2 p-Toluolsulfonsaeure-<6-endo-brom-2exo-norbornyl>ester 
• 71338-98-2 p-Toluolsulfonsaeure-<6endo-brom-2endo-norbornyl>ester 

Downstream Products

• 2534-77-2 exo-2-bromonorbornane 
• 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

The Surface Nature of Grignard Reagent Formation

The reaction of exo-2-norbornyl bromide with Rieke magnesium in ether at -70 deg C in the presence of tert-butyl alcohol-O-d gave exclusively exo-2-deuterionorbornane whereas the epimer endo-2-norbornyl bromide yielded a 1:1 mixture of endo- and exo-2-deu

Synthesis of some 1,2-Dihalogenonorbornanes

The synthesis of 1,2exo-dibromo-norbornane as well as the preparation of the configurational isomers of 2-bromo-1-iodo- and 2-chloro-1-iodo-norbornane are described.

Carbon Participation in the Solvolysis of 6-exo-substituted 2-exo- and 2-endo-Norbornyl p-Toluenesulfonates. Norbornanes Part 5

The solvolysis rates and products of the 6-exo-substituted 2-exo- 1a-1u, and 2-endo-norbornyl p-toluenesulfonates 2a-2u, have been determined.In general, the rate constants for 1 and 2 (log k) correlate well with the inductive constants ?qI of the substituents at C(6); however, their sensitivity to ?qI is much larger in the 2-exo-series 1 than in the 2-endo-series 2.This differential transmission of polar effects is the cause of decreasing 2-exo/2-endo rate ratios from 2388 for R=t-C4H9 to 0.37 for R=Br, i.e., with increasing electron attraction by the substituent.The high sensitivity of the rate constants for the 2-exo-p-toluenesulfonates 1 to ?qI indicates an unusually strong inductive interaction between C(6) and the incipient cationic center at C(2).This interaction is ascribed to the participation of the pentacoordinate C(6)-atom, i.e. to 1,3-bridging, a consequence of steric hindrance of nucleophilic solvent participation in norbornanes.Donor substituents enhanche 1,3-bridging, lead to faster reactions and to the formation of 2-exo substitution products.Conversely, acceptor substituents reduce 1,3-bridging, decrease rates and facilitate the formation of 2-endo substitution products.Graded 1,3-bridging is discussed in the light of Winstein's nonclassical ion concept.