1-Bromoadamantane
Names
Preferred IUPAC name
1-Bromoadamantane
Other names
1-Adamantyl bromide, adamantane, 1-bromo-, adamantyl bromide, tricyclo[3.3.1.1(3,7)]decane, 1-bromo-
Identifiers
3D model (JSmol)
1098857
ChemSpider
ECHA InfoCard 100.011.091
EC Number
  • 230-777-3
UNII
  • InChI=1S/C10H15Br/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6H2
    Key: VQHPRVYDKRESCL-UHFFFAOYSA-N
  • InChI=1/C10H15Br/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6H2
    Key: VQHPRVYDKRESCL-UHFFFAOYAL
  • C1C2CC3CC1CC(C2)(C3)Br
Properties
C10H15Br
Molar mass 215.134 g·mol−1
Appearance Solid
Melting point 117 °C (243 °F)
Boiling point 226 °C (439 °F)
Insoluble
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
1
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1-Bromoadamantane is the organobromine compound with the formula (CH2)6(CH)3CBr. A colorless solid, the compound is a derivative of adamantane with a bromine atom at one of the four equivalent methine positions.

Reactions

Although of no commercial value, 1-bromoadamantane has often been employed for testing methodology. Hydrolysis of this bromide gives the alcohol 1-hydroxyadamantane.[1]

It reacts with phenol to give para-adamantylphenol.[2]

Classified as a tertiary alkyl bromide, it is reluctant to form organometallic derivatives. With Rieke calcium however it forms the organocalcium derivative, which functions like a Grignard reagent.[3]

References

  1. ↑ Ōsawa, Eiji (1974). "Bromination of adamantane and bicyclo(2.2.2)octane with liquid bromine". Tetrahedron Letters. 15: 115–117. doi:10.1016/S0040-4039(01)82150-X.
  2. ↑ V. Prakash Reddy. G. K. Surya Prakash (2003). "Electrophilic reactions of phenols". In Zvi Rappoport (ed.). The Chemistry of Phenols. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. pp. 605–660. doi:10.1002/0470857277.ch9. ISBN 0471497371.
  3. ↑ Reuben D. Rieke; Tse-Chong Wu; Loretta I. Rieke (1995). "Highly Reactive Calcium for the Preparation of Organocalcium Reagents: 1-Adamantyl Calcium Halides and Their Addition to Ketones: 1-(1-Adamantyl)cyclohexanol". Organic Syntheses. 72: 147. doi:10.15227/orgsyn.072.0147.



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