1-Bromoadamantane is the

organobromine compound Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromometh ...

with the formula (CH₂)₆(CH)₃CBr. A colorless solid, the compound is a

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

adamantane Adamantane is an organic compound with formula C10H16 or, more descriptively, (CH)4(CH2)6. Adamantane molecules can be described as the fusion of three cyclohexane rings. The molecule is both rigid and virtually stress-free. Adamantane is the mo ...

with a bromine atom at one of the four equivalent

methine In organic chemistry, a methine group or methine bridge is a trivalent functional group , derived formally from methane. It consists of a carbon atom bound by two single bonds and one double bond, where one of the single bonds is to a hydrogen. ...

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. It reacts with

phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...

to give para-adamantylphenol. 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 Grignard reagents or Grignard compounds are chemical compounds with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromi ...

References

Organobromides Adamantanes {{Organohalide-stub