A | B | C | D | E | F | G | H | CH | I | J | K | L | M | N | O | P | Q | R | S | T | U | V | W | X | Y | Z | 0 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9
Names | |
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Preferred IUPAC name
1-Bromoadamantane | |
Other names
1-Adamantyl bromide, adamantane, 1-bromo-, adamantyl bromide, tricyclodecane, 1-bromo-
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Identifiers | |
3D model (JSmol)
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1098857 | |
ChemSpider | |
ECHA InfoCard | 100.011.091 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
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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
- ^ 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.
- ^ 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.
- ^ 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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