1-Bromoadamantane

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
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 Edit this at Wikidata
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 diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

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