1-bromoadamantane

• ChemBase ID: 80001
• Molecular Formular: C10H15Br
• Molecular Mass: 215.1301
• Monoisotopic Mass: 214.03571248
• SMILES: BrC12CC3CC(C1)CC(C2)C3
• Canonical SMILES: BrC12CC3CC(C2)CC(C1)C3
• InChI: InChI=1S/C10H15Br/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6H2
• InChIKey: VQHPRVYDKRESCL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-bromoadamantane
• IUPAC Traditional name: 1-bromoadamantane
• Synonyms: 1-bromoadamantane; 1-BROMO ADAMANTANE; 1-Adamantyl bromide; 1-Bromoadamantane; 1-溴金刚烷

Database IDs

• CAS Number: 768-90-1
• EC Number: 212-200-7
• MDL Number: MFCD00074721
• Beilstein Number: 1098857
• PubChem SID: 162067121
• PubChem CID: 79106

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.1129165
• LogD (pH = 7.4): 3.1129165
• Log P: 3.1129165
• Molar Refractivity: 49.9126 cm^3
• Polarizability: 19.623222 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 116-118°C; 117-121°C

Safety Information

• TSCA Listed: 否

Product Information

• Purity: 98%; 99%

DETAILS

MP Biomedicals - 05221753

MP Biomedicals Rare Chemical collection

REFERENCES

• Reduction with Tri-n-butyltin hydride, A13298, generates the 1-adamantyl radical which, e.g. adds to Michael acceptors in good yield: J. Org. Chem., 53, 1285 (1988).
• With activated Ca metal (prepared from CaBr₂ and Li biphenylide), forms an organocalcium reagent which reacts with ketones to give tertiary alcohols; the preparation and reactivity of these intermediates is discussed: Org. Synth. Coll., 9, 9 (1998).
• Undergoes Heck-type coupling with styrenes and arenes, catalyzed by Pd on carbon: Synthesis, 148 (1998).