adamantane-1-carboxylic acid

• ChemBase ID: 63993
• Molecular Formular: C11H16O2
• Molecular Mass: 180.24354
• Monoisotopic Mass: 180.11502975
• SMILES: C12CC3(CC(CC(C1)C3)C2)C(=O)O
• Canonical SMILES: OC(=O)C12CC3CC(C2)CC(C1)C3
• InChI: InChI=1S/C11H16O2/c12-10(13)11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2,(H,12,13)
• InChIKey: JIMXXGFJRDUSRO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: adamantane-1-carboxylic acid
• IUPAC Traditional name: adamantanecarboxylic acid
• Synonyms: (3r,5r,7r)-adamantane-1-carboxylic acid; 1-Adamantanecarboxylic acid; 1-Carboxyadamantane; Tricyclo[3.3.1.1~3,7~]decane-1-carboxylic acid; Adamantane-1-carboxylic acid 99%; adamantane-1-carboxylic acid; Adamantane-1-carboxylic acid; 金刚烷-1-甲酸

Database IDs

• CAS Number: 828-51-3
• EC Number: 212-584-6
• MDL Number: MFCD00074720
• Beilstein Number: 1910637
• PubChem SID: 162029732
• PubChem CID: 13235

CALCULATED PROPERTIES

• Acid pKa: 4.6242127
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.4506795
• LogD (pH = 7.4): -0.3262101
• Log P: 2.3797762
• Molar Refractivity: 48.3883 cm^3
• Polarizability: 19.32288 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 172-176°C; 173-176°C

Safety Information

• Storage Warning: IRRITANT; Irritant
• RTECS: AU4452200
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: >95%; 95+%; 97%; 99%

REFERENCES

• Reaction with alkaline permanganate gives the 3-hydroxy derivative in good yield. Further modification leads to 1,3-disubstituted adamantanes: Synth. Commun., 18, 1967 (1988):