dicyclopropylmethanol

• ChemBase ID: 301896
• Molecular Formular: C7H12O
• Molecular Mass: 112.16958
• Monoisotopic Mass: 112.088815
• SMILES: C1CC1C(C1CC1)O
• Canonical SMILES: OC(C1CC1)C1CC1
• InChI: InChI=1S/C7H12O/c8-7(5-1-2-5)6-3-4-6/h5-8H,1-4H2
• InChIKey: PIXLZMHERIHLJL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dicyclopropylmethanol
• IUPAC Traditional name: dicyclopropyl carbinol
• Synonyms: Dicyclopropyl carbinol; Dicyclopropylmethanol; 二环丙基甲醇

Database IDs

• CAS Number: 14300-33-5
• EC Number: 238-236-3
• MDL Number: MFCD00019249
• Beilstein Number: 2203215

CALCULATED PROPERTIES

• Acid pKa: 18.779552
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.1023445
• LogD (pH = 7.4): 1.1023445
• Log P: 1.1023445
• Molar Refractivity: 31.8155 cm^3
• Polarizability: 12.7828245 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 99-100°C/12mm
• Flash Point: >110°C(230°F)
• Refractive Index: 1.4650

Safety Information

• TSCA Listed: 否

Product Information

• Purity: 97%

REFERENCES

• Esters of this alcohol undergo extremely rapid solvolysis under mildly acidic conditions such as 1% TFA in dichloromethane. This is due to the effective stabilization of a cation ɑAlpha/D to the cyclopropyl group. Carpino has shown that the dicyclopropylmethyl (Dcpm) group is therefore a potentially very useful, low molecular weight protecting group for the carboxyl function, particularly in peptide synthesis; selective removal in the presence of such acid-sensitive groups as t-butyl, N-Trt, etc. can be achieved: J. Org. Chem., 60, 7718 (1995). See Appendix 6.