[2-(hydroxymethyl)phenyl]methanol

• ChemBase ID: 88138
• Molecular Formular: C8H10O2
• Molecular Mass: 138.1638
• Monoisotopic Mass: 138.06807956
• SMILES: OCc1ccccc1CO
• Canonical SMILES: OCc1ccccc1CO
• InChI: InChI=1S/C8H10O2/c9-5-7-3-1-2-4-8(7)6-10/h1-4,9-10H,5-6H2
• InChIKey: XMUZQOKACOLCSS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(hydroxymethyl)phenyl]methanol
• IUPAC Traditional name: 1,2-benzenedimethanol
• Synonyms: 1,2-Bis(hydroxymethyl)benzene; o-Xylene-α,α′-diol; 1,2-Benzenedimethanol; Benzene-1,2-diyldimethanol; o-Xylene-alpha,alpha'-diol; Phthalyl alcohol; 1,2-Bis(hydroxymethyl)benzene 98%; 1,2-双(羟基甲基)苯; 邻二甲苯-α,α′-二醇; 邻苯二甲醇; 1,2-苯二甲醇; 邻苯二甲醇

Database IDs

• CAS Number: 612-14-6
• EC Number: 210-293-9
• MDL Number: MFCD00004626
• Beilstein Number: 508775
• PubChem SID: 24847532; 162075170; 24851134
• PubChem CID: 69153

CALCULATED PROPERTIES

• Acid pKa: 14.62035
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.43854627
• LogD (pH = 7.4): 0.43854624
• Log P: 0.43854627
• Molar Refractivity: 39.6898 cm^3
• Polarizability: 15.235643 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 59-64°C; 61-64 °C; 63-65 °C(lit.); 63-65°C

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95.0% (HPLC); 97%
• Grade: purum
• Linear Formula: C6H4(CH2OH)2

DETAILS

Sigma Aldrich - 184829

Packaging
1, 10 g in glass bottle

Sigma Aldrich - 12570

Other Notes
Reagent for the protection of carbonyl compounds as 7-membered acetals1,2

REFERENCES

• The 7-membered cyclic orthoformates, formed with triethyl or trimethyl orthoformate, are superior reagents for the protection of carbonyl groups as their 2,4-benzodioxepine derivatives. These can be readily cleaved in high yield by Pd-catalyzed hydrogenolysis: Tetrahedron Lett., 30, 4165 (1989); J. Am. Chem. Soc., 116, 558 (1994).
• Has also been employed for the protection of boronic acids, by reaction in THF in the presence of a dehydrating agent, e.g. Na₂SO₄. These derivatives can be readily cleaved by hydrogenolysis or hydrolysis: Tetrahedron Lett., 37, 6705 (1996).