(3-methyloxetan-3-yl)methanol

• ChemBase ID: 67660
• Molecular Formular: C5H10O2
• Molecular Mass: 102.1317
• Monoisotopic Mass: 102.06807956
• SMILES: C(O)C1(COC1)C
• Canonical SMILES: OCC1(C)COC1
• InChI: InChI=1S/C5H10O2/c1-5(2-6)3-7-4-5/h6H,2-4H2,1H3
• InChIKey: NLQMSBJFLQPLIJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-methyloxetan-3-yl)methanol
• IUPAC Traditional name: (3-methyloxetan-3-yl)methanol
• Synonyms: 3-Hydroxymethyl-3-methyl-oxetane; 3-Methyl-3-oxetanemethanol; (3-Methyloxetan-3-yl)methanol; 3-METHYL-3-OXETANEMETHANOL; 3-Hydroxymethyl-3-methyloxetane; 3-羟甲基-3-甲基氧杂环丁烷; 3-甲基-3-羟甲基氧杂环丁烷; 3-甲基-3-氧杂环丁烷甲醇

Database IDs

• CAS Number: 3143-02-0
• EC Number: 000-000-0
• MDL Number: MFCD00010273
• Beilstein Number: 102773
• PubChem SID: 162033395; 24856780
• PubChem CID: 137837

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.2961118
• LogD (pH = 7.4): -0.2961118
• Log P: -0.2961118
• Molar Refractivity: 26.4429 cm^3
• Polarizability: 10.544464 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 14.977656

PROPERTIES

Physical Property

• Boiling Point: 79-80°C/40mm; 80 °C/40 mmHg(lit.)
• Flash Point: 206.6 °F; 97 °C; 98°C(208°F)
• Density: 1.02 g/ml; 1.024; 1.024 g/mL at 25 °C(lit.)
• Refractive Index: 1.4460; n20/D 1.446(lit.)

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 43
• Safety Statements: 36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 95+%; 97%; 98%
• Empirical Formula (Hill Notation): C5H10O2

DETAILS

MP Biomedicals - 02155616

1 ml = approx. 1.02 g

Sigma Aldrich - 277681

Application
Carboxyl protecting group used recently in a synthesis of δ-lactams.1
Packaging
10, 50 g in glass bottle

REFERENCES

• Reacts with nucleophiles to give 2-substituted 2-methyl-1,3-propanediols; e.g. dialkylamines, on heating under pressure at 180^o, give 2-(N,N-dialkylaminomethyl)-2-methylpropane-1,3-diols, and aqueous hydrogen halides give the corresponding 2-halomethyl compounds: Liebigs Ann. Chem., 365 (1973).
• Valuable protecting agent for carboxylic acids, introduced by Corey. The oxetane ester, formed from the acid chloride, rearranges with BF₃ etherate to the bridged 2,6,7-trioxabicyclo[2.2.2]octane [OBO] orthoester, stable to strong bases and nucleophiles, e.g. Grignards, but readily cleaved by mild acid, followed by saponification of the ester: J. Am. Chem. Soc., 103, 4618 (1991); 106, 2735 (1984); Tetrahedron Lett., 23, 1651 (1982); 24, 5571 (1983); 27, 2199 (1986):