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3143-02-0 - 3-Methyl-3-oxetanemethanol, 97% - 3-Hydroxymethyl-3-methyloxetane - B25111 - Alfa Aesar

B25111 3-Methyl-3-oxetanemethanol, 97%

CAS Number
3143-02-0
Synonyms
3-Hydroxymethyl-3-methyloxetane

Size Price ($) Quantity Availability
25g 58.50
100g 188.00
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3-Methyl-3-oxetanemethanol, 97%

MDL
MFCD00010273
EINECS
000-000-0

Chemical Properties

Formula
C5H10O2
Formula Weight
102.13
Boiling Point
79-80°/40mm
Flash Point
98°(208°F)
Density
1.024
Refractive Index
1.4460
Solubility
Soluble in chloroform, methanol.

Applications

3-Methyl-3-oxetanemethanol has been used in the preparation of star-shaped copolymer consisting of a hyperbranched poly(3-methyl-3-oxetanemethanol) core and polytetrahydrofuran arms, pyridyl disulfide-functionalized cyclic carbonate monomer, required for the synthesis of of functional poly(ε-caprolactone) containing pendant pyridyl disulphide groups and δ-lactams. It is used to synthesize octahydroindole alkaloids and γ-butenolides.

Notes

Protect from heat. Store away from oxidizing agents. Store at 4°C.

Literature References

Jian Hou and Deyue Yan. Synthesis of a Star-Shaped Copolymer with a Hyperbranched Poly(3-methyl-3-oxetanemethanol) Core and Tetrahydrofuran Arms by One-Pot Copolymerization. Macromolecular Rapid Communications.2002, 23, 456-459.

Bhooma Raghavan; Rodney L Johnson. Short stereoselective synthesis of alpha-substituted gamma-lactams. Journal of Organic Chemistry .2006, 71, (5), 2151-2154.

Reacts with nucleophiles to give 2-substituted 2-methyl-1,3-propanediols; e.g. dialkylamines, on heating under pressure at 180o, 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):

Other References

Beilstein
102773
Harmonized Tariff Code
2932.99
TSCA
No

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