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29943-42-8 - Tetrahydro-4H-pyran-4-one, 98% - A19010 - Alfa Aesar

A19010 Tetrahydro-4H-pyran-4-one, 98%

CAS Number
29943-42-8
Synonyms

Size Price ($) Quantity Availability
1g 34.00
5g 113.69
25g 518.40
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Tetrahydro-4H-pyran-4-one, 98%

MDL
MFCD00006581
EINECS
249-967-2

Chemical Properties

Formula
C5H8O2
Formula Weight
100.12
Boiling Point
165-167°
Flash Point
62°(144°F)
Density
1.084
Refractive Index
1.4530
Solubility
Very soluble in water.

Applications

It is employed in the preparation of 4-methoxytetrahydropyran-4-yl protecting group, synthesis of symmetric tetra substituted methanes. The methyl enol ether is a useful protecting agent for alcohols, e.g. in nucleotide synthesis, with the advantage over 3,4-Dihydro-2H-pyran. It is also employed in a study of the enantioselective alpha-aminoxylation of ketones with nitrosobenzene and L-proline in an ionic liquid. It undergoes condensation reactions in the preparation of dipeptides and spiroimidazolones. It is also employed in wittig reactions for the synthesis of Penicillins and in a ring of vitamin D3

Notes

Store away from strong bases and oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.

Literature References

Colin B. Reese.; R. Saffhill.; J. E. Sulston. Symmetrical alternative to the tetrahydropyranyl protecting group.J. Am. Chem. Soc.,1967,89(13), 3366-3368.

George R. Newkome.; Sadao Arai.; V. K. Gupta.; Rodger W. Griffin. Chemistry of micelles series. 4. A convenient synthesis of tetrakis(2-bromoethyl)methane.J. Org. Chem.,1987,52(24), 5480-5482.

The methyl enol ether is a useful protecting agent for alcohols, e.g. in nucleotide synthesis, with the advantage over 3,4-Dihydro-2H-pyran, L02731, that no new asymmetric center is introduced on reaction with a chiral alcohol: J. Am. Chem. Soc., 89, 3366 (1967); Tetrahedron, 26, 1023, 1031 (1970).

GHS Hazard and Precautionary Statements

Hazard Statements: H227

Combustible liquid.

Precautionary Statements: P210-P280-P370+P378a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. In case of fire: Use for extinction: CO2, powder or water spray. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
106463
Harmonized Tariff Code
2932.99
TSCA
No

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