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B25686 2,5-Hexanedione, 97%

CAS Number
110-13-4
Synonyms
Acetonylacetone

Stock No. Size Price ($) Quantity Availability
B25686-14 25g 27.50
B25686-22 100g 54.00
B25686-36 500g 164.00
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2,5-Hexanedione, 97%

MDL
MFCD00008792
EINECS
203-738-3

Chemical Properties

Formula
C6H10O2
Formula Weight
114.15
Melting point
-6°
Boiling Point
192-193°
Flash Point
78°(172°F)
Density
0.976
Refractive Index
1.4250
Storage & Sensitivity
Ambient temperatures.
Solubility
Miscible with alcohol, water and diethyl ether.

Applications

2,5-Hexanedione is used as a reagent in the preparation of trans-2,5-dimethylpyrrolidine. It is also used in the synthesis of 2,5-dimethylpyrroles. Further, it plays an important role as a reagent used for the protection of amino groups in amino sugars and nucleosides. In addition to this, it is used in the preparation of five-membered heterocycles like indane-type and benzannulated systems. It is also employed as a precursor in Diels-alder cycloaddition reactions.

Notes

Incompatible with strong oxidizing agents, strong bases, metals and strong reducing agents.

Literature References

Primary amines can be protected by conversion to 2,5-dimethylpyrroles, from which they can be released by reaction with hydroxylamine hydrochloride: J. Chem. Soc., Perkin 1, 2801 (1984). The method has been found useful for protecting amino sugars in oligosaccharide synthesis: J. Org. Chem., 63, 4570 (1998), and also in the protection of an arylamine during Cu(I) promoted methoxylation of a ring bromo or iodo substituent; Synthesis, 1599 (1998).

Sacia, E. R.; Deaner, M. H.; Louie, Y. L.; Bell, A. T. Synthesis of biomass-derived methylcyclopentane as a gasoline additivevia aldol condensation/hydrodeoxygenation of 2,5-hexanedione. Green Chem. 2015, 17 (4), 2393-2397.

Chambon, F.; Rataboul, F.; Pinel, C.; Cabiac, A.; Guillon, E.; Essayem, N. Conversion of cellulose to 2,5-hexanedione using tungstated zirconia in hydrogen atmosphere. Appl. Catal., A 2015, 504, 664-671.

GHS Hazard and Precautionary Statements

Hazard Statements: H227-H315-H319-H373

Combustible liquid. Causes skin irritation. Causes serious eye irritation. May cause damage to organs through prolonged or repeated exposure.

Precautionary Statements: P210-P260-P264b-P280-P302+P352-P305+P351+P338-P314-P332+P313-P337+P313-P362-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Get medical advice/attention if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,71
Beilstein
506525
Harmonized Tariff Code
2914.19
TSCA
Yes
RTECS
MO3150000

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