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77-76-9 - 2,2-Dimethoxypropane, 98% - Acetone dimethyl acetal - A13810 - Alfa Aesar

A13810 2,2-Dimethoxypropane, 98%

CAS Number
77-76-9
Synonyms
Acetone dimethyl acetal

Size Price ($) Quantity Availability
100ml 16.92
500ml 35.66
2500ml 114.33
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2,2-Dimethoxypropane, 98%

MDL
MFCD00008479
EINECS
201-056-0

Chemical Properties

Formula
(CH3O)2C(CH3)2
Formula Weight
104.15
Melting point
-47°
Boiling Point
79-81°
Flash Point
-11°(12°F)
Density
0.848
Refractive Index
1.3780
Solubility
Soluble in benzene, carbon tetrachloride, ethyl ether and n-butane, methanol. Moderately soluble in water.

Applications

2,2-Dimethoxypropane acts as a dehydrating agent. It also serves as an intermediate in the synthesis of vitamin E, vitamin A and various carotenoids such as astaxanthin. It is used as a reagent for the preparation of 1,2-diols, acetonides, isopropylidene derivatives of sugars, nucleosides, methyl esters of amino acids and enol ethers.

Notes

Incompatible with oxidizing agents and acids.

Literature References

Methoxylating agent for preparation of acetals by acid-catalyzed exchange: J. Org. Chem., 25, 521 (1960). Also used as a water-scavenger in the preparation of acetals from higher-boiling alcohols and ketones: Org. Synth. Coll., 5, 292 (1973).

Widely used for the isopropylidenation of diols; see, e.g.: Org. Synth. Coll., 9, 450, 717 (1998). Isopropylidenation of acid-sensitive carbohydrates in the presence of 2,3-Dichloro-5,6-dicyanobenzoquinone, A11879: Acta Chem. Scand., 47, 843 (1993); preparation of acyclic mixed acetals of carbohydrates: Acta Chem. Scand., 48, 80 (1994). For use in the cyclization of N-Boc serine methyl ester to the oxazolidine, see: Org. Synth. Coll., 9, 300 (1998).

Methyl ester hydrochlorides of amino acids can be conveniently prepared with excess reagent in combination with conc. HCl. Water is removed in situ, thus displacing the equilibrium in favor of the ester: J. Org. Chem., 28, 3898 (1963). Methyl esters of non-aromatic acids can also be prepared with the reagent in MeOH with a catalytic amount of HCl or TMS chloride: Tetrahedron Lett., 38, 2685 (1997).

/n

Urosa, A.; Marcos, I. S.; Díez, D.; Padrón, J. M.; Pilar Basabe, P. Synthesis of Luffarin L and 16-epi-Luffarin L Using a Temporary Silicon-Tethered Ring-Closing Metathesis Reaction. J. Org. Chem. 2015, 80 (12), 6447-6455.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H319

Highly flammable liquid and vapour. Causes serious eye irritation.

Precautionary Statements: P210-P305+P351+P338

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Other References

Beilstein
635678
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2911.00
TSCA
Yes

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