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6279-86-3 - Triethyl methanetricarboxylate, 98% - Methanetricarboxylic acid triethyl ester - Tris(carboethoxy)methane - L08356 - Alfa Aesar

L08356 Triethyl methanetricarboxylate, 98%

CAS Number
6279-86-3
Synonyms
Methanetricarboxylic acid triethyl ester
Tris(carboethoxy)methane

Size Price ($) Quantity Availability
5g 21.60
25g 62.50
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Triethyl methanetricarboxylate, 98%

MDL
MFCD00009150
EINECS
228-477-2

Chemical Properties

Formula
C10H16O6
Formula Weight
232.23
Melting point
26-29°
Boiling Point
253°
Flash Point
>110°(230°F)
Density
1.095
Refractive Index
1.4255
Solubility
Insoluble in water.

Applications

Methanetricarboxylates have been used as "blocked" malonic esters, restricting reaction with alkyl halides to monoalkylation. The unwanted carboxyl group can be removed by treatment with Na alkoxide, LDA or BCl3. Provides a useful 2-carbon chain extension method that adds to Michael acceptors under phase-transfer conditions. Triethyl Methanetricarboxylate is used in the synthesis of novel inhibitors of Hsp90. It is also used in the preparation of novel dihydroquinoline-3-carboxylic acids that function as HIV-1 integrase inhibitors.

Notes

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

Literature References

Giancarlo Cravotto, et al. Dehydrative alkylation of alcohols with triethyl methanetricarboxylate under Mitsunobu conditions.Tetrahedron.,1996,50(40), 13007-13016.

Teruaki Mukaiyama, et al. Stereoselective Carbon-Carbon Bond Forming Reactions between Various Chiral Alkyl Aryl Carbinols and Triethyl Methanetricarboxylate by Oxidation-Reduction Condensation Using Alkyl Diphenylphosphinites.Chem. Lett.,2005,34(12), 1676-1677.

Methanetricarboxylates have been used as "blocked" malonic esters, restricting reaction with alkyl halides to monoalkylation. The unwanted carboxyl group can be removed by treatment with Na alkoxide, LDA or BCl3: J. Org. Chem., 44, 3492 (1979). Adds to Michael acceptors under phase-transfer conditions, providing a useful 2-carbon chain extension method: Synthesis, 1125 (1990):

Under similar conditions, diethyl malonate gives only 36% yield.

The tricarboxylate also undergoes free-radical addition to the terminal position of alkenes: Angew. Chem. Int. Ed., 5, 586 (1966). Arylation with electron-rich aromatics is promoted by Mn(III): Synthesis, 567 (1991).

Other References

Beilstein
1793645
Harmonized Tariff Code
2917.19
TSCA
No

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