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294632

Sigma-Aldrich

Methyl dimethoxyacetate

97%

Synonym(s):

Glyoxylic acid methyl ester dimethyl acetal

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About This Item

Linear Formula:
(CH3O)2CHCOOCH3
CAS Number:
89-91-8
Molecular Weight:
134.13
Beilstein:
1757582
EC Number:
201-950-0
MDL number:
MFCD00008484
UNSPSC Code:
12352100
PubChem Substance ID:
24857724
NACRES:
NA.22

Assay

97%

refractive index

n20/D 1.405 (lit.)

bp

67 °C/18 mmHg (lit.)

density

1.096 g/mL at 25 °C (lit.)

functional group

acetal
ester
ether

storage temp.

2-8°C

SMILES string

COC(OC)C(=O)OC

InChI

1S/C5H10O4/c1-7-4(6)5(8-2)9-3/h5H,1-3H3

InChI key

NZTCVGHPDWAALP-UHFFFAOYSA-N

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Application

Methyl dimethoxyacetate has been used:
  • in Claisen acylation of active hydrogen compounds
  • in preparation of 3, 9-disubstituted 2,4,8,10-tetroxaspiro [5.5] undecane
  • as Lithium enolate precursor
  • as acylating reagent for cycloalkanone enolates and amino alcohols

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

152.6 °F - closed cup

Flash Point(C)

67 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000194516
0000190021
MKBJ8624V
MKBB9042
06208MH

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Tetrahedron, 46, 6799-6799 (1990)
Synthetic Communications, 23, 1003-1003 (1993)
Some 3, 9-Dicarboxylic Acids of 2, 4, 8, 10-Tetroxaspiro [5.5] undecane.
CLEMENTS JB and RICE LM.
The Journal of Organic Chemistry, 24(12), 1958-1961 (1959)
P J Connolly et al.
Journal of medicinal chemistry, 36(23), 3674-3685 (1993-11-12)
Compounds comprising a series of 7-[2-(4-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-3,5- dihydroxy-6-heptenoic acid sodium salts (18) were synthesized and tested for their ability to inhibit HMG-CoA reductase in a partially purified enzyme preparation and cholesterol biosynthesis from acetate in cultured HEP-G2 cells. Changing the size
Studies in Mixed Ester Condensations. IV. Acylations with Methyl Dimethoxyacetate1.
Royals EE and Robinson AG.
Journal of the American Chemical Society, 78(16), 4161-4164 (1956)

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