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305847

Sigma-Aldrich

Dihydro-4,4-dimethyl-2,3-furandione

97%

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About This Item

Empirical Formula (Hill Notation):
C6H8O3
CAS Number:
Molecular Weight:
128.13
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

solid

mp

67-69 °C (lit.)

solubility

dichloromethane: soluble 25 mg/mL, clear, colorless to yellow

SMILES string

CC1(C)COC(=O)C1=O

InChI

1S/C6H8O3/c1-6(2)3-9-5(8)4(6)7/h3H2,1-2H3

InChI key

HRTOQFBQOFIFEE-UHFFFAOYSA-N

General description

Dihydro-4,4-dimethyl-2,3-furandione is an activated keto compound and its enantioselective hydrogenation was reported. Neutral Rhodium (I) aminophosphine-phosphinite complex calatyzed asymmetric hydrogenation of dihydro-4,4-dimethyl-2,3-furandione was reported. Asymmetric hydrogenation of dihydro-4,4-dimethyl-2,3-furandione gives D-(-)-pantoyl lactone, a key intermediate in the synthesis of pantothenic acid.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Neutral Rhodium (I) Aminophosphine-Phosphinite Complexes: Synthesis, Structure, and Use in Catalytic Asymmetric Hydrogenation of Activated Keto Compounds.
Agbossou F, et al.
Organometallics, 14(5), 2480-2489 (1995)
Organic Syntheses, 63, 18-18 (1985)
S Shimizu et al.
European journal of biochemistry, 174(1), 37-44 (1988-05-16)
A novel enzyme which specifically catalyzes the reduction of conjugated polyketones was purified to homogeneity from cells of Mucor ambiguus AKU 3006. The enzyme has a strict requirement for NADPH and irreversibly reduces a number of quinones such as p-benzoquinone
Norberto Bonalumi et al.
Journal of the American Chemical Society, 125(44), 13342-13343 (2003-10-30)
The combination of ATR-IR and modulation spectroscopy allowed for the study of the interaction of ketopantolactone with Pt/Al2O3 films chirally modified by cinchonidine under hydrogenation conditions. The spectra reveal a significant influence of ketopantolactone on the adsorption of the modifier
Rhodium (I) bis (aminophosphane) complexes as catalysts for asymmetric hydrogenation of activated ketones.
Roucoux A, et al.
Tetrahedron Asymmetry, 7(2), 379-382 (1996)

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