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MilliporeSigma

592498

Dimethyl itaconate

99%

Synonym(s):

2-(Methylene)butanedioic dimethyl ester

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25 G

$146.00

100 G

$482.00

$146.00


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About This Item

Linear Formula:
CH3O2CCH2C(=CH2)CO2CH3
CAS Number:
Molecular Weight:
158.15
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
210-519-6
Beilstein/REAXYS Number:
386674
MDL number:
Assay:
99%
Form:
solid

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InChI key

ZWWQRMFIZFPUAA-UHFFFAOYSA-N

InChI

1S/C7H10O4/c1-5(7(9)11-3)4-6(8)10-2/h1,4H2,2-3H3

SMILES string

COC(=O)CC(=C)C(=O)OC

assay

99%

form

solid

bp

208 °C (lit.)

mp

37-41 °C (lit.)

density

1.124 g/mL at 25 °C (lit.)

functional group

ester

Quality Level

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1 of 4

This Item
109533476196149012
assay

99%

assay

97%

assay

96%

assay

99%

bp

208 °C (lit.)

bp

208 °C (lit.)

bp

284 °C (lit.)

bp

268 °C (lit.)

form

solid

form

solid

form

-

form

liquid

mp

37-41 °C (lit.)

mp

37-41 °C (lit.)

mp

-

mp

-

density

1.124 g/mL at 25 °C (lit.)

density

1.124 g/mL at 25 °C (lit.)

density

0.985 g/mL at 25 °C (lit.)

density

1.014 g/mL at 25 °C (lit.)

functional group

ester

functional group

ester

functional group

-

functional group

ester

General description

Dimethyl itaconate can be synthesized via esterification of itaconic acid.[1]

Application

Dimethyl itaconate can be used for the rhodium catalyzed asymmetric hydrogenation of (S)-dimethyl-2-methylsuccinate[2] and (R)-methyl succinic acid dimethyl ester.[3]

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Skin Irrit. 2 - Skin Sens. 1B

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

212.0 °F - closed cup

flash_point_c

100 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)


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?Modification of poly(propylene) through grafting with dimethyl
itaconate in solution?
Yazdani-Pedram M, et al.
Macromolecular Chemistry and Physics, 199(11), 2495- 2500 (1998)
?New ferrocenyl ligands with broad applications in asymmetric catalysis?
Lotz M, et al.
Angewandte Chemie (International Edition in English), 41(24), 4708-4711 (2002)
"Catalytic asymmetric hydrogenation of dimethyl itaconate with trans-chelating chiral diphosphine ligands TRAP-rhodium complexes"
Kuwano R, et al.
Tetrahedron Asymmetry, 6(10), 2521- 2526 (1995)
Yepin Zhao et al.
Advanced materials (Deerfield Beach, Fla.), 32(17), e1907769-e1907769 (2020-03-10)
Intrinsically, detrimental defects accumulating at the surface and grain boundaries limit both the performance and stability of perovskite solar cells. Small molecules and bulkier polymers with functional groups are utilized to passivate these ionic defects but usually suffer from volatility
Vittoria Chimisso et al.
Langmuir : the ACS journal of surfaces and colloids, 35(41), 13413-13420 (2019-10-05)
Poly(N-vinylcaprolactam-co-itaconate) (P(VCL-co-IADME) microgels were synthesized varying the molar ratio between VCL and IADME via free radical precipitation polymerization in the presence of quaternary ammonium surfactant. In order to determine the effect of the divalent metal ions on the structure and

Questions

1–5 of 5 Questions  
  1. If I would like to dilute DMI for in vitro experiments, what solvent(s) would you recommend for proper dilution?

    1 answer
    1. This product is not tested directly for solubility in any solvent. An online search for solubility indicates this compound is soluble in ethanol, acetone, ether, methanol, chloroform, and ethyl acetate. Specific testing will be necessary to ensure this property.

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  2. I would like to ask whether it is possible to dilute in PBS or sterile water instead of DMSO. If so, would the storage conditions be the same as for the DMSO solution?

    1 answer
    1. This product has not been tested for solubility, solution stability, or storage requirements after dissolution in any of the mentioned solvents. The compound is reported to be water soluble at 35.1 g/L at 20 °C. Verification of these details through testing is necessary.

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  3. How to store 592498-25G which comes as liquid? alliquoted and store at -20C? How long it can be stored at this condition?which solvent to use to dilute it?

    1 answer
    1. The undiluted form of this product may be stored at room temperature. The stability of this material following dilution has not been evaluated. However, external source indicate that when diluted with an appropriate solvent such as DMSO, solutions may be stored at -20°C for 1 month or -80°C for 6 months.

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  4. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  5. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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