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242926

Sigma-Aldrich

Dimethyl fumarate

97%

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Linear Formula:
CH3OCOCH=CHCOOCH3
CAS Number:
Molecular Weight:
144.13
Beilstein:
774590
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

Assay

97%

form

solid

bp

192-193 °C (lit.)

mp

102-106 °C (lit.)

SMILES string

[H]\C(=C(\[H])C(=O)OC)C(=O)OC

InChI

1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+

InChI key

LDCRTTXIJACKKU-ONEGZZNKSA-N

Gene Information

human ... KEAP1(9817)

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This Item
50744PHR2118D95654
Dimethyl fumarate 97%

Sigma-Aldrich

242926

Dimethyl fumarate

Dimethyl fumarate certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

Supelco

50744

Dimethyl fumarate

Dimethyl Fumarate Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR2118

Dimethyl Fumarate

Diethyl fumarate 98%

Sigma-Aldrich

D95654

Diethyl fumarate

form

solid

form

-

form

-

form

liquid

bp

192-193 °C (lit.)

bp

192-193 °C (lit.)

bp

192-193 °C (lit.)

bp

218-219 °C (lit.)

mp

102-106 °C (lit.)

mp

102-106 °C (lit.)

mp

102-106 °C (lit.)

mp

1-2 °C (lit.)

Gene Information

human ... KEAP1(9817)

Gene Information

human ... KEAP1(9817)

Gene Information

human ... KEAP1(9817)

Gene Information

-

Application

Dimethyl fumarate can be used:
  • In the preparation of an adduct [dimethyl-(+)-(11R,12R)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate].
  • As a ligand in the synthesis of Ni(II)-based catalytic system applicable in the Negishi alkylations of N-sulfonyl aziridines with organozinc reagents.
  • As a ligand to synthesize zerovalent ruthenium metal complex namely Ru(η6-1,3,5-cyclooctatriene)(η2-dimethyl fumarate)2.

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Aquatic Chronic 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Importance of c*--h based modes and large amplitude motion effects in vibrational circular dichroism spectra: the case of the chiral adduct of dimethyl fumarate and anthracene
Passarello M, et al.
The Journal of Physical Chemistry A, 118, 4339-4350 (2014)
Ru (η6-1, 3, 5-cyclooctatriene)(η2-dimethyl fumarate) 2: a novel, versatile zerovalent ruthenium complex with electron-deficient olefinic ligands
Mitsudo T, et al.
Journal of Organometallic Chemistry, 689, 4530-4539 (2004)
Marco Passarello et al.
The journal of physical chemistry. A, 118(24), 4339-4350 (2014-05-21)
The role played by the C*-H based modes (C* being the chiral carbon atom) and the large amplitude motions in the vibrational absorption (VA) and vibrational circular dichroism (VCD) spectra is investigated. The example of an adduct of dimethyl fumarate
Giovanna Casili et al.
Journal of neurotrauma, 35(13), 1437-1451 (2018-01-25)
Traumatic brain injury (TBI) is a serious neuropathology that causes secondary injury mechanisms, including dynamic interplay between ischemic, inflammatory, and cytotoxic processes. Fumaric acid esters (FAEs) showed beneficial effects in pre-clinical models of neuroinflammation and toxic oxidative stress, so the
Chung-Yang Huang et al.
Journal of the American Chemical Society, 134(23), 9541-9544 (2012-03-15)
A nickel-catalyzed cross-coupling reaction between N-sulfonyl aziridines and organozinc reagents is reported. The catalytic system comprises an inexpensive and air-stable Ni(II) source and dimethyl fumarate as ligand. Regioselective synthesis of β-substituted amines is possible under mild and functional-group-tolerant conditions. The

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