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Sigma-Aldrich

Dimethyl fumarate

97%

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Synonym(s):
(2E)-2-Butenedioic acid dimethyl ester, (E)-But-2-enedioic acid dimethyl ester, Allomaleic acid dimethyl ester, Boletic acid dimethyl ester, Dimethyl trans-ethylenedicarboxylate, Methyl fumarate, trans-1,2-Ethylenedicarboxylic acid dimethyl ester, trans-Butenedioic acid dimethyl ester
Linear Formula:
CH3OCOCH=CHCOOCH3
CAS Number:
624-49-7
Molecular Weight:
144.13
Beilstein:
774590
EC Number:
210-849-0
MDL number:
MFCD00064438
UNSPSC Code:
12352100
PubChem Substance ID:
24854591
NACRES:
NA.22

Quality Level

200

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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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
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H312,H315,H317,H335,H411

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
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
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)
Yanwen Chen et al.
Redox biology, 32, 101485-101485 (2020-03-17)
NRF2 is a master regulator of cellular anti-oxidant and anti-inflammatory responses, and strategies to augment NRF2-dependent responses may beneficial in many diseases. Basal NRF2 protein level is constrained by constitutive KEAP1-mediated degradation, but in the presence of electrophiles, NRF2 ubiquitination
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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