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242926

Sigma-Aldrich

Dimethyl fumarate

97%

Sinónimos:

(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

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About This Item

Fórmula lineal:
CH3OCOCH=CHCOOCH3
Número de CAS:
624-49-7
Peso molecular:
144.13
Beilstein/REAXYS Number:
774590
EC Number:
210-849-0
MDL number:
MFCD00064438
UNSPSC Code:
12352100
PubChem Substance ID:
24854591
NACRES:
NA.22

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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Categorías relacionadas

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

signalword

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

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
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
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
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)
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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