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M0375

Sigma-Aldrich

Maleic acid

ReagentPlus®, ≥99% (HPLC)

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Synonym(s):
cis-Butenedioic acid, Toxilic acid
Linear Formula:
HO2CCH=CHCO2H
CAS Number:
110-16-7
Molecular Weight:
116.07
Beilstein/REAXYS Number:
605762
EC Number:
203-742-5
MDL number:
MFCD00063177
UNSPSC Code:
12352100
PubChem Substance ID:
24896549
NACRES:
NA.21

Quality Level

200

product line

ReagentPlus®

assay

≥99% (HPLC)

form

powder

impurities

≤2.0% water

ign. residue

≤0.1%

pKa (25 °C)

(1) 1.97, (2) 6.24

mp

130-135 °C (lit.)

density

1.59 g/mL at 25 °C (lit.)

SMILES string

OC(=O)\C=C/C(O)=O

InChI

1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-

InChI key

VZCYOOQTPOCHFL-UPHRSURJSA-N

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General description

Maleic acid (MA) is a dicarboxylic acid that undergoes esterification with ethanol in the presence of cation-exchange resin catalysts to form diethyl maleate. Its crystalline structure has been analyzed. Reaction kinetics and mechanism of the isomerization of maleic acid to fumaric acid in the presence of ceric and bromide ions has been investigated. The reaction mechanism and reactivity ratios for the radical copolymerization of maleic acid with styrene have been determined.

Application

Maleic acid has been used in the preparation of tris-maleate buffer and sodium maleate buffer. It has also been used for the pretreatment of poplar tracheid cell walls for the spectroscopic analysis of lignin. It may be used to synthesize superswelling acrylamide/maleic acid hydrogels.

Quality

Repurified

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 1

Certificates of Analysis (COA)

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Esterification of maleic acid with ethanol over cation-exchange resin catalysts.
Yadav GD and Thathagar MB.
Reactive functional Polymers, 52(2), 99-110 (2002)
Swelling equilibria and dye adsorption studies of chemically crosslinked superabsorbent acrylamide/maleic acid hydrogels.
Karadag E, et al.
Eur. Polymer J., 38(11), 2133-2141 (2002)
Bromine-Catalyzed Isomerization of Maleic Acid to Fumaric Acid.
Jwo JJ.
J. Chin. Chem. Soc., 28(1), 34-41 (1981)
A refinement of the crystal structure of maleic acid.
James MNG and Williams GJB.
Acta Crystallographica Section B, Structural Science, 30(5), 1249-1257 (1974)
Determination of total dietary fibre and available carbohydrates: A rapid integrated procedure that simulates in vivo digestion.
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