Maleic Acid

Base Information

• Chemical Name: Maleic Acid
• CAS No.: 110-16-7
• Deprecated CAS: 1975169-66-4
• Molecular Formula: C4H4O4
• Molecular Weight: 116.073
• Hs Code.: 29173990
• European Community (EC) Number: 203-742-5,607-861-7
• ICSC Number: 1186
• NSC Number: 25940
• UN Number: 2215,3261
• UNII: 91XW058U2C
• DSSTox Substance ID: DTXSID8021517
• Nikkaji Number: J2.446E
• Wikipedia: Maleic_acid
• Wikidata: Q42038
• NCI Thesaurus Code: C25951
• RXCUI: 1426330
• Pharos Ligand ID: G85TY71W8BTL
• Metabolomics Workbench ID: 37118
• ChEMBL ID: CHEMBL539648
• Mol file: 110-16-7.mol

Synonyms:hydrogen maleate;maleate;maleic acid;maleic acid, ammonium salt;maleic acid, calcium salt;maleic acid, dipotassium salt;maleic acid, disodium salt;maleic acid, iron salt;maleic acid, monoammonium salt;maleic acid, monocopper (2+) salt;maleic acid, monosodium salt;maleic acid, neodymium salt;maleic acid, potassium salt;maleic acid, sodium salt;sodium maleate

Chemical Property of Maleic Acid

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 137-140 °C(lit.)
• Refractive Index: 1.526
• Boiling Point: 355.5 °C at 760 mmHg
• PKA: 1.83(at 25℃)
• Flash Point: 183 °C
• PSA: 74.60000
• Density: 1.499 g/cm³
• LogP: -0.28820
• Storage Temp.: Store at RT.
• Solubility.: 478.8g/l
• Water Solubility.: 790 g/L (25 ºC)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 116.01095860
• Heavy Atom Count: 8
• Complexity: 119
• Transport DOT Label: Corrosive

Purity/Quality:

99% ^*data from raw suppliers

Maleic acid 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn
• Statements: 22-36/37/38-43
• Safety Statements: 26-28-37-28A-46-24

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: UVCB,Other Classes -> Organic Acids
• Canonical SMILES: C(=CC(=O)O)C(=O)O
• Isomeric SMILES: C(=C\C(=O)O)\C(=O)O
• Recent ClinicalTrials: Comparing Different Single and Combination Chelating Agents on Sealer Penetration and Dentin Erosion.
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes. The substance is irritating to the skin and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. Repeated or prolonged contact may cause skin sensitization.
• Description: Maleic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Its chemical formula is HO2CCHCHCO2H. Maleic acid is the cis-isomer of butenedioic acid, where as fumaric acid is the trans-isomer. It is mainly used as a precursor to fumaric acid, and relative to its parent maleic anhydride, maleic acid has few applications.
• Physical properties: Maleic acid is a less stable molecule than fumaric acid. The difference in heat of combustion is 22.7 kJ·mol?1. The heat of combustion is -1355 kJ / mole. Maleic acid is more soluble in water than fumaric acid. The melting point of maleic acid (135 °C) is also much lower than that of fumaric acid (287 °C). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place in maleic acid at the expense of intermolecular interactions, and that are not possible in fumaric acid for geometric reasons.
• Uses: Maleic acid is used as a precursor to fumaric acid, dimethyl maleate and glyoxalic acid. It is an electrophile and acts as dienophine in Diels-Alder reactions. It reacts with drugs to form more stable addition salts like indacaterol maleate, carfenazine, chlorpheniramine, pyrilamine, methylergonovine and thiethylperazine. Its maleate ion is useful in biochemistry as an inhibitor of transaminase reactions.

Technology Process of Maleic Acid

There total 427 articles about Maleic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

sulfuric acid (7664-93-9) + p-benzoquinone (106-51-4) → formic acid (64-18-6) + DL-tartaric acid (133-37-9,138508-61-9) + maleic acid (110-16-7,26099-09-2)

Guidance literature:

Electrolysis;

Reference yield:

nitrobenzene (98-95-3,26969-40-4) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + malonic acid (141-82-2) + 1,2-dihydroxy-4-nitrobenzene (3316-09-4) + meta-nitrophenol (554-84-7) + oxalic acid (144-62-7,97993-78-7) + maleic acid (110-16-7,26099-09-2) + hydroquinone (123-31-9,8027-02-9) + p-benzoquinone (106-51-4) + 2-hydroxynitrobenzene (88-75-5,78813-12-4) + phenol (108-95-2,27073-41-2)

Guidance literature:

With ozone; In water; at 24.84 ℃; Mechanism; Ultrasound irradiation;

DOI:10.1016/j.ultsonch.2009.07.001

Reference yield:

furan (110-00-9) + maleic anhydride (108-31-6) → exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) + maleic acid (110-16-7,26099-09-2)

Guidance literature:

With water; for 1h; Inert atmosphere; Darkness;

DOI:10.1039/c3gc41655k

upstream raw materials:

tetrahydrofuran

piperidine

pyridine

malonic acid

Downstream raw materials:

endo, cis-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dicarboxylic acid

7-Oxa-bicyclo-<2.2.1>-hept-5-en-2,3-exo,exo-dicarbonsaeure

(+/-)-6t-Brom-5c-hydroxy-7-oxa-(1rH.4cH)-bicyclo<2.2.1>heptan-2c.3c-dicarbonsaeure-3-lacton

(+/-)-5endo,6exo-dibromo-7-oxa-norbornane-2exo,3exo-dicarboxylic acid

Refernces

Sonochemical synthesis of a new nano-plate lead(II) coordination polymer constructed of maleic acid

10.1016/j.ica.2010.04.024

The research focuses on the synthesis and characterization of a novel nano-sized lead(II) coordination polymer, [Pb(l7-Mal)]n (1), using maleic acid (H2Mal) as the organic ligand. The polymer was synthesized through a sonochemical method, which involves the application of ultrasound to induce chemical reactions. The study utilized various analytical techniques, including scanning electron microscopy (SEM), X-ray powder diffraction (XRD), elemental analyses, and IR spectroscopy, to characterize the structure and properties of the synthesized polymer. The research also compared the thermal stability of the nano-sized polymer with its bulk counterpart, finding that the nano-sized material decomposes at a lower temperature, likely due to its higher surface-to-volume ratio. Upon calcination at 600 °C, the nano-sized polymer was converted into pure phase micro-sized lead(II) oxide (PbO). The study highlights the potential of sonochemical synthesis as an efficient method for producing nano-structured coordination polymers with unique properties suitable for nanotechnological applications.

Facile one-pot synthesis of tetrahydroisoquinolines from amino acids via hypochlorite-mediated decarboxylation and Pictet-Spengler condensation

10.1016/j.tetlet.2014.07.043

The study presents an optimized biomimetic method for the conversion of various α-amino acids to aldehydes using sodium hypochlorite (NaOCl), which serves as an oxidizing agent for the decarboxylation of amino acids. The aldehyde products can then be transformed into tetrahydroisoquinolines, either racemic or (S)-enantiomer forms, through the Pictet–Spengler reaction with dopamine. The study utilizes a phosphate buffer to maximize regioselectivity for the racemic products and a maleic acid buffer for the enantioselective enzymatic synthesis of (S)-enantiomer products using norcoclaurine synthase. The purpose of these chemicals is to facilitate the synthesis of tetrahydroisoquinolines, which are found in numerous natural products and synthetic compounds with pharmacological activity, including benzoisoquinoline alkaloids. The study aims to synthesize novel BIAs with potential pharmacological utility by employing precursor-directed biosynthesis, avoiding the need for chromatography and ensuring the preparations are free of toxic chemical species.