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Home> Encyclopedia >Organic Acid>Pharmaceutical Intermediates>Organic Intermediate
Maleic acid structure
Maleic acid structure

Maleic acid

Iupac Name:(Z)-but-2-enedioic acid
CAS No.: 110-16-7
Molecular Weight:116.072
Modify Date.: 2022-11-06 17:25
Introduction: 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. View more+
1. Names and Identifiers
1.1 Name
Maleic acid
1.2 Synonyms

(2Z)-2-Butenedioic acid (2Z)-Butene-2-dioic acid (Z)-2-Butenedioic acid (z)-butenedioicaci 1,2-Ethylenedicarboxylic acid, (Z) 1,2-ethylenedicarboxylicacid,(z) 2-Butenedioic acid (2Z)- 2-Butenedioic acid (Z)- 2-Butenedioic acid, (Z)- 2-Butenedioicacid(Z)- acidemaleique Butenedioic acid,(Z)- cis-1,2-Ethylenedicarboxylic acid cis-2-Butenedioic Acid cis-Butenedioic acid cis-Ethylene-1,2-dicar-boxylicacid Kyselina maleinova Maleinic acid Malezid CM Scotchbond Multipurpose Etchant Toxilic acid

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1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C4H4O4 (isomer)
1.7 Inchi
1.8 InChIkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
2.1 Boiling point
266 to 268° F (NTP, 1992)
2.1 Refractive index
2.1 Flash Point
2.2 PSA
2.2 logP
2.2 Solubility
2.3 VaporDensity
4 (NTP, 1992) (Relative to Air)
2.4 Appearance
White solid
2.5 Storage
Ambient temperatures.
2.6 Chemical Properties
Maleic acid, HOOCCH:CHCOOH, also known as maleinic acid and toxilic acid,is a colorless crystalline dibasic acid. It is soluble in water and alcohol. Maleic acid is used in manufacturing synthetic resins, in textile processing, and in preserving oils and fats.
2.7 Color/Form
Monoclinic prisms from water
White crystals from water, alcohol & benzene
Colorless crystals
2.8 Corrosivity
May corrode metals when wet.
2.9 Decomposition
When heated to decomp it emits acrid smoke and irritating fumes.
2.10 Heat of Combustion
-1355.2 kJ/mol
2.11 Odor
Faint acidulous odor
2.12 PH
1.3 (100g/l, H2O, 20℃)
2.13 pKa
1.83(at 25℃)
2.14 Water Solubility
790 g/L (25 oC)
2.15 Spectral Properties
IR: 15240 (Sadtler Research Laboratories IR Grating Collection)
UV: 6-18 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: 4532 (Sadtler Research Laboratories Spectral Collection)
MASS: 465 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
2.16 Stability
Stable. Combustible. Incompatible with strong oxidizing agents, bases.
2.17 StorageTemp
Store at RT.
3. Use and Manufacturing
3.1 Definition
ChEBI: A butenedioic acid in which the double bond has cis- (Z)-configuration.
3.2 General Description
Maleic acid is a colorless crystalline solid having a faint odor. Maleic acid is combustible though Maleic acid may take some effort to ignite. Maleic acid is soluble in water. Maleic acid is used to make other chemicals and for dyeing and finishing naturally occurring fibers.
3.3 Potential Exposure
Maleic acid is used to make artificialresins, antihistamines, and to preserve (retard rancidity) offats and oils
3.4 Produe Method
Maleic anhydride is the main source of maleic acid produced byhydration. Maleic anhydride is prepared commercially by theoxidation of benzene or by the reaction of butane with oxygen in thepresence of a vanadium catalyst.
3.5 Purification Methods
Crystallise the acid from acetone/pet ether (b 60-80o) or hot water. Dry it at 100o. [Beilstein 2 H 748, 2 I 303, 2 II 641, 2 III 1911, 2 IV 2199.]
3.6 Shipping
UN2215 Maleic acid, Hazard class: 8; Labels:8-Corrosive material.
3.7 Usage
Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. Maleic acid may be used to form acid addition salts with drugs to make them more stable, such as indacaterol maleate.
3.8 Waste Disposal
Dissolve or mix the materialwith a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal,state, and local environmental regulations must beobserved. Liquid: incinerate after mixing with a flammablesolvent. Use afterburner for complete combustion. Solid:dissolve in a flammable solvent or package in paper andburn. See above
4. Safety and Handling
4.1 Hazard Codes
4.1 Risk Statements
4.1 Safety Statements
4.1 Exposure Standards and Regulations
Maleic acid is an indirect food additive for use only as a component of adhesives.
4.2 Packing Group
4.2 Octanol/Water Partition Coefficient
log Kow= -0.48
4.3 Fire Hazard
Special Hazards of Combustion Products: Irritating smoke containing maleic anhydride may form in fire.
4.4 Other Preventative Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Local exhaust.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary.
Personnel protection: Avoid breathing vapors or dust. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
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4.5 Hazard Class
4.5 Cleanup Methods
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner. Cover solids wil a plastic sheet to prevent dissolving in rain or fire fighting water.
Environmental considerations: Water spill: If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at 10 times the spilled amount. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
4.6 DOT Emergency Guidelines
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Health: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat which will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Public Safety: CALL Emergency Response Telephone Number. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Evacuation: Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Fire: Note: Most foams will react with the material and release corrosive/toxic gases. Small fires: CO2, dry chemical, dry sand, alcohol-resistant foam. Large fires: Water spray, fog or alcohol-resistant foam. Move containers from fire area if you can do it without risk. Use water spray or fog; do not use straight streams. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. A vapor suppressing foam may be used to reduce vapors. DO NOT GET WATER on spilled substance or inside containers. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material. Prevent entry into waterways, sewers, basements or confined areas. Small spills: Cover with DRY earth, DRY sand, or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. Use clean non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.
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UN 2215
4.7 Fire Fighting Procedures
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use "alcohol" foam, carbon dioxide or dry chemical.
4.8 FirePotential
It is combustible though it may take some effort to ignite.
4.9 Safety Profile
Moderately toxic by ingestion and skin contact. Passes through intact skin. A skin and severe eye irritant and a corrosive. Believed to be more toxic than its isomer, fumeric acid. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritating fumes.
4.10 Formulations/Preparations
Grades of purity: Reagent; Technical
4.11 Incompatibilities
Dust may form explosive mixture withair, Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine,fluorine, etc.); contact may cause fires or explosions.Keep away from alkaline materials, strong bases, amines,reducing agents; alkali metals
4.12 WGK Germany
4.12 RTECS
4.12 Protective Equipment and Clothing
/NIOSH certified respirator/; goggles or face shield; protective gloves.
Compatible protective equipment construction materials include: natural rubber, neoprene, nitrile rubber, nitrile rubber/polyvinyl chloride, polyethylene, polyurethane, polyvinyl chloride, and viton.
4.13 Skin, Eye, and Respiratory Irritations
Dust: Irritating to eyes, nose and throat.
Solid: Irritating to skin and eyes.

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Skin sensitization, Category 1

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Signal word


Hazard statement(s)

H302 Harmful if swallowed

H315 Causes skin irritation

H319 Causes serious eye irritation

H317 May cause an allergic skin reaction

H335 May cause respiratory irritation

Precautionary statement(s)

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P271 Use only outdoors or in a well-ventilated area.


P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.


P403+P233 Store in a well-ventilated place. Keep container tightly closed.

P405 Store locked up.


P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification


8. Other Information
8.0 Usage
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.
9. Computational chemical data
  • Molecular Weight: 116.072g/mol
  • Molecular Formula: C4H4O4
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 116.01095860
  • Monoisotopic Mass: 116.01095860
  • Complexity: 119
  • Rotatable Bond Count: 2
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Topological Polar Surface Area: 74.6
  • Heavy Atom Count: 8
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
10. Question & Answer
  • Maleic acid is an organic chemical substance widely used in the pharmaceutical and food additive industries. It has various pharmacological effects, with its most prominent being its antibacterial and..
  • Maleic acid, an unsaturated organic dibasic acid, plays a crucial role in the production of polyesters for fiber-reinforced laminated moldings and paint vehicles. It is also used in the manufacturing ..
  • Maleic acid, also known as cis-butenedioic acid, is an organic compound with the chemical formula HO2CCHCHCO2H. It is a dicarboxylic acid, meaning it contains two carboxylic acid functional groups. Ma..
  • Maleic acid, also known as cis-butenedioic acid, with the molecular formula C4H4O4, is a dicarboxylic acid commonly used in pharmaceuticals, resin synthesis, and as a preservative for oils and fats. B..
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