malonic acid
malonic acid
CAS: 141-82-2;156-80-9
Molecular Formula: C3H4O4
malonic acid - Names and Identifiers
| Name | malonic acid |
| Synonyms | malonic acid propanedioate Propanedioic acid Carboxyacetic acid Malonic acid 141-82-2 Methane dicardonic acid Methanadicarboxylic acid Sodium Valproate Impurity 24 Valproic Acid Impurity 2 (Malonic Acid) 141-82-2 Malonic acid 1,3-Propanedioic acid |
| CAS | 141-82-2 156-80-9 |
| EINECS | 205-503-0 |
| InChI | InChI=1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)/p-2 |
| InChIKey | OFOBLEOULBTSOW-UHFFFAOYSA-N |
malonic acid - Physico-chemical Properties
| Molecular Formula | C3H4O4 |
| Molar Mass | 104.06 |
| Density | 1.619 g/cm3 at 25 °C |
| Melting Point | 132-135 °C (dec.) (lit.) |
| Boling Point | 140℃（decomposition） |
| Flash Point | 157°C |
| Water Solubility | 1400 g/L (20 ºC) |
| Solubility | Soluble in ether, pyridine, methanol and propanol, solubility in water: 1400g/L (20°C) |
| Vapor Presure | 0-0.2Pa at 25℃ |
| Appearance | White crystal |
| Color | White |
| Merck | 14,5710 |
| BRN | 1751370 |
| pKa | 2.83(at 25℃) |
| PH | 3.17(1 mM solution);2.5(10 mM solution);1.94(100 mM solution) |
| Storage Condition | Sealed in dry,Room Temperature |
| Stability | Stable. Incompatible with oxidizing agents, reducing agents, bases. |
| Refractive Index | 1.4780 |
| MDL | MFCD00002707 |
| Physical and Chemical Properties | Character: white crystal. soluble in water, soluble in ethanol and ether, pyridine. |
| Use | Mainly used in pharmaceutical intermediates, but also for spices, adhesives, resin additives, electroplating polishing agents; For the production of barbiturates and other drugs |
malonic acid - Risk and Safety
| Risk Codes | R20/22 - Harmful by inhalation and if swallowed. R41 - Risk of serious damage to eyes R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/39 - S37/39 - Wear suitable gloves and eye/face protection S36 - Wear suitable protective clothing. |
| UN IDs | 3261 |
| WGK Germany | 1 |
| RTECS | OO0175000 |
| TSCA | Yes |
| HS Code | 29171910 |
| Packing Group | III |
malonic acid - Upstream Downstream Industry
| Raw Materials | Ethyl malonate Acetone Chloroacetic acid Sodium cyanide Hydrochloric acid |
| Downstream Products | 2-Methyl-4,6-dichloro-5-aminopyrimidine Methyl 2-nonenoate |
malonic acid - Reference
| Reference Show more | 1. Gong Fangfang, Fan Weiguo. Effects of Exogenous Citric Acid on Nutrient Activation in Calcareous Yellow Soil and Nutrient Absorption and Growth of Rosa roxburghii Seedlings [J]. Chinese Agricultural Sciences, 2018. 2. Yuan Qifeng, Yan Jiawen, Wang Honglin, Li Shipin, Chen Nan, Wang Yu, Han Xiumei, Ma Yuhua. Analysis of Sugar, Acid and Vitamin Components in Peach Fruit Varieties 'Zixiang 1' [J]. Chinese Fruit Trees, 2019(04):43-47. |
malonic acid - Nature
Open Data Verified Data
white crystals. Melting point 135.6 °c (small amount of sublimation). Boiling point 140 degrees C (decomposition). The relative density was 1. 619. Soluble in water, soluble in ethanol and ether, pyridine. After dehydration to produce malonic anhydride, decarboxylation of acetic acid.
Last Update：2025-06-10 22:55:16
malonic acid - Preparation Method
Open Data Verified Data
The use of malonic acid in industry is less, generally not as a product, but directly produced into malonic acid ester. If necessary, malonic acid is produced by hydrolysis of the ester. Malonate production methods for chloroacetic acid and sodium cyanide in alkaline conditions to generate sodium cyanoacetate, and then with sulfuric acid to get malonic acid, Further esterification of malonate.
Last Update：2022-01-01 10:31:49
malonic acid - Application
Open Data Verified Data
raw materials for organic synthesis. The main derivative product is diethyl malonate, which is used in the production of barbiturates in medicine. In addition, malonic acid can be used as electroplating polishing agent, explosive control agent and thermal welding flux additive.
Last Update：2025-08-19 16:24:40
malonic acid - Safety
Open Data Verified Data
low toxicity. The skin and mucous membranes have a stimulating effect, but less serious than oxalic acid. The oral LD50 for mice was 1.54g/kg. When producing malonic acid, special protection is generally not required, but cyanoacetic acid and sodium cyanide are strong poisons, so special care must be taken when handling compounds containing cyano groups, and wear good anti-virus equipment, at the same time to develop appropriate security measures.
Packed with a woven bag lined with a plastic liner, net weight 25kg. According to the general provisions of the storage and transportation of chemicals.
Last Update：2022-01-01 10:31:50
malonic acid - Reference Information
| LogP | -0.81 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Dibasic acid | Malonic acid is also called methanedicarboxylic acid, carrot acid, malic acid, beet acid. There are 3 crystal types, two of which are triclinic and one is monoclinic. Crystallized from ethanol is triclinic white crystal. Relative molecular mass 104.06. Relative density 1.631(15 ℃). Melting point 135.6 ℃. Decompose to acetic acid and carbon dioxide at 140 ℃. It does not decompose under a vacuum of 1.067 × 103~1.333 × 103Pa, but sublimates directly. Insoluble in benzene, soluble in water 61.1(0 ℃), 73.5(20 ℃), 92.6(50 ℃), ethanol 57(20 ℃), ether 5.7(20 ℃), slightly soluble in pyridine. In case of potassium permanganate, it is decomposed into formic acid and carbon dioxide. Malonic acid is a dibasic acid, which has the typical reactivity of dibasic acid. For example, the methylene group of malonic acid is active and can undergo addition, alkylation, amination, halogenation and other reactions; its two carboxyl groups are very close apart and can be dehydrated; it can be esterified with alcohol; it is heated to decarboxylate; it is condensed with carbonyl compounds; it is added with compounds containing active double bonds. The hydroxyl groups in the two carboxyl groups of malonic acid are all substituted by ethoxy (see substitution reaction) to form the compound diethyl malonate. Diethyl malonate is an important organic synthesis raw material for dye and drug synthesis. Because the molecule contains active methylene group, it can first react with sodium alkoxide to form sodium malonate, and then interact with various active halides to form substituted malonate. It can be hydrolyzed and carboxylated to produce various Monobasic, dicarboxylic acid and other keto acids and other compounds. For example, the substituted malonate can be reacted with urea to produce a commonly used hypnotic barbital. Since malonic acid is heated to generate carbon dioxide and water, there is no pollution problem, so it can be directly used as an aluminum surface treatment agent; it is also a raw material for the production of pesticide fungicide Fuji No. 1 and herbicide Kukeda; the pharmaceutical industry uses malonic acid to prepare diuretics benzoxazolone, anti-inflammatory drug oxyphenylbutazone, sedative drug bromomethyloctine, etc. In addition, malonic acid and its esters are widely used as pharmaceutical intermediates, such as barbiturates, vitamins B1 and B6, etc., malonic acid esters are commonly used in organic synthesis, and are also used as adhesives, fragrances, resin additives, electroplating polishing agents, welding fluxes, etc. |
| preparation method | the laboratory uses chloroacetic acid as raw material, neutralizes with NaOH or Na2CO3 to generate sodium chloroacetate salt, which reacts with KCN (or NaCN) to obtain sodium α-cyanoacetate, and then transforms malonic acid after alkaline hydrolysis, calcium salt replacement and acidification. The chemical reaction equation is as follows: |
| use | mainly used in pharmaceutical intermediates, as well as fragrances, adhesives, resin additives, electroplating and polishing agents, etc. used as complexing agent, It is also used for the preparation of barbi soil salt, etc. Malonic acid is an intermediate of the fungicide Paisanaphrin and an intermediate of the plant growth regulator indenyl. malonic acid and its esters are mainly used in spices, adhesives, resin additives, pharmaceutical intermediates, electroplating polishing agents, explosion control agents, thermal welding fluxing additives, etc. In the pharmaceutical industry, it is used to produce Lumina, barbital, vitamin B1, vitamin B2, vitamin B6, phenylbutazone, amino acids, etc. Malonic acid is used as an aluminum surface treatment agent. Since only water and carbon dioxide are generated during heating and decomposition, there is no pollution problem. In this regard, it has great advantages over acid-type treatment agents such as formic acid used in the past. Determination of complexing agent of beryllium and copper. Calibration of standard alkali solution. Biochemical research. Organic synthesis. To make barbiturates. Standard for analysis by gas chromatography. |
| production method | malonic acid is prepared by hydrolyzing cyanacetic acid or diethyl malonate in industry. Since malonic acid itself is not very stable, it is carried out through diethyl malonate in organic synthesis. Malonic acid exists in beetroot in the form of calcium salt, and the scale deposited in the deep shrinkage tank of sugar beet is calcium malonate. Malonic acid is a metabolic intermediate, and its derivatives have biological activity. Malonate, especially diethyl malonate and ethyl acetoacetate, are extremely important intermediates in organic synthesis. The intermediate for the preparation of malonic acid and its derivatives is cyanoacetic acid. Cyanoacetic acid is converted into free malonic acid by hydrolysis. Generally, it is directly esterified without separation. It is usually converted to diethyl ester, and free malonic acid is usually made by hydrolysis of diethyl malonate. the preparation method is to add sodium carbonate aqueous solution to the reaction kettle to form sodium chloroacetate aqueous solution, and then slowly add 30% sodium cyanide solution dropwise, and proceed at a given temperature to generate sodium cyanide. After the cyanidation reaction is completed, sodium hydroxide is added to heat up and hydrolyze to generate sodium malonate solution, which is concentrated, and then sulfuric acid is added dropwise to acidify to generate malonic acid, which is filtered and dried to obtain the product. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:06
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Raw Materials for malonic acid
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