Grundinformationen
- CAS
141-82-2- Standard-SMILES
O=C([O-])CC(=O)[O-].[H+].[H+]- InChIKey
OFOBLEOULBTSOW-UHFFFAOYSA-N- Summenformel
- C3H4O4
- Durchschnittliche Molmasse
- 104,06 g/mol
- Monoisotopische Masse
- 104,0109586
Überblick
malonic acid has been reported in Camellia sinensis, Meum athamanticum, and other organisms with data available.
Namen und Bezeichner
- Bevorzugter Name
- CID 23511544
- IUPAC
- hydron;propanedioate
- Lokaler Name
- Malonsäure
- Englischer Name
- Malonic acid
- Summenformel
- C3H4O4
- Molmasse
- 104.06
Namen und Synonyme
118690-08-7SCHEMBL66611PROPANEDIOIC ACIDMAACDaucic acidCH2(COOH)2Methane acidMETHANEDICARBOXYLIC ACIDPropandioic acidMethanedicarbonic acidMALONIC ACID, 99%MALONIC ACID, 99%MALONIC ACID, 99%MALONIC ACID, 99%Malonsure
Datenbank-Bezeichner
- CAS
141-82-2- PubChem CID
- 23511544
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 80,3 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 7
- Formalladung
- 0
- Komplexität
- 72,1
Experimentelle und physikochemische Eigenschaften
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]
LogP-0.81
Solubility763.0 mg/mL
Melting Point135 °C
Physical DescriptionSolid
Dissociation Constants2.85 (at 25 °C)
Physikochemische Eigenschaften
- Schmelzpunkt
- 135 to · 135 to 137 °C (275 to 279 °F; 408 to 410 K) (decomposes)
- Siedepunkt
- decomposes
- Dichte
- 1.619 g/cm3 · 1.619 g/cm3
- Dampfdruck
- 0 · 0-0.2Pa at 25℃
- Brechungsindex
- 1.478 · 1.4780
- Flammpunkt
- 157 °C · 157 °C - closed cup
- storage temp.
- Sealed in dry,Room Temperature
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Gefahrenhinweise
CSL Reaction Information
CSL00132
WATER + Ammonium cerium(IV) nitrate + MALONIC ACID + POTASSIUM BROMATE
Chemical & Engineering News (15 Jun 1998) Vol. 76, No. 24, pp. 4. We wish to point out a safety hazard with a widely performed standard chemical demonstration that caused significant damage recently in a teaching laboratory in the chemistry department at the University of Tennessee, Knoxville. The Belousov-Zhabotinsky oscillator reaction described in Bassam Shakhashiri's" Chemical Demonstrations: A Handbook for Teachers of Chemistry," Vol. 2, involves the cerium ammonium nitrate-catalyzed redox reaction of potassium bromate with malonic acid. This reaction was carried out in an honors general chemistry laboratory without incident during the afternoon, but a fire was discovered in the lab two hours after everyone had left. It destroyed the wooden drawers beneath a stone benchtop before being extinguished by the fire department. Investigation revealed that the three chemicals used are stable when mixed dry, and react as expected when in dilute solution. However, when 0.5 g of each are mixed together, and between one drop and 3 mL of water added, a very exothermic reaction occurs with considerable fuming. All three chemicals are needed for this to initiate. When carried out on a piece of filter paper, ignition of the paper occurred. We suspect that in the teaching laboratory, dry chemicals were spilled during weighing, and, rather than being disposed of in the aqueous heavy-metal waste container, were placed in a trash can. This was stored under a sink with a leaky drainpipe, and the critical amount of moisture set off the reaction after everyone had left the room. There is a safety warning in the experimental procedure regarding bromates being strong oxidizing agents and indicating that mixtures with finely divided organic materials are easily ignited. The catalytic nature of the cerium salt on this is not indicated, however. We alert people to the hazardous nature of this particular mixture, under conditions that are not unusual.
Flammable,Oxidizer
bromate
Not Available
Sicherheitsdaten
- wgk
- 1
Chemie und Industrie
Pharmakologische Informationen
Tissue LocationsKidney
Cellular LocationsCytoplasm
Metabolite PathwaysAspartate Metabolism
Anwendungen
BeschreibungMalonic acid (MA), also known as propanedioic acid, is a dicarboxylic acid with structure CH2(COOH)2. It have three kinds of crystal forms, of which two are triclinic, and one is monoclinic. That crystallized from ethanol is white triclinic crystals.It decomposes to acetic acid and carbon dioxide at 140℃. It does not decompose at 1.067×103~1.333×103Pa vacuum, but directly sublimates. The ionised form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's ethyl ester. The name originates from Latin malum, meaning apple.
VerwendenMalonic acid is used as an intermediate in the manufacture of barbiturates and other pharmaceuticals. It is a component used as a stabilizer in many high-end cosmetic and pharmaceutical products. Malonic acid is also used as building block in chemical synthesis, specifically to introduce the molecular group -CH2-COOH. It is used for the introduction of an acetic acid moiety under mild conditions by Knoevenagel condensation and subsequent decarboxylation.
Darstellung
synthetischeMalonic acid is usually produced from chloroacetic acid.Reaction: The chloroacetic acid is added to the reaction kettle by adding sodium carbonate aqueous solution to generate sodium chloroacetate aqueous solution, and then 30% sodium cyanide solution is slowly added dropwise, and the reaction is carried out at a predetermined temperature to generate sodium cyanoacetate. After the cyanation reaction is completed, add sodium hydroxide for heating and hydrolysis to generate sodium malonate solution, concentrate, then dropwise add sulfuric acid for acidification to generate malonic acid, filter and dry to obtain the product.This method often does not produce a pure enough product or the pure product has an extremely low yield. Industrially, malonic acid is also produced by hydrolyzing dimethyl malonate or diethyl malonate. This manufacturing method is able to bring about a higher yield and purity, but the organic synthesis of malonic acid through these processes is extremely costly and environmentally hazardous.
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