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Malonic acid information


Malonic acid
Skeletal formula of malonic acid
Ball-and-stick model of the malonic acid molecule
Names
Preferred IUPAC name
Propanedioic acid[1]
Other names
Methanedicarboxylic acid
Identifiers
CAS Number
  • 141-82-2 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:30794 checkY
ChEMBL
  • ChEMBL7942 checkY
ChemSpider
  • 844 checkY
DrugBank
  • DB02175 checkY
ECHA InfoCard 100.005.003 Edit this at Wikidata
PubChem CID
  • 867
UNII
  • 9KX7ZMG0MK checkY
CompTox Dashboard (EPA)
  • DTXSID7021659 Edit this at Wikidata
InChI
  • InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7) checkY
    Key: OFOBLEOULBTSOW-UHFFFAOYSA-N checkY
  • InChI=1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
    Key: OFOBLEOULBTSOW-UHFFFAOYAJ
SMILES
  • O=C(O)CC(O)=O
  • C(C(=O)O)C(=O)O
Properties
Chemical formula
C3H4O4
Molar mass 104.061 g·mol−1
Density 1.619 g/cm3
Melting point 135 to 137 °C (275 to 279 °F; 408 to 410 K) (decomposes)
Boiling point decomposes
Solubility in water
763 g/L
Acidity (pKa) pKa1 = 2.83[2]
pKa2 = 5.69[2]
Magnetic susceptibility (χ)
-46.3·10−6 cm3/mol
Related compounds
Other anions
Malonate
Related carboxylic acids
Oxalic acid
Propionic acid
Succinic acid
Fumaric acid
Related compounds
Malondialdehyde
Dimethyl malonate
Hazards
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. The name originates from the Greek word μᾶλον (malon) meaning 'apple'.

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 746. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ a b pKa Data Compiled by R. Williams (pdf; 77 kB) Archived 2010-06-02 at the Wayback Machine

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Malonic acid

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Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as...

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Diethyl malonate

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Diethyl malonate, also known as DEM, is the diethyl ester of malonic acid. It occurs naturally in grapes and strawberries as a colourless liquid with an...

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Methylmalonic acid

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Methylmalonic acid (MMA) (conjugate base methylmalonate) is a dicarboxylic acid that is a C-methylated derivative of malonic acid. Methylmalonic acid is a by-product...

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Fatty acid synthesis

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cytosolic fatty acid synthesis, there is also mitochondrial fatty acid synthesis (mtFASII), in which malonyl-CoA is formed from malonic acid with the help...

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Combined malonic and methylmalonic aciduria

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by elevated levels of malonic acid and methylmalonic acid. However, the methylmalonic acid levels exceed those of malonic acid. CMAMMA is not only an...

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Malonic ester synthesis

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The malonic ester synthesis is a chemical reaction where diethyl malonate or another ester of malonic acid is alkylated at the carbon alpha (directly adjacent)...

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Barbituric acid

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Édouard Grimaux synthesized barbituric acid from malonic acid, urea, and phosphorus oxychloride (POCl3). Malonic acid has since been replaced by diethyl malonate...

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Dimethyl malonate

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of malonic acid. It is a common reagent for organic synthesis used, for example, as a precursor for barbituric acid. It is also used in the malonic ester...

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Malonic aciduria

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calculating the malonic acid to methylmalonic acid ratio in blood plasma, malonic aciduria can be clearly distinguished from combined malonic and methylmalonic...

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Maleic acid

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acid salt, e.g. carfenazine, chlorpheniramine, pyrilamine, methylergonovine, and thiethylperazine. Fumaric acid Malic acid Malonic acid Succinic acid...

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Knoevenagel condensation

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Z−CHR−Z for instance diethyl malonate, Meldrum's acid, ethyl acetoacetate or malonic acid, or cyanoacetic acid. Z−CHRR', for instance nitromethane. where Z...

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Michael addition reaction

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side-products earlier in 1883 while investigating condensation reactions of malonic acid with aldehydes. However, according to biographer Takashi Tokoroyama,...

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Cyanoacetic acid

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is 1.5 g/kg. Harald Strittmatter, Stefan Hildbrand and Peter Pollak Malonic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2007...

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Tartronic acid

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Tartronic acid or 2-hydroxymalonic acid is an organic compound with the structural formula of HOHC(CO2H)2. This dicarboxylic acid is related to malonic acid. It...

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Cinnamic acid

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of preparing cinnamic acid is by the Knoevenagel condensation reaction. The reactants for this are benzaldehyde and malonic acid in the presence of a weak...

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Malic acid

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William B. (June 2007). "The Origin of the Names Malic, Maleic, and Malonic Acid". Journal of Chemical Education. 84 (6): 924. Bibcode:2007JChEd..84....

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Acrylic acid

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Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of...

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List of carboxylic acids

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Carboxylic acids are organic acids characterized by a carboxyl (-COOH) functional group. The naming of these compounds is governed by IUPAC nomenclature...

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Dicarboxylic acid

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a dicarboxylic acid is an organic compound containing two carboxyl groups (−COOH). The general molecular formula for dicarboxylic acids can be written...

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Diethyl acetamidomalonate

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derivative of malonic acid diethyl ester. Formally, it is derived through the acetylation of ester from the unstable aminomalonic acid. DEAM serves as...

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Lactic acid

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Lactic acid is an organic acid. It has the molecular formula CH3CH(OH)COOH. It is white in the solid state and it is miscible with water. When in the...

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Oxalic acid

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Emanuel (1987). "Solubility of oxalic, malonic, succinic, adipic, maleic, malic, citric, and tartaric acids in water from 278.15 to 338.15 K". The Journal...

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Succinic acid

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Succinic acid (/səkˈsɪnɪk/) is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2. In living organisms, succinic acid takes the form of an anion...

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IUPAC nomenclature of organic chemistry

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Malonic acid, CH2(COOH)2, is systematically named propanedioic acid. Alternatively, the suffix "-carboxylic acid" can be used in place of "oic acid"...

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Malonic anhydride

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CH2(CO)2O. It can be viewed as the anhydride of malonic acid, or a double ketone of oxetane. Malonic anhydride was first synthesized in 1988 by ozonolysis...

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Ester

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condensation. This conversion is exploited in the malonic ester synthesis, wherein the diester of malonic acid reacts with an electrophile (e.g., alkyl halide)...

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