malonic acid


malonic acid
a white, crystalline, water-soluble, dibasic acid, C3H4O4, easily decomposed by heat: used chiefly as an intermediate in the synthesis of barbiturates.
[1885-90]

* * *

also called  Propanedioic Acid 

      (HO2CCH2CO2H), a dibasic organic acid whose diethyl ester is used in syntheses of vitamins B1 and B6, barbiturates (barbiturate), and numerous other valuable compounds.

      Malonic acid itself is rather unstable and has few applications. Its calcium salt occurs in beetroot, but the acid itself is usually prepared by hydrolyzing diethyl malonate. It undergoes the usual reactions of carboxylic acids as well as facile cleavage into acetic acid and carbon dioxide.

      Diethyl malonate, CH2(CO2C2H5)2, also called malonic ester, is prepared by the reaction of ethyl alcohol with cyanoacetic acid. Its utility in synthesis arises from the reactivity of its methylene (CH2) group; a hydrogen atom is easily removed by sodium ethoxide or other strong base, and the resulting derivative reacts readily with an alkyl halide to form a diethyl alkylmalonate. A second alkyl group may be similarly introduced. The diethyl dialkylmalonates are converted by reaction with urea to barbiturates. Diethyl malonate is a colourless, fragrant liquid boiling at 181.4° C.

* * *


Universalium. 2010.

Look at other dictionaries:

  • Malonic acid — Malonic acid …   Wikipedia

  • malonic acid — [mə lō′nik, məlän′ik] n. [Fr malonique, altered < malique: see MALIC ACID] a crystalline, dibasic acid, HOOCCH2COOH, obtained from malic acid by oxidation and used in synthesizing barbiturates …   English World dictionary

  • malonic acid — məˈlōnik , länik noun Etymology: malonic from F. malonique (in acide malonique malonic acid), alteration of malique malic (in acide malique malic acid) more at malic acid : a crystalline dicarboxylic acid CH2(COOH)2 obtained by oxidation of malic …   Useful english dictionary

  • malonic acid — malono rūgštis statusas T sritis chemija formulė CH₂(COOH)₂ atitikmenys: angl. malonic acid rus. малоновая кислота ryšiai: sinonimas – propano dirūgštis …   Chemijos terminų aiškinamasis žodynas

  • malonic acid — A dicarboxylic acid of importance in intermediary metabolism; an inhibitor of succinate dehydrogenase. SYN: propanedioic acid. * * * ma·lo·nic acid mə lōn ik , län n a crystalline dicarboxylic acid CH2(COOH)2 used esp. in the form of its diethyl… …   Medical dictionary

  • malonic acid — noun a white crystalline dicarboxylic acid, CH(COOH), used in making barbiturates See Also: malonate …   Wiktionary

  • malonic acid — ma•lo′nic ac′id [[t]məˈloʊ nɪk, ˈlɒn ɪk[/t]] n. chem. a white, crystalline, water soluble, dibasic acid, C3H4O4, used chiefly in the synthesis of barbiturates • Etymology: < F (acide) malonique (1858), alter. ofmalique malic …   From formal English to slang

  • malonic acid — /məˌlɒnɪk ˈæsəd/ (say muh.lonik asuhd), /məˌloʊnɪk/ (say muh.lohnik) noun a dibasic acid, CH2(COOH)2, easily decomposed by heat. {French malonique, alteration of malique malic} …   Australian English dictionary

  • malonic — MALÓNIC adj. (chim.; în sintagma) Acid malonic = acid dicarboxilic folosit împreună cu derivaţii săi în sinteze organice şi farmaceutice. – Din fr. malonique. Trimis de claudia, 13.09.2007. Sursa: DEX 98  malónic adj. m. Trimis de siveco,… …   Dicționar Român

  • Malonic anhydride — Malonic anhydride …   Wikipedia