Cyanessigsäure Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R31:Entwickelt bei Berührung mit Säure giftige Gase.
R34:Verursacht Verätzungen.
R52/53:Schädlich für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R20/22:Gesundheitsschädlich beim Einatmen und Verschlucken.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S20:Bei der Arbeit nicht essen und trinken.
Beschreibung
Cyanoacetic acid is an organic compound. It is a white, hygroscopic solid. The compound contains two functional groups, a nitrile (C≡N) and a carboxylic acid. It is a precursor to cyanoacrylates, components of adhesives.
Cyanoacetic acid is used in pharmaceutical industry for producing vitamin B6 and caffeine. It is also used in making dyes, agricultural chemicals, and in the synthesis of phenylacetic acid esters. It acts as a precursor cyanoacrylates viz. ethyl cyanoacrylate.
Chemische Eigenschaften
white to light beige adhering crystalline solid
Verwenden
Cyanoacetic acid was used in the synthesis of N-piperidine-cyanacetamide and N-morpholyl-cyanacetamide. It was also used in the preparation of a panchromatic dye for dye-sensitized solar cells.
Definition
ChEBI: A monocarboxylic acid that consists of acetic acid bearing a cyano substituent.
Application
Cyanoacetic acid can be used as a reagent:
Along with acetic anhydride for cyanoacetylation of various pyrroles, indoles, and aniline derivatives. It can also be used in other reactions such as cyclizations, syntheses of coumarins and other heterocycles.
To prepare of key intermediate via Knoevenagel condensation in the total synthesis of 5-acetamido-substituted melatonin derivatives as MT3 receptor ligands.
In the synthesis of aminopyrrolinone derivatives by reacting Ugi adducts of cyanoacetic acid and aromatic aldehydes.
synthetische
Cyanoacetic acid is prepared by treatment of chloroacetate salts with sodium cyanide followed by acidification. Electrosynthesis by cathodic reduction of carbon dioxide and anodic oxidation of acetonitrile also affords cyanoacetic acid.
Allgemeine Beschreibung
Yellow-brown liquid with an unpleasant odor. Sinks and mixes with water.
Air & Water Reaktionen
Water soluble.
Reaktivität anzeigen
White, moderately toxic solid, combustible. When heated to decomposition Cyanoacetic acid emits toxic fumes of nitrile and oxides of nitrogen. A stirred mixture with furfuryl alcohol exploded violently upon heating [MCA Case History No 858].
Health Hazard
Contact irritates eyes and may irritate skin.
Brandgefahr
Special Hazards of Combustion Products: Toxic oxides of nitrogen and toxic and flammable acetonitrile vapors may form in fire.
läuterung methode
Recrystallise the acid to constant melting point from *benzene/acetone (2:3), and dry it over silica gel. [Beilstein 2 H 583, 2 I 253, 2 II 530, 2 III 1626, 2 IV 1888.]
Cyanessigsäure Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
Enprofyllin
Coffein
3,3,3-Tris(p-chlorphenyl)propionsure
2-Cyan-N-methyl-N-[(methylamino)carbonyl]acetamid
1-methyl-4-[3,3,3-tris(4-chlorophenyl)propionyl]piperazine
2-Cyan-N-[(ethylamino)carbonyl]acetamid
Sulindac
Dimethylmalonat
3,3,3-tris(p-chlorphenyl)propionylchlorid
4-PYRIDIN-2-YLISOXAZOL-5-AMINE
5,6-Diamino-1,3-dimethylpyrimidin-2,4(1H,3H)-dion
2-Cyan-N-((ethylamino)carbonyl)-2-(methoxyimino)acetamid
6-Amino-1,3-dimethyl-5-nitrosouracil
2,4-Dichloro-5-cyanopyrimidine
2,2-Dibrom-2-cyanacetamid
Octyl cyanoacetate
Dichloracetonitril
Dinatriummalonat
Diethylmalonat
Malonsäure
Ethylcyanacetat
