Cyanoacetic acid
Synonym(s):Cyanoacetic acid;Malonic acid mononitrile
- CAS NO.:372-09-8
- Empirical Formula: C3H3NO2
- Molecular Weight: 85.06
- MDL number: MFCD00002677
- EINECS: 206-743-9
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-11-28 16:31:43
What is Cyanoacetic acid?
Description
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.
Chemical properties
white to light beige adhering crystalline solid
The Uses of Cyanoacetic acid
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.
The Uses of Cyanoacetic acid
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.
The Uses of Cyanoacetic acid
Synthesis of intermediates; manufacture of barbital.
Definition
ChEBI: A monocarboxylic acid that consists of acetic acid bearing a cyano substituent.
What are the applications of 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.
Preparation
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.
General Description
Yellow-brown liquid with an unpleasant odor. Sinks and mixes with water.
Air & Water Reactions
Water soluble.
Reactivity Profile
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.
Fire Hazard
Special Hazards of Combustion Products: Toxic oxides of nitrogen and toxic and flammable acetonitrile vapors may form in fire.
Purification Methods
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.]
Properties of Cyanoacetic acid
Melting point: | 65 °C |
Boiling point: | 108 °C0.15 mm Hg(lit.) |
Density | 1.3676 (rough estimate) |
vapor pressure | 0.1 mm Hg ( 100 °C) |
refractive index | 1.3764 (estimate) |
Flash point: | 226 °F |
storage temp. | Store below +30°C. |
solubility | H2O: soluble50mg/mL, clear, colorless to very faintly yellow |
form | Adhering Crystalline Solid |
pka | 2.45(at 25℃) |
color | White to light beige |
PH | 1.6 (50g/l, H2O, 20℃) |
Water Solubility | 1000 g/L (20 ºC) |
Sensitive | Hygroscopic |
Merck | 14,2689 |
BRN | 506325 |
Dielectric constant | 33.0(4℃) |
CAS DataBase Reference | 372-09-8(CAS DataBase Reference) |
NIST Chemistry Reference | Acetic acid, cyano-(372-09-8) |
EPA Substance Registry System | Cyanoacetic acid (372-09-8) |
Safety information for Cyanoacetic acid
Signal word | Danger |
Pictogram(s) |
Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H314:Skin corrosion/irritation |
Precautionary Statement Codes |
P260:Do not breathe dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Cyanoacetic acid
InChIKey | MLIREBYILWEBDM-UHFFFAOYSA-N |
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