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Cyanoacetic acid

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Cyanoacetic acid
Names
Preferred IUPAC name 2-Cyanoacetic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 506325
ChEBI
ChemSpider
ECHA InfoCard 100.006.131 Edit this at Wikidata
EC Number
  • 206-743-9
PubChem CID
UNII
UN number 1759
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H3NO2/c4-2-1-3(5)6/h1H2,(H,5,6)Key: MLIREBYILWEBDM-UHFFFAOYSA-N
  • InChI=1/C3H3NO2/c4-2-1-3(5)6/h1H2,(H,5,6)Key: MLIREBYILWEBDM-UHFFFAOYAD
SMILES
  • C(C#N)C(=O)O
Properties
Chemical formula C3H3NO2
Molar mass 85.06 g/mol
Appearance colorless solid
Density 1.287 g/cm
Melting point 69-70 °C
Boiling point 108 °C (15 mm Hg)
Solubility in water 1000 g/L (20 °C) in water
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS07: Exclamation mark
Signal word Danger
Hazard statements H302, H314, H332
Precautionary statements P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P405, P501
Flash point 107 °C (225 °F; 380 K)
Related compounds
Related Ethyl cyanoacetate
Cyanoacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

Preparation and reactions

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.

Cyanoacetic acid is used to do cyanoacetylation, first convenient method described by J. Slätt.

It is about 1000x more acidic than acetic acid, with a pKa of 2.5. Ka=2.8x10^-3

Upon heating at 160 °C, it undergoes decarboxylation to give acetonitrile:

HO2CCH2CN → CO2 + CH3CN

Applications

In its largest scale application, cyanoacetic acid is first esterified to give ethyl cyanoacetate. Condensation of that ester with formaldehyde gives ethyl cyanoacrylate, which used as superglue. As of 2007, more than 10,000 tons of cyanoacetic acid were produced annually.

Cyanoacetic acid is a versatile intermediate in the preparation of other chemicals. it is a precursor to synthetic caffeine via the intermediacy of theophylline. It is a building block for many drugs, including dextromethorphan, amiloride, sulfadimethoxine, and allopurinol.

Safety

The LD50 (oral, rats) is 1.5 g/kg.

References

  1. ^ Harald Strittmatter, Stefan Hildbrand and Peter Pollak Malonic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a16_063.pub2
  2. Inglis, J. K. H. (1928). "Ethyl Cyanoacetate". Organic Syntheses. 8: 74. doi:10.15227/orgsyn.008.0074.
  3. Barba, Fructuoso; Batanero, Belen (2004). "Paired Electrosynthesis of Cyanoacetic Acid". The Journal of Organic Chemistry. 69 (7): 2423–2426. doi:10.1021/jo0358473. PMID 15049640.
  4. Bergman, Jan; Romero, Ivan; Slätt, Johnny (2004). "Cyanoacetylation of indoles, pyrroles and aromatic amines with the combination cyanoacetic acid and acetic anhydride". Synthesis. 2004 (16): 2760–2765. doi:10.1055/s-2004-831164. hdl:10616/37961.
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