Cyanoacetic acid

Cyanoacetic acid
Names
	IUPAC name 2-cyanoacetic acid
Identifiers
CAS Number	372-09-8 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	506325
ChEBI	CHEBI:51889;
ChemSpider	9357;
ECHA InfoCard	100.006.131
EC Number	206-743-9;
PubChem CID	9740;
UNII	QZT550H2Y9 ;
UN number	1759
CompTox Dashboard (EPA)	DTXSID0027149 ;
	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/cm3
Melting point	69-70 ℃
Boiling point	108 ℃ (15 mm Hg)
Solubility in water	1000 g/L (20 ℃) in water
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H302, H302, H314, H318, H332
GHS precautionary statements	P260, P261, P264, P270, P271, P280, P301+312, P301+330+331, P303+361+353, P304+312, P304+340, P305+351+338, 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 [77 °F], 100 kPa).
	Infobox references

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.[1]

Preparation and reactions

Cyanoacetic acid is prepared by treatment of chloroacetate salts with sodium cyanide followed by acidification.[1][2] Electrosynthesis by cathodic reduction of carbon dioxide and anodic oxidation of acetonitrile also affords cyanoacetic acid.[3]

Cyanoacetic acid is used to do cyanoacetylation, first convenient method described by J. Slätt.[4]

It is about 1000x more acidic than acetic acid, with a pK_a of 2.5. Upon heating at 160 °C, it undergoes decarboxylation to give acetonitrile:

C₃H₃NO₂ → C₂H₃N + CO₂

Applications

The largest scale reaction is its esterification to give the corresponding ester ethyl cyanoacetate, which is then transformed to ethyl cyanoacrylate used as superglue, via reaction with formaldehyde. As of 2007, more than 10,000 tons of cyanoacetic acid were produced annually.

Cyanoacetic acid is a versatile intermediate in the preparation of 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,[1] and also for Peldesine.

Safety

The LD50 (oral, rats) is 1.5 g/kg.[1]

References

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
Inglis, J. K. H. (1928). "Ethyl Cyanoacetate". Organic Syntheses. 8: 74. doi:10.15227/orgsyn.008.0074.
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.
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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[Ullm-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.