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| Names | |
|---|---|
| Preferred IUPAC name
2-Cyanoacetic acid | |
| Identifiers | |
3D model (JSmol)
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| 506325 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.006.131 |
| EC Number |
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PubChem CID
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| UNII | |
| UN number | 1759 |
CompTox Dashboard (EPA)
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| Properties | |
| C3H3NO2 | |
| Molar mass | 85.06 g/mol |
| Appearance | colorless solid |
| Density | 1.287 g/cm3 |
| Melting point | 69-70 °C |
| Boiling point | 108 °C (15 mm Hg) |
| 1000 g/L (20 °C) in water | |
| Hazards | |
| GHS labelling: | |
 
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| Danger | |
| H302, H314, H332 | |
| 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
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Ethyl cyanoacetate Cyanoacetamide |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
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Transcription
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 pKa of 2.5.
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,[1] and also for Peldesine.
Safety
The LD50 (oral, rats) is 1.5 g/kg.[1]
References
- ^ a b c d 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.
This page was last edited on 11 May 2024, at 22:21