Chemistry:Isonicotinic acid
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| Names | |||
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| Preferred IUPAC name
Pyridine-4-carboxylic acid | |||
| Other names
Isonicotinic acid
4-Pyridinecarboxylic acid p-Pyridinecarboxylic acid 4-Picolinic acid | |||
| Identifiers | |||
3D model (JSmol)
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| KEGG | |||
PubChem CID
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| Properties | |||
| C6H5NO2 | |||
| Molar mass | 123.111 g·mol−1 | ||
| Appearance | White to off-white crystalline solid | ||
| Density | Solid | ||
| Melting point | 310 °C (590 °F; 583 K) (sublimes) | ||
| Hazards | |||
| Safety data sheet | http://datasheets.scbt.com/sc-250188.pdf | ||
| NFPA 704 (fire diamond) | |||
| Related compounds | |||
Related compounds
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nicotinic acid, pyridine isoniazid | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
 verify (what is   ?)
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| Infobox references | |||
Isonicotinic acid or pyridine-4-carboxylic acid is an organic compound with the formula C5H4N(CO2H). It is a derivative of pyridine with a carboxylic acid substituent at the 4-position. It is an isomer of picolinic acid and nicotinic acid, which have the carboxyl group at the 2- and 3-position respectively compared to the 4-position for isonicotinic acid.
Production
On a commercial scale, isonicotinic acid, like other pyridine carboxylic acid is produced by ammoxidation of 4-picoline (4-methylpyridine) followed by hydrolysis of the resulting nitrile:
- NC
5H
4CH
3 + 1.5 O
2 + NH
3 → NC
5H
4C≡N + 3 H
2O - NC
5H
4C≡N + 2 H
2O → NC
5H
4CO
2H + NH
3
It is also produced by oxidation of 4-picoline with nitric acid.[2]
Derivatives
Isonicotinic acids is a term loosely used for derivatives of isonicotinic acid. Hydrazide derivatives include isoniazid, iproniazid, and nialamide. Amide and ester derivatives include ethionamide and dexamethasone isonicotinate.
Its conjugate base forms coordination polymers[3] and MOFs[4] by binding metal ions through both the N and carboxylate.
See also
References
- ↑ Isonicotinic acid at chemicalland21.com
- ↑ Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399.
- ↑ Huang, Wei; Zhu, Hai-Bin; Gou, Shao-Hua (2006). "Self-assembly directed by dinuclear zinc(II) macrocyclic species". Coordination Chemistry Reviews 250 (3–4): 414–423. doi:10.1016/j.ccr.2005.07.008.
- ↑ Lin, Rui-Biao; Wu, Hui; Li, Libo; Tang, Xiao-Liang; Li, Zhiqiang; Gao, Junkuo; Cui, Hui; Zhou, Wei et al. (2018). "Boosting Ethane/Ethylene Separation within Isoreticular Ultramicroporous Metal–Organic Frameworks". Journal of the American Chemical Society 140 (40): 12940–12946. doi:10.1021/jacs.8b07563. PMID 30216725.
External links
- Isonicotinic+Acids at the US National Library of Medicine Medical Subject Headings (MeSH)
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