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Isonicotinic acid

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Isonicotinic acid[1]
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
Pyridine-4-carboxylic acid
Other names
Isonicotinic acid
4-Pyridinecarboxylic acid
p-Pyridinecarboxylic acid
4-Picolinic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.208 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9) checkY
    Key: TWBYWOBDOCUKOW-UHFFFAOYSA-N checkY
  • InChI=1/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9)
    Key: TWBYWOBDOCUKOW-UHFFFAOYAV
  • c1cnccc1C(=O)O
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
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Safety data sheet (SDS) http://datasheets.scbt.com/sc-250188.pdf
Related compounds
Related compounds
 nicotinic acid, pyridine isoniazid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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

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On a commercial scale, isonicotinic acid, like other pyridine carboxylic acid is produced by ammoxidation of 2-picoline followed by hydrolysis of the resulting nitrile:

NC5H4CH3 + 1.5 O2 + NH3 → NC5H4C≡N + 3 H2O
NC5H4C≡N + 2 H2O → NC5H4CO2H + NH3

It is also produced by oxidation of 4-picoline with nitric acid.[2]

Derivatives

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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

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References

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  1. ^ Isonicotinic acid at chemicalland21.com
  2. ^ Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399. ISBN 978-3527306732.
  3. ^ 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.
  4. ^ Lin, Rui-Biao; Wu, Hui; Li, Libo; Tang, Xiao-Liang; Li, Zhiqiang; Gao, Junkuo; Cui, Hui; Zhou, Wei; Chen, Banglin (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.
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