isonicotinic acid

{{chembox

|Watchedfields = changed

|verifiedrevid = 443884866

|Reference =[http://chemicalland21.com/lifescience/phar/ISONICOTINIC%20ACID.htm Isonicotinic acid] at chemicalland21.com

|Name = Isonicotinic acid

|ImageFileL1 = Isonicotinic acid.png

|ImageNameL1 = Skeletal formula

|ImageFileR1 = Isonicotinic-acid-3D-balls.png

|ImageNameR1 = Ball-and-stick model

|PIN = Pyridine-4-carboxylic acid

|OtherNames = Isonicotinic acid
4-Pyridinecarboxylic acid
p-Pyridinecarboxylic acid
4-Picolinic acid

|Section1={{Chembox Identifiers

|ChEBI_Ref = {{ebicite|correct|EBI}}

|ChEBI = 6032

|SMILES = c1cnccc1C(=O)O

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 5709

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = Y8SYN761TQ

|KEGG_Ref = {{keggcite|correct|kegg}}

|KEGG = C07446

|InChI = 1/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9)

|InChIKey = TWBYWOBDOCUKOW-UHFFFAOYAV

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 1203

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9)

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = TWBYWOBDOCUKOW-UHFFFAOYSA-N

|CASNo_Ref = {{cascite|correct|CAS}}

|CASNo = 55-22-1

|PubChem = 5922

}}

|Section2={{Chembox Properties

|C=6|H=5|N=1|O=2

|Appearance = White to off-white crystalline solid

|Density = Solid

|MeltingPtC = 310

|MeltingPt_notes = (sublimes)

}}

|Section7={{Chembox Hazards

|ExternalSDS =http://datasheets.scbt.com/sc-250188.pdf

|NFPA-F = 1

|NFPA-H = 3

|NFPA-R = 0

}}

|Section8={{Chembox Related

| OtherCompounds = nicotinic acid, pyridine isoniazid

}}

}}

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:

:{{chem2|NC5H4CH3 + 1.5 O2 + NH3 -> NC5H4C\tN + 3 H2O}}

:{{chem2|NC5H4C\tN + 2 H2O -> NC5H4CO2H + NH3}}

It is also produced by oxidation of 4-picoline with nitric acid.{{Ullmann|first1=Shinkichi|last1=Shimizu|first2=Nanao|last2=Watanabe|first3=Toshiaki|last3=Kataoka|first4=Takayuki|last4= Shoji|first5=Nobuyuki|last5=Abe|first6=Sinji|last6=Morishita|first7=Hisao|last7=Ichimura|title=Pyridine and Pyridine Derivatives|year=2007|doi=10.1002/14356007.a22_399}}

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{{cite journal |doi=10.1016/j.ccr.2005.07.008 |title=Self-assembly directed by dinuclear zinc(II) macrocyclic species |date=2006 |last1=Huang |first1=Wei |last2=Zhu |first2=Hai-Bin |last3=Gou |first3=Shao-Hua |journal=Coordination Chemistry Reviews |volume=250 |issue=3–4 |pages=414–423 }} and MOFs{{cite journal |doi=10.1021/jacs.8b07563 |title=Boosting Ethane/Ethylene Separation within Isoreticular Ultramicroporous Metal–Organic Frameworks |date=2018 |last1=Lin |first1=Rui-Biao |last2=Wu |first2=Hui |last3=Li |first3=Libo |last4=Tang |first4=Xiao-Liang |last5=Li |first5=Zhiqiang |last6=Gao |first6=Junkuo |last7=Cui |first7=Hui |last8=Zhou |first8=Wei |last9=Chen |first9=Banglin |journal=Journal of the American Chemical Society |volume=140 |issue=40 |pages=12940–12946 |pmid=30216725 }} by binding metal ions through both the N and carboxylate.

See also

References

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