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55-22-1

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55-22-1 Usage

Chemical Properties

isonicotinic acid is also known as pyridine-4-carboxylic acid. white to light yellow crystal powder or white needle crystals. odorless, sublimable. molecular weight 123.11. melting point 319°C . slightly soluble in cold water, soluble in hot water, insoluble in alcohol, benzene and ether. isonicotinic acid is an amphoteric compound that is soluble in both acids and bases. soluble in hot water and ethanol, slightly soluble in cold water and ether. stable to heat and oxidation.

Uses

Isonicotinic acid is a metabolite of isoniazid. It is an isomer of nicotinic acid. The chronic toxicity of isonicotinic acid is slightly higher than that of isonicotinic acid hydrazide ( INH ) .Isonicotinic acid is a moderately basic compound (based on its pKa). Isonicotinic acid is an organic compound with a carboxyl group on a pyridine ring. The carboxyl group for isonicotinic acid is on the 4-position instead of the 3-position for nicotinic acid. It is an isomer of nicotinic acid. Isonicotinic acid is a metabolite of isoniazid.Isonicotinic acid considered to be inactive isomer of nicotinic acid. Isonicotinic acid is a metabolite of pyridine-4-carboxy hydrazide (isonicotinyl hydrazide; isoniazid) a front-line weapon in the battle against tuberculosis. Isonicotinic acid and its derivatives are used in manufacturing pharmaceuticals and agrochemicals.Used in the biological study of differentiation induced by nicotinic acid, nicotinamide and isonicotinic acid in human leukemia cell lines

Definition

ChEBI: Isonicotinic acid is a pyridinemonocarboxylic acid in which the carboxy group is at position 4 of the pyridine ring. It has a role as a human metabolite and an algal metabolite. It is a conjugate acid of an isonicotinate.

Preparation

Isonicotinic acid is synthesized by continuous oxidation with 4-methylpyridine as raw material and vanadium pentoxide as catalyst. The purity of the industrial product isonicotinic acid is more than 95%, and the yield of the above method is 70-75%. The consumption of 4-methylpyridine per ton of product is 1070kg.

Application

Isonicotinic acid (IN) can be used as:An organocatalyst in the one pot four component condensation reaction, to synthesize pyranopyrazoles based heterocyclic compounds.An organic ligand for the preparation of copper(I) halide coordination polymer [CuBr(IN)]n, by hydrothermal method.As a starting material for the synthesis of cation-dimers with potent antimalarial activity.

Purification Methods

Crystallise the acid repeatedly from water and dry it under vacuum at 110o or sublime it at 260o/15mm (m 319o). [Beilstein 22 III/IV 518, 22/2 V 188.]

Check Digit Verification of cas no

The CAS Registry Mumber 55-22-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 5 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 55-22:
(4*5)+(3*5)+(2*2)+(1*2)=41
41 % 10 = 1
So 55-22-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9)/p-1

55-22-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A18109)  Isonicotinic acid, 99%   

  • 55-22-1

  • 100g

  • 201.0CNY

  • Detail
  • Alfa Aesar

  • (A18109)  Isonicotinic acid, 99%   

  • 55-22-1

  • 500g

  • 573.0CNY

  • Detail
  • Alfa Aesar

  • (A18109)  Isonicotinic acid, 99%   

  • 55-22-1

  • 2500g

  • 2282.0CNY

  • Detail
  • Aldrich

  • (I17508)  Isonicotinicacid  99%

  • 55-22-1

  • I17508-5G

  • 228.15CNY

  • Detail
  • Aldrich

  • (I17508)  Isonicotinicacid  99%

  • 55-22-1

  • I17508-100G

  • 263.25CNY

  • Detail
  • Aldrich

  • (I17508)  Isonicotinicacid  99%

  • 55-22-1

  • I17508-500G

  • 742.95CNY

  • Detail

55-22-1Synthetic route

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With formic acid; dihydrogen peroxide at 0 - 4℃; for 12h; other aromatic aldehydes;100%
With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide In water; acetonitrile at 10℃; for 1h;100%
With formic acid; dihydrogen peroxide at 0 - 4℃; for 12h;100%
picoline
108-89-4

picoline

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With sulfuric acid; ozone; acetic acid; manganese(II) acetate at 16℃; for 1h;97%
Stage #1: picoline With β‐cyclodextrin In water at 60℃; for 0.5h;
Stage #2: With sulfuric acid; dihydrogen peroxide; boric acid In water at 40℃; for 6h;
94.7%
With potassium hydroxide; oxygen; 18-crown-6 ether In 1,2-dimethoxyethane at 25℃; for 96h;80%
pyridine-4-methanol
586-95-8

pyridine-4-methanol

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In aq. buffer at 20℃; for 13h; pH=9.8 - 10.1; Catalytic behavior; Electrolysis;97%
With oxygen at 120℃; for 12h; Green chemistry;92%
With Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Sealed tube;90%
isonicotinate tert-butyl ester
81660-73-3

isonicotinate tert-butyl ester

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With water; iodine In acetonitrile for 4h; Heating;92%
at 324.9℃; Rate constant; Thermodynamic data; Kinetics; gas-phase pyrolysis; other temperatures between 549-602 K; ΔH(excit.), ΔS(excit.);
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

A

pyridine-4-methanol
586-95-8

pyridine-4-methanol

B

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 25℃; for 4h; Cannizzaro Reaction;A n/a
B 91%
With aluminum oxide; water; sodium hydroxide at 100℃; for 0.0333333h; Cannizzaro Reaction; Microwave irradiation;A 47%
B 47%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In chloroform at 0℃; for 2h;A 45 % Chromat.
B 41%
With N,N,N',N'-tetramethylguanidine In water at 20℃; for 5h; Cannizzaro reaction;A 40%
B 35%
isonicotinamide
1453-82-3

isonicotinamide

A

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

B

isoniazid
54-85-3

isoniazid

Conditions
ConditionsYield
With hydrazine dihydrochloride In aq. phosphate buffer at 30℃; for 1h; pH=7; Kinetics; Concentration; Time; Temperature; Enzymatic reaction;A n/a
B 90.4%
Isonicotinic acid N-oxide
13602-12-5

Isonicotinic acid N-oxide

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol at 30℃; for 0.25h;90%
With Dimethylphenylsilane In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;79%
With ammonium formate; nickel In methanol at 50℃; for 3h;74%
3-methylbut-2-enyl isonicotinate
638203-02-8

3-methylbut-2-enyl isonicotinate

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With sodium iodide; zirconium(IV) chloride In acetonitrile for 1.5h; Heating;90%
pyridine
110-86-1

pyridine

carbon dioxide
124-38-9

carbon dioxide

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With [NiII(Me4-(NO2Bzo)2[14]tetraeneN4)]; tetrabutylammonium perchlorate In acetonitrile at 20℃; Electrochemical reaction; Inert atmosphere;90%
With C28H20N2O2; tetrabutylammonium perchlorate In acetonitrile at 20℃; Mechanism; Electrolysis;75%
4-(bromomethyl)pyridine
54751-01-8

4-(bromomethyl)pyridine

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With 5,10,15,20-tetra(4-nitrophenyl) porphyrinato iron chloride; [bis(acetoxy)iodo]benzene; water In methanol at 50℃; for 12h;87%
isonicotinic acid ethylester
1570-45-2

isonicotinic acid ethylester

ethyl acetate
141-78-6

ethyl acetate

A

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

B

ethyl 3-oxo-3-(4-pyridyl)propanoate
26377-17-3

ethyl 3-oxo-3-(4-pyridyl)propanoate

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 10 - 20℃; for 2.5h; Reagent/catalyst; Solvent;A n/a
B 86%
picoline
108-89-4

picoline

A

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

B

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With water; oxygen; CrV0.95P0.05O4 at 324.84℃;A 8.9%
B 84.3%
With tert.-butylhydroperoxide; selenium(IV) oxide In 1,4-dioxane for 24h;A 34%
B 11%
With selenium(IV) oxide In 1,4-dioxane for 24h;A 2%
B 19%
isoniazid
54-85-3

isoniazid

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With water; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In chloroform at 20℃; for 1h;75%
With cetyl-trimethylammonium dichromate; acetic acid In chloroform at 50℃; for 3h; Kinetics; Mechanism; Reagent/catalyst; Temperature; Solvent;64%
With triiodide(1-); water; sodium chloride In hydrogenchloride at 24.9℃; Rate constant;
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With ((1,2-bis(diisopropylphosphino)ethane)NiH)2; water at 180℃; for 72h;74%
With phosphate buffer at 30℃; for 72h; rhodococcus rhodocrous AJ270, pH 7.0;50%
With potassium phosphate buffer at 30℃; for 72h; Rhodococcus sp. AJ270 cells;50.1%
4-methoxybenzyl isonicotinate
71653-47-9

4-methoxybenzyl isonicotinate

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With zirconium(IV) chloride In acetonitrile at 20℃; for 1.5h;67%
2,2,2-trichloroethyl isonicotinate

2,2,2-trichloroethyl isonicotinate

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With indium; ammonium chloride In tetrahydrofuran for 12h; Heating;62%
4-Ethylpyridine
536-75-4

4-Ethylpyridine

A

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

B

oxo-pyridin-4-yl-acetic acid
71708-14-0

oxo-pyridin-4-yl-acetic acid

Conditions
ConditionsYield
With potassium hydroxide; potassium permanganate at 45℃; for 1.5h;A 61.9%
B 5.2%
4-vinylpyridine
100-43-6

4-vinylpyridine

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: 4-vinylpyridine With ozone In water; acetonitrile at 0℃; Inert atmosphere;
Stage #2: With sodium chlorite In water; acetonitrile at 15 - 20℃; under 760.051 Torr; Inert atmosphere;
Stage #3: With sodium hydrogen sulfate In water; acetonitrile at 35℃; for 0.166667h; Inert atmosphere;
59%
With sodium periodate; 2C16H13N2O10Ru2(1-)*Ca(2+) In water at 45℃; for 16h; Green chemistry;57%
With nitric acid
isoniazid
54-85-3

isoniazid

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical
2564-83-2, 45842-10-2

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

A

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

B

2,2,6,6-tetramethylpiperidino isonicotinate
1020092-80-1

2,2,6,6-tetramethylpiperidino isonicotinate

Conditions
ConditionsYield
With water; periodic acid In acetonitrile at 0 - 20℃; Product distribution; Further Variations:; Reagents; nitrogen bubbling;A n/a
B 58%
picoline
108-89-4

picoline

2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
2196-95-4, 17213-48-8

2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide

A

pyridine
110-86-1

pyridine

B

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

C

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

D

2,2'-diphenyl-1H,1'H-3,3'-biindole
2415-33-0

2,2'-diphenyl-1H,1'H-3,3'-biindole

Conditions
ConditionsYield
at 140℃; for 14h; Further byproducts given;A 31%
B 13%
C 10%
D 55%
picoline
108-89-4

picoline

2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
2196-95-4, 17213-48-8

2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide

A

pyridine
110-86-1

pyridine

B

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

C

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

D

formaldehyd
50-00-0

formaldehyd

E

2,2'-diphenyl-1H,1'H-3,3'-biindole
2415-33-0

2,2'-diphenyl-1H,1'H-3,3'-biindole

Conditions
ConditionsYield
at 140℃; for 14h; Product distribution;A 31%
B 13%
C 10%
D n/a
E 55%
2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
2196-95-4, 17213-48-8

2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide

A

pyridine
110-86-1

pyridine

B

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

C

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

D

2,2'-diphenyl-1H,1'H-3,3'-biindole
2415-33-0

2,2'-diphenyl-1H,1'H-3,3'-biindole

Conditions
ConditionsYield
With picoline at 140℃; for 14h; Further byproducts given;A 31%
B 13%
C 10%
D 55%
picoline
108-89-4

picoline

A

pyridine
110-86-1

pyridine

B

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

C

pyridine-4-methanol
586-95-8

pyridine-4-methanol

D

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With oxygen; CrV0.95P0.05O4 at 325℃; Product distribution; Further Variations:; Temperatures; Reagents; atmospheric pressure;A n/a
B 38.5%
C n/a
D 42.1%
methanol
67-56-1

methanol

isoniazid
54-85-3

isoniazid

A

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

B

4-pyridinecarboxylic acid, methyl ester
2459-09-8

4-pyridinecarboxylic acid, methyl ester

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene at 10℃; for 6h;A n/a
B 40%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

4-(chlorocarbonyl)pyridine
14254-57-0

4-(chlorocarbonyl)pyridine

Conditions
ConditionsYield
With thionyl chloride for 2h; Reflux;100%
With thionyl chloride In neat (no solvent) at 20℃; for 48h; Inert atmosphere;100%
With thionyl chloride at 80℃; for 2h;83%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

copper diacetate
142-71-2

copper diacetate

copper(II) isonicotinate

copper(II) isonicotinate

Conditions
ConditionsYield
for 0.166667 - 6h; Product distribution / selectivity; Neat (no solvent); Mechanochemistry;100%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

3-[4-(3-amino-phenylsulfanyl)-2,3-bis-trifluoromethyl-phenyl]-1-morpholin-4-yl-propenone

3-[4-(3-amino-phenylsulfanyl)-2,3-bis-trifluoromethyl-phenyl]-1-morpholin-4-yl-propenone

C27H21F6N3O3S

C27H21F6N3O3S

Conditions
ConditionsYield
Stage #1: pyridine-4-carboxylic acid With N-ethyl-N,N-diisopropylamine; HATU In DMF (N,N-dimethyl-formamide) at 20℃;
Stage #2: 3-[4-(3-amino-phenylsulfanyl)-2,3-bis-trifluoromethyl-phenyl]-1-morpholin-4-yl-propenone In DMF (N,N-dimethyl-formamide)
100%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

1-(piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea

1-(piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea

1-(1-isonicotinoylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea
1191908-84-5

1-(1-isonicotinoylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;100%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

1-(3,4-dichlorophenyl)-4-[2-(tetrahydro-2H-pyran-2-yloxy)-ethyl]-4,5-dihydro-1H-pyrazol-3-amine

1-(3,4-dichlorophenyl)-4-[2-(tetrahydro-2H-pyran-2-yloxy)-ethyl]-4,5-dihydro-1H-pyrazol-3-amine

N-{1-(3,4-dichlorophenyl)-4-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-4,5-dihydro-1H-pyrazol-3-yl}-4-pyridinecarboxamide

N-{1-(3,4-dichlorophenyl)-4-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-4,5-dihydro-1H-pyrazol-3-yl}-4-pyridinecarboxamide

Conditions
ConditionsYield
Stage #1: pyridine-4-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 0.0833333h;
Stage #2: 1-(3,4-dichlorophenyl)-4-[2-(tetrahydro-2H-pyran-2-yloxy)-ethyl]-4,5-dihydro-1H-pyrazol-3-amine In dichloromethane at 40℃;
100%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

C79H98N4O2Ru

C79H98N4O2Ru

C83H97N5O3Ru

C83H97N5O3Ru

Conditions
ConditionsYield
In tetrahydrofuran Inert atmosphere; Reflux;100%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

cadmium(II) nitrate tetrhydrate

cadmium(II) nitrate tetrhydrate

ethanol
64-17-5

ethanol

potassium thioacyanate
333-20-0

potassium thioacyanate

Cd(2+)*CNS(1-)*C6H4NO2(1-)*2C2H6O

Cd(2+)*CNS(1-)*C6H4NO2(1-)*2C2H6O

Conditions
ConditionsYield
In water at 30℃; for 1h; Solvent; Time; Sonication; Green chemistry;100%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

isonicotinoyl chloride hydrochloride
39178-35-3

isonicotinoyl chloride hydrochloride

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide at 20℃; Reflux;99%
With thionyl chloride In 1,2-dichloro-ethane for 2h; Heating;98.1%
With thionyl chloride In N,N-dimethyl-formamide at 20 - 40℃; for 0.5h;98%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

aniline
62-53-3

aniline

N-phenylisonicotinamide
3034-31-9

N-phenylisonicotinamide

Conditions
ConditionsYield
Stage #1: pyridine-4-carboxylic acid With thionyl chloride for 2h; Reflux;
Stage #2: aniline With potassium carbonate In tetrahydrofuran at 20℃; for 24h;
99%
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;90%
Stage #1: pyridine-4-carboxylic acid With 1,1'-carbonyldiimidazole at 50℃; for 0.5h;
Stage #2: aniline at 50℃; for 20h;
70%
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 100℃;17%
With cyanuric chloride - DMF; triethylamine 1) heating, 2h, 2) heating, 3h; Yield given. Multistep reaction;
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

trans-4,4'-benzophenonebis[(triflate)bis(triphenylphosphine)]diplatinum(II)

trans-4,4'-benzophenonebis[(triflate)bis(triphenylphosphine)]diplatinum(II)

trans-4,4'-benzophenonebis[(nicotinic acid)bis(triphenylphosphine)]diplatinum(II) bis(triflate)

trans-4,4'-benzophenonebis[(nicotinic acid)bis(triphenylphosphine)]diplatinum(II) bis(triflate)

Conditions
ConditionsYield
In dichloromethane (N2); addn. of ligand and CH2Cl2 to platinum complex, stirring at room temp. for 6 h; evapn.; elem. anal.;99%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

meso-5,10,15,20-tetrakis(3,5-di-tert-butylphenyl)porphyrinato ruthenium(II) carbonyl

meso-5,10,15,20-tetrakis(3,5-di-tert-butylphenyl)porphyrinato ruthenium(II) carbonyl

(5,10,15,20-tetrakis(3,5-di-tert-butylphenyl)porphyrinato)ruthenium(II) carbonyl(pyridine carboxylic acid)
1449131-63-8, 358974-35-3

(5,10,15,20-tetrakis(3,5-di-tert-butylphenyl)porphyrinato)ruthenium(II) carbonyl(pyridine carboxylic acid)

Conditions
ConditionsYield
In dichloromethane Sonication; to Ru complex in CH2Cl2 added ligand, sonicated and heated to 40°C for a few min; filtered(Celite), evapd.;99%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

2,12-bis[trans-Pt(PEt3)2NO3]-[7-(3,5-di-tert-butylphenyl)-5,6,8,9-tetrahydro-dibenzo[c,h]acridine]
869641-37-2

2,12-bis[trans-Pt(PEt3)2NO3]-[7-(3,5-di-tert-butylphenyl)-5,6,8,9-tetrahydro-dibenzo[c,h]acridine]

cyclo-bis[(2,12-bis(trans-Pt(PEt3)2)-7-(3,5-di-tert-butylphenyl)-5,6,8,9-tetrahydrodibenzo[c,h]acridine)(isonicotinic acid)2](NO3)4

cyclo-bis[(2,12-bis(trans-Pt(PEt3)2)-7-(3,5-di-tert-butylphenyl)-5,6,8,9-tetrahydrodibenzo[c,h]acridine)(isonicotinic acid)2](NO3)4

Conditions
ConditionsYield
In water; acetone (N2); a flask charged with Pt complex and ligand, a mixt. of acetone andH2O added, heated at 50-55°C; recrystd. (CH2Cl2/hexane); elem. anal.;99%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

sodium pyridine-4-carboxylate
16887-79-9

sodium pyridine-4-carboxylate

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 0.5h;99%
With sodium hydroxide
With sodium hydroxide
With sodium hydroxide In water
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

2-aminoacetonitrile hydrochloride
6011-14-9

2-aminoacetonitrile hydrochloride

N-(cyanomethyl)isonicotinamide
1184796-18-6

N-(cyanomethyl)isonicotinamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;99%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

N-tert-butyl-N'-phenyl-S-phenylisothiourea

N-tert-butyl-N'-phenyl-S-phenylisothiourea

N-phenylisonicotinamide
3034-31-9

N-phenylisonicotinamide

Conditions
ConditionsYield
With iron(III)-acetylacetonate In iso-butanol at 98℃; for 48h; Microwave irradiation;99%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

1,1,1,2,2,2-hexamethyldisilane
1450-14-2

1,1,1,2,2,2-hexamethyldisilane

trimethylsilyl 4-pyridinecarboxylate
25436-39-9

trimethylsilyl 4-pyridinecarboxylate

Conditions
ConditionsYield
RT, then warmed slowly until violent gas evolution occured;98%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

(3R,4S)-3-Amino-4-hydroxy-azepane-1-carboxylic acid tert-butyl ester
198419-20-4

(3R,4S)-3-Amino-4-hydroxy-azepane-1-carboxylic acid tert-butyl ester

(3R,4S)-4-hydroxy-3-[(pyridine-4-carbonyl)amino]azepane-1-carboxylic acid tert-butyl ester
602277-74-7

(3R,4S)-4-hydroxy-3-[(pyridine-4-carbonyl)amino]azepane-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;98%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Pyridine-2,6-dicarboxylic acid
499-83-2

Pyridine-2,6-dicarboxylic acid

palladium dichloride

palladium dichloride

(NC5H4COOH)Pd(NC5H3(COO)2)
236750-15-5

(NC5H4COOH)Pd(NC5H3(COO)2)

Conditions
ConditionsYield
In nitric acid dissoln. Pd-compd. in aq. HNO3, addn. of ligands aq. soln.; ppt. washing, drying; elem. anal.;98%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

1,3-propanesultone
1120-71-4

1,3-propanesultone

3-(4-carboxypyridinium-1-yl)propane-1-sulfonate
1151655-30-9

3-(4-carboxypyridinium-1-yl)propane-1-sulfonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 60℃; for 24h;98%
at 140℃;62%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

piperidine-4-carboxylic acid hydrochloride
5984-56-5

piperidine-4-carboxylic acid hydrochloride

Conditions
ConditionsYield
Stage #1: pyridine-4-carboxylic acid With hydrogen In water at 160℃; under 45004.5 Torr; for 24h; Autoclave;
Stage #2: With hydrogenchloride chemoselective reaction;
98%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

ethanol
64-17-5

ethanol

isonicotinic acid ethylester
1570-45-2

isonicotinic acid ethylester

Conditions
ConditionsYield
With pyrographite In toluene at 130℃; for 0.166667h; Claisen Condensation; Irradiation;97.2%
With N-dodecanoyl-N-methyl-1-glucamine In water at 45℃; for 5h; Green chemistry;90%
With sulfuric acid for 12h; Reflux;90%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

ethanol
64-17-5

ethanol

isonicotinic acid ethyl ester; hydrochloride
58827-14-8

isonicotinic acid ethyl ester; hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 30℃; for 6h; Reflux;97.07%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

2,2'-biimidazole
492-98-8

2,2'-biimidazole

water
7732-18-5

water

nickel(II) acetate tetrahydrate
6018-89-9

nickel(II) acetate tetrahydrate

[Ni(2,2'-biimidazole)2(OH2)2](isonicotinate)2*4H2O

[Ni(2,2'-biimidazole)2(OH2)2](isonicotinate)2*4H2O

Conditions
ConditionsYield
In water 2,2'-biimidazole added to a soln. of metal acetate in hot water, a soln.of isonicotinic acid in hot water added; concn., controlled evapn. at room temp. for 2-3 wk; elem. anal.;97%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

{Cu2(μ-bis(diphenylphosphino)methane)2(CH3CN)2}{BF4}2

{Cu2(μ-bis(diphenylphosphino)methane)2(CH3CN)2}{BF4}2

[(Cu2(bis(diphenylphosphino)methane)2(μ-4-pyridylcarboxylato))4][BF4]4

[(Cu2(bis(diphenylphosphino)methane)2(μ-4-pyridylcarboxylato))4][BF4]4

Conditions
ConditionsYield
In dichloromethane under N2; suspn. of (Cu(dppm)MeCN))2(BF4)2 and 4-pyridinecarboxylic acidin CH2Cl2 was stirred at ambient temp. for 30 min, resulting soln. was stirred for 10 min; evapn. under vac., ppt was washed with Et2O, recrystn. from CH2Cl2/hexane; elem. anal.;97%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

zinc(II) acetate dihydrate
5970-45-6

zinc(II) acetate dihydrate

pyridine-4-carboxylic acid zinc salt

pyridine-4-carboxylic acid zinc salt

Conditions
ConditionsYield
In neat (no solvent) at 200℃; for 16h; Green chemistry;97%
In neat (no solvent, solid phase) stoich., mixed, ground in agate mortar for 10 min, heated at 180°C for 2 h; XRD;96%
With CH3OH In neat (no solvent, solid phase) stoich., mixed, ground in agate mortar for 10 min, immerced in CH3OH, dried at 40°C; XRD;
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

C7β-Hydroxyobacunone

C7β-Hydroxyobacunone

C32H35NO8

C32H35NO8

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;97%

55-22-1Relevant articles and documents

STABILITY OF WATER-SOLUBLE VITAMINS AND COENZYMES. VIII. KINETICS OF ACID HYDROLYSIS OF NICOTINOYL-γ-AMINOBUTYRIC ACID

Kozlov, E. I.,L'vova, M. Sh.,Garber, N. I.

, p. 328 - 333 (1988)

-

Continuous flow metal-free oxidation of picolines using air

Hamano, Masaya,Nagy, Kevin D.,Jensen, Klavs F.

, p. 2086 - 2088 (2012)

The metal free, direct oxidation of 2-, 3-, and 4-picoline to the corresponding carboxylic acid using either oxygen or air has been developed under continuous flow conditions. Complete conversion for all three substrates was obtained at moderate temperatures and pressures within minutes.

-

Trubnikov et al.

, (1968)

-

-

Bartok et al.

, p. 410 (1963)

-

-

v.Euler,Hasselquist

, p. 439,445 (1958)

-

-

Toma,Malin

, p. 288 (1975)

-

Decoration of copper foam with Ni nanorods and copper oxide nanosheets to produce a high-stability electrocatalyst for the reduction of CO2: Characterization of the electrosynthesis of isonicotinic acid

Mohammadzadeh, Safoora,Zare, Hamid R.,Khoshro, Hossein

, p. 678 - 685 (2019)

CuO–Cu2O (CuxO) nanosheets were coated on a copper foam substrate by the electrochemical anodization method in an alkaline solution. Constant current coulometry was performed to electrodeposit Ni nanorods on the surface of a Cu/CuxO electrode. Scanning electron microscopy (SEM) and X-ray diffraction (XRD) proved that the copper oxide nanosheets were anchored on the copper foam substrate and modified by Ni nanorods (Cu/CuxO/Ni). The process took place via a facile and inexpensive electrodeposition method. As the results indicate, owing to the synergistic effect of adjacent CuxO and Ni sites, a Cu/CuxO/Ni electrode has a very good and stable electrocatalytic activity to reduce CO2. As tested in this study, the product of the electrocatalytic reduction of CO2 (i.e. activated CO2, or CO2 ??) can be used for the electrocarboxylation of pyridine in mild conditions. Once an electron is transferred from CO2 ?? to pyridine, a pyridine radical anion is formed. Based on the EC'C′CC mechanism, this radical anion reacts with CO2 ?? and produces isonicotinic acid as the main product. In addition, two pyridine radical anions react together and produce a 4,4′-bipyridine dimer. The high stability of the electrocatalyst during the electrolysis process and the simplicity of the workup make the proposed modified electrode appropriate for the electrosynthesis of some organic compounds.

Kinetics of the highly selective liquid-phase oxidation of side chain alkyl groups in 2-methylpyrazine and picolines by selenium dioxide

Mukhopadhyay, Sudip,Chandalia, Sampatraj B.

, p. 455 - 459 (1999)

Kinetics of the liquid-phase oxidation of alkyl groups in 2-methylpyrazine and picolines with selenium dioxide at moderate conditions were studied. Thus, 2-methylpyrazine was oxidized to pyrazinoic acid with selenium dioxide in pyridine at 115 °C with 99% selectivity at a 2-methylpyrazine conversion of 100% in 8 h. It was deduced that the reaction follows secondorder kinetics and the activation energy was found to be 35 kcal/mol. The same reaction-scheme was found to hold for picolines oxidation to obtain picolinic acids. The byproduct selenium, formed in the reaction, was converted back to selenium dioxide by nitric acid oxidation with 100% selectivity.

Oxidation of Antitubercular Drug Isoniazid by a Lipopathic Oxidant, Cetyltrimethylammonium Dichromate: A Mechanistic Study

Garnayak, Sarita,Patel, Sabita

, p. 32 - 44 (2016)

The oxidation of an antitubercular drug isoniazid by a lipopathic oxidant cetyltrimethylammonium dichromate (CTADC) in a nonpolar medium generates isonicotinic acid both in the presence and the absence of acetic acid. The conventional UV–vis spectrophotometric method is used to study the reaction kinetics. The occurrence of the Michaelis–Menten–type kinetics with respect to isoniazid confirms the binding of oxidant and substrate to form a complex before the rate-determining step. The existence of the inverse solvent kinetic isotope effect, k(H2O)/ k(D2O) = 0.7, in an acid-catalyzed reaction proposes a multistep reaction mechanism. A decrease in the rate constant with an increase in [CTADC] reveals the formation of reverse micellar–type aggregates of CTADC in nonpolar solvents. In the presence of different ionic and nonionic surfactants, CTADC forms mixed aggregates and controls the reaction due to the charge on the interface and also due to partition of oxidant and substrate in two different domains. High negative entropy of activation (ΔS? = –145 and –159 J K?1 mol?1 in the absence and presence of acetic acid) proposes a more ordered and highly solvated transition state than the reactants. Furthermore, the solvent polarity-reactivity relationship reveals (i) the presence of less polar and less ionic transition state compared to the reactants during the oxidation, (ii) differential contribution from nonpolar and dipolar aprotic solvents toward the reaction process, and (iii) the existence of polarity/hydrophobic switch at log P = 0.73. A suitable mechanism has been proposed on the basis of experimental results. These results may provide insight into the mechanism of isoniazid oxidation in hydrophobic environment and may assist in understanding the drug resistance in different location.

Oxidation of isoniazid by N-haloarenesulfonamidates in alkaline medium: A kinetic and mechanistic study

Puttaswamy,Anuradha,Ramachandrappa,Made Gowda

, p. 221 - 230 (2000)

The kinetics of oxidation of Isoniazid (INH) by sodium N-haloarenesulfonamidates, chloramine-T (CAT), bromamine-T (BAT), chloramine-B (CAB), and bromamine-B (BAB), has been studied in alkaline medium at 303 K. The oxidation reaction follows identical kinetics with a first-order dependence on each [oxidant] and [INH] and an inverse fractional-order on [OH-]. Addition of the reaction product (p-toluenesulfonamide or benzenesulfonamide) had no significant effect on the reaction rate. Variation of ionic strength and addition of halide ions have no influence on the rate. There is a negative effect of dielectric constant of the solvent. Studies of solvent isotope effects using D2O showed a retardation of rate in the heavier medium. The reaction was studied at different temperatures, and activation parameters have been computed from the Arrhenius and Eyring plots. Isonicotinic acid was identified as the oxidation product by GC-MS. A two-pathway mechanism is proposed in which RNHX and the anion RNX- interact with the substrate in the rate-limiting steps. The mechanism proposed and the derived rate laws are consistent with the observed kinetics. The rate of oxidation of INH increases in the order: BAT>BAB>CAT>CAB. This effect is mainly due to electronic factors.

An ESIPT-based colorimetric and fluorescent probe with large Stokes shift for the sensitive detection of hypochlorous acid and its bioimaging in cells

Ren, Haixian,Huo, Fangjun,Yin, Caixia

, p. 4724 - 4728 (2021)

Hypochlorous acid (HOCl), with a low physiological concentration, plays a vital role in killing the pathogens and anti-inflammation in the human immune system. Deviation from the normal concentration is directly related to the inflammation-associated diseases and even cancer. Thus, it is necessary to sensitively detect the tiny concentration changes of HOCl. However, few of the reported probes could practically work well due to small Stokes shift, high detection of limits, and low SNR. In this study, HBT (2-(2′-Hydroxyphenyl)benzothiazole) was used as the candidate for the ESIPT-based fluorophore and connected to pyridinevia“CC” bonds. The “CC” bonds are the reaction site for HOCl and are activated by the strong electron-withdrawing CN group located on the double-bond carbon atom, resulting in a high sensitivity towards HOCl. Thereby, the probe's emission shifted effectively to the red channel avoiding the interference from biological autofluorescence. The excellent response of the probeJBDtowards HOCl enables it to detect endogenous hypochlorous acid in the cells and provides an ideal molecular tool for exploring the mechanism of hypochlorous acid in oxidative stress and its immune role.

SYNTHESIS OF PYRIDYL(TRICHLOROMETHYL)CARBINOLS UNDER INTERPHASE-CATALYSIS CONDITIONS

Iovel', I. G.,Gol'dberg, Yu. Sh.,Gaukhman, A. P.,Shimanskaya, M. V.

, p. 40 - 43 (1990)

The corresponding pyridyl(trichloromethyl)carbinols were obtained by reactions of 2- and 3-formylpyridine and 6-methyl-2-formylpyridine with chloroform in the presence of aqueous or solid alkali and an interphase catalyst.It is shown that carrying out the reaction in a liquid-solid system is more efficient than in a liquid-liquid system.

MOF-Zn-NHC as an efficient N-heterocyclic carbene catalyst for aerobic oxidation of aldehydes to their corresponding carboxylic acids: Via a cooperative geminal anomeric based oxidation

Babaee, Saeed,Zarei, Mahmoud,Zolfigol, Mohammad Ali

, p. 36230 - 36236 (2021/12/02)

As an efficient heterogenous N-heterocyclic carbene (NHC) catalyst, MOF-Zn-NHC was used in the aerobic oxidation of aryl aldehydes to their corresponding carbocyclic acids via an anomeric based oxidation. Features such as mild reaction conditions and no need for a co-catalyst or oxidative reagent can be considered as the major advantages of the presented method in this study. This journal is

Photo-induced deep aerobic oxidation of alkyl aromatics

Wang, Chang-Cheng,Zhang, Guo-Xiang,Zuo, Zhi-Wei,Zeng, Rong,Zhai, Dan-Dan,Liu, Feng,Shi, Zhang-Jie

, p. 1487 - 1492 (2021/07/10)

Oxidation is a major chemical process to produce oxygenated chemicals in both nature and the chemical industry. Presently, the industrial manufacture of benzoic acids and benzene polycarboxylic acids (BPCAs) is mainly based on the deep oxidation of polyalkyl benzene, which is somewhat suffering from environmental and economical disadvantage due to the formation of ozone-depleting MeBr and corrosion hazards of production equipment. In this report, photo-induced deep aerobic oxidation of (poly)alkyl benzene to benzene (poly)carboxylic acids was developed. CeCl3 was proved to be an efficient HAT (hydrogen atom transfer) catalyst in the presence of alcohol as both hydrogen and electron shuttle. Dioxygen (O2) was found as a sole terminal oxidant. In most cases, pure products were easily isolated by simple filtration, implying large-scale implementation advantages. The reaction provides an ideal protocol to produce valuable fine chemicals from naturally abundant petroleum feedstocks. [Figure not available: see fulltext.].

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