Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
pyridine-4-carboxylic acid
Conditions | Yield |
---|---|
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
A
pyridine-4-methanol
B
pyridine-4-carboxylic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
pyridine-4-carboxylic acid
Conditions | Yield |
---|---|
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
pyridine-4-carboxylic acid
Conditions | Yield |
---|---|
With sodium iodide; zirconium(IV) chloride In acetonitrile for 1.5h; Heating; | 90% |
Conditions | Yield |
---|---|
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
pyridine-4-carboxylic acid
Conditions | Yield |
---|---|
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
ethyl acetate
A
pyridine-4-carboxylic acid
B
ethyl 3-oxo-3-(4-pyridyl)propanoate
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 10 - 20℃; for 2.5h; Reagent/catalyst; Solvent; | A n/a B 86% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
pyridine-4-carboxylic acid
Conditions | Yield |
---|---|
With zirconium(IV) chloride In acetonitrile at 20℃; for 1.5h; | 67% |
pyridine-4-carboxylic acid
Conditions | Yield |
---|---|
With indium; ammonium chloride In tetrahydrofuran for 12h; Heating; | 62% |
4-Ethylpyridine
A
pyridine-4-carboxylic acid
B
oxo-pyridin-4-yl-acetic acid
Conditions | Yield |
---|---|
With potassium hydroxide; potassium permanganate at 45℃; for 1.5h; | A 61.9% B 5.2% |
Conditions | Yield |
---|---|
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
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical
A
pyridine-4-carboxylic acid
B
2,2,6,6-tetramethylpiperidino isonicotinate
Conditions | Yield |
---|---|
With water; periodic acid In acetonitrile at 0 - 20℃; Product distribution; Further Variations:; Reagents; nitrogen bubbling; | A n/a B 58% |
picoline
2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
A
pyridine
B
pyridine-4-carbaldehyde
C
pyridine-4-carboxylic acid
D
2,2'-diphenyl-1H,1'H-3,3'-biindole
Conditions | Yield |
---|---|
at 140℃; for 14h; Further byproducts given; | A 31% B 13% C 10% D 55% |
picoline
2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
A
pyridine
B
pyridine-4-carbaldehyde
C
pyridine-4-carboxylic acid
D
formaldehyd
E
2,2'-diphenyl-1H,1'H-3,3'-biindole
Conditions | Yield |
---|---|
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
A
pyridine
B
pyridine-4-carbaldehyde
C
pyridine-4-carboxylic acid
D
2,2'-diphenyl-1H,1'H-3,3'-biindole
Conditions | Yield |
---|---|
With picoline at 140℃; for 14h; Further byproducts given; | A 31% B 13% C 10% D 55% |
picoline
A
pyridine
B
pyridine-4-carbaldehyde
C
pyridine-4-methanol
D
pyridine-4-carboxylic acid
Conditions | Yield |
---|---|
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
isoniazid
A
pyridine-4-carboxylic acid
B
4-pyridinecarboxylic acid, methyl ester
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene at 10℃; for 6h; | A n/a B 40% |
pyridine-4-carboxylic acid
4-(chlorocarbonyl)pyridine
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
for 0.166667 - 6h; Product distribution / selectivity; Neat (no solvent); Mechanochemistry; | 100% |
pyridine-4-carboxylic acid
Conditions | Yield |
---|---|
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
1-(1-isonicotinoylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; | 100% |
pyridine-4-carboxylic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In tetrahydrofuran Inert atmosphere; Reflux; | 100% |
Conditions | Yield |
---|---|
In water at 30℃; for 1h; Solvent; Time; Sonication; Green chemistry; | 100% |
pyridine-4-carboxylic acid
isonicotinoyl chloride hydrochloride
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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
(5,10,15,20-tetrakis(3,5-di-tert-butylphenyl)porphyrinato)ruthenium(II) carbonyl(pyridine carboxylic acid)
Conditions | Yield |
---|---|
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
2,12-bis[trans-Pt(PEt3)2NO3]-[7-(3,5-di-tert-butylphenyl)-5,6,8,9-tetrahydro-dibenzo[c,h]acridine]
Conditions | Yield |
---|---|
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
sodium pyridine-4-carboxylate
Conditions | Yield |
---|---|
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
2-aminoacetonitrile hydrochloride
N-(cyanomethyl)isonicotinamide
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate In iso-butanol at 98℃; for 48h; Microwave irradiation; | 99% |
pyridine-4-carboxylic acid
1,1,1,2,2,2-hexamethyldisilane
trimethylsilyl 4-pyridinecarboxylate
Conditions | Yield |
---|---|
RT, then warmed slowly until violent gas evolution occured; | 98% |
pyridine-4-carboxylic acid
(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
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; | 98% |
pyridine-4-carboxylic acid
Pyridine-2,6-dicarboxylic acid
(NC5H4COOH)Pd(NC5H3(COO)2)
Conditions | Yield |
---|---|
In nitric acid dissoln. Pd-compd. in aq. HNO3, addn. of ligands aq. soln.; ppt. washing, drying; elem. anal.; | 98% |
pyridine-4-carboxylic acid
1,3-propanesultone
3-(4-carboxypyridinium-1-yl)propane-1-sulfonate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 60℃; for 24h; | 98% |
at 140℃; | 62% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
ethanol
isonicotinic acid ethyl ester; hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride at 30℃; for 6h; Reflux; | 97.07% |
pyridine-4-carboxylic acid
2,2'-biimidazole
water
nickel(II) acetate tetrahydrate
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 97% |
Molecular Structure of Isonicotinic acid (CAS NO.55-22-1):
IUPAC Name: pyridine-4-carboxylic acid
Molecular formula: C6H5NO2
Molecular Weight: 123.11
EINECS: 200-228-2
Melting point: ≥300 °C(lit.)
H bond acceptors: 3
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 39.19Å2
Index of Refraction: 1.57
Molar Refractivity: 31.27 cm3
Molar Volume: 95.1 cm3
Surface Tension: 58.7 dyne/cm
Density: 1.293 g/cm3
Flash Point: 193.3 °C
Enthalpy of Vaporization: 68.15 kJ/mol
Boiling Point: 396 °C at 760 mmHg
Vapour Pressure: 5.56E-07 mmHg at 25°C
Water Solubility: 5.2 g/L (20°C)
Merck: 14,5187
BRN: 109599
InChI
InChI=1/C6H5NO2/c8-6(9)5-1-3-7-4-2-5/h1-4H,(H,8,9)
Smiles
c1(ccncc1)C(O)=O
Product Categories: Nitrogen cyclic compounds; Pyridine; API intermediates; API's
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 436mg/kg (436mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Pharmaceutical Chemistry Journal Vol. 11, Pg. 481, 1977. |
mouse | LD50 | intravenous | 5gm/kg (5000mg/kg) | Therapie. Vol. 23, Pg. 1343, 1968. | |
mouse | LD50 | oral | 3123mg/kg (3123mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Pharmaceutical Chemistry Journal Vol. 11, Pg. 481, 1977. |
rat | LD50 | oral | 5gm/kg (5000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Pharmaceutical Chemistry Journal Vol. 11, Pg. 481, 1977. |
Reported in EPA TSCA Inventory.
Moderately toxic by ingestion and intraperitoneal routes. Mildly toxic by intravenous route. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: Xi
Risk Statements information:
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements information:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
WGK Germany: 2
Isonicotinic acid , with CAS number of 55-22-1, can be called 4-Pyridinecarboxylic acid ; p-Pyridinecarboxylic acid ; 1,4-Dihydroisonicotinic acid ; gamma-Picolinic acid ; 4-Picolinic acid ; pyridine-4-carboxylate ; gamma-Pyridinecarboxylic acid . It is a white to light yellow crystal powder.
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