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98-98-6

Basic Information
CAS No.: 98-98-6
Name: Picolinic acid
Article Data: 236
Cas Database
Molecular Structure:
Molecular Structure of 98-98-6 (Picolinic acid)
Formula: C6H5NO2
Molecular Weight: 123.111
Synonyms: Pyridine-2-carboxylic acid;pyridine-2-carboxylic acid hydrochloride;2-pyridinecarboxylate;2-Carboxypyridine;pyridine-2-carboxylate;alpha-Picolinic acid hydrochloride;2-Pyridinecarboxylic acid, hydrochloride;.alpha.-Pyridinecarboxylic acid;o-Pyridinecarboxylic acid;PLA;2-Picolinic acid;2-pyridine carboxylic acid;Sodium picolinate;alpha-Pyridinecarboxylic acid;alpha-Picolinic acid;2-pyridinecarboxylic acid;Sodium pyridine-2-carboxylate;2-Pyridinecarboxylic acid, sodium salt;Picolinate;2-Pyridinecarboxylic Aicd;Alpha Picolinic Acid;Picolinic Acid (P521);
EINECS: 202-719-7
Density: 1.293 g/cm3
Melting Point: 139-142 °C(lit.)
Boiling Point: 292.467 °C at 760 mmHg
Flash Point: 130.68 °C
Solubility: water: 50 mg/mL, clear
Appearance: Off-white to tan powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36-36/37/38
Safety: 26-36-33-24/25
Transport Information: N/A
PSA: 50.19000
LogP: 0.77980
Synthetic route
586-98-1

2-Hydroxymethylpyridine

98-98-6

2-Picolinic acid

Conditions
ConditionsYield
With Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Sealed tube;98%
With tert-butyldimethylsilyl chloride In methanol; water at 20℃; for 0.5h; Green chemistry;97%
Stage #1: 2-Hydroxymethylpyridine With sodium hydroxide; Rh(trop2NH)(PPh3)(OTf); water; cyclohexanone at 25℃; for 16h; Inert atmosphere;
Stage #2: With hydrogenchloride; water chemoselective reaction;
96%
98-98-6

2-Picolinic acid

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; copper diacetate; potassium hydroxide In dimethyl sulfoxide at 130℃; under 3000.3 Torr; for 12h; Autoclave;79%
100-70-9

2-Cyanopyridine

98-98-6

2-Picolinic acid

Conditions
ConditionsYield
With potassium phosphate buffer at 30℃; for 144h; Rhodococcus sp. AJ270 cells;46.3%
With phosphate buffer at 30℃; for 144h; rhodococcus rhodocrous AJ270, pH 7.0;30%
With acetic acid tert-butyl ester; sulfuric acid In acetic acid at 45℃; for 0.1h; Ritter reaction; In flow;
1309453-54-0

C16H17NO2

A

98-98-6

2-Picolinic acid

B

338415-92-2

C16H15NO2

C

100-09-4

4-methoxybenzoic acid

Conditions
ConditionsYield
Stage #1: C16H17NO2 With oxygen; sodium hydride In tetrahydrofuran at 0 - 20℃; for 6h;
Stage #2: With hydrogenchloride In water
A 18%
B 84%
C 18%
109-06-8

α-picoline

98-98-6

2-Picolinic acid

Conditions
ConditionsYield
With sulfuric acid; ozone; acetic acid; manganese(II) acetate at 16℃; for 1h;97%
Stage #1: α-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;
89.3%
With potassium hydroxide; oxygen; 18-crown-6 ether In 1,2-dimethoxyethane at 25℃; for 96h;85%
1121-60-4

pyridine-2-carbaldehyde

98-98-6

2-Picolinic acid

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor; oxygen In water at 20℃; for 12h; Temperature; Enzymatic reaction;99%
With 3-bromo-2-(1-hydroxycyclohexyl)[1,2]selenazolo[2,3-a]pyridinium chloride; dihydrogen peroxide In water; tert-butyl alcohol at 20℃; for 2h;96%
With oxygen; Langlois reagent In acetonitrile at 25℃; under 760.051 Torr; for 12h; Irradiation; Green chemistry;95%
1309453-49-3

C15H14ClNO

A

98-98-6

2-Picolinic acid

B

1309453-57-3

C15H12ClNO

C

74-11-3

para-chlorobenzoic acid

Conditions
ConditionsYield
Stage #1: C15H14ClNO With oxygen; sodium hydride In tetrahydrofuran at 0 - 20℃; for 10h;
Stage #2: With hydrogenchloride In water
A 51%
B 45%
C 51%
1121-60-4

pyridine-2-carbaldehyde

A

586-98-1

2-Hydroxymethylpyridine

B

98-98-6

2-Picolinic acid

Conditions
ConditionsYield
With aluminum oxide; water; sodium hydroxide at 100℃; for 0.0333333h; Cannizzaro Reaction; Microwave irradiation;A 47%
B 47%
With N,N,N',N'-tetramethylguanidine In water at 20℃; for 7h; Cannizzaro reaction;A 39%
B 36%
626-61-9

4-Chloropyridine

617-35-6

2-oxo-propionic acid ethyl ester

ferrous(II) sulfate heptahydrate

98-98-6

2-Picolinic acid

Conditions
ConditionsYield
With sodium hydroxide; sulfuric acid; dihydrogen peroxide In water; toluene50%
626-61-9

4-Chloropyridine

617-35-6

2-oxo-propionic acid ethyl ester

ferrous(II) sulfate heptahydrate

conc. H2 SO4

conc. H2 SO4

98-98-6

2-Picolinic acid

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide In water; toluene50%
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Chemistry


IUPAC Name: Pyridine-2-carboxylic acid
Canonical SMILES: C1=CC=NC(=C1)C(=O)O
InChI: InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
InChIKey: SIOXPEMLGUPBBT-UHFFFAOYSA-N
Molecular Weight: 123.1094 [g/mol]
Molecular Formula: C6H5NO2
XLogP3: 0.8
H-Bond Donor: 1
H-Bond Acceptor: 3 
storage temp.: Store at RT.
solubility: H2O: 50 mg/mL, clear
Water Solubility: 887 g/L (20 °C) 
Appearance: Off-white to tan powder
Melting Point: 139-142 °C
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: 130.7 °C
Enthalpy of Vaporization: 56.18 kJ/mol
Boiling Point: 292.5 °C at 760 mmHg
Vapour Pressure: 0.000836 mmHg at 25 °C 
EINECS: 202-719-7
Product Categories: Nitrogen cyclic compounds; Pyridine; Organic acids; API intermediates; Pyridine series
Classification Code of Picolinic acid (CAS NO.98-98-6): Chelating Agents; Iron chelating agents

Uses

 Picolinic acid (CAS NO.98-98-6) acts as a chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body. It is involved in phenylalanine, tryptophan, and alkaloid production, and for the quantitative detection of calcium.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 178mg/kg (178mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
mouse LD50 intraperitoneal 360mg/kg (360mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 17, Pg. 2377, 1969.
mouse LD50 intravenous 487mg/kg (487mg/kg)   Therapie. Vol. 23, Pg. 1343, 1968.
quail LD50 oral 562mg/kg (562mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by intravenous route. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 22-36-36/37/38 
R22:Harmful if swallowed. 
R36:Irritating to eyes. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-33-24/25 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S33:Take precautionary measures against static discharges. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: TJ7344000

Specification

 Picolinic acid (CAS NO.98-98-6), its Synonyms are 2-Carboxypyridine ; 2-Pyridinecarboxylic acid ; Acide picolique ; Pyridine-carboxylique-2 ; alpha-Pyridinecarboxylic acid ; o-Pyridinecarboxylic acid .