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498-94-2

Basic Information
CAS No.: 498-94-2
Name: Isonipecotic acid
Article Data: 30
Molecular Structure:
Molecular Structure of 498-94-2 (Isonipecotic acid)
Formula: C6H11NO2
Molecular Weight: 129.159
Synonyms: Hexahydroisonicotinic acid;Acide piperidine-carboxylique-4 [French];5-22-01-00244 (Beilstein Handbook Reference);4-Piperidinecarboxylic acid;Acide isonipecotique [French];4-Hexahydroisonicotinic acid;Isonicotinic acid, hexahydro-;4-Carboxypiperidine;3,4,5,6-tetrahydro-2H-pyridine-4-carboxylate;Piperidine-4-carboxylic acid;4-piperidine carboxylic acid;H-Pic(4)-OH;4-nipecotic acid(Isonipecotic acid);
EINECS: 207-872-3
Density: 1.125 g/cm3
Melting Point: >300 °C(lit.)
Boiling Point: 265.8 °C at 760 mmHg
Flash Point: 114.5 °C
Solubility: Soluble in water
Appearance: white to faint pink-beige powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
PSA: 49.33000
LogP: 0.39940
Synthetic route

Piperidine-4-carboxylic acid 3-methyl-but-2-enyl ester

498-94-2

isonipecotic acid

Conditions
ConditionsYield
With diethylamine; Pd(0) (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) In water; acetonitrile for 0.166667h; 5 molpercent catalyst;100%
13602-12-5

Isonicotinic acid N-oxide

498-94-2

isonipecotic acid

Conditions
ConditionsYield
With ammonium formate; 10percent palladium on carbon In methanol at 20℃; for 16h;99%
10314-99-5

benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate

A

498-94-2

isonipecotic acid

B

138163-08-3

N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde

C

4-(4-Formyl-piperidine-1-carbonyl)-piperidine-1-carboxylic acid benzyl ester

Conditions
ConditionsYield
With methyl-phenyl-thioether; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal In toluene at 20℃; under 2068.6 Torr; for 22h; Yields of byproduct given;A n/a
B 94%
C n/a
3731-38-2

3-Quinuclidinone

498-94-2

isonipecotic acid

Conditions
ConditionsYield
With dihydrogen peroxide In ethanol for 2h;72%
110-89-4

piperidine

64-18-6

formic acid

A

498-94-2

isonipecotic acid

B

56-40-6

glycine

C

4043-87-2

pipecolic Acid

D

498-95-3

nipecotic acid

Conditions
ConditionsYield
In water at 10 - 20℃; for 1h; contact glow discharge electrolysis (500-600 V, 45 mA);A 4.3%
B 0.1%
C 0.8%
D 2.9%
55-22-1

pyridine-4-carboxylic acid

498-94-2

isonipecotic acid

Conditions
ConditionsYield
With i-Amyl alcohol; sodium
With acetic acid; platinum at 40℃; under 2280 Torr; Hydrogenation;
With acetic acid; platinum Hydrogenation;
857778-39-3

4-bromo-2-(2-bromo-ethyl)-butyric acid ethyl ester

498-94-2

isonipecotic acid

Conditions
ConditionsYield
With ammonia at 130 - 140℃;
5398-44-7

2,6-dichloropyridine-4-carboxylic acid

498-94-2

isonipecotic acid

Conditions
ConditionsYield
With acetic acid; platinum Hydrogenation;
Multi-step reaction with 2 steps
1: Raney nickel; aqueous NaOH / Hydrogenation.unter Druck
2: platinum; acetic acid / Hydrogenation
View Scheme
N-nitroso-isonipecotic acid
6238-69-3, 67659-29-4, 67659-30-7

N-nitroso-isonipecotic acid

498-94-2

isonipecotic acid

Conditions
ConditionsYield
With perchloric acid; ammonium sulfamate; sodium thiocyanide at 50℃; Rate constant; piperidinium perchlorate, 18h; transnitrosating studies;

Piperidine-4-carboxylic acid 4-nitro-phenyl ester; hydrobromide

A

498-94-2

isonipecotic acid

B

100-02-7

4-nitro-phenol

Conditions
ConditionsYield
With Cu complex of polymer from 2,6-bis-aminomethylpyridine and 4,4'-bis-aminomethyldiphenylmethane; water In dimethyl sulfoxide at 25℃; Rate constant; var.reag.: Cu(2+) complex of 2,6-bis-benzylaminomethylpyridine; oligomers of 2,6-bis-aminomethylpyridine and 4,4'-bis-aminomethyldiphenylmethane;
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    Product Name: Isonipecotic acid Synonyms: Inp-OH;Isonipecotic acid≥ 99% (Titration);4-Piperidinecarboxylic acid for synthesis;IsonipecoticAcid98%;4-PiperidinecarboxylicAcid/IsonipecoticAcid;(n)-piperidine-4-carboxylic acid;h-dl-inp-oh;Piperid

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Chemistry

IUPAC Name: piperidine-4-carboxylic acid 
Empirical Formula: C6H11NO2
Molecular Weight: 129.157g/mol
EINECS: 207-872-3 
Structure of Isonipecotic acid (CAS NO.498-94-2):

Index of Refraction: 1.478
Molar Refractivity: 32.51 cm3
Molar Volume: 114.7 cm3
Polarizability: 12.88×10-24cm3
Surface Tension: 40.3 dyne/cm
Density: 1.125 g/cm3
Flash Point: 114.5 °C
Enthalpy of Vaporization: 55.45 kJ/mol 
Melting Point: >300 °C(lit.)
Boiling Point: 265.8 °C at 760 mmHg
Vapour Pressure: 0.0026 mmHg at 25°C 
Water Solubility: soluble
Product Categories: Nitrogen cyclic compounds;blocks;Carboxes;Heterocycles;Acids and Derivatives;Amines and Anilines;Carboxylic Acids;Pyrans, Piperidines &Piperazines;Piperidine;Organic acids;Terfenadine Fexofenadine Ketanserin;Carboxylic Acids;Pyrans, Piperidines & Piperazines 
Canonical SMILES: C1CNCCC1C(=O)O
InChI: InChI=1S/C6H11NO2/c8-6(9)5-1-3-7-4-2-5/h5,7H,1-4H2,(H,8,9)
InChIKey: SRJOCJYGOFTFLH-UHFFFAOYSA-N

Toxicity Data With Reference

1.    

ivn-mus LD50:2100 mg/kg

    THERAP    Therapie. 23 (1968),1343.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by intravenous route. When heated to decomposition it emits toxic vapors of NOx.
Hazard Codes:  Xi
Hazard Note: Irritant
The Risk Statements information of Isonipecotic acid (CAS NO.498-94-2):
36/37/38:  Irritating to eyes, respiratory system and skin 
The Safety Statements information of Isonipecotic acid (CAS NO.498-94-2):
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing 
37/39:  Wear suitable gloves and eye/face protection 
WGK Germany: 3
RTECS: NS5150000
Hazard Note: Irritant
TSCA: T
HazardClass: IRRITANT
HS Code: 29333999

Specification

  Isonipecotic acid , its cas register number is 498-94-2. It also can be called 4-Carboxypiperidine ; 4-Hexahydroisonicotinic acid ; 5-22-01-00244 (Beilstein Handbook Reference) ; Acide isonipecotique ; Acide piperidine-carboxylique-4 ;
 Hexahydroisonicotinic acid ; Isonicotinic acid, hexahydro- ; NSC 61049 ; Piperidine-4-carboxylic acid . Isonipecotic acid (CAS NO.498-94-2) is a white to faint pink-beige powder.