Isonipecotic acid supplier

Name
Isonipecotic acid
EINECS 207-872-3
CAS No. 498-94-2
Article Data30
CAS DataBase
Density 1.125 g/cm³
Solubility Soluble in water
Melting Point >300 °C(lit.)
Formula C₆H₁₁NO₂
Boiling Point 265.8 °C at 760 mmHg
Molecular Weight 129.159
Flash Point 114.5 °C
Transport Information
Appearance white to faint pink-beige powder
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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);
PSA 49.33000
LogP 0.39940

Synthetic route

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

: 498-94-2
isonipecotic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 3731-38-2
3-Quinuclidinone

: 498-94-2
isonipecotic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 55-22-1
pyridine-4-carboxylic acid

: 498-94-2
isonipecotic acid

Conditions

Conditions	Yield
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

Conditions	Yield
With ammonia at 130 - 140℃;

: 5398-44-7
2,6-dichloropyridine-4-carboxylic acid

: 498-94-2
isonipecotic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

: 55-22-1
pyridine-4-carboxylic acid

: 64-19-7
acetic acid

platinum: platinum

: 498-94-2
isonipecotic acid

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 55-22-1
pyridine-4-carboxylic acid

: 71-41-0
pentan-1-ol

sodium: sodium

: 498-94-2
isonipecotic acid

...Expand

: 10314-98-4
1-benzyloxycarbonylpiperidine-4-carboxylic acid

: 498-94-2
isonipecotic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (COCl)2 / toluene; dimethylformamide / 16 h / 18 °C 2: H2, DIEA, thioanisole / Pd/C / toluene / 22 h / 20 °C / 2068.6 Torr View Scheme

: Piperidine-1,4-dicarboxylic acid 1-allyl ester 4-(3-methyl-but-2-enyl) ester

: 498-94-2
isonipecotic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / diethylamine / Pd(0) (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) / acetonitrile; H2O / 0.33 h / 1 molpercent catalyst 2: 100 percent / diethylamine / Pd(0) (in situ from Pd(OAc)2 and m.sulfonated triphenylphosphine) / acetonitrile; H2O / 0.17 h / 5 molpercent catalyst View Scheme

A

B 1-(dimethylcarbamoyl)piperidine-4-carboxylic acid: 1-(dimethylcarbamoyl)piperidine-4-carboxylic acid

C: 632-22-4
tetramethylurea

...Expand

: 39546-32-2
4-carboxamidopiperidine

: 498-94-2
isonipecotic acid

Conditions

Conditions	Yield
With amidase from Cupriavidus necator JMP134; water In aq. phosphate buffer at 30℃; pH=7; Enzymatic reaction; stereoselective reaction;

: 498-94-2
isonipecotic acid

: 501-53-1
benzyl chloroformate

: 10314-98-4
1-benzyloxycarbonylpiperidine-4-carboxylic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate; sodium carbonate In water; acetonitrile at 0 - 20℃; for 2h; pH=10 - 11;	100%
With potassium carbonate In water at 22℃; for 58h;	97%
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃;	96%

: 498-94-2
isonipecotic acid

: 95-54-5
1,2-diamino-benzene

: 38385-95-4
2-(4-piperidinyl)-1H-benzimidazole

Conditions

Conditions	Yield
Stage #1: isonipecotic acid; 1,2-diamino-benzene at 190℃; for 14h; Stage #2: isonipecotic acid; 1,2-diamino-benzene With phosphoric acid	100%
With PPA at 100℃; for 2h;	92%
With PPA at 180℃; for 2h;	85%

: 498-94-2
isonipecotic acid

: 24424-99-5
di-tert-butyl dicarbonate

: 84358-13-4
N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

Conditions

Conditions	Yield
In dichloromethane	100%
In sodium hydroxide; tert-butyl alcohol	100%
In sodium hydroxide; tert-butyl alcohol	100%

: 498-94-2
isonipecotic acid

: 40320-60-3
N-benzhydryl 3-azetidinone

: 874800-95-0
1-[1-(diphenylmethyl)azetidin-3-yl]piperidine-4-carboxylic acid

Conditions

Conditions	Yield
With methanol; polymer-bound trimethyl ammonium cyanoborohydride; acetic acid at 120℃; for 0.0833333h; Polystyrene; Microwave irradiation;	100%

: 498-94-2
isonipecotic acid

: 1885-14-9
phenyl chloroformate

: 10314-98-4
1-benzyloxycarbonylpiperidine-4-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide In water at 0 - 25℃; for 18h;	100%

: 498-94-2
isonipecotic acid

: 1-[3-chloro-5-(5-ethyl-1,2,4-oxadiazol-3-yl)pyridin-2-yl]piperazine bis(trifluoroacetate)

: 898227-66-2
1-(3-cyano-5-(isopropoxycarbonyl)-6-methylpyridin-2-yl)piperidine-4-carboxylic acid

Conditions

Conditions	Yield
Stage #1: isonipecotic acid; 1-[3-chloro-5-(5-ethyl-1,2,4-oxadiazol-3-yl)pyridin-2-yl]piperazine bis(trifluoroacetate) With N-ethyl-N,N-diisopropylamine In ethanol for 1h; Heating / reflux; Stage #2: With potassium hydrogensulfate In ethanol; water at 20℃;	100%

: 498-94-2
isonipecotic acid

: 898229-16-8
2-chloro-5-(5-ethyl-1,3-oxazol-2-yl)-6-methylnicotinonitrile

: 898229-21-5
1-[3-cyano-5-(5-ethyl-1,3-oxazol-2-yl)-6-methylpyridin-2-yl]piperidine-4-carboxylic acid

Conditions

Conditions	Yield
at 120℃; for 0.666667h; Microwave irradiation;	100%

: 498-94-2
isonipecotic acid

: 898227-65-1
isopropyl 6-chloro-3-cyano-2-methylnicotinate

: 898227-66-2
1-(3-cyano-5-(isopropoxycarbonyl)-6-methylpyridin-2-yl)piperidine-4-carboxylic acid

Conditions

Conditions	Yield
Stage #1: isonipecotic acid; isopropyl 6-chloro-3-cyano-2-methylnicotinate With N-ethyl-N,N-diisopropylamine In ethanol for 1h; Heating / reflux; Stage #2: With potassium hydrogensulfate In ethanol; water at 20℃;	100%
Stage #1: isonipecotic acid; isopropyl 6-chloro-3-cyano-2-methylnicotinate With N-ethyl-N,N-diisopropylamine In ethanol for 1h; Heating / reflux; Stage #2: With potassium hydrogensulfate In ethanol; water	100%

: 498-94-2
isonipecotic acid

: 108-77-0
1,3,5-trichloro-2,4,6-triazine

: 74-89-5
methylamine

: 1141894-74-7
1-[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylicacid

Conditions

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; methylamine With sodium hydroxide In water; acetonitrile at 0℃; for 0.5h; pH=9 - 10; Stage #2: isonipecotic acid In water; acetonitrile at 0 - 20℃; for 1h; pH=9 - 10;	100%

...Expand

: 498-94-2
isonipecotic acid

: 625826-69-9
4-(chloromethyl)-2-(4-fluorophenyl)-5-methyl-1,3-oxazole

: 1-((2-(4-fluorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 16h;	100%

: 498-94-2
isonipecotic acid

: 4-(chloromethyl)-5-methyl-2-(2,6-difluorophenyl)oxazole

: 1-((2-(2,6-difluorolphenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 16h;	100%

: 498-94-2
isonipecotic acid

: 4-(chloromethyl)-5-methyl-2-(2,6-dibromophenyl)oxazole

: 1-((2-(2,6-dibromophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 16h;	100%

: 498-94-2
isonipecotic acid

: 4-(chloromethyl)-5-methyl-2-(2-fluoro-6-methylphenyl)oxazole

: 1-((2-(2-fluoro-6-methylphenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 16h;	100%

: 498-94-2
isonipecotic acid

: 4-(chloromethyl)-5-methyl-2-(2-methoxy-6-methylphenyl)oxazole

: 1-((2-(2-methoxy-6-methylphenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 16h;	100%

: 498-94-2
isonipecotic acid

: 374776-34-8
4-(5-chlorosulfonyl-2-n-propoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide

: 4-(5-(4-(hydroxycarbonyl)piperidinylsulfonyl)-2-n-propoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide

Conditions

Conditions	Yield
With triethylamine In ethanol at 20℃; for 2h;	99%

: 498-94-2
isonipecotic acid

: 64-17-5
ethanol

: piperidine-4-carboxylic acid ethyl ester hydrochloride

Conditions

Conditions	Yield
With thionyl chloride for 3.83333h; Cooling with ice; Reflux;	99%
With thionyl chloride at 0℃; for 3h; Reflux;	96%
Stage #1: isonipecotic acid; ethanol With thionyl chloride at 0℃; for 3h; Heating / reflux; Stage #2: With hydrogenchloride In ethanol	90.2%
With thionyl chloride at 0 - 90℃; for 6h;	80.05%
With thionyl chloride Inert atmosphere; Reflux;

: 498-94-2
isonipecotic acid

: copper(II) perchlorate hexahydrate

: [Cu(piperidine-4-carboxylic acid)4][ClO4]2

Conditions

Conditions	Yield
In water soln. of metal compd. added to aq. soln. of ligand (1:4), stirred at 70°C for 10 min; crystd. on storage for several h, elem. anal.;	99%

: 498-94-2
isonipecotic acid

: 4-(chloromethyl)-5-methyl-2-(2,6-dichlorophenyl)oxazole

: 1-((2-(2,6-dichlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 16h;	99%

: 498-94-2
isonipecotic acid

: 4-(chloromethyl)-5-methyl-2-(2-fluoro-6-methoxyphenyl)oxazole

: 1-((2-(2-fluoro-6-methoxyphenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 16h;	99%

Isonipecotic acid Chemical Properties

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

Isonipecotic acid Toxicity Data With Reference

ivn-mus LD50:2100 mg/kg

THERAP Therapie. 23 (1968),1343.

Isonipecotic acid Consensus Reports

Reported in EPA TSCA Inventory.

Isonipecotic acid Safety Profile

Moderately toxic by intravenous route. When heated to decomposition it emits toxic vapors of NO_x.
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

Isonipecotic acid 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.

Product Name

Isonipecotic acid

Synthetic route

Isonipecotic acid Chemical Properties

Isonipecotic acid Toxicity Data With Reference

Isonipecotic acid Consensus Reports

Isonipecotic acid Safety Profile

Isonipecotic acid Specification

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