Product Name

  • Name

    Methyl 6-aminonicotinate

  • EINECS 629-051-2
  • CAS No. 36052-24-1
  • Article Data30
  • CAS DataBase
  • Density 1.238 g/cm3
  • Solubility
  • Melting Point 158-162 °C(lit.)
  • Formula C7H8N2O2
  • Boiling Point 304.5 °C at 760 mmHg
  • Molecular Weight 152.153
  • Flash Point 137.9 °C
  • Transport Information UN 2811
  • Appearance off-white solid
  • Safety 26-36-36/37
  • Risk Codes 36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 36052-24-1 (Methyl 6-aminonicotinate)
  • Hazard Symbols IrritantXi, HarmfulXn
  • Synonyms Nicotinicacid, 6-amino-, methyl ester (6CI,8CI);2-Amino-5-(methoxycarbonyl)pyridine;3-Pyridinecarboxylicacid, 6-amino-, methyl ester;6-Aminopyridine-3-carboxylic acid methylester;Methyl 2-aminopyridine-5-carboxylate;6-Aminonicotinic acid methyl ester;Methyl6-aminopyridine-3-carboxylate;
  • PSA 65.21000
  • LogP 1.03160

Synthetic route

methanol
67-56-1

methanol

6-aminonicotinic acid
3167-49-5

6-aminonicotinic acid

methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

Conditions
ConditionsYield
With hydrogenchloride for 18h; Reflux;98%
With thionyl chloride at 80℃; for 12h; Inert atmosphere;89%
With sulfuric acid at 0 - 80℃;81.5%
6-aminonicotinic acid
3167-49-5

6-aminonicotinic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

Conditions
ConditionsYield
In methanol; chloroform; cyclohexane at 20℃; for 1h;66%
With acetic acid In methanol; chloroform
6-(acetylamino)pyridine-3-carboxylic acid
21550-48-1

6-(acetylamino)pyridine-3-carboxylic acid

methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

Conditions
ConditionsYield
With hydrogenchloride; methanol
(5-methyl-pyridin-2-yl)amine
1603-41-4

(5-methyl-pyridin-2-yl)amine

methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid
2: aqueous KMnO4
3: methanol; HCl
View Scheme
N-(5-methylpyridin-2-yl)acetamide
4931-47-9

N-(5-methylpyridin-2-yl)acetamide

methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous KMnO4
2: methanol; HCl
View Scheme
6-aminonicotinic acid
3167-49-5

6-aminonicotinic acid

methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

Conditions
ConditionsYield
With hydrogenchloride In methanol; water
With sulfuric acid In methanol; water-EtOAc
With thionyl chloride In methanol; water
6-aminonicotinic acid
3167-49-5

6-aminonicotinic acid

MeOH-HCl

MeOH-HCl

methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

Conditions
ConditionsYield
In hydrogenchloride; methanol; water
6-aminonicotinic acid
3167-49-5

6-aminonicotinic acid

MeOH-HCl

MeOH-HCl

methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

Conditions
ConditionsYield
In hydrogenchloride; methanol; water
In hydrogenchloride; methanol; water
In hydrogenchloride; methanol; water
In hydrogenchloride; methanol; water
In hydrogenchloride; methanol; water
6-aminonicotinic acid
3167-49-5

6-aminonicotinic acid

sulfuric acid
7664-93-9

sulfuric acid

methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

Conditions
ConditionsYield
In methanol
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

methyl 6-<(tert-butyloxycarbonyl)amino>nicotinoate
144186-11-8

methyl 6-<(tert-butyloxycarbonyl)amino>nicotinoate

Conditions
ConditionsYield
With dmap In tetrahydrofuran at 20℃;100%
With dmap In acetonitrile for 4h; Ambient temperature;79%
With dmap In acetone; tert-butyl alcohol for 20h;78%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

methyl 6-cyanopyridine-3-carboxylate
89809-65-4

methyl 6-cyanopyridine-3-carboxylate

Conditions
ConditionsYield
In methanol; diethyl ether at 0 - 20℃; for 2h;100%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide
1211443-61-6

2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide

6-(7-cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-nicotinic acid methyl ester
1211444-01-7

6-(7-cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-nicotinic acid methyl ester

Conditions
ConditionsYield
With caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; for 2.2h; Product distribution / selectivity; Sealed tube; Inert atmosphere;100%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

2,4-dichlorobenzoyl chloride
89-75-8

2,4-dichlorobenzoyl chloride

6-(2,4-dichlorobenzoylamino)nicotinic acid methyl ester
735351-60-7

6-(2,4-dichlorobenzoylamino)nicotinic acid methyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 4h;96%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

2-bromo-4'-fluoroacetophenone
403-29-2

2-bromo-4'-fluoroacetophenone

2-(4-fluoro-phenyl)-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester
866133-01-9

2-(4-fluoro-phenyl)-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester

Conditions
ConditionsYield
In 1,4-dioxane for 8.5h; Heating / reflux;96%
With sodium carbonate In ethanol at 70℃;
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

acetyl chloride
75-36-5

acetyl chloride

6-acetamide-nicotinic acid methyl ester
98953-23-2

6-acetamide-nicotinic acid methyl ester

Conditions
ConditionsYield
Stage #1: methyl 6-aminonicotinoate; acetyl chloride With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -20 - 20℃;
Stage #2: With sodium methylate In dichloromethane at 20℃; for 14h;		96%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

hexadecanyl bromide
112-82-3

hexadecanyl bromide

methyl 6-hexadecylamino-3-pyridinecarboxylate
73781-92-7

methyl 6-hexadecylamino-3-pyridinecarboxylate

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide at 120℃; for 22h;95%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

6-[(Z)-Toluene-4-sulfonylimino]-1,6-dihydro-pyridine-3-carboxylic acid methyl ester
209971-44-8

6-[(Z)-Toluene-4-sulfonylimino]-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With pyridine at 80 - 90℃;93%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

Ethoxycarbonyl isothiocyanate
16182-04-0

Ethoxycarbonyl isothiocyanate

methyl 6-{[(ethoxycarbonyl)carbamothioyl]amino}pyridine-3-carboxylate

methyl 6-{[(ethoxycarbonyl)carbamothioyl]amino}pyridine-3-carboxylate

Conditions
ConditionsYield
In tetrahydrofuran at 45 - 50℃; for 15h;91%
In 1,4-dioxane at 20 - 50℃; for 1.5h;66%
In 1,4-dioxane at 20 - 50℃; for 1.5h;66%
In 1,4-dioxane at 20℃; for 15h;
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

2-isopropoxy-6-methoxyisonicotinic acid
1168143-78-9

2-isopropoxy-6-methoxyisonicotinic acid

6-[(2-isopropoxy-6-methoxy-pyridine-4-carbonyl)-amino]-nicotinic acid methyl ester
1168143-79-0

6-[(2-isopropoxy-6-methoxy-pyridine-4-carbonyl)-amino]-nicotinic acid methyl ester

Conditions
ConditionsYield
Stage #1: 2-isopropoxy-6-methoxyisonicotinic acid With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: methyl 6-aminonicotinoate In N,N-dimethyl-formamide at 100℃; for 1h;		90.62%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

2-Phenylbutyryl chloride
36854-57-6

2-Phenylbutyryl chloride

C17H18N2O3

C17H18N2O3

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;88.2%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

bromoacetaldehyde
17157-48-1

bromoacetaldehyde

methyl 6-imidazo<1,2-a>pyridinecarboxylate
136117-69-6

methyl 6-imidazo<1,2-a>pyridinecarboxylate

Conditions
ConditionsYield
With sodium hydrogencarbonate at 60℃; for 1h;88%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

methyl 6-((3-oxocyclohex-1-en-1-yl)amino)nicotinate

methyl 6-((3-oxocyclohex-1-en-1-yl)amino)nicotinate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In water; toluene for 3h; Dean-Stark; Reflux; Inert atmosphere;88%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

2-bromo-1-(1-hydroxycyclohexyl)ethanone
23386-72-3

2-bromo-1-(1-hydroxycyclohexyl)ethanone

methyl 2-(1-hydroxycyclohexyl)imidazo[1,2-a]pyridine-6-carboxylate

methyl 2-(1-hydroxycyclohexyl)imidazo[1,2-a]pyridine-6-carboxylate

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane at 110℃; for 12h; Sealed tube; Inert atmosphere;88%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

phenylacetyl chloride
103-80-0

phenylacetyl chloride

C15H14N2O3

C15H14N2O3

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;87.3%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

benzyl alcohol
100-51-6

benzyl alcohol

methyl 6-(benzylamino)nicotinate

methyl 6-(benzylamino)nicotinate

Conditions
ConditionsYield
With palladium diacetate; sodium 3-(diphenylphosphanyl)benzenesulfonate In water at 120℃; for 16h; Sealed tube;86%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

methylmagnesium chloride
676-58-4

methylmagnesium chloride

2-(6-aminopyridin-3-yl)propan-2-ol
843643-03-8

2-(6-aminopyridin-3-yl)propan-2-ol

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere;85.7%
Stage #1: methyl 6-aminonicotinoate; methylmagnesium chloride In tetrahydrofuran at 10 - 20℃; for 15h;
Stage #2: With water; ammonium chloride In tetrahydrofuran at 0℃;
In tetrahydrofuran at 10 - 20℃; for 15h;
In tetrahydrofuran at 0 - 25℃; for 15h; Inert atmosphere;
formaldehyd
50-00-0

formaldehyd

methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

methyl 6-(dimethylamino)nicotinate
26218-81-5

methyl 6-(dimethylamino)nicotinate

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid at 20℃; for 23h;85.5%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

2,3-diphenylpropionyl chloride
56042-76-3

2,3-diphenylpropionyl chloride

C22H20N2O3

C22H20N2O3

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;85%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

methyl 6-amino-5-bromopyridine-3-carboxylate

methyl 6-amino-5-bromopyridine-3-carboxylate

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrahydrofuran at 0 - 20℃;84.8%
With N-Bromosuccinimide In tetrahydrofuran at 0 - 20℃;84.8%
With N-bromobutyramide In tetrahydrofuran at 0 - 25℃; for 2h;80.91%
2-naphthylacetyl chloride
37859-25-9

2-naphthylacetyl chloride

methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

C19H16N2O3

C19H16N2O3

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;83.4%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

methyl 6-{[(1Z)-(hydroxyamino)methylene]amino}nicotinate

methyl 6-{[(1Z)-(hydroxyamino)methylene]amino}nicotinate

Conditions
ConditionsYield
Stage #1: methyl 6-aminonicotinoate; N,N-dimethyl-formamide dimethyl acetal In isopropyl alcohol Heating;
Stage #2: With hydroxylamine hydrochloride In isopropyl alcohol at 50℃;		80%
2-chloroethanal
107-20-0

2-chloroethanal

methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

methyl 6-imidazo<1,2-a>pyridinecarboxylate
136117-69-6

methyl 6-imidazo<1,2-a>pyridinecarboxylate

Conditions
ConditionsYield
With sodium hydrogencarbonate In methanol for 8h; Reflux;80%
In ethanol; water for 4h; Reflux;63%
In ethanol for 18h; Heating / reflux;
Stage #1: 2-chloroethanal; methyl 6-aminonicotinoate In ethanol; water for 4h; Reflux;
Stage #2: With sodium hydrogencarbonate In water pH=> 7;
In ethanol; water for 4h; Reflux;
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

pivaloyl chloride
3282-30-2

pivaloyl chloride

C12H16N2O3
1439929-96-0

C12H16N2O3

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃;80%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

α-isopropyl-α-phenylacetyl chloride
51631-26-6

α-isopropyl-α-phenylacetyl chloride

methyl 6-(3-methyl-2-phenylbutanamido)nicotinate

methyl 6-(3-methyl-2-phenylbutanamido)nicotinate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;78.4%
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

2-amino-3-iodo-5-nicotinic methyl ester
211308-80-4

2-amino-3-iodo-5-nicotinic methyl ester

Conditions
ConditionsYield
With iodine; silver trifluoroacetate In methanol at 25℃; for 72h;77%
With iodine; silver sulfate In ethanol at 20℃; for 42h;62%
With iodine; silver sulfate In ethanol at 20℃; for 24h;57%
With N-iodo-succinimide; trifluoroacetic acid In acetic acid at 20℃;50%
With trifluorormethanesulfonic acid; [bis(pyridine)iodine]+ tetrafluoroborate In dichloromethane at 0 - 20℃; for 26h;
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

(6-amino-3-pyridinyl)methanol
113293-71-3

(6-amino-3-pyridinyl)methanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 24h; Inert atmosphere;76%
Stage #1: methyl 6-aminonicotinoate With lithium aluminium tetrahydride In tetrahydrofuran
Stage #2: With methanol In tetrahydrofuran at 0℃;		67%
With lithium aluminium tetrahydride In tetrahydrofuran at 70℃; for 16h; Inert atmosphere;2.6 g
methyl 6-aminonicotinoate
36052-24-1

methyl 6-aminonicotinoate

C13H10ClN3
1204527-15-0

C13H10ClN3

C20H17N5O2
1204527-58-1

C20H17N5O2

Conditions
ConditionsYield
With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium diacetate In 1,4-dioxane at 20 - 100℃;76%

Methyl 6-aminonicotinate Chemical Properties

The molecular structure of 6-Aminonicotinic acid methyl ester (CAS NO.36052-24-1):

IUPAC Name: Methyl 6-aminopyridine-3-carboxylate 
Molecular Weight: 152.15062 g/mol
Molecular Formula: C7H8N2O2 
Density: 1.238 g/cm3 
Melting Point: 158-162 °C(lit.)
Boiling Point: 304.5 °C at 760 mmHg 
Flash Point: 137.9 °C
Index of Refraction: 1.57
Molar Refractivity: 40.35 cm3
Molar Volume: 122.8 cm3
Surface Tension: 53.4 dyne/cm 
Enthalpy of Vaporization: 54.48 kJ/mol
Vapour Pressure: 0.000872 mmHg at 25 °C
XLogP3: 1.7
H-Bond Donor: 1
H-Bond Acceptor: 4
Rotatable Bond Count: 2
Tautomer Count: 4
Exact Mass: 152.058578
MonoIsotopic Mass: 152.058578
Topological Polar Surface Area 65.2
Heavy Atom Count 11
Canonical SMILES: COC(=O)C1=CN=C(C=C1)N
InChI: InChI=1S/C7H8N2O2/c1-11-7(10)5-2-3-6(8)9-4-5/h2-4H,1H3,(H2,8,9)
InChIKey: JACPDLJUQLKABC-UHFFFAOYSA-N
Product Categories: Amines; blocks; Carboxes; Pyridines; pharmacetical; Esters; Heterocycles; Heterocyclic Building Blocks

Methyl 6-aminonicotinate Uses

 6-Aminonicotinic acid methyl ester (CAS NO.36052-24-1) is used in ointments for treatment of psoriasis.

Methyl 6-aminonicotinate Safety Profile

Hazard Codes: IrritantXi, HarmfulXn
Risk Statements: 36/37/38-20/21/22 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36-36/37 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S36/37:Wear suitable protective clothing and gloves.
RIDADR: 2811
WGK Germany: 3
Hazard Note: Irritant
HazardClass: IRRITANT

Methyl 6-aminonicotinate Specification

 6-Aminonicotinic acid methyl ester (CAS NO.36052-24-1) is also named as 3-Pyridinecarboxylic acid, 6-amino-, methyl ester ; 6-Amino-nicotinic acid methyl ester ; Methyl 6-aminonicotinate ; Methyl 2-amino-5-pyridinecarboxylate ; Methyl 2-aminopyridine-5-carboxylate ; Methyl 6-Aminopyridine-3-carboxylate . 6-Aminonicotinic acid methyl ester (CAS NO.36052-24-1) is off-white solid.

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