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Name	3-(Aminomethyl)pyridine	EINECS	223-091-0
CAS No.	3731-52-0	Density	1.053 g/cm³
PSA	38.91000	LogP	1.24060
Solubility	Freely soluble in water	Melting Point	-21 °C(lit.)
Formula	C₆H₈N₂	Boiling Point	226 °C at 760 mmHg
Molecular Weight	108.143	Flash Point	100.6 °C
Transport Information	UN 2735 8/PG 2	Appearance	Clear colourless to slighly yellow liquid
Safety	26-36/37/39-45-25-36	Risk Codes	Statements 34-37-36/37/38
Molecular Structure		Hazard Symbols	C, Xi
Synonyms	3-Aminomethylpyridine;2-Aminomethyl pyridine;Pyridine, 3- (aminomethyl)-;Picolaminum [INN-Latin];pyridin-3-ylmethanamine;3-Pyridinemethanamine;Picolamine;Picolamine [DCF:INN];3-Picolylamine;3-Pyridylmethylamine;Pyridine, 3-(aminomethyl)- (8CI);Picolamina [INN-Spanish];pyridin-3-ylmethylazanium;1-pyridin-3-ylmethanamine;3-Pyridinemethylamine;	Article Data	72

3-(Aminomethyl)pyridine Synthetic route

: 100-54-9
pyridine-3-carbonitrile

: 3731-52-0
3-Aminomethylpyridine

Conditions

Conditions	Yield
With sodium tetrahydroborate In water; dimethyl sulfoxide at 60℃; for 6h; High pressure; Green chemistry;	99.9%
With palladium 10% on activated carbon; ammonia; hydrogen In methanol at 30℃; under 7500.75 Torr; for 4h; Reagent/catalyst; Temperature; Pressure; Autoclave;	93.44%
With hydrogen; silica gel; nickel In methanol; ammonia at 120℃; under 7600 Torr; for 6h;	86%

: 500-22-1
3-pyridinecarboxaldehyde

: 3731-52-0
3-Aminomethylpyridine

Conditions

Conditions	Yield
With ammonia; hydrogen In methanol at 30℃; for 20h; Autoclave;	97%
With N,N'-bis(salicylidene)-1,2-phenylene-diaminocobalt(II); ammonia; hydrogen In water at 120℃; for 24h; Autoclave;	84%
Multi-step reaction with 2 steps 1: water; potassium carbonate; hydroxylamine hydrochloride 2: ethanol; zinc; acetic acid View Scheme

: 100-55-0
3-hydroxymethylpyridin

: 3731-52-0
3-Aminomethylpyridine

Conditions

Conditions	Yield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tert-Amyl alcohol at 140℃; for 20h; Inert atmosphere; Cooling;	96%
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tert-Amyl alcohol at 140℃; under 12001.2 Torr; for 20h; Inert atmosphere; Autoclave; chemoselective reaction;	96 %Chromat.

: 100-54-9
pyridine-3-carbonitrile

ammoniacal methanol: ammoniacal methanol

: 3731-52-0
3-Aminomethylpyridine

Conditions

Conditions	Yield
	85.6%
	84.2%

: 33252-28-7
6-chloronicotinonitrile

A: 3731-52-0
3-Aminomethylpyridine

B: 23100-12-1
6-chloronicotinylaldehyde

C: bis(6-chloro-3-pyridylmethyl)amine

D: 97004-04-1
5-(aminomethyl)-2-chloropyridine

Conditions

Conditions	Yield
With ammonia; hydrogen; Sponge Ni In ethanol at 50℃; under 760 Torr; for 5h; Reduction;	A 3% B 5% C 8% D 75%
With ammonia; hydrogen; Sponge Ni In ethanol at 50℃; under 912 - 1064 Torr; for 9h; Product distribution; Further Variations:; Catalysts; Pressures; Temperatures; Reduction;	A 2% B 1% C 2% D 73%
With ammonia; hydrogen; Sponge Ni In ethanol at 50℃; under 912 - 1064 Torr; Reduction;	A 2% B 2% C 2% D 73%
With hydrogen; Raney Nickel R-100 In methanol; ammonium hydroxide at 25℃; under 760 Torr; for 9h; Product distribution; Further Variations:; Catalysts; Pressures; Solvents; Temperatures; Hydrogenation;	A 11% B 3% C 17% D 59%

: 51892-16-1
nicotinaldehyde oxime

: 3731-52-0
3-Aminomethylpyridine

Conditions

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol for 0.5h; Ambient temperature;	74%
With ethanol; acetic acid; zinc

: 33252-28-7
6-chloronicotinonitrile

A: 3731-52-0
3-Aminomethylpyridine

B: bis(6-chloro-3-pyridylmethyl)amine

C: 97004-04-1
5-(aminomethyl)-2-chloropyridine

Conditions

Conditions	Yield
With ammonia; hydrogen; Sponge Ni In ethanol at 50℃; under 760 Torr; for 1.5h; Reduction;	A 17% B 3% C 62%

: 100-54-9
pyridine-3-carbonitrile

A: 3731-52-0
3-Aminomethylpyridine

B: 1656-94-6
bis(pyridin-3-ylmethyl)amine

Conditions

Conditions	Yield
With 1,4-dioxane; nickel at 130℃; under 147102 Torr; Hydrogenation;
With ethanol; nickel at 130℃; under 147102 Torr; Hydrogenation;
With ammonia; nickel at 70 - 80℃; under 77228.3 Torr; Hydrogenation;

: 108-99-6
3-Methylpyridine

A: 100-54-9
pyridine-3-carbonitrile

B: 3731-52-0
3-Aminomethylpyridine

C: 124-38-9
carbon dioxide

D: 98-92-0
nicotinamide

Conditions

Conditions	Yield
With ammonia; oxygen; vanadia at 375℃; Product distribution; other catalysts, effect of the presence of O2;

: 100-54-9
pyridine-3-carbonitrile

chromium (II)-acetate: chromium (II)-acetate

aq.-ethanolic KOH-solution: aq.-ethanolic KOH-solution

hydrogen: hydrogen

: 3731-52-0
3-Aminomethylpyridine

3-(Aminomethyl)pyridine Chemical Properties

MF: C₆H₈N₂
Synonyms: C-PYRIDIN-3-YL-METHYLAMINE;3-(AMINOMETHYL)PYRIDINE;3AMPY;3-PYRIDINEMETHANAMINE;3-PYRIDYLMETHYLAMINE;3-PICOLYLAMINE;AKOS BBS-00003679;Picolamine
MW: 108.14
EINECS: 223-091-0
mp : ?21 °C(lit.)
bp : 73-74 °C1 mm Hg(lit.)
density : 1.062 g/mL at 25 °C(lit.)
refractive index : n20/D 1.551(lit.)
Fp : 213 °F
Water Solubility : FREELY SOLUBLE
BRN : 108056

3-(Aminomethyl)pyridine Safety Profile

Risk Statements : 34-37-36/37/38
Safety Statements :26-36/37/39-45-25-36
Hazard Codes : C,Xi
RIDADR : UN 2735 8/PG 2
WGK Germany : 3
Hazard Note :Irritant
HazardClass : 8
PackingGroup : III
HS Code : 29333999

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