2-Amino-4-picoline supplier

Name
4-Methylpyridin-2-amine
EINECS 211-780-9
CAS No. 695-34-1
Article Data25
CAS DataBase
Density 1.068 g/cm³
Solubility Soluble in water
Melting Point 96-101 °C
Formula C₆H₈N₂
Boiling Point 227.4 °C at 760 mmHg
Molecular Weight 108.143
Flash Point 114 °C
Transport Information UN 3086 6.1/PG 1
Appearance Light yellow to brown flakes
Safety 53-45-60-61-37/39-28A-26-36/37/39
Risk Codes 45-46-60-61-8-21-25-26-34-42/43-48/23-50/53-36/37/38-33-23/24/25
Molecular Structure
Hazard Symbols T
Synonyms 4-Picoline, 2-amino-;4-Picolylamine;4-methyl-1H-pyridin-2-amine;RA 1226;2-Amino-4-methylpyridine;2-Pyridinamine,4-methyl-;Methyl-4 amino-2-pyridine;4-Methyl-2-aminopyridine;2-Pyridinamine, 4-methyl-;Pyridine, 2-amino-4-methyl-;4-Methyl-2-pyridinamine;4-Methyl-2-pyridylamine;alpha-Amino-gamma-picoline;4-methylpyridin-2-amine;4-Methyl-pyridin-2-ylamine;2-Amino-4-Methyl pyridine;
PSA 38.91000
LogP 1.55340

Synthetic route

: 76809-23-9
2,2-dimethyl-3-(4-methylpyrid-2-yl)-4-oxo-4H-1,3-benzoxazine

A: 695-34-1
2-Amino-4-methylpyridine

B: 69-72-7
salicylic acid

Conditions

Conditions	Yield
With hydrogenchloride for 3h; Heating;	A 94% B n/a

: 4926-28-7
2-Bromo-4-picoline

: 695-34-1
2-Amino-4-methylpyridine

Conditions

Conditions	Yield
With ammonium hydroxide; L-2-O-methyl-chiro-inositol; copper(II) acetate monohydrate In 1-methyl-pyrrolidin-2-one at 110℃; for 20h;	91%

: 18368-71-3
4-methyl-2-nitropyridine

: 695-34-1
2-Amino-4-methylpyridine

Conditions

Conditions	Yield
With C36H56Cl3CrN2O; magnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; chemoselective reaction;	90%

: 56960-76-0
2-amino-3-chloro-4-methylpyridine

: 695-34-1
2-Amino-4-methylpyridine

Conditions

Conditions	Yield
With copper; benzoic acid at 150℃; for 1h;	87.2%

: 95337-78-3
2-(2,5-dimethyl-pyrrol-1-yl)-4-methyl-pyridine

: 695-34-1
2-Amino-4-methylpyridine

Conditions

Conditions	Yield
With hydroxylamine hydrochloride In ethanol; water for 24h; Heating;	82%

: 461-87-0
2-fluoro-4-methylpyridine

: 695-34-1
2-Amino-4-methylpyridine

Conditions

Conditions	Yield
With acetamidine hydrochloride; sodium hydroxide In water; dimethyl sulfoxide at 130℃; for 24h; Schlenk technique; chemoselective reaction;	46%

: 108-89-4
picoline

: 695-34-1
2-Amino-4-methylpyridine

Conditions

Conditions	Yield
With sodium amide; xylene
With sodium amide; decalin at 140 - 150℃;

: 79917-38-7
4-methyl(2-nitroso)pyridine

: 695-34-1
2-Amino-4-methylpyridine

Conditions

Conditions	Yield
With zinc In acetic acid

: 108-89-4
picoline

: 56-23-5
tetrachloromethane

: sodium amide

: 695-34-1
2-Amino-4-methylpyridine

...Expand

: 76809-23-9
2,2-dimethyl-3-(4-methylpyrid-2-yl)-4-oxo-4H-1,3-benzoxazine

: 695-34-1
2-Amino-4-methylpyridine

Conditions

Conditions	Yield
With hydrogenchloride Hydrolysis;

: 4-methyl-pyridin-2-yl-(tert-butyl)-amine

: 695-34-1
2-Amino-4-methylpyridine

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 70℃;

: 1003-67-4
4-methylpyridine-1-oxide

: 695-34-1
2-Amino-4-methylpyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Ts2O / various solvent(s); CH2Cl2 / 0.25 h 2: TFA / various solvent(s); CH2Cl2 / 70 °C View Scheme
Multi-step reaction with 2 steps 1: CH2Cl2 / Heating 2: conc. HCl View Scheme

: N-2-(4-methylpyridyl)-2-hydroxy-1-naphthaldiamine

A: 695-34-1
2-Amino-4-methylpyridine

B: 708-06-5
2-hydroxynaphthalene-1-carbaldehyde

Conditions

Conditions	Yield
In methanol; water at 20℃; for 0.5h;

: N-(4-methylpyridin-2-yl)butyramide

: 5123-13-7
5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane

A: 695-34-1
2-Amino-4-methylpyridine

B: 103392-72-9
butyl-(4-methyl-[2]pyridyl)-amine

C: C16H20N2

Conditions

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; isopropyl alcohol at 140℃; for 24h; Inert atmosphere; Sealed tube;	A 10 %Spectr. B 18 %Spectr. C 53 %Spectr.

...Expand

: 695-34-1
2-Amino-4-methylpyridine

: 62266-36-8
(+/-)-methylenecyclopropanecarboxylic acid

: 2-methylene-cyclopropanecarboxylic acid (4-methyl-pyridin-2-yl)-amide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; for 9.5h;	100%

: 695-34-1
2-Amino-4-methylpyridine

: 4-hydroxy-1-(4-nitrophenylsulphonyl)pyrrolidine-2-carboxylic acid

: (2S)-4-hydroxy-N-(4-methylpyridin-2-yl)-1-(4-nitrobenzenesulfonyl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux;	100%

: 695-34-1
2-Amino-4-methylpyridine

: 909262-73-3
4-hydroxy-1-tosylpyrrolidine-2-carboxylic acid

: (2S)-4-hydroxy-1-(4-methylbenzenesulfonyl)-N-(4-methylpyridin-2-yl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux;	100%

: 695-34-1
2-Amino-4-methylpyridine

: 88867-96-3
1-(4-nitrophenylsulphonyl)pyrrolidine-2-carboxylic acid

: (2S)-N-(4-methylpyridin-2-yl)-1-(4-nitrobenzenesulfonyl)pyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux;	99.9%

: 695-34-1
2-Amino-4-methylpyridine

: 3-(1H-indol-2-yl)-2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]propanoic acid

: (2S)-3-(1H-indol-2-yl)-2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]-N-(4-methylpyridin-2-yl)propanamide

Conditions

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux;	99.6%

: 695-34-1
2-Amino-4-methylpyridine

: 3-(1H-indol-2-yl)-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]propanoic acid

: (2S)-3-(1H-indol-2-yl)-N-(4-methylpyridin-2-yl)-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]propanamide

Conditions

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux;	99.4%

: 695-34-1
2-Amino-4-methylpyridine

: {benzoyl[(4-methylphenyl)sulfonyl]amino}acetic acid

: 2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]-N-(4-methylpyridin-2-yl)acetamide

Conditions

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux;	99.3%

: 695-34-1
2-Amino-4-methylpyridine

: 135-73-9
2-Bromo-4'-phenylacetophenone

: 65964-64-9
7-methyl-2-(biphenyl-4-yl)imidazo[1,2-a]pyridine

Conditions

Conditions	Yield
In neat (no solvent) at 25 - 30℃; Milling; Green chemistry;	99%
In ethanol for 4h; Heating;	77%

: 695-34-1
2-Amino-4-methylpyridine

: 619-41-0
4-(bromoacetyl)toluene

: 65964-61-6
2-(4-methylphenyl)-7-methylimidazo[1,2-a]pyridine

Conditions

Conditions	Yield
In neat (no solvent) at 25 - 30℃; Milling; Green chemistry;	99%
In water; isopropyl alcohol at 75℃; Microwave irradiation; Green chemistry;	95%
With ethanol

: 695-34-1
2-Amino-4-methylpyridine

: 536-38-9
4-chlorobenzoylmethyl bromide

: 65964-62-7
2-(4-chlorophenyl)-7-methyl-imidazo[1,2-a]pyridine

Conditions

Conditions	Yield
In neat (no solvent) at 25 - 30℃; Milling; Green chemistry;	99%
With sodium hydrogencarbonate In ethanol for 20h; Reflux;	79%
With ethanol
With sodium carbonate In ethanol for 1h; Reflux;

: 695-34-1
2-Amino-4-methylpyridine

: 2632-13-5
2-Bromo-4'-methoxyacetophenone

: 65964-63-8
2-(4-methoxyphenyl)-7-methyl-imidazo[1,2-a]pyridine

Conditions

Conditions	Yield
In neat (no solvent) at 25 - 30℃; Milling; Green chemistry;	99%
In water; isopropyl alcohol at 75℃; Microwave irradiation; Green chemistry;	96%
In neat (no solvent) at 65℃; under 750.075 Torr; for 0.3h; Microwave irradiation; Green chemistry;	83%

: 695-34-1
2-Amino-4-methylpyridine

: 99-81-0
4-Nitrophenacyl bromide

: 961-82-0
2-(4-nitrophenyl)-7-methylimidazo[1,2-a]pyridine

Conditions

Conditions	Yield
In neat (no solvent) at 25 - 30℃; Milling; Green chemistry;	99%
With hydrogen bromide 1) acetone, reflux, 3 h, 2) methanol, reflux, 60 min; Yield given. Multistep reaction;

: 695-34-1
2-Amino-4-methylpyridine

: 70-11-1
α-bromoacetophenone

: 885-91-6
2-phenyl-7-methylimidazo[1,2-a]pyridine

Conditions

Conditions	Yield
In neat (no solvent) at 25 - 30℃; Milling; Green chemistry;	99%
In neat (no solvent) at 65℃; under 750.075 Torr; for 0.333333h; Microwave irradiation; Green chemistry;	85%
Stage #1: 2-Amino-4-methylpyridine; α-bromoacetophenone In ethanol for 5h; Reflux; Stage #2: With hydrogenchloride In ethanol; water for 3h; Reflux;	80%

: 695-34-1
2-Amino-4-methylpyridine

: 613-54-7
2-Bromo-2'-acetonaphthone

: 240135-98-2
7-methyl-2-(naphthalen-2-yl)imidazo[1,2-a]pyridine

Conditions

Conditions	Yield
In neat (no solvent) at 25 - 30℃; Milling; Green chemistry;	99%
With sodium carbonate In ethanol for 24h; Cyclization; Tschitschibabin reaction; Heating;	62%
In ethanol for 8h; Heating;	54%
In ethanol for 4h; Heating;	54%

: 695-34-1
2-Amino-4-methylpyridine

: 94-02-0
ethyl 3-oxo-3-phenylpropionate

: 137997-34-3
ethyl 7-methyl-2-phenylimidazo[1,2-a]pyridine-3-carboxylate

Conditions

Conditions	Yield
With carbon tetrabromide In acetonitrile at 80℃;	99%
With tert.-butylhydroperoxide; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide In water; acetonitrile at 80℃; for 10h;	83%
With [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate In tetrahydrofuran at 7℃; for 2h;	75%
Multi-step reaction with 2 steps 1: copper(l) iodide / N,N-dimethyl-formamide / 70 °C / Green chemistry 2: copper(l) iodide / N,N-dimethyl-formamide / 70 °C / Green chemistry View Scheme

: 695-34-1
2-Amino-4-methylpyridine

: 67-56-1
methanol

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

: 551911-78-5
methyl (4-methylpyridin-2-yl)carbamate

Conditions

Conditions	Yield
at 0 - 20℃; for 4h; Inert atmosphere;	99%

...Expand

: 695-34-1
2-Amino-4-methylpyridine

: 931-53-3
Cyclohexyl isocyanide

: 1122-91-4
4-bromo-benzaldehyde

: 1538557-71-9
C20H22BrN3

Conditions

Conditions	Yield
With LaMnO3 In neat (no solvent) at 35℃; for 1.5h; Catalytic behavior; Green chemistry;	99%

...Expand

: 695-34-1
2-Amino-4-methylpyridine

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

: 2-(4-fluorophenyl)-7-methylimidazo[1,2-a]pyridine

Conditions

Conditions	Yield
In neat (no solvent) at 25 - 30℃; Milling; Green chemistry;	99%
With sodium hydrogencarbonate In ethanol for 3h; Reflux;
Stage #1: 2-Amino-4-methylpyridine With sodium hydrogencarbonate In ethanol at 20℃; for 0.0833333h; Stage #2: 2-bromo-4'-fluoroacetophenone In ethanol at 65℃;

: 695-34-1
2-Amino-4-methylpyridine

: 20099-89-2
4-Cyanophenacyl bromide

: 118000-54-7
4-(7-methylimidazo[1,2-a]pyridin-2-yl)benzonitrile

Conditions

Conditions	Yield
In neat (no solvent) at 25 - 30℃; Milling; Green chemistry;	99%
In neat (no solvent) at 65℃; under 750.075 Torr; for 0.333333h; Microwave irradiation; Green chemistry;	86%

: 695-34-1
2-Amino-4-methylpyridine

: tetrakis-pivaloyloxymethyl ester of vinylidene-1,1-bisphosphonate

: tetrakispivaloyloxymethyl 2-(4-methylpyridine-2-ylamino)ethylidene-1,1-bisphosphonate

Conditions

Conditions	Yield
In chloroform at 20℃; for 1h;	99%

: 695-34-1
2-Amino-4-methylpyridine

: 4-(chlorosulfonyl)benzenesulfonyl fluoride

: 4-(N-(4-methylpyridin-2-yl)sulfamoyl)benzene-1-sulfonyl fluoride

Conditions

Conditions	Yield
With pyridine In chloroform at 20℃; for 48h; chemoselective reaction;	99%

: 695-34-1
2-Amino-4-methylpyridine

: 2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]acetic acid

: N-(4-methylpyridin-2-yl)-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]acetamide

Conditions

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux;	98.5%

: 695-34-1
2-Amino-4-methylpyridine

: 3-methyl-2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]pentanoic acid

: (2S)-3-methyl-2-[N-(4-methylbenzenesulfonyl)-1-phenylformamido]-N-(4-methylpyridin-2-yl)pentanamide

Conditions

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux;	98.3%

: 695-34-1
2-Amino-4-methylpyridine

: 3-methyl-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]pentanoic acid

: (2S)-3-methyl-N-(4-methylpyridin-2-yl)-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]pentanamide

Conditions

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux;	98.2%

: 695-34-1
2-Amino-4-methylpyridine

: 3-methyl-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]butanoic acid

: (2S)-3-methyl-N-(4-methylpyridin-2-yl)-2-[N-(4-nitrobenzenesulfonyl)-1-phenylformamido]butanamide

Conditions

Conditions	Yield
With boric acid In toluene for 6h; Dean-Stark; Reflux;	98.2%

: 695-34-1
2-Amino-4-methylpyridine

: 99-73-0
para-bromophenacyl bromide

: 838-32-4
2-(4-bromophenyl)-7-methylimidazo[1,2-a]pyridine

Conditions

Conditions	Yield
In neat (no solvent) at 25 - 30℃; Milling; Green chemistry;	98%
With sodium hydrogencarbonate In ethanol for 20h; Reflux;	79%
In ethanol for 18h; Heating;	58%

: 695-34-1
2-Amino-4-methylpyridine

: 2401-73-2
1,1,3,3-tetramethyl-1,3-dichlorodisiloxane

: 182245-12-1
[(NC5H3(CH3))NHSi(CH3)2]2O

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran; diethyl ether	98%

: 886981-23-3
benzyl (2S)-2-(1H-1,2,3-benzotriazol-1-ylcarbonyl)tetrahydro-1H-pyrrole-1-carboxylate

: 695-34-1
2-Amino-4-methylpyridine

: benzyl (2S)-2-[(4-methyl-2-pyridinyl)amino]carbonyl-tetrahydro-1H-pyrrole-1-carboxylate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 70℃; for 0.5h; microwave irradiation;	98%

: 695-34-1
2-Amino-4-methylpyridine

: 2033-24-1
cycl-isopropylidene malonate

: 100-52-7
benzaldehyde

: 1135400-33-7
C15H16N2O2

Conditions

Conditions	Yield
With potassium hydroxide; water at 100℃; for 1.5h;	98%

...Expand

: 695-34-1
2-Amino-4-methylpyridine

: 1147550-11-5
ammonium thiocyanate

: 122-04-3
4-nitro-benzoyl chloride

: 1403962-22-0
8-methyl-4-(4-nitrophenyl)-2H-pyrido[1,2-a][1,3,5]triazine-2-thione

Conditions

Conditions	Yield
Stage #1: ammonium thiocyanate; 4-nitro-benzoyl chloride In neat (no solvent) at 90℃; for 0.0833333h; Stage #2: 2-Amino-4-methylpyridine In neat (no solvent) at 20℃; for 3h;	98%

...Expand

2-Amino-4-picoline Consensus Reports

Reported in EPA TSCA Inventory.

2-Amino-4-picoline Specification

The IUPAC name of 2-Amino-4-methylpyridine is 4-methylpyridin-2-amine. With the CAS registry number 695-34-1, it is also named as alpha-Amino-gamma-picoline. The product's categories are Variousamine; Fine Chemical & Intermediates; Pyridines, Pyrimidines, Purines and Pteredines; Pyridines Derivates; Pyridines. It is light yellow to brown flakes which is highly toxic and flammable. When heated to decomposition it emits toxic fumes of NO_x. So the storage environment should be well- ventilated, low-temperature and dry.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.08; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.71; (4)ACD/LogD (pH 7.4): 0.79; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 2; (7)ACD/KOC (pH 5.5): 1.49; (8)ACD/KOC (pH 7.4): 47.27; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.574; (13)Molar Refractivity: 33.4 cm³; (14)Molar Volume: 101.2 cm³; (15)Polarizability: 13.24×10^-24 cm³; (16)Surface Tension: 46.9 dyne/cm; (17)Enthalpy of Vaporization: 46.39 kJ/mol; (18)Vapour Pressure: 0.0778 mmHg at 25°C; (19)Tautomer Count: 2; (20)Exact Mass: 108.068748; (21)MonoIsotopic Mass: 108.068748; (22)Topological Polar Surface Area: 38.9; (23)Heavy Atom Count: 8; (24)Complexity: 72.9.

Uses of 2-Amino-4-methylpyridine: It is used as pharmaceutical intermediate. And it also can react with 2-bromo-1-thiophen-2-yl-ethanone to get 7-methyl-2-[2]thienyl-imidazo[1,2-a]pyridine. This reaction needs solvent ethanol by heating. The reaction time is 4.0 hours. The yield is 75%.

When you are using this chemical, please be cautious about it as the following:
It is not only toxic by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. And it is very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. What's more, this chemical cam cause burns and may cause harm to the unborn child. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) This material and its container must be disposed of as hazardous waste. Avoid release to the environment. Refer to special instructions / safety data sheets.

People can use the following data to convert to the molecule structure.
1. SMILES:n1ccc(cc1N)C
2. InChI:InChI=1/C6H8N2/c1-5-2-3-8-6(7)4-5/h2-4H,1H3,(H2,7,8)
3. InChIKey:ORLGLBZRQYOWNA-UHFFFAOYAS

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LD50	skin	500mg/kg (500mg/kg)		"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 841, 1986.
mouse	LD50	intravenous	39mg/kg (39mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Annales Pharmaceutiques Francaises. Vol. 26, Pg. 345, 1968.
mouse	LD50	subcutaneous	64mg/kg (64mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT	Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 227S, 1957.
rat	LD50	oral	200mg/kg (200mg/kg)		"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 841, 1986.
rat	LD50	subcutaneous	160mg/kg (160mg/kg)		Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 227, Pg. 234, 1955.

Product Name

4-Methylpyridin-2-amine

Synthetic route

2-Amino-4-picoline Consensus Reports

2-Amino-4-picoline Specification

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