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2-Amino-6-methylpyridine

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Name

2-Amino-6-methylpyridine

EINECS 217-360-1
CAS No. 1824-81-3 Density 1.068 g/cm3
PSA 38.91000 LogP 1.55340
Solubility Soluble in water, but soluble in ethanol, ethyl ether, acetone, benzene and hot ligroin Melting Point 40-44 °C(lit.)
Formula C6H8N2 Boiling Point 208.499 °C at 760 mmHg
Molecular Weight 108.143 Flash Point 103.333 °C
Transport Information UN 2811 6.1/PG 3 Appearance yellowish crystalline low melting solid
Safety 26-36/37/39-45-28A Risk Codes 36/37/38-23/24/25
Molecular Structure Molecular Structure of 1824-81-3 (2-Amino-6-methylpyridine) Hazard Symbols ToxicT
Synonyms

2-Picoline,6-amino- (7CI,8CI);2-Amino-6-methylpyridine;2-Amino-6-picoline;6-Amino-2-methylpyridine;6-Amino-2-picoline;6-Methyl-2-aminopyridine;6-Methyl-2-pyridinamine;6-Methylpyridin-2-ylamine;NSC 1488;NSC 176163;NSC 6971;

Article Data 41

2-Amino-6-methylpyridine Synthetic route

25063-84-7

2-amino-6-methylpyridine 1-oxide

1824-81-3

2-Amino-6-methylpyridine

Conditions
ConditionsYield
With titanium tetrachloride; tin(ll) chloride In diethyl ether for 0.5h; Ambient temperature;98%
860460-70-4

N-cyclohexyl-5-methyl-2-phenylimidazo[1,2-a]pyridine-3-amine

A

1824-81-3

2-Amino-6-methylpyridine

B

724-92-5

N-cicloesil-α-ossofenilacetamide

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;A n/a
B 98%
18368-61-1

2-methyl-6-nitropyridine

1824-81-3

2-Amino-6-methylpyridine

Conditions
ConditionsYield
With sodium hydride; bis(pinacol)diborane In 1-methyl-pyrrolidin-2-one at 100℃; for 15h; Schlenk technique; Inert atmosphere; Sealed tube;93%
5315-25-3

2-bromo-6-methylpyridine

1824-81-3

2-Amino-6-methylpyridine

Conditions
ConditionsYield
With copper(I) oxide; potassium carbonate; ammonium hydroxide; N,N-dimethylethylenediamine In ethylene glycol at 60℃; for 16h; Inert atmosphere;88%
With ammonium hydroxide; copper(I) iodide; 1-ethylacetoacetate-3-methyl imidazolium hydroxide In acetonitrile at 80℃; for 12h; Inert atmosphere;75%
With ammonia; copper(I) oxide In ethylene glycol at 100℃; for 24h;62%
32570-89-1

2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyridine

1824-81-3

2-Amino-6-methylpyridine

Conditions
ConditionsYield
With hydroxylamine hydrochloride In ethanol; water for 24h; Heating;83%
With hydroxylamine hydrochloride In ethanol Heating; Yield given;
76809-21-7

2,2-dimethyl-3-(6-methylpyrid-2-yl)-4-oxo-4H-1,3-benzoxazine

A

1824-81-3

2-Amino-6-methylpyridine

B

69-72-7

salicylic acid

Conditions
ConditionsYield
With hydrogenchloride for 3h; Heating;A 82%
B n/a
62674-71-9

2-iodo-6-methyl-pyridine

1824-81-3

2-Amino-6-methylpyridine

Conditions
ConditionsYield
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide In dimethyl sulfoxide at 25℃; for 24h; Inert atmosphere; Sealed tube;81%
1218934-33-8

N-cyclohexyl-2-isopropyl-5-methylimidazo[1,2-a]pyridin-3-amine

A

1824-81-3

2-Amino-6-methylpyridine

B

32998-89-3

N-cyclohexyl-3-methyl-2-oxobutanamide

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;A n/a
B 80%

N-cyclohexyl-2-ethyl-5-methylimidazo[1,2-a]pyridin-3-amine

A

1824-81-3

2-Amino-6-methylpyridine

B

5070-30-4

N-cyclohexyl-2-oxobutanamide

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;A n/a
B 78%
5327-33-3

2-acetylamino-6-methylpyridine

A

1824-81-3

2-Amino-6-methylpyridine

B

39179-00-5

N-ethyl-6-methylpyridin-2-amine

Conditions
ConditionsYield
With dihydridocarbonyl(1,1,1-tris(diphenylphosphinomethyl)ethane)ruthenium(II) complex; boron trifluoride diethyl etherate; hydrogen; toluene-4-sulfonic acid In tetrahydrofuran at 120℃; under 38002.6 Torr; for 16h; Glovebox; Autoclave; Inert atmosphere;A n/a
B 75%

2-Amino-6-methylpyridine Consensus Reports

Reported in EPA TSCA Inventory.

2-Amino-6-methylpyridine Specification

The 2-Amino-6-methylpyridine, with the CAS registry number 1824-81-3, is also known as 6-Amino-2-picoline. It belongs to the product categories of Variousamine; Pyridine; Pyridines, Pyrimidines, Purines and Pteredines; Pyridines derivates. Its EINECS number is 217-360-1. This chemical's molecular formula is C6H8N2 and molecular weight is 108.14. What's more, its systematic name is 6-Methyl-2-pyridinamine. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides, moisture and fire. It is used in organic synthesis, and it is also used to prepare photographic developer, dye and medicine. This chemical can be prepared by 2-methylpyridine.

Physical properties of 2-Amino-6-methylpyridine are: (1)ACD/LogP: 0.912; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.52; (4)ACD/LogD (pH 7.4): 0.78; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 2.14; (7)ACD/KOC (pH 5.5): 2.76; (8)ACD/KOC (pH 7.4): 54.99; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 38.91 Å2; (13)Index of Refraction: 1.574; (14)Molar Refractivity: 33.405 cm3; (15)Molar Volume: 101.213 cm3; (16)Polarizability: 13.243×10-24cm3; (17)Surface Tension: 46.92 dyne/cm; (18)Density: 1.068 g/cm3; (19)Flash Point: 103.333 °C; (20)Enthalpy of Vaporization: 44.476 kJ/mol; (21)Boiling Point: 208.499 °C at 760 mmHg; (22)Vapour Pressure: 0.21 mmHg at 25°C.

Uses of 2-Amino-6-methylpyridine: it can be used to produce N-(6-methyl-[2]pyridyl)-phthalimide by heating. It will need solvent acetic acid with the reaction time of 24 hours. The yield is about 65%.

2-Amino-6-methylpyridine can be used to produce N-(6-methyl-[2]pyridyl)-phthalimide by heating

When you are using this chemical, please be cautious about it as the following:
This chemical is toxic by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: n1c(cccc1N)C
(2)Std. InChI: InChI=1S/C6H8N2/c1-5-3-2-4-6(7)8-5/h2-4H,1H3,(H2,7,8)
(3)Std. InChIKey: QUXLCYFNVNNRBE-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 skin 200mg/kg (200mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 841, 1986.
mouse LD50 intravenous 18mg/kg (18mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00148,
mouse LD50 subcutaneous 52mg/kg (52mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR
Australian Journal of Experimental Biology and Medical Science. Vol. 36, Pg. 491, 1958.
rabbit LD50 skin 125mg/kg (125mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
National Technical Information Service. Vol. OTS0571973,
rat LD50 oral 100mg/kg (100mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 841, 1986.

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