| Identification | More | [Name]
2-Amino-6-methylpyridine | [CAS]
1824-81-3 | [Synonyms]
2A6PC
2-Amino-6-merthyl pyridine
2-AMINO-6-METHYLPYRIDINE
2-AMINO-6-PICOLINE
6-AMINO-2-PICOLINE
6-AMINO-ALPHA-PICOLINE
6-METHYL-2-PYRIDYLAMINE
6-METHYLPYRIDIN-2-AMINE
6-METHYLPYRIDIN-2-YLAMINE
AKOS 91157
AKOS BBS-00004344
TIMTEC-BB SBB004355
2-amino-6-methyl-pyridin
2-Picoline, 6-amino-
2-Pyridinamine,6-methyl-
6-Amino-2-methylpyridine
6-Methyl-2-aminopyridine
6-methyl-2-pyridinamin
6-Methyl-2-pyridinamine
6-Methyl-2-pyridinamine, | [EINECS(EC#)]
217-360-1 | [Molecular Formula]
C6H8N2 | [MDL Number]
MFCD00006331 | [Molecular Weight]
108.14 | [MOL File]
1824-81-3.mol |
| Chemical Properties | Back Directory | [Appearance]
YELLOWISH CRYSTALLINE LOW MELTING SOLID | [Melting point ]
40-44 °C(lit.)
| [Boiling point ]
208-209 °C(lit.)
| [density ]
1.0275 (estimate) | [refractive index ]
1.5560 (estimate) | [Fp ]
218 °F
| [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
Crystalline Low Melting Solid | [pka]
pK1: 7.41(+1) (25°C) | [color ]
Yellow | [Water Solubility ]
very faint turbidity | [Sensitive ]
Hygroscopic | [Detection Methods]
HPLC,GC,NMR | [BRN ]
107048 | [InChI]
1S/C6H8N2/c1-5-3-2-4-6(7)8-5/h2-4H,1H3,(H2,7,8) | [InChIKey]
QUXLCYFNVNNRBE-UHFFFAOYSA-N | [SMILES]
Cc1cccc(N)n1 | [CAS DataBase Reference]
1824-81-3(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Pyridinamine, 6-methyl-(1824-81-3) | [Storage Precautions]
Moisture sensitive | [EPA Substance Registry System]
1824-81-3(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS06 | [Signal word ]
Danger | [Hazard statements ]
H301-H310-H315-H319-H335 | [Precautionary statements ]
P262-P280-P301+P310+P330-P302+P352+P310-P305+P351+P338 | [Hazard Codes ]
T | [Risk Statements ]
R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R24/25:Toxic in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S37/39:Wear suitable gloves and eye/face protection . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
US1885000
| [F ]
10-21 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29333999 | [Storage Class]
6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | [Hazard Classifications]
Acute Tox. 2 Dermal
Acute Tox. 3 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
YELLOWISH CRYSTALLINE LOW MELTING SOLID | [Uses]
Intermediate. | [Application]
2-Amino-6-methylpyridine (2A6MPy) can be used as an electron donor and reacts with the π-acceptors tetracyanoethylene (TCNE), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and 2,4,4,6-tetrabromo-2,5-cyclohexanediene dione (TBCHD) to form a solid charge transfer molecule in chloroform at 25 ℃. complex (CT), and the chemical formulae of the solid CT complexes were [(2A6MPy)(TCNE)2], [(2A6MPy)2(DDQ)], [(2A6MPy)4(TBCHD)], respectively[2]. | [Definition]
2-amino-6-methylpyridine, a colorless organic crystalline solid, is a prominent candidate to be exploited for the manufacturing of valuable compounds with biological activity. This synthetic nucleus can be used as precursor for the construction of diversified valuable scaffolds, e.g., 5-methyl-2-phenyl-3H-imidazo[4,5-b]pyridine and 6?bromo-5-methyl-2-phenylthiazolo[4,5-b]pyridine. The nitration of this nucleus in the presence of H2SO4 can yield N-(6-methyl-5-nitropyridin-2-yl)nitramide. It is also an important precursor for the generation of N-linked aminopiperidine-based gyrase inhibitors where during the course of reactions bromination of this nucleus was performed. Importantly, the amino group can be replaced by different halogen atoms, i.e. F, Cl, Br, or even by a nitroso group. Additionally, the methyl group on an aromatic system can be modified to the routine functional groups like aldehyde and carboxylic acid, or even bromination can be performed on this particular carbon[1].
| [Description]
2-amino-6-methylpyridine, a colorless organic crystalline solid, is a prominent candidate to be exploited for the manufacturing of valuable compounds with biological activity. | [Reactions]
2-Amino-6-methylpyridine can be used as precursor for the construction of diversified valuable scaffolds, e.g., 5-methyl-2-phenyl-3H-imidazo[4,5-b]pyridine and 6-bromo-5-methyl-2-phenylthiazolo[4,5-b]pyridine. The nitration of this nucleus in the presence of H2SO4 can yield N-(6-methyl-5-nitropyridin-2-yl)nitramide. It is also an important precursor for the generation of N-linked aminopiperidine-based gyrase inhibitors where during the course of reactions bromination of this nucleus was performed. Importantly, the amino group can be replaced by different halogen atoms, i.e. F, Cl, Br, or even by a nitroso group. Additionally, the methyl group on an aromatic system can be modified to the routine functional groups like aldehyde and carboxylic acid, or even bromination can be performed on this particular carbon[1]. | [Synthesis]
The general procedure for the synthesis of 2-bromo-6-methylpyridine from 2-bromo-6-methylpyridine was as follows: 2-bromo-6-methylpyridine (1.0 mmol), aqueous ammonia solution (28%, 1.5 mmol), cuprous iodide nanoparticles (0.02 mmol), ligand 4a (3.0 mmol) and acetonitrile (2 mL) were added to an oven-dried flask. The reaction mixture was stirred at room temperature for 12 h under argon protection. The reaction process was monitored by thin layer chromatography (TLC). After completion of the reaction, the product was extracted with ether (5 x 5 mL). The organic layers were combined, washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography using mixed ethyl acetate-hexane solvent as eluent gave 2-amino-6-methylpyridine. All the products are known compounds and their structures were confirmed by 1H NMR, 13C NMR and mass spectrometry, see Supplementary Material for detailed data. | [Purification Methods]
Crystallise it three times from acetone and dry it under vacuum at ca 45o. Alternatively, keep it in contact with NaOH pellets for 3hours, with occasional shaking, decant and fractionally distil it [Mod et al. J Phys Chem 60 1651 1956]. It also recrystallises from CH2Cl2 on addition of pet ether. [Marzilli et al. J Am Chem Soc 108 4830 1986, Beilstein 22/9 V 210.] | [References]
[1] Ali A, et al. 2-Amino-6-methylpyridine based co-crystal salt formation using succinic acid: Single-crystal analysis and computational exploration. Journal of Molecular Structure, 2021; 1230: 129893. |
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