2-Amino-6-methylpyridine
Synonym(s):6-Amino-2-picoline
- CAS NO.:1824-81-3
- Empirical Formula: C6H8N2
- Molecular Weight: 108.14
- MDL number: MFCD00006331
- EINECS: 217-360-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-08 14:53:31
What is 2-Amino-6-methylpyridine?
Chemical properties
YELLOWISH CRYSTALLINE LOW MELTING SOLID
The Uses of 2-Amino-6-methylpyridine
Intermediate.
The Uses of 2-Amino-6-methylpyridine
2-Amino-6-methylpyridine is a reagent used in the identification of selective inhibitor for phosphatidylinositol 3-kinase (PI3Ka).
What are the applications of Application
2-Amino-6-methylpyridine is a pyridine building block
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].
What are the applications of 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].
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.
[2] SHERZOD MADRAHIMOV . Electronic, infrared, mass spectrometry and thermal studies on the reaction of 2-amino-6-methylpyridine with π-acceptors[J]. Journal of Molecular Structure, 2020. DOI:10.1016/j.molstruc.2019.127021.
Properties of 2-Amino-6-methylpyridine
Melting point: | 40-44 °C(lit.) |
Boiling point: | 208-209 °C(lit.) |
Density | 1.0275 (estimate) |
refractive index | 1.5560 (estimate) |
Flash point: | 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 |
BRN | 107048 |
CAS DataBase Reference | 1824-81-3(CAS DataBase Reference) |
NIST Chemistry Reference | 2-Pyridinamine, 6-methyl-(1824-81-3) |
EPA Substance Registry System | 2-Pyridinamine, 6-methyl- (1824-81-3) |
Safety information for 2-Amino-6-methylpyridine
Signal word | Danger |
Pictogram(s) |
Skull and Crossbones Acute Toxicity GHS06 |
GHS Hazard Statements |
H301:Acute toxicity,oral H310:Acute toxicity,dermal H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P262:Do not get in eyes, on skin, or on clothing. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 2-Amino-6-methylpyridine
InChIKey | QUXLCYFNVNNRBE-UHFFFAOYSA-N |
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