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2-Amino-6-methylpyridine

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2-Amino-6-methylpyridine Basic information

Product Name:
2-Amino-6-methylpyridine
Synonyms:
  • 2-amino-6-methyl-pyridin
  • 2-Picoline, 6-amino-
  • 2-Pyridinamine,6-methyl-
  • 6-Amino-2-methylpyridine
  • 6-Methyl-2-aminopyridine
  • 2-AMINO-6-METHYL PYRIDINE 6-METHYLPYRIDIN-2-YLAMINE
  • 2-AMINO-6-METHYLPYRIDINE (2-AMINO-6-PICOLINE)
  • 2-Amino-6-picoline ,98%
CAS:
1824-81-3
MF:
C6H8N2
MW:
108.14
EINECS:
217-360-1
Product Categories:
  • VARIOUSAMINE
  • Pyridine
  • Pyridines, Pyrimidines, Purines and Pteredines
  • Pyridines derivates
  • Heterocycle-Pyridine series
Mol File:
1824-81-3.mol
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2-Amino-6-methylpyridine Chemical Properties

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
pka
pK1: 7.41(+1) (25°C)
form 
Crystalline Low Melting Solid
color 
Yellow
Water Solubility 
very faint turbidity
Sensitive 
Hygroscopic
BRN 
107048
InChIKey
QUXLCYFNVNNRBE-UHFFFAOYSA-N
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)
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Safety Information

Hazard Codes 
T
Risk Statements 
25-36/37/38-24/25-23/24/25-24
Safety Statements 
26-36/37/39-45-37/39-28A
RIDADR 
UN 2811 6.1/PG 3
WGK Germany 
3
RTECS 
US1885000
10-21
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
II
HS Code 
29333999

MSDS

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2-Amino-6-methylpyridine Usage And Synthesis

Chemical Properties

YELLOWISH CRYSTALLINE LOW MELTING SOLID

Uses

Intermediate.

Uses

2-Amino-6-methylpyridine is a reagent used in the identification of selective inhibitor for phosphatidylinositol 3-kinase (PI3Ka).

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].

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.

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