2-Amino-6-methylpyridine Property

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)

Safety

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

F 

10-21

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29333999

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H310Fatal in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P262Do not get in eyes, on skin, or on clothing.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Amino-6-methylpyridine Chemical Properties,Usage,Production

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.