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HomeProduct name list2-Amino-6-methylpyridine

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
2-Amino-6-methylpyridine Structural

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)
ghs
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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