ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Methylpyridine 4-Methylpyridin-2-amine

4-Methylpyridin-2-amine

Product Name4-Methylpyridin-2-amine
CAS695-34-1
MFC6H8N2
MW108.14
EINECS211-780-9
MOL File695-34-1.mol

Chemical Properties

Melting point	96-99 °C (lit.)
Boiling point	230 °C (lit.)
Density	1.0275 (estimate)
vapor pressure	3.71Pa at 25℃
refractive index	1.5560 (estimate)
Flash point	118 °C
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	DMF: freely soluble
form	Flakes
pka	pK1: 7.48(+1) (25°C)
color	Slightly yellow to beige or brown
Water Solubility	SOLUBLE
Sensitive	Hygroscopic
Merck	14,466
BRN	107066
InChI	1S/C6H8N2/c1-5-2-3-8-6(7)4-5/h2-4H,1H3,(H2,7,8)
InChIKey	ORLGLBZRQYOWNA-UHFFFAOYSA-N
SMILES	Cc1ccnc(N)c1
LogP	0.56-1.08
CAS DataBase Reference	695-34-1(CAS DataBase Reference)
NIST Chemistry Reference	2-Pyridinamine, 4-methyl-(695-34-1)
EPA Substance Registry System	2-Pyridinamine, 4-methyl- (695-34-1)

Safety Information

Hazard Codes	T
Risk Statements	45-46-60-61-8-21-25-26-34-42/43-48/23-50/53-36/37/38-33-23/24/25
Safety Statements	53-45-60-61-37/39-28A-26-36/37/39
RIDADR	UN 3086 6.1/PG 1
WGK Germany	3
RTECS	TJ5150000
TSCA	TSCA listed
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. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Aquatic Chronic 3 Eye Dam. 1 Skin Corr. 1B
Toxicity	LD50 oral in rat: 200mg/kg

MSDS

Provider	Language
4-Methylpyridin-2-amine	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

Light yellow to brown flakes

Uses

Intermediate, medicine.

Uses

4-Methylpyridin-2-amine has been used in the synthesis of 2-amino-4-methyl-pyridinium 2-hy-droxy-benzoate. It is potent inhibitor of NOS2 (iNOS) in vitro. It is used as pharmaceutical intermediate.

Synthesis Reference(s)

The Journal of Organic Chemistry, 72, p. 4554, 2007 DOI: 10.1021/jo070189y

General Description

4-Methylpyridin-2-amine acts as ligand and forms methoxo-bridged copper(II) complexes.

Biochem/physiol Actions

4-Methylpyridin-2-amine inhibits the activity of inducible NO synthase isolated from mouse RAW 264.7 cells in vitro.

Synthesis

A mixture of 2-amino-3-chloro-4-methylpyridine 0.96 g (0. 0067πο1) and benzoic acid, 1.83 g (0.015 mol) was added, the copper powder was added, reacted at 150 ° C for 1 h, and the reaction solution was added to water, Adding the decolorizer, adjusting the pH of the filtered solution to pH 9, filtering and drying the filter cake to obtain 0.65 g of crude 4-Methylpyridin-2-amine as a yellow solid, the yield was 89.3percent. The crude 0.65g dissolved in dilute hydrochloric acid solution to the crude product completely dissolved to obtain a salt solution, adding ethyl acetate to the salt solution to extract the water phase, slowly adding sodium bicarbonate to the aqueous phase Solution to pH 9, the solid was completely precipitated, filtered, and the filtrate was washed with distilled water and dried in vacuo to give 0.53 g of 4-Methylpyridin-2-amine as a pale yellow solid.

Purification Methods

Crystallise it from EtOH or a 2:1 *benzene/acetone mixture, and dry it under vacuum as in the prevous entry. [Beilstein 22/9 V 325.]

References

[1] Patent: CN107011254, 2017, A. Location in patent: Paragraph 0022; 0042; 0043; 0046; 0047