ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Aminopyridine 4-Amino-2-chloropyridine

4-Amino-2-chloropyridine

Product Name4-Amino-2-chloropyridine
CAS14432-12-3
MFC5H5ClN2
MW128.56
EINECS238-403-0
MOL File14432-12-3.mol

Chemical Properties

Melting point	90-94 °C(lit.)
Boiling point	153°C 5mm
Density	1.2417 (rough estimate)
refractive index	1.5110 (estimate)
Flash point	153°C/5mm
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	DMSO (Slightly), Methanol (Slightly)
pka	4.73±0.30(Predicted)
form	Crystalline Powder
color	Light yellow
Water Solubility	Slightly soluble in water.
BRN	108671
InChI	1S/C5H5ClN2/c6-5-3-4(7)1-2-8-5/h1-3H,(H2,7,8)
InChIKey	BLBDTBCGPHPIJK-UHFFFAOYSA-N
SMILES	Nc1ccnc(Cl)c1
CAS DataBase Reference	14432-12-3(CAS DataBase Reference)
NIST Chemistry Reference	4-Amino-2-chloropyridine(14432-12-3)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36-37/39-36/37/39
RIDADR	2811
WGK Germany	3
HazardClass	IRRITANT
HS Code	29333999
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
2-Chloro-4-pyridinamine	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Description

4-Amino-2-chloropyridine is an important pharmaceutical and pesticide intermediate. It can synthesize N-(2-chloro-4-pyridyl)urea regulators that promote plant growth. It is also a key substance in the synthesis of KT-30 (Forchlorfenuron, IUPAC name N-(2-chloro-4-pyridyl)-N'-phenylurea). KT-30 is a highly active cytokinin, which has the biological activity of promoting tissue growth, promoting bud development and green preservation; it has an effect of increasing yield on apple, pear, grape, peach and other fruit crops.
4-Amino-2-chloropyridine itself can also be used as a pesticide alone, and has high activity against various pathogens such as rust, powdery mildew, rice blast, and apple downy mildew. 4-Amino-2-chloropyridine and its pharmaceutical and pesticide intermediates have the advantages of high biological activity, low toxicity, long-lasting period and easy degradation in the environment, so they have broad application prospects in agricultural production.

Chemical Properties

White powder.

Uses

An aminopyridine derivative with potential herbicidal activity.

Uses

4-Amino-2-chloropyridine may be used in the preparation of:

3-deazacytosine
7-substituted 1-alky-1,4-dihydro-4-oxo-1,6-naphthyridine-3-carboxylic acids
1,6-naphthyridines

Definition

ChEBI: 4-Amino-2-chloropyridine is an aminopyridine.

Reactions

4-amino-2-chloropyridine (3 b) can be used as starting compound in the synthesis of novel cyclin-dependent kinase (CDK2) inhibitors and high-energy compounds.^[1]

General Description

4-Amino-2-chloropyridine is a chloroaminoheterocyclic compound. It readily undergoes Suzuki-Miyaura coupling with phenylboronic acid.

References

[1] Dinitropyridines: Synthesis and Reactions. Asian J. Org. Chem. 2024, e202400304. DOI:10.1002/ajoc.202400304