2-Chloro-5-nitropyrimidine Chemical Properties

Melting point:

105-110 °C

Boiling point:

345.4±15.0 °C(Predicted)

Density 

1.600±0.06 g/cm3(Predicted)

storage temp. 

-20°C

pka

-4.60±0.22(Predicted)

form 

powder to crystal

color 

Light orange to Yellow to Green

InChI

InChI=1S/C4H2ClN3O2/c5-4-6-1-3(2-7-4)8(9)10/h1-2H

InChIKey

OFCBNMYNAHUDGE-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C([N+]([O-])=O)C=N1

CAS DataBase Reference

10320-42-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-43-41-37/38-22-20/21/22

Safety Statements 

26-36-37/39-36/37/39-36/37-24/25

RIDADR 

UN 3335

WGK Germany 

3

RTECS 

US7175000

HazardClass 

IRRITANT

HS Code 

29335990

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2
Skin Sens. 1
STOT SE 3

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloro-5-nitropyrimidine Usage And Synthesis

Chemical Properties

Light yellow solid

Uses

2-Chloro-5-nitropyrimidine is an advanced intermediate for kinase/PRMT1 inhibitors, antiviral drugs, and other purine drugs. It can also be converted into herbicides, fungicides, and insecticides, providing targeted crop protection while maintaining good environmental friendliness.

Synthesis

Example 1 Preparation of 2-chloro-5-nitropyrimidine: 5-nitropyrimidin-2-amine (0.98 g, 7 mmol, 1 eq.) was added to a solution of acetonitrile containing anhydrous copper(II) chloride (1.12 g, 8.4 mmol, 1.2 eq.), tert-butyl nitrite (1.24 mL, 10.5 mmol, 1.5 eq.), and MgSO4 (~300 mg) ( 40 mL) solution, and the reaction was stirred at 65-80 °C (bath temperature).After 30 min, the reaction mixture was cooled to room temperature and ether (100 mL) was added. The organic layer was separated and washed sequentially with aqueous 1N HCl (2 x 20 mL), H2O (50 mL) and brine (20 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (eluent: hexane/ether=3:1) to afford the target product 2-chloro-5-nitropyrimidine as a light yellow solid (0.56 g, 50% yield).

References

[1] Patent: US2003/181465, 2003, A1

2-Chloro-5-nitropyrimidine(10320-42-0)Related Product Information

• 2-Chloro-5-nitropyrimidine-4-amine,4-AMINO-2-CHLORO-5-NITROPYRIMIDINE
• 2,4,6-TRICHLORO-5-NITROPYRIMIDINE
• 2-Chloro-5-nitropyrimidine
• 2,4-Dichloro-6-methyl-5-nitropyrimidine
• 2,4-Dichloro-5-nitropyrimidine
• 5-Chloro-2-nitropyridine
• 2-Chloro-4-nitropyridine
• 2-Amino-6-chloro-3-nitropyridine
• 4,6-Dichloro-5-nitropyrimidine
• 2-Chloro-3-nitropyridine
• 4-CHLORO-5-NITROPYRIMIDINE
• Methyl 2-(2-chloro-5-nitropyrimidin-4-ylamino)acetate
• 4-Chloro-3-nitropyridine
• 4,6-Dichloro-2-methyl-5-nitropyrimidine
• 2-Chloropyrimidine
• ETHYL 2,6-DICHLORO-5-NITROPYRIMIDINE-4-CARBOXYLATE
• 2-chloro-N-methyl-5-nitropyrimidin-4-amine
• 2-CHLORO-6-METHYL-5-NITRO-4(1H)-PYRIMIDINONE