4-Amino-2-chloropyrimidine Chemical Properties

Melting point:

197-205 °C

Boiling point:

338.8±15.0 °C(Predicted)

Density 

1.437±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

2.30±0.10(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C4H4ClN3/c5-4-7-2-1-3(6)8-4/h1-2H,(H2,6,7,8)

InChIKey

LPBDZVNGCNTELM-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC(N)=N1

CAS DataBase Reference

7461-50-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-36-22

Safety Statements 

26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT-HARMFUL

HS Code 

29335990

4-Amino-2-chloropyrimidine Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

4-Amino-2-chloropyrimidine is a chloropyrimidine compound, which is widely used in the synthesis of various medicines and pesticides. It can be used to transform functional groups, such as amino groups, or to remove chlorine by hydrogenolysis; chlorine can also be used to couple various carbon-carbon bonds.

Synthesis

2,4-Dichloropyrimidine (1.0 g, 6.7 mmol) was used as starting material and 28% w/v aqueous ammonium hydroxide solution (20 mL) was added. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The obtained residue was dried and subsequently purified by fast column chromatography (FCC) with the eluent being chloroform solution containing 2-10% ethanol, resulting in the isolation of 2-amino-4-chloropyrimidine and 2-chloro-4-aminopyrimidine. Product yields: 200 mg of 2-amino-4-chloropyrimidine in 23% yield and 600 mg of 2-chloro-4-aminopyrimidine in 69% yield.

References

[1] Patent: WO2010/20556, 2010, A1. Location in patent: Page/Page column 62
[2] Journal of the American Chemical Society, 2003, vol. 125, # 33, p. 9970 - 9982
[3] Tetrahedron, 2010, vol. 66, # 6, p. 1280 - 1288
[4] Patent: WO2006/114409, 2006, A1. Location in patent: Page/Page column 18
[5] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 1973 - 1978

4-Amino-2-chloropyrimidine(7461-50-9)Related Product Information

• 4-Aminopyrimidine
• MCPA SODIUM
• 4-Aminoantipyrine
• 2-Chloropyrimidine
• 4,4'-Diaminodiphenylsulfone
• MCPB
• Glycine
• ALTRENOGEST
• Betaine
• 2-Aminobenzylchloride
• Difluorochloromethane
• 5-Chloropyrimidine-2,4,6-triamine
• 4-AMINO-2-CHLOROPYRIMIDINE-5-CARBONITRILE,4-AMINO-2-CHLOROPYRIMIDINE-5-CARBOXNITR&,4-Amino-2-chloropyrimidine-5-carbonitrile ,97%
• 4-Amino-6-chloropyrimidine-5-carboxaldehyde
• 2-AMINO-5-CHLOROPYRIMIDINE
• 2,4,5-Triamino-6-chloropyrimidine hydrochloride
• 4-AMINO-6-CHLOROPYRIMIDIN-5-YLAMINE
• N-(tert-Butyl)-6-chloropyrimidin-4-amine