2-Amino-4-chloropyrimidine Chemical Properties

Melting point:

155-160 °C (dec.)

Boiling point:

314.6±34.0 °C(Predicted)

Density 

1.437±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in dimethyl sulfoxide.

pka

3.55±0.10(Predicted)

form 

Solid

color 

White

InChI

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

InChIKey

DBGFGNCFYUNXLD-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

3993-78-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-37/38-22

Safety Statements 

26-36/37/39-36/39-60

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29335990

2-Amino-4-chloropyrimidine Usage And Synthesis

Chemical Properties

White Solid

Uses

2-Amino-4-chloropyrimidine is a substrate used in a palladium-catalyzed cyanation with zinc(II) cyanide. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff fields.

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 concentration 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.

Purification Methods

It has also been purified by sublimation in a vacuum and recrystrallisation from H2O. [Hilbert & Johnson J Am Chem Soc 52 1155 1930, Beilstein 24 H 80, 25 III/IV 2117.]

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

2-Amino-4-chloropyrimidine(3993-78-0)Related Product Information

• 2-Aminopyrimidine
• 6-Aminocaproic acid
• ALTRENOGEST
• 3-Aminophenol
• MCPA SODIUM
• Acetaminophen
• 2-Chloropyrimidine
• Glycine
• 4-Chloropyrimidine
• Tris(hydroxymethyl)aminomethane
• 4-Chloro-2,6-diaminopyrimidine
• 2-Amino-4-chloro-6-methylpyrimidine
• Chlorimuron-ethyl
• 2-AMINO-4-CHLORO-6-PHENYLPYRIMIDINE
• 2-Amino-4,6-dichloropyrimidine
• 2-AMINO-4,6-DIHYDROXY-5-METHYLPYRIMIDINE
• 2-Amino-6-chloropurine Riboside
• 2-Amino-6-chloro-4-pyrimidinol