2-Amino-4-chloro-6-methylpyrimidine Chemical Properties

Melting point:

183-186 °C (lit.)

Boiling point:

234.32°C (rough estimate)

Density 

1.2986 (rough estimate)

refractive index 

1.6000 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

acetic acid: soluble50mg/mL, clear, colorless to faintly yellow

pka

4.26±0.10(Predicted)

form 

Solid

color 

White to Off-White

biological source

rabbit

Water Solubility 

Insoluble in water.

BRN 

114297

InChI

InChI=1S/C5H6ClN3/c1-3-2-4(6)9-5(7)8-3/h2H,1H3,(H2,7,8,9)

InChIKey

NPTGVVKPLWFPPX-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

5600-21-5(CAS DataBase Reference)

NIST Chemistry Reference

2-Amino-4-chloro-6-methylpyrimidine(5600-21-5)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

22-24/25-37/39-26-36

WGK Germany 

3

RTECS 

UV6329600

HazardClass 

IRRITANT, AVOID SKIN CONTACT

HS Code 

29335995

MSDS

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2-Amino-4-chloro-6-methylpyrimidine Usage And Synthesis

Chemical Properties

WHITE TO LIGHT YELLOW NEEDLE-LIKE CRYST. POWDER

Uses

2-Amino-4-chloro-6-methylpyrimidine was used to study the influence of chlorine substitution in pyrimidine ring on proton donor ability of amino group in 2-aminopyrimidine.

Definition

ChEBI: An aminopyrimidine compound having its amino group at position 2 and chloro and methyl substituents at positions 4 and 6 respectively.

General Description

2-Amino-4-chloro-6-methylpyrimidine is a nitification inhibitor.

Synthesis

General procedure for the synthesis of 2-amino-4-chloro-6-methylpyrimidine from 2-amino-4-hydroxy-6-methylpyrimidine: 6 g of 2-amino-4-hydroxy-6-methylpyrimidine (IV) was mixed with 35 mL of freshly distilled phosphorous trichloride and the reaction was carried out by refluxing the mixture until it was homogeneous. Upon completion of the reaction, the excess phosphorous trichloride was removed under vacuum. The reaction mixture was cooled and the residue was mixed with ice water and the pH was adjusted with 25% ammonia to 8. The resulting suspension was filtered and the precipitate was washed with water. The crude product was recrystallized from 50% ethanol and dried to constant weight at constant temperature. A final 3.7 g of the target product (54% yield) was obtained with a melting point of 188°C (literature value 182-183°C [7]) and a thin-layer chromatographic Rf value of 0.79 (Expander D). Elemental analysis results: 41.74% C, 4.05% H, 29.35% N. Theoretically calculated values for the molecular formula C5H6ClN3: C 41.83%, H 4.21%, N 29.27%.

Purification Methods

Recrystallise it from EtOH. [Beilstein 24 H 84.]

References

[1] Russian Journal of General Chemistry, 2015, vol. 85, # 1, p. 79 - 87
[2] Zhurnal Obshchei Khimii, 2015, vol. 85, # 1, p. 79 - 87,9

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