2-Chloro-5-methylpyrimidine Chemical Properties

Melting point:

89-92℃

Boiling point:

239.2±9.0 °C(Predicted)

Density 

1.234±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

-1.03±0.22(Predicted)

form 

Solid

color 

White to Light yellow

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C5H5ClN2/c1-4-2-7-5(6)8-3-4/h2-3H,1H3

InChIKey

APRMCBSTMFKLEI-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

22536-61-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37/39

HS Code 

29335990

2-Chloro-5-methylpyrimidine Usage And Synthesis

Uses

Used in organic synthesis, catalytic agent, petrochemical additive and synthetic chemistry. Also used as intermediate for pharmaceutical.

Synthesis

Step 1. Synthesis of 2-chloro-5-methylpyrimidine To a stirred solution of 2,4-dichloro-5-methylpyrimidine (4.00 g, 24.5 mmol) dissolved in a solvent mixture of benzene (16.0 mL) and water (40.0 mL) was added zinc powder (4.81 g, 73.6 mmol) and ammonia (8.80 mL, 24.5 mmol) sequentially at room temperature. The reaction mixture was heated and refluxed for 18 hours, then cooled to room temperature and filtered through a diatomaceous earth pad. The filtrate was extracted with ether (Et2O), and the combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 1:1) to afford the target compound 2-chloro-5-methylpyrimidine (2.44 g, 77% yield) as a yellow oil.1H NMR (400 MHz, CDCl3) δ 2.33 (3H, s), 8.47 (2H, s).

References

[1] Patent: WO2013/132376, 2013, A1. Location in patent: Page/Page column 224
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4720 - 4744
[3] Patent: US2012/53180, 2012, A1. Location in patent: Page/Page column 8
[4] Patent: US2010/190771, 2010, A1. Location in patent: Page/Page column 33
[5] Patent: US2008/306082, 2008, A1. Location in patent: Page/Page column 26-27

2-Chloro-5-methylpyrimidine(22536-61-4)Related Product Information

• 4-(Chloromethyl)benzoic acid
• Pirimiphos-methyl
• 2-Chloro-5-nitropyrimidine
• 2-Chloropyrimidine
• tert-Butyldimethylsilyl chloride
• Sulfamerazine
• Chloromethane
• 2-CHLORO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBONYL CHLORIDE
• 4-AMINO-2-CHLOROPYRIMIDINE-5-CARBONITRILE
• Difluorochloromethane
• 2,4,6-Trichloro-5-methylpyrimidine
• 2-Chloro-5-ethylpyrimidine
• Methyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate
• 2-Chloro-5-propylpyrimidine
• 2,4-Dichloro-5-methylpyrimidine
• 5-Amino-4,6-dichloro-2-methylpyrimidine
• 2-CHLORO-4-METHYLPYRIMIDINE 98%,2-CHLORO-4-METHYLPYRIMIDINE
• 4,6-Dichloro-5-methylpyrimidine