2-Chloro-4-methylpyrimidine Chemical Properties

Melting point:

35-36°C

Boiling point:

94°C/17mmHg(lit.)

Density 

1.234±0.06 g/cm3(Predicted)

Flash point:

98℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform

form 

Solid

pka

-0.93±0.20(Predicted)

color 

Pale Yellow to Beige

Sensitive 

Moisture Sensitive

Stability:

Toxic

InChI

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

InChIKey

BHAKRVSCGILCEW-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

13036-57-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-41-37/38

Safety Statements 

26-39

WGK Germany 

3

TSCA 

N

HazardClass 

IRRITANT

HS Code 

29335990

2-Chloro-4-methylpyrimidine Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

2-Chloro-4-methylpyrimidine (cas# 13036-57-2) is a compound useful in organic synthesis.

Application

2-chloro-4-methylpyrimidine could be used to synthesis 4-Methyl-2-vinylpyrimidine which is a intermediate of pyrimidinyl trans-cyclopropane carboxylic acid (rac-1)[1].

Synthesis

Step A: Synthesis of 2-chloro-4-methylpyrimidine To a vigorously stirred slurry containing 50.0 g (0.31 mol) of 2,6-dichloro-4-methylpyrimidine, 250 mL of ethanol (EtOH), and 250 mL of water, 41 g (0.63 mol) of zinc powder and 0.78 g (3.08 mmol) of iodine were sequentially added. The reaction mixture was heated to reflux at 70°C for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure to remove ethanol and subsequently extracted with dichloromethane (DCM). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to remove solvent. The residue was purified by silica gel column chromatography using a hexane/DCM solvent mixture as eluent, resulting in 20.6 g (53% yield) of 2-chloro-4-methylpyrimidine as a white solid. The structure of the product was confirmed by 1H-NMR (d6-DMSO, 400 MHz) δ 8.59 (d, 1H, J=4.9 Hz), 7.44 (d, 1H, J=4.9 Hz), and 3.29 (s, 3H), and ESIMS: 129.11 (M+H+).

References

[1] M. Fray. “N-Ylide Mediated Synthesis and Resolution of a Chiral Pyrimidinyl Cyclopropane Carboxylic Acid.” Organic Process Research &Development 19 1 (2023).

2-Chloro-4-methylpyrimidine(13036-57-2)Related Product Information

• 4-Methylpyridine
• 2,5-Dimethylpyridine
• 2,6-Lutidine
• 2-Chloro-4-nitropyridine
• Chromium picolinate
• 2,4,6-Collidine
• 2-chloro-6-trichloromethylpyridine
• 2-(Chloromethyl)pyridine
• 2-CHLORO-4-METHYL-THIAZOLE
• Methyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate
• 2,4-Dichloro-6-methyl-5-nitropyrimidine
• 2-CHLORO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBONYL CHLORIDE
• 2-Chloro-4-(trifluoromethyl)pyrimidine
• CRIMIDINE
• 2-Chloro-4,6-dimethylpyrimidine
• 2,4-Dichloro-6-methylpyrimidine
• METHYL 2-CHLORO-6-METHYLPYRIMIDINE-4-CARBOXYLATE,Methyl 2-chloro-4-methylpyrimidine-6-carboxylate, HPLC +97%
• Difluorochloromethane