4,6-Dichloro-2-(methylthio)pyrimidine Chemical Properties

Melting point:

38-42 °C(lit.)

Boiling point:

135-136 °C14 mm Hg(lit.)

Density 

1.502 (estimate)

refractive index 

1.6300 (estimate)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform, Dichloromethane, Ethyl Acetate

pka

-4.86±0.30(Predicted)

form 

Powder or Crystals

color 

White to yellow or orange

BRN 

127664

CAS DataBase Reference

6299-25-8(CAS DataBase Reference)

NIST Chemistry Reference

Pyrimidine, 4,6-dichloro-2-(methylthio)-(6299-25-8)

Safety Information

Hazard Codes 

C

Risk Statements 

34-36/37

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3263 8/PG 2

WGK Germany 

3

F 

10-19

HazardClass 

8

PackingGroup 

III

HS Code 

29335990

MSDS

• Language:English Provider:4,6-Dichloro-2-(methylthio)pyrimidine
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4,6-Dichloro-2-(methylthio)pyrimidine Usage And Synthesis

Chemical Properties

White Crystalline Solid

Uses

4,6-Dichloro-2-(methylthio)pyrimidine (cas# 6299-25-8) is a compound useful in organic synthesis.

General Description

4,6-Dichloro-2-(methylthio)pyrimidine reacts with (η⁵-C₅H₅)Fe(CO)₂ to form monometallic and bimetallic complexes.

Synthesis

Step b: Synthesis of 4,6-dichloro-2-methylthiopyrimidine (19b); 2-methylthiopyrimidine-4,6-diol (30.0 g, 189 mmol) was slowly added to phosphorochloride (350 mL) under cooling in an ice bath, followed by the slow addition of N,N-diethylaniline (52.5 mL) while maintaining cooling. The reaction mixture was gradually warmed to reflux and maintained at reflux for 2.5 hours. Upon completion of the reaction, the mixture was concentrated and subsequently poured into crushed ice for quenching. The aqueous phase was extracted three times with ethyl acetate, and the organic phases were combined and washed sequentially three times with water and once with brine, after which the organic phase was concentrated. The crude product was purified by silica gel column chromatography using hexane-ethyl acetate as eluent to afford 4,6-dichloro-2-methylthiopyrimidine (36 g, 97% yield).

References

[1] Patent: WO2008/95999, 2008, A1. Location in patent: Page/Page column 96
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 29, p. 6547 - 6556
[3] Organic and Biomolecular Chemistry, 2003, vol. 1, # 19, p. 3353 - 3361
[4] ACS Combinatorial Science, 2014, vol. 16, # 4, p. 168 - 175
[5] Journal of Medicinal Chemistry, 1984, vol. 27, # 12, p. 1621 - 1629

4,6-Dichloro-2-(methylthio)pyrimidine(6299-25-8)Related Product Information

• 4,6-Dichloropyrimidine
• 2-Methylsulfonyl-4,6-dimethoxypyrimidine
• 4,6-Dichloro-2-methylpyrimidine
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBONITRILE
• Pyrimidine
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXYLIC ACID
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXAMIDE
• 4,6-DICHLORO-2-METHYLTHIO-PYRIMIDINE, [4,6-14C]
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBALDEHYDE 5-PHENYLHYDRAZONE
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBALDEHYDE 5-(2,4-DICHLOROPHENYL)HYDRAZONE, TECH
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBALDEHYDE 5-[3-(TRIFLUOROMETHYL)PHENYL]HYDRAZONE
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBALDEHYDE 5-(2,4-DICHLOROPHENYL)HYDRAZONE
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXALDEHYDE 5-(4-ISOPROPYLPHENYL)HYDRAZONE
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBALDEHYDE 5-(4-ISOPROPYLPHENYL)HYDRAZONE, TECH
• 5-(([(ANILINOCARBONYL)OXY]IMINO)METHYL)-4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBALDEHYDE 5-PHENYLHYDRAZONE, TECH
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXALDEHYDE 5-PHENYLHYDRAZONE
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXALDEHYDE 5-(2,4-DICHLOROPHENYL)HYDRAZONE