2,4-Dichloropyrimidine Property

Melting point:

57-61 °C (lit.)

Boiling point:

101 °C/23 mmHg (lit.)

Density 

1.6445 (rough estimate)

refractive index 

1.6300 (estimate)

Flash point:

101°C/23mm

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Powder, Crystals and/or Chunks

pka

-2.84±0.20(Predicted)

color 

White to yellow to beige or grayish

Water Solubility 

Soluble in water (partly), methanol, chloroform, and ethyl acetate.

Sensitive 

Moisture Sensitive

BRN 

110911

InChIKey

BTTNYQZNBZNDOR-UHFFFAOYSA-N

CAS DataBase Reference

3934-20-1(CAS DataBase Reference)

NIST Chemistry Reference

Pyrimidine, 2,4-dichloro-(3934-20-1)

EPA Substance Registry System

Pyrimidine, 2,4-dichloro- (3934-20-1)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-28A

RIDADR 

1759

WGK Germany 

3

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29335990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2,4-Dichloropyrimidine Chemical Properties,Usage,Production

Chemical Properties

White Solid

Uses

2,4-Dichloropyrimidine was used in the synthesis of medicinally important 4-aryl-5-pyrimidinylimidazoles.

Preparation

Obtained by chlorination of uracil. Add uracil, phosphorus trichloride, and xylene amine into the reaction pot, heat to 130 ℃, reflux for about 45min, slightly cool, put in crushed ice, that is, the precipitation of purple solid, filtered while hot and not dissolved, washed with ice water, vacuum drying, a kind of purple crude, decolorized with petroleum ether (boiling range of 60-90 ℃), recrystallized, obtained 2,4-dichloropyrimidine.

General Description

2,4-Dichloropyrimidine is a human skin sensitizer. It undergoes effective one-pot, regioselective double Suzuki coupling reaction to yield diarylated pyrimidines.

Reactivity Profile

The reaction of N-substituted cyclic amines with 2,4-dichloroquinazoline and 2,4-dichloro-5-methyl-pyrimidine afforded 2-amino-4-chloroquinazolines and 2-amino-4-chloro-5-methylpyrimidines, respectively—the reaction of these amines with 2,4-dichloropyrimidine 3a afforded not only 2-amino-4-chloropyrimidines but also the isomeric 4-amino-2-chloropyrimidines. An effective one-pot, regioselective double Suzuki coupling of 2,4-dichloropyrimidine has been developed. This method enables the quick and efficient synthesis of diarylated pyrimidines. The choice of solvent proved critical to the success of this reaction sequence, with alcoholic solvent mixtures affording much greater reactivity and correspondingly lower temperatures than polar aprotic solvents[5-6].

References

[1] DR. AGNES FIZIA. Cyclopalladation in the Periphery of a NHC Ligand as the Crucial Step in the Synthesis of Highly Active Suzuki–Miyaura Cross-Coupling Catalysts[J]. Chemistry - A European Journal, 2017. DOI:10.1002/chem.201702877.
[2] FABIAN BRUENING  Lucie E L. Highly Regioselective Organocatalytic SNAr Amination of 2,4-Dichloropyrimidine and Related Heteroaryl Chlorides[J]. European Journal of Organic Chemistry, 2017. DOI:10.1002/ejoc.201700459.
[3] ANDERSONSAMANTHA C   HandyScott T. One-pot Double Suzuki Couplings of Dichloropyrimidines.[J]. Synthesis-Stuttgart, 2010. DOI:10.1055/s-0030-1258150.
[4] TOMá? KUBELKA. Synthesis of 2,4-Disubstituted Pyrimidin-5-yl C-2′-Deoxyribonucleosides by Sequential Regioselective Reactions of 2,4-Dichloropyrimidine Nucleosides[J]. European Journal of Organic Chemistry, 2010. DOI:10.1002/ejoc.201000164.
[5] Kenji Yoshida, M. Taguchi. “Reaction of N-substituted cyclic amines with 2,4-dichloroquinazoline, 2,4-dichloropyrimidine, and its 5-methyl derivative.” Journal of The Chemical Society-perkin Transactions 1 102 1 (1992): 919–922.
[6] Samantha C Anderson, Scott T Handy. “One-pot Double Suzuki Couplings of Dichloropyrimidines.” Synthesis-Stuttgart 2010 16 (2010): 2721–2724.