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HomeProduct name list2,4-Dichloropyrimidine

2,4-Dichloropyrimidine

  • CAS NO.:3934-20-1
  • Empirical Formula: C4H2Cl2N2
  • Molecular Weight: 148.98
  • MDL number: MFCD00006061
  • EINECS: 223-508-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-15 16:24:08
2,4-Dichloropyrimidine Structural

What is 2,4-Dichloropyrimidine?

Chemical properties

White Solid

The Uses of 2,4-Dichloropyrimidine

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].

Description

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

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.

Properties of 2,4-Dichloropyrimidine

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)
pka -2.84±0.20(Predicted)
form  Powder, Crystals and/or Chunks
color  White to yellow to beige or grayish
Water Solubility  Soluble in water (partly), methanol, chloroform, and ethyl acetate.
Sensitive  Moisture Sensitive
BRN  110911
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 information for 2,4-Dichloropyrimidine

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 2,4-Dichloropyrimidine

InChIKey BTTNYQZNBZNDOR-UHFFFAOYSA-N

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