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: 2024-11-13 18:13:23
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) |
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 |
Abamectin manufacturer
Sanpra Synthesis Private Limited
Kalam Sai Life Sciences Pvt Ltd
PALEM ORGANICS PVT LTD
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Shreyasvi Lifesciences Pvt Ltd
Covalent Incorporation
Avra Laboratories Pvt Ltd
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