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2,4-Dichloropyrimidine

CAS No.3934-20-1
Chemical Name:2,4-Dichloropyrimidine
CBNumber:CB6202781
Molecular Formula:C4H2Cl2N2
Formula Weight:148.98
MOL File:3934-20-1.mol

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)
FDA UNII YV96122OCD
NIST Chemistry Reference Pyrimidine, 2,4-dichloro-(3934-20-1)
EPA Substance Registry System Pyrimidine, 2,4-dichloro- (3934-20-1)
UNSPSC Code 12352100
NACRES NA.22

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

NFPA 704:

	1
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H319-H335
Precautionary statements P261-P264-P271-P280-P302+P352-P305+P351+P338

2,4-Dichloropyrimidine Price More Price(4)

Brand: Sigma-Aldrich(India)
Product number: 143847
Product name : 2,4-Dichloropyrimidine
Purity: 98%
Packaging: 10G
Price: ₹4940
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 143847
Product name : 2,4-Dichloropyrimidine
Purity: 98%
Packaging: 50G
Price: ₹13860
Updated: 2022/06/14
Buy: Buy

Brand: TCI Chemicals (India)
Product number: D2310
Product name : 2,4-Dichloropyrimidine
Purity: min. 98.0 %
Packaging: 5G
Price: ₹3400
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: D2310
Product name : 2,4-Dichloropyrimidine
Purity: min. 98.0 %
Packaging: 25G
Price: ₹8200
Updated: 2022/05/26
Buy: Buy

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.