ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyrimidines Chloropyrimidine 2,4,6-Trichloropyrimidine

2,4,6-Trichloropyrimidine

Product Name2,4,6-Trichloropyrimidine
CAS3764-01-0
MFC4HCl3N2
MW183.42
EINECS223-183-0
MOL File3764-01-0.mol

Chemical Properties

Melting point	23-25 °C (lit.)
Boiling point	210-215 °C (lit.)
Density	1.595 g/mL at 20 °C (lit.)
refractive index	n20/D 1.57(lit.)
Flash point	>230 °F
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	Chloroform, Ethyl Acetate
form	Liquid After Melting
pka	-7.14±0.30(Predicted)
color	Clear colorless to yellow
Water Solubility	Insoluble in water.
FreezingPoint	21.0 to 23.0 ℃
BRN	118284
InChI	1S/C4HCl3N2/c5-2-1-3(6)9-4(7)8-2/h1H
InChIKey	DPVIABCMTHHTGB-UHFFFAOYSA-N
SMILES	Clc1cc(Cl)nc(Cl)n1
CAS DataBase Reference	3764-01-0(CAS DataBase Reference)
NIST Chemistry Reference	Pyrimidine, 2,4,6-trichloro-(3764-01-0)
EPA Substance Registry System	Pyrimidine, 2,4,6-trichloro- (3764-01-0)

Safety Information

Hazard Codes	Xn,Xi,T
Risk Statements	20/21/22-36/37/38
Safety Statements	26-36-24/25-23
RIDADR	UN1759
WGK Germany	3
TSCA	TSCA listed
HazardClass	8
PackingGroup	III
HS Code	29335990
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
2,4,6-Trichloropyrimidine	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

clear colorless to yellowish liquid after melting

Uses

It is applied In selective Suzuki coupling with arylboronic acids has been reported to give 6-arylpyrimidines.

Uses

Fungitoxic substance.

Synthesis Reference(s)

Journal of the American Chemical Society, 80, p. 5481, 1958 DOI: 10.1021/ja01553a042

Synthesis

67-52-7

3764-01-0

Example 2: 128.1 g (1 mol) of barbituric acid and 500 ml (5.5 mol) of phosphorus trichloride were sequentially added to a reaction flask, heated to reflux and maintained for 4 hours. Subsequently, 270 ml (3.1 mol) of phosphorus trichloride and 213 g (3 mol) of chlorine were slowly added dropwise to the reaction system, and the reaction solution was kept as a light yellow suspension during the treatment. The amount of chlorine gas should be strictly controlled during the titration process to avoid overdose, and the specific operation was referred to Example 1. After the titration was completed, the reaction was continued to reflux for 1 hour. After completion of the reaction, phosphorus trichloride is removed by distillation. Finally, 2,4,6-trichloropyrimidine was obtained by distillation under pump vacuum according to the method described in Example 1. The yield of the product was 148 g, the yield was 81% of the theoretical value (in terms of barbituric acid), and the absence of 2,4,5,6-tetrachloropyrimidine in the product was confirmed by GC assay.

Toxics Screening Level

The initial threshold screening level (ITSL) for 2,4,6-trichloropyrimidine is 0.1 μg/m3 based on an annual averaging time.

References

[1] Journal of the American Chemical Society, 1980, vol. 102, # 15, p. 5036 - 5044
[2] Patent: US5898073, 1999, A
[3] Patent: US5712394, 1998, A
[4] Polyhedron, 2014, vol. 81, p. 316 - 322
[5] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 159 - 174

2,4,6-Trichloropyrimidine

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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