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2,4-Dichloro-5-nitropyrimidine

Product Name2,4-Dichloro-5-nitropyrimidine
CAS49845-33-2
MFC4HCl2N3O2
MW193.98
EINECS629-447-5
MOL File49845-33-2.mol

Chemical Properties

Melting point	28-32 °C
Boiling point	0.9 °C0.5 mm Hg
Density	2.0263 (rough estimate)
refractive index	1.6100 (estimate)
Flash point	>230 °F
storage temp.	Inert atmosphere,Store in freezer, under -20°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Liquid or Low Melting Solid
pka	-6.02±0.29(Predicted)
color	Clear yellow
Sensitive	Moisture Sensitive
InChI	InChI=1S/C4HCl2N3O2/c5-3-2(9(10)11)1-7-4(6)8-3/h1H
InChIKey	INUSQTPGSHFGHM-UHFFFAOYSA-N
SMILES	C1(Cl)=NC=C([N+]([O-])=O)C(Cl)=N1
CAS DataBase Reference	49845-33-2(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	3
Hazard Note	Irritant/Moisture Sensitive/Keep under Argon
HazardClass	IRRITANT, LACHRYMATOR
HS Code	29335990
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
2,4-Dichloro-5-nitropyrimidine	English
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

Intermediate in a solid-phase synthesis of diaminopurines.1

Uses

2,4-Dichloro-5-nitropyrimidine (cas# 49845-33-2) is a compound useful in organic synthesis.

Anticancer Research

Molecular docking analysis has shown that 2,4-dichloro-5-nitropyrimidine can bind to EGF receptor sites on the surface of tumor cells, thereby inhibiting their growth.

Synthesis

611-08-5

49845-33-2

General procedure for the synthesis of 2,4-dichloro-5-nitropyrimidine from 5-nitropyrimidine-2,4(1H,3H)-dione: 5-nitrouracil (6.28 g, 0.040 mol) was mixed with phosphorus triclosan (26 mL), and N,N-dimethylaniline (8 mL) was slowly added under stirring conditions. The reaction mixture was then heated to 110 °C and maintained at this temperature for 8 hours. Upon completion of the reaction, the excess trichlorophosphorus was removed by distillation. The remaining mixture was ground and separated by silica gel column chromatography. Finally, the collected fractions were concentrated to give 6.2 g of yellow oily liquid product in 94% yield.

References

[1] Patent: CN106432239, 2017, A. Location in patent: Paragraph 0066; 0071; 0072
[2] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 2, p. 321 - 328
[3] Tetrahedron Letters, 2006, vol. 47, # 50, p. 8897 - 8900
[4] Patent: WO2010/83645, 2010, A1. Location in patent: Page/Page column 27
[5] Patent: US7256196, 2007, B1. Location in patent: Page/Page column 8; 9-10

2,4-Dichloro-5-nitropyrimidine

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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