4,6-Dichloro-5-nitropyrimidine Chemical Properties

Melting point:

100-103 °C (lit.)

Boiling point:

325.8±37.0 °C(Predicted)

Density 

1.737±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform, Ethyl Acetate, Methanol, Toluene

form 

Solid

pka

-7.48±0.26(Predicted)

color 

White to Off-White

BRN 

162029

InChI

InChI=1S/C4HCl2N3O2/c5-3-2(9(10)11)4(6)8-1-7-3/h1H

InChIKey

HCTISZQLTGAYOX-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=C([N+]([O-])=O)C(Cl)=N1

CAS DataBase Reference

4316-93-2(CAS DataBase Reference)

NIST Chemistry Reference

Pyrimidine, 4,6-dichloro-5-nitro-(4316-93-2)

EPA Substance Registry System

Pyrimidine, 4,6-dichloro-5-nitro- (4316-93-2)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-23/24/25

Safety Statements 

26-36-45-36/37/39-7/9

RIDADR 

UN 3335

WGK Germany 

3

RTECS 

UV8258000

TSCA 

Yes

HS Code 

29335990

MSDS

• Language:English Provider:SigmaAldrich

4,6-Dichloro-5-nitropyrimidine Usage And Synthesis

Chemical Properties

Yellow Crystalline Solid

Uses

4,6-Dichloro-5-nitropyrimidine (cas# 4316-93-2) is a compound useful in organic synthesis.

Synthesis

The general procedure for the synthesis of 4,6-dichloro-5-nitropyrimidine using 5-nitro-4,6-dihydroxypyrimidine as starting material was as follows: to a suspension of phosphoryl chloride (96 mL, 1056 mmol) containing 4,6-dihydroxy-5-nitropyrimidine (25 g, 160 mmol) was added dimethylaniline (32.6 mL, 246 mmol). The reaction mixture was heated in an oil bath at 125 °C and subsequently warmed to 130 °C and held for 1 hour. Upon completion of the reaction, excess trichlorophosphorus oxide was removed by evaporation. The residue was slowly poured onto ice (300 g) and the solid formed was subsequently collected by filtration. The filtrate was extracted with ether and the combined organic layers were washed sequentially with water and brine and dried with anhydrous sodium sulfate. After removal of the solvent by evaporation, the residue was purified by fast column chromatography in dichloromethane to afford the light brown solid product 4,6-dichloro-5-nitropyrimidine (21.5 g, 70% yield). The 1H NMR (DMSO-D6) data of the product were as follows: δ 8.3 (s, 1H, Ar).

Purification Methods

If too impure, then dissolve it in Et2O, wash it with H2O, dry it over MgSO4, evaporate it to dryness and recrystallise it from pet ether (b 85-105o) to give a light tan solid. It is soluble in ca 8 parts of MeOH [Boon et al. J Chem Soc 96 1951, Montgomery et al. in Synthetic Procedures in Nucleic Acid Chemistry Zorbach & Tipson eds, Wiley & Sons, NY, p76 1968]. [Beilstein 23 III/IV 899.]

References

[1] Journal of Labelled Compounds and Radiopharmaceuticals, 2008, vol. 51, # 1, p. 54 - 58
[2] Patent: EP1598354, 2005, A1. Location in patent: Page/Page column 90
[3] Pharmaceutical Chemistry Journal, 2000, vol. 34, # 3, p. 110 - 112
[4] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4288 - 4312

4,6-Dichloro-5-nitropyrimidine(4316-93-2)Related Product Information

• 4,6-Dichloro-5-fluoropyrimidine
• 4,6-Dichloropyrimidine
• Thionyl chloride
• 2-Chloro-5-nitropyrimidine
• Sodium dichloroisocyanurate
• Dichloroethane
• Nitromethane
• 2,6-DINITROPHENOL
• 2,4-DICHLORO-5-NITROPYRIMIDINE 97%,2,4-Dichloro-5-nitropyrimidine ,97%,2,4-DICHLORO-5-NITROPYRIMIDINE
• TRITON
• Nitrobenzene
• 2,4,6-Trinitrotoluene
• 2-Methyl-4,6-dichloro-5-nitropyrimidine
• 2,4,6-TRICHLORO-5-NITROPYRIMIDINE
• 4,6-DICHLORO-5-NITRO-2-PROPYLTHIOPYRIMIDINE
• 4,6-DICHLORO-5-NITRO-2-(TRIFLUOROMETHYL)PYRIMIDINE
• 4,6-Dichloro-5-nitro-2-(pyridin-2-yl)pyrimidine
• 2,6-dichloro-5-nitropyrimidine-4-carboxylic acid ethyl ester,ETHYL 2,6-DICHLORO-5-NITROPYRIMIDINE-4-CARBOXYLATE