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145378

Sigma-Aldrich

4,6-Dichloropyrimidine

97%

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Empirical Formula (Hill Notation):
C4H2Cl2N2
CAS Number:
Molecular Weight:
148.98
Beilstein/REAXYS Number:
111195
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

solid

bp

176 °C (lit.)

mp

65-67 °C (lit.)

solubility

95% ethanol: soluble 50 mg/mL, clear to very slightly hazy, colorless to yellow

SMILES string

Clc1cc(Cl)ncn1

InChI

1S/C4H2Cl2N2/c5-3-1-4(6)8-2-7-3/h1-2H

InChI key

XJPZKYIHCLDXST-UHFFFAOYSA-N

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1 of 4

This Item
143847193291193763
4,6-Dichloropyrimidine 97%

145378

4,6-Dichloropyrimidine

2,4-Dichloropyrimidine 98%

143847

2,4-Dichloropyrimidine

2-Chloropyrimidine 95%

193291

2-Chloropyrimidine

2,5-Dichloropyridine 98%

193763

2,5-Dichloropyridine

solubility

95% ethanol: soluble 50 mg/mL, clear to very slightly hazy, colorless to yellow

solubility

-

solubility

-

solubility

-

form

solid

form

solid

form

crystals

form

solid

mp

65-67 °C (lit.)

mp

57-61 °C (lit.)

mp

63-66 °C (lit.)

mp

59-62 °C (lit.)

bp

176 °C (lit.)

bp

101 °C/23 mmHg (lit.)

bp

75-76 °C/10 mmHg (lit.)

bp

-

General description

Cyclic voltammograms of 4,6-dichloropyrimidine shows three cathodic waves, arising from sequential cleavage of carbon-chlorine bonds as well as the reduction of pyrimidine.

Application

4,6-Dichloropyrimidine was used in the synthesis of N-substituted azacalix[4]pyrimidines. It was used as starting reagent for the synthesis of disubstituted pyrimidines by tandem amination and Suzuki-Miyaura cross-coupling. It was also used in a biarylpyrimidine synthesis involving biaryl cross-coupling.

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Customers Also Viewed

Slide 1 of 4

1 of 4

Richard T Wheelhouse et al.
Journal of medicinal chemistry, 49(17), 5187-5198 (2006-08-18)
Biarylpyrimidines are characterized as selective ligands for higher-order nucleic acid structures. A concise and efficient synthesis has been devised incorporating Suzuki biaryl cross-coupling of dihalopyrimidines. Two ligand series are described based on the parent thioether 4,6-bis[4-[[2-(dimethylamino)ethyl]mercapto]phenyl]pyrimidine (1a) and amide 4,6-bis(4[(2-(dimethylamino)ethyl)carboxamido]phenyl)pyrimidine
Electrochemical reduction of halogenated pyrimidines at mercury cathodes in acetonitrile.
Ji C, et al.
Journal of Electroanalytical Chemistry, 500(1), 3-11 (2001)
Li-Xia Wang et al.
The Journal of organic chemistry, 75(3), 741-747 (2010-01-02)
A number of N-substituted azacalix[4]pyrimidines were synthesized by two methods. While straightforward condensation reaction between 4,6-dichloropyrimidine and 4,6-bis(alkylamino)pyrimidines gave identically N-substituted azacalix[4]pyrimidines in low yields, a general and moderate-to-high yielding 1 + 3 macrocyclic fragment coupling reaction afforded azacalix[4]pyrimidines that
Tetrahedron, 62, 10055-10055 (2006)

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