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145378

Sigma-Aldrich

4,6-Dichloropyrimidine

97%

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About This Item

Empirical Formula (Hill Notation):
C4H2Cl2N2
CAS Number:
1193-21-1
Molecular Weight:
148.98
Beilstein:
111195
EC Number:
214-770-2
MDL number:
MFCD00006109
UNSPSC Code:
12352100
PubChem Substance ID:
24848721
NACRES:
NA.22

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

functional group

chloro

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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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
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Tetrahedron, 62, 10055-10055 (2006)
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

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