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143847

Sigma-Aldrich

2,4-Dichloropyrimidine

98%

Synonym(s):

2,6-Dichloropyrimidine, 2-Chloropyrimidin-4-yl chloride

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About This Item

Empirical Formula (Hill Notation):
C4H2Cl2N2
CAS Number:
3934-20-1
Molecular Weight:
148.98
Beilstein:
110911
EC Number:
223-508-6
MDL number:
MFCD00006061
UNSPSC Code:
12352100
PubChem Substance ID:
24848616
NACRES:
NA.22

Quality Level

200

Assay

98%

form

solid

bp

101 °C/23 mmHg (lit.)

mp

57-61 °C (lit.)

functional group

chloro

SMILES string

Clc1ccnc(Cl)n1

InChI

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

InChI key

BTTNYQZNBZNDOR-UHFFFAOYSA-N

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General description

2,4-Dichloropyrimidine is a human skin sensitizer. It undergoes effective one-pot, regioselective double Suzuki coupling reaction to yield diarylated pyrimidines.

Application

2,4-Dichloropyrimidine was used in the synthesis of medicinally important 4-aryl-5-pyrimidinylimidazoles.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000354327
BCCL4488
0000289053
0000253670
0000216807

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Charles Q Huang et al.
Bioorganic & medicinal chemistry letters, 14(9), 2083-2086 (2004-04-15)
A series of 2-dialkylamino-4-phenylpyrimidines (7) was designed and synthesized as CRF(1) antagonists. SAR studies of this series resulted in the discovery of potent and selective antagonists 7b and 7n bearing a 4-(2,4,6-trisubstituted-phenyl) ring and a bulky 2-(N-bis(cyclopropane)methyl-N-propyl)amino group.
D W Roberts et al.
Chemical research in toxicology, 24(7), 1003-1011 (2011-06-16)
There is a strong impetus to develop nonanimal based methods to predict skin sensitization potency. An approach based on physical organic chemistry, whereby chemicals are classified into reaction mechanistic domains and quantitative models or read-across methods are derived for each
Xiaohu Deng et al.
Organic letters, 8(2), 269-272 (2006-01-18)
[reaction: see text] Starting from 2,4-dichloropyrimidine, a concise synthetic route to medicinally important 4-aryl-5-pyrimidinylimidazoles is described. Sequential substitution of the 4- and 2-chloro groups using a regioselective Sonogashira coupling, followed by nucleophilic substitution, led to pyrimidinylalkyne derivatives, which were then
Samantha C Anderson et al.
Synthesis, 2010(16), 2721-2724 (2010-08-01)
An effective one-pot, regioselective double Suzuki coupling of 2,4-dichloropyrimidine has been developed, which enables the quick and efficient synthesis of diarylated pyrimidines. The choice of solvent proved critical to the success of this reaction sequence, with alcoholic solvent mixtures affording
Bodo Scheiper et al.
The Journal of organic chemistry, 69(11), 3943-3949 (2004-05-22)
Cheap, readily available, air stable, nontoxic, and environmentally benign iron salts such as Fe(acac)(3) are excellent precatalysts for the cross-coupling of Grignard reagents with alkenyl triflates and acid chlorides. Moreover, it is shown that dichloroarene and -heteroarene derivatives as the
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