143847
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:
Molecular Weight:
148.98
Beilstein:
110911
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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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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
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
Mahbub Alam et al.
Bioorganic & medicinal chemistry letters, 17(12), 3463-3467 (2007-04-27)
The development of a series of novel aminopyrimidines as inhibitors of c-Jun N-terminal kinases is described. The synthesis, in vitro inhibitory values for JNK1, JNK2 and CDK2, and the in vitro inhibitory value for a c-Jun cellular assay are discussed.
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
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