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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
223-508-6
Beilstein/REAXYS Number:
110911
MDL number:
Assay:
98%
Form:
solid
InChI key
BTTNYQZNBZNDOR-UHFFFAOYSA-N
InChI
1S/C4H2Cl2N2/c5-3-1-2-7-4(6)8-3/h1-2H
SMILES string
Clc1ccnc(Cl)n1
assay
98%
form
solid
bp
101 °C/23 mmHg (lit.)
Quality Level
functional group
chloro
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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
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
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
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.
Mark H Norman et al.
Journal of medicinal chemistry, 50(15), 3497-3514 (2007-06-26)
The vanilloid receptor-1 (VR1 or TRPV1) is a member of the transient receptor potential (TRP) family of ion channels and plays a role as an integrator of multiple pain-producing stimuli. From a high-throughput screening assay, measuring calcium uptake in TRPV1-expressing
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