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Merck
CN

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:
3934-20-1
Molecular Weight:
148.98
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24848616
EC Number:
223-508-6
Beilstein/REAXYS Number:
110911
MDL number:
MFCD00006061

Key Documents

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Product Name

2,4-Dichloropyrimidine, 98%

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.)

mp

57-61 °C (lit.)

functional group

chloro

Quality Level

200

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Application

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

General description

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

pictograms

Exclamation mark
GHS07

signalword

Warning

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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Certificates of Analysis (COA)

Lot/Batch Number
0000522776
0000522776
0000503030
0000503036
0000503036

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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
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.
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.
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
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