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143847

Sigma-Aldrich

2,4-Dichlor-pyrimidin

98%

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C4H2Cl2N2
CAS-Nummer:
3934-20-1
Molekulargewicht:
148.98
Beilstein:
110911
EG-Nummer:
223-508-6
MDL-Nummer:
MFCD00006061
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24848616
NACRES:
NA.22

Assay

98%

Form

solid

bp

101 °C/23 mmHg (lit.)

mp (Schmelzpunkt)

57-61 °C (lit.)

SMILES String

Clc1ccnc(Cl)n1

InChI

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

InChIKey

BTTNYQZNBZNDOR-UHFFFAOYSA-N

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Allgemeine Beschreibung

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

Anwendung

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

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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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.
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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