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193291

Sigma-Aldrich

2-Chloropyrimidine

95%

Synonym(s):

2-Chloro-1,3-pyrimidine, Pyrimidin-2-yl chloride

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About This Item

Empirical Formula (Hill Notation):
C4H3ClN2
CAS Number:
1722-12-9
Molecular Weight:
114.53
Beilstein:
107171
EC Number:
217-020-2
MDL number:
MFCD00006060
UNSPSC Code:
12352100
PubChem Substance ID:
24851590
NACRES:
NA.22

Quality Level

100

Assay

95%

form

crystals

bp

75-76 °C/10 mmHg (lit.)

mp

63-66 °C (lit.)

functional group

chloro

SMILES string

Clc1ncccn1

InChI

1S/C4H3ClN2/c5-4-6-2-1-3-7-4/h1-3H

InChI key

UNCQVRBWJWWJBF-UHFFFAOYSA-N

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General description

2-Chloropyrimidine undergoes cobalt-catalyzed cross-coupling reaction with aryl halides.

Application

2-Chloropyrimidine was used in the synthesis of:
  • novel bis(2-(pyrimidin-2-yl)ethoxy)alkanes
  • 4′-(1,1′-(5-(2-methoxyphenoxy)-[2,2′-bipyrimidine]-4,6-diyl)bis(1H-pyrazol-3,1-diyl)) dianiline fluorescent dye, biosensor for protein assay
  • cis- and trans-octahydropyrrolo[2,3]pyridine derivatives
  • 2-amino-4-heteroarylpyrimidines

Other Notes

Remainder 2-hydroxypyrimidine

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

208.4 °F - closed cup

Flash Point(C)

98 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000227070
MKCT6758
MKCT8025
MKCN7697
MKCL8106

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Vikas S Padalkar et al.
Chemistry Central journal, 5, 72-72 (2011-11-10)
Fluorescent dyes with biocompatible functional group and good fluorescence behavior are used as biosensor for monitoring different biological processes as well as detection of protein assay. All reported fluorophore used as sensors are having high selectivity and sensitivity but till
Matthew G Bursavich et al.
Organic letters, 7(19), 4113-4116 (2005-09-09)
[reaction: see text] An expedient synthesis of diverse 2-amino-4-heteroarylpyrimidines via a 2-chloropyrimidine intermediate is described. A series of potentially biologically active analogues have been synthesized in two parallel steps to afford focused arrays.
Vangavaragu Jhansi Rani et al.
Archiv der Pharmazie, 345(8), 663-669 (2012-05-18)
The pyrimidine nucleus is an important component of nucleic acids (DNA and RNA) and vitamins (B(2) and folic acid). It is evident from the literature that pyrimidine derivatives possess a wide spectrum of biological activities such as antioxidant, anticancer, antibacterial
Carina Sollert et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 21(14), 5380-5386 (2015-02-18)
The Ru-catalysed C2-H arylation of indoles and pyrroles by using boronic acids under oxidative conditions is reported. This reaction can be applied to tryptophan derivatives and tolerates a wide range of functional groups on both coupling partners, including bromides and
Igor Goljer et al.
Chirality, 21(7), 681-691 (2008-09-17)
Reaction of (S)- or (R)-3-aminoquinuclidine with 2-chloropyrimidine or 2-bromopyrimidine led to an unexpected formation of both cis- and trans-octahydropyrrolo [2,3]pyridine derivatives. A single-step synthesis of two of the four stereoisomers of these octahydropyrrolo[2,3]pyridine derivatives provides a convenient way of generating
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