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1722-12-9 - 2-Chloropyrimidine, 98% - A15394 - Alfa Aesar

A15394 2-Chloropyrimidine, 98%

CAS Number
1722-12-9
Synonyms

Size Price ($) Quantity Availability
10g 54.38
25g 92.08
100g 258.30
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2-Chloropyrimidine, 98%

MDL
MFCD00006060
EINECS
217-020-2

Chemical Properties

Formula
C4H3ClN2
Formula Weight
114.54
Melting point
64-67°
Boiling Point
75-76°/10mm
Flash Point
98°(208°F)
Sensitivity
Moisture Sensitive
Solubility
Slightly soluble in water. 33.3 mg soluble in 1 mL of alcohol.

Applications

2-Chloropyrimidine is a useful reagent in the preparation of antivirals and other biologically active compounds. It was used in the synthesis of 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, 2-amino-4-heteroarylpyrimidines, cis- and trans-octahydropyrrolo[2,3]pyridine derivatives.

Notes

Moisture sensitive. Store under inert gas. Store away from moisture, oxidizing agents. Store in refrigerator.

Literature References

Jeanne-Marie Bégouin and Corinne Gosmini. Cobalt-Catalyzed Cross-Coupling Between In Situ Prepared Arylzinc Halides and 2-Chloropyrimidine or 2-Chloropyrazine. J. Org. Chem. 2009, 74 (8), 3221-3224.

Y.Anantharama Sarma. Planar vibrations of 2-chloropyrimidine. Spectrochimica Acta Part A: Molecular Spectroscopy. 1974, 30 (9), 1801-1806.

Alkoxylation with 3-butyn-1-ol, followed by intramolecular Diels-Alder reaction, leads to a fused pyridine system, by a sequence analogous to that shown for 2-Chloropyrazine, A10108: Tetrahedron, 45, 803 (1989). For a similar sequence using the anion of an alkynylmalononitrile, see: Tetrahedron, 45, 5151 (1989). For synthesis of a benzofuropyridine by the cyclization of a 2-(alkynylphenoxy)pyrimidine, see: Tetrahedron, 45, 6511 (1989).

Organolithium reagents add to the 1,6-imine bond, giving, after aromatization with DDQ, 6-substituted 2-chloropyrimidines: J. Org. Chem., 53, 4137 (1988).

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H319-H317-H335

Harmful if swallowed. Causes serious eye irritation. May cause an allergic skin reaction. May cause respiratory irritation.

Precautionary Statements: P261-P280h-P305+P351+P338-P304+P340-P301+P312-P312-P363-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Wash contaminated clothing before reuse. Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
107171
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2933.59
TSCA
No

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