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144185

Sigma-Aldrich

2,4-Dichloro-6-methylpyrimidine

98%

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About This Item

Empirical Formula (Hill Notation):
C5H4Cl2N2
CAS Number:
5424-21-5
Molecular Weight:
163.00
EC Number:
226-563-4
MDL number:
MFCD00006064
UNSPSC Code:
12352100
PubChem Substance ID:
24848638
NACRES:
NA.22

Quality Level

100

Assay

98%

form

solid

bp

219 °C (lit.)

mp

44-47 °C (lit.)

functional group

chloro

SMILES string

Cc1cc(Cl)nc(Cl)n1

InChI

1S/C5H4Cl2N2/c1-3-2-4(6)9-5(7)8-3/h2H,1H3

InChI key

BTLKROSJMNFSQZ-UHFFFAOYSA-N

General description

2,4-Dichloro-6-methylpyrimidine undergoes double cross-coupling reaction with 2-(tributylstannyl)pyridine, followed by aldol condensation to yield 4-arylvinyl-2,6-di(pyridin-2-yl)pyrimidines. It reacts with 1H,1H,2H,2H-perfluorodecanethiol during fluorous synthesis of disubstituted pyrimidines.

Application

2,4-Dichloro-6-methylpyrimidine was used in the synthesis of (2-chloro-6-methyl-pyrimidin-4-yl)-(2,3-dihydro-benzothiazol-6-yl)-amine.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT1680
MKCM7826
MKCF3396
MKBZ0325V
STBB0071V

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Caroline Hadad et al.
The Journal of organic chemistry, 76(10), 3837-3845 (2011-04-06)
A series of 4-arylvinyl-2,6-di(pyridin-2-yl)pyrimidines have been efficiently prepared by a double cross-coupling reaction between 2,4-dichloro-6-methylpyrimidine and 2-(tributylstannyl)pyridine, followed by aldol condensation with the appropriate aromatic aldehyde substituted with electron-donating, electron-withdrawing, dendritic, or water-soluble groups. The effect of different protic and
Eliud Hernández et al.
Puerto Rico health sciences journal, 29(4), 348-356 (2011-01-26)
Rho family GTPases are molecular switches that control signaling pathways regulating a myriad of cellular functions. Rac1, a Rho family member, plays a critical role in several aspects of tumorigenesis, cancer progression, invasion, and metastasis. Rac proteins are not mutated
Wei Zhang
Organic letters, 5(7), 1011-1013 (2003-03-28)
[reaction: see text] The fluorous synthesis of disubstituted pyrimidines is carried out by attaching 2,4-dichloro-6-methylpyrimidine with 1H,1H,2H,2H-perfluorodecanethiol. The tagged substrate is substituted with 3-(trifluoromethyl)pyrazole followed by thioether oxidation and tag displacement with amines or thiols. The fluorous chain serves as

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