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653233

Sigma-Aldrich

2,4-Dichloro-5-fluoropyrimidine

97%

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About This Item

Empirical Formula (Hill Notation):
C4HCl2FN2
CAS Number:
2927-71-1
Molecular Weight:
166.97
MDL number:
MFCD00233551
UNSPSC Code:
12352100
PubChem Substance ID:
24883938
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

mp

37-41 °C (lit.)

functional group

chloro
fluoro

SMILES string

Fc1cnc(Cl)nc1Cl

InChI

1S/C4HCl2FN2/c5-3-2(7)1-8-4(6)9-3/h1H

InChI key

WHPFEQUEHBULBW-UHFFFAOYSA-N

Related Categories

Application

2,4-Dichloro-5-fluoropyrimidine can be used as a starting material to synthesize:
  • 5-fluoropyrimidine-2-carboxamides and 5-fluoropyrimidine-4-carboxamides as potential kinase inhibitors.
  • A series of 2,4-diamino-5-fluoropyrimidine derivatives as potential protein kinase Cθ inhibitors.
  • 2,4-Bisanilinopyrimidine derivatives as potential aurora kinases inhibitors.
  • 5-fluoro-N,N-bis(4-methoxyphenyl)-2,4-pyrimidinediamine by reacting with p-methoxy aniline in the presence of DIPEA.
  • 2-chloro-5-fluoro-4-(4-fluorophenyl)pyrimidine by Suzuki coupling reaction in the presence of (4-fluorophenyl)boronic acid triphenylphosphine, and palladium(II) acetate catalyst.
  • 5-fluoro-2-(piperidin-4-yloxy)pyrimidin-4-amine, a scaffold, which is used in the preparation of potent deoxycytidine kinase inhibitors.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314,H317

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1A

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

222.8 °F - closed cup

Flash Point(C)

106 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW7663
MKCT6079
MKCQ4906
MKCP1812
MKCG6231

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Practical synthesis of 5-fluoro-2-(piperidin-4-yloxy) pyrimidin-4-amine, a key intermediate in the preparation of potent deoxycytidine kinase inhibitors
Zhang H, et al.
Organic Process Research & Development, 13(4), 807-811 (2009)
Ignacio Aliagas-Martin et al.
Journal of medicinal chemistry, 52(10), 3300-3307 (2009-05-01)
The two major Aurora kinases carry out critical functions at distinct mitotic stages. Selective inhibitors of these kinases, as well as pan-Aurora inhibitors, show antitumor efficacy and are now under clinical investigation. However, the ATP-binding sites of Aurora A and
Design, synthesis, and biological evaluation of a series of novel AXL kinase inhibitors
Mollard A, et al.
ACS Medicinal Chemistry Letters, 2(12), 907-912 (2011)
Optimization of 2, 4-diamino-5-fluoropyrimidine derivatives as protein kinase C theta inhibitors with mitigated time-dependent drug-drug interactions and P-gp liability
Kunikawa S, et al.
Bioorganic & Medicinal Chemistry, 23(13), 3269-3277 (2015)
Facile and regioselective synthesis of novel 2, 4-disubstituted-5-fluoropyrimidines as potential kinase inhibitors
Wada H, et al.
Tetrahedron Letters, 53(14), 1720-1724 (2012)

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