| Identification | More | [Name]
4-(PYRIMIDIN-5-YL)BENZALDEHYDE | [CAS]
198084-12-7 | [Synonyms]
AKOS BAR-0648
5-(4-FORMYLPHENYL)PYRIMIDINE
4-(5-PYRIMIDINYL)BENZALDEHYDE
4-(PYRIMIDIN-5-YL)BENZALDEHYDE
Benzaldehyde, 4-(5-pyrimidinyl)-
4-PYRIMIDIN-5-YL-BENZALDEHYDE, 95+%
4-(2-Chloropyrimidin-5-yl)benzaldehyde
5-(4-Formylphenyl)pyrimidine
4-(2-(Dimethylamino)pyrimidin-5-yl)benzaldehyde
4-(PYRIMIDIN-5-YL)BENZALDEHYDE ISO 9001：2015 REACH | [Molecular Formula]
C11H8N2O | [MDL Number]
MFCD02684108 | [Molecular Weight]
184.19 | [MOL File]
198084-12-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
145-149 °C (lit.) | [Boiling point ]
369.1±35.0 °C(Predicted) | [density ]
1.205±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C, stored under nitrogen | [form ]
solid | [pka]
1.52±0.10(Predicted) | [Appearance]
Off-white to light brown Solid | [InChI]
InChI=1S/C11H8N2O/c14-7-9-1-3-10(4-2-9)11-5-12-8-13-6-11/h1-8H | [InChIKey]
BXNXTOLXLPQMHS-UHFFFAOYSA-N | [SMILES]
C(=O)C1=CC=C(C2=CN=CN=C2)C=C1 | [CAS DataBase Reference]
198084-12-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36:Irritating to the eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
2913000090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2 |
| Hazard Information | Back Directory | [Uses]
4-(Pyrimidin-5-yl)benzaldehyde is a useful reactant and reagent in organic reactions such as the synthesis of 1,?2-?difluorination of alkenes, and β-?Cyanoacrylamides. | [Synthesis]
To a stirred solution of 5-bromopyrimidine (1 eq.), 4-formylphenylboronic acid (1.3-3.0 eq.), and sodium carbonate monohydrate (1.3-3.0 eq.) in a mixed solvent of dimethoxyethane/water (4:1, v/v) (concentration of about 0.05-0.2 M) was added tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.1 eq.). The reaction mixture was stirred at 90 °C for about 18 h and subsequently quenched with water. The mixture was extracted with dichloromethane (CH2Cl2) according to standard post-treatment steps and the organic layer was dried over anhydrous sodium sulfate (Na2SO4) or anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. The crude product was purified by fast column chromatography or silica gel radial chromatography. According to the above general method, 4-(5-pyrimidinyl)benzaldehyde (162 mg, 99% yield) was obtained from 5-bromopyrimidine (199 mg, 1.25 mmol) and 4-formylphenylboronic acid (469 mg, 3.13 mmol). | [References]
[1] Patent: WO2007/22371, 2007, A2. Location in patent: Page/Page column 25; 71
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 8049 - 8065 |
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