| Identification | More | [Name]
4,6-Dichloro-5-pyrimidinecarbaldehyde | [CAS]
5305-40-8 | [Synonyms]
4,6-DICHLORO-5-PYRIMIDINECARBALDEHYDE
4,6-DICHLORO-5-PYRIMIDINE CARBOXALDEHYDE
4,6-DICHLORO-PYRIMIDINE-5-CARBALDEHYDE
ASISCHEM C51985
TIMTEC-BB SBB005606
4,6-Dichloropyrimidine-5-carboxaldehyde
4,6-Dichloropyrimidine-5-carboxaldehyde 97%
4,6-DICHLOROPYRIMIDINE-5-CARBALDEHYDE,PURITY:97% MIN(HPLC)
4,6-Dichloro-5-formylpyrimidine
4,6-Dichloro-5-pyrimidinecarbaldehyde ,96% | [Molecular Formula]
C5H2Cl2N2O | [MDL Number]
MFCD02257701 | [Molecular Weight]
176.99 | [MOL File]
5305-40-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White to off-white solid | [Melting point ]
66-71 °C | [Boiling point ]
92-93 °C(Press: 0.05 Torr) | [density ]
1.588±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
solid | [pka]
-5.90±0.26(Predicted) | [color ]
Yellow | [Detection Methods]
HPLC | [InChI]
InChI=1S/C5H2Cl2N2O/c6-4-3(1-10)5(7)9-2-8-4/h1-2H | [InChIKey]
XQSJHQXYQAUDFC-UHFFFAOYSA-N | [SMILES]
C1=NC(Cl)=C(C=O)C(Cl)=N1 | [CAS DataBase Reference]
5305-40-8(CAS DataBase Reference) | [Storage Precautions]
Store under nitrogen |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact.
R36/38:Irritating to eyes and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29335990 |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white solid | [Uses]
4,6-Dichloropyrimidine-5-carboxaldehyde is used as a substrate in the synthesis of N-terminal surrogate in amino acid and peptide analogues. | [Synthesis]
General procedure for the synthesis of 4,6-dichloro-5-pyrimidinecarboxaldehyde from N,N-dimethylformamide (DMF) and 4,6-dihydroxypyrimidine: First, DMF (64 mL) was mixed with phosphorus oxychloride (POCl3) (200 mL) and stirred for 1 hr at 0 °C. Subsequently, 4,6-dihydroxypyrimidine (50.0 g, 446 mmol) was added to the mixture and stirring was continued for 0.5 h at room temperature. Next, the resulting non-homogeneous mixture was heated to reflux for 3 hours. After completion of the reaction, the volatiles were removed by distillation under reduced pressure and the residue was carefully poured into ice water. The aqueous phase was extracted six times with ether and the organic phases were combined. The organic phase was washed sequentially with aqueous sodium bicarbonate (NaHCO3) and pure water and dried over anhydrous sodium sulfate (Na2SO4). The dried organic phase was concentrated under reduced pressure and finally crystallized by ethyl acetate (EtOAc)-petroleum ether mixed solvent to afford the target product 4,6-dichloro-5-pyrimidinecarboxaldehyde (43.5 g, 55% yield). The product was analyzed by LC-MS (ESI), m/z 177 [M+H]+. | [References]
[1] Patent: US2006/281700, 2006, A1. Location in patent: Page/Page column 34
[2] Patent: US2006/281755, 2006, A1. Location in patent: Page/Page column 40
[3] Patent: US2006/281764, 2006, A1. Location in patent: Page/Page column 25
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 16, p. 3353 - 3358
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 12, p. 2936 - 2941 |
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