4,6-Dichloro-5-pyrimidinecarbaldehyde Chemical Properties

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

pka

-5.90±0.26(Predicted)

form 

solid

color 

Yellow

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)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-43-36/38-22

Safety Statements 

26-36-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29335990

4,6-Dichloro-5-pyrimidinecarbaldehyde Usage And Synthesis

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

4,6-Dichloro-5-pyrimidinecarbaldehyde(5305-40-8)Related Product Information

• 4,6-Dichloropyrimidine
• Sulfadiazine
• Sodium dichloroisocyanurate
• Dichloroethane
• 4,6-Dichloro-5-fluoropyrimidine
• Thionyl chloride
• 2,4,6-TRICHLORO-PYRIMIDINE-5-CARBALDEHYDE
• 4,6-DICHLORO-2-METHYLPYRIMIDINE-5-CARBALDEHYDE
• 2-Amino-4,6-dichloro-pyrimidine-5-carbaldehyde
• 4,6-DICHLORO-2-METHYLSULFANYL-PYRIMIDINE-5-CARBALDEHYDE
• Pyrimidine-5-carboxaldehyde
• 4,6-dichloropyrimidine-5-carboxylic acid
• (4,6-Dichloropyrimidin-5-yl)(quinolin-4-yl)methanone
• 4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE-5-CARBOXYLIC ACID
• 5-Pyrimidinecarbonyl chloride, 4,6-dichloro- (9CI)
• (4,6-Dichloropyrimidin-5-yl)(4-methoxy-2-(trifluoromethyl)phenyl)methanone
• 5-PYRIMIDINECARBOXYLIC ACID, 4,6-DICHLORO-,METHYL ESTER
• 4,6-DICHLORO-5-PYRIMIDINECARBOXAMIDE