2,4-Dichloro-5-thiazolecarboxaldehyde

2,4-Dichloro-5-thiazolecarboxaldehyde Property

Melting point:

47-53℃

Boiling point:

307.1±45.0 °C(Predicted)

Density 

1.690±0.06 g/cm3(Predicted)

Flash point:

>110°C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

-3.71±0.10(Predicted)

color 

Pale Beige

CAS DataBase Reference

92972-48-0(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-36-22

Safety Statements 

26-36/37/39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

HS Code 

29341000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2,4-Dichloro-5-thiazolecarboxaldehyde Chemical Properties,Usage,Production

Uses

2,4-Dichloro-5-thiazolecarboxaldehyde is used in the synthesis of some novel thiazolidine-2,4-dione derivatives having antimicrobial activity.

Synthesis

General procedure for the synthesis of 2,4-dichlorothiazole-5-carboxaldehyde (330): 2,4-thiazolidinedione (329, 2.7 g, 23.07 mmol) was dissolved in N,N-dimethylformamide (DMF, 1.23 mL, 15.98 mmol) at 0 °C and protected by argon and slowly added dropwise to phosphorus trichloride (8.15 mL, 87.17 mmol) (8.15 mL, 87.17 mmol), and the dropwise addition time was controlled at 15 min. Subsequently, the reaction mixture was gradually warmed to room temperature and stirred continuously for 1 hour. Next, the reaction system was heated to 120 °C and stirring was continued for 4 hours. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was carefully poured into pre-cooled ice water and extracted with dichloromethane (CH2Cl2, 3 x 100 mL). The organic phases were combined, washed sequentially with saturated sodium bicarbonate solution (100 mL) and water (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with 5% ethyl acetate/hexane as eluent, and the target compound 330 (1.4 g, 33% yield) was finally obtained as a brown oil.TLC conditions: 30% ethyl acetate/hexane (Rf=0.8).1H NMR (500 MHz, DMSO-d6): δ9.87 (s, 1H).

References

[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 8, p. 973 - 978
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 235 - 238
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 10, p. 2435 - 2444
[4] Patent: US2010/298334, 2010, A1. Location in patent: Page/Page column 78
[5] Chemistry of Heterocyclic Compounds, 2010, vol. 46, # 3, p. 334 - 341