4-Chlorothiazole-5-carboxaldehyde

4-Chlorothiazole-5-carboxaldehyde Property

storage temp. 

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

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C4H2ClNOS/c5-4-3(1-7)8-2-6-4/h1-2H

InChIKey

GJTWEAFBOIYNLZ-UHFFFAOYSA-N

SMILES

S1C(C=O)=C(Cl)N=C1

Safety

HS Code 

2934999090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

4-Chlorothiazole-5-carboxaldehyde Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 4-chlorothiazole-5-carbaldehyde (333): to a stirred solution of 4-chloro-5-(1,3-dioxolan-2-yl)thiazole (332, 1.1 g, 5.75 mmol) in THF (10 mL) was slowly added an aqueous 5N HCl solution (6 mL) at 0°C. The reaction mixture was gradually warmed up to room temperature and stirred continuously for 3 hours. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was poured into brine (20 mL) and extracted with EtOAc (2 x 50 mL). The organic phases were combined, washed with saturated sodium bicarbonate solution (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product 4-chlorothiazole-5-carbaldehyde (333, 800 mg, 95%) as a yellow oil.TLC conditions: 10% EtOAc/hexanes (Rf=0.3); 1H NMR (CDCl3, 500 MHz): δ 10.11 (s, 1H), 9.00 (s, 1H).

References

[1] Patent: WO2015/138895, 2015, A1. Location in patent: Paragraph 000273
[2] Patent: US2010/298334, 2010, A1. Location in patent: Page/Page column 78
[3] Patent: WO2005/92885, 2005, A1. Location in patent: Page/Page column 94
[4] Patent: US2003/45546, 2003, A1
[5] Patent: WO2010/132999, 2010, A1. Location in patent: Page/Page column 148