2-Chloro-5-thiophenecarboxaldehyde

2-Chloro-5-thiophenecarboxaldehyde Property

Boiling point:

99 °C/21 mmHg (lit.)

Density 

1.376 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.604(lit.)

Flash point:

208 °F

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Crystalline Powder or Solid

color 

White to tan

Sensitive 

Air Sensitive

InChI

InChI=1S/C5H3ClOS/c6-5-2-1-4(3-7)8-5/h1-3H

InChIKey

VWYFITBWBRVBSW-UHFFFAOYSA-N

SMILES

C1(C=O)SC(Cl)=CC=1

CAS DataBase Reference

7283-96-7(CAS DataBase Reference)

NIST Chemistry Reference

2-Thiophenecarboxaldehyde, 5-chloro-(7283-96-7)

EPA Substance Registry System

2-Thiophenecarboxaldehyde, 5-chloro- (7283-96-7)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-43-36-36/37/38

Safety Statements 

36-36/37/39-26-24-37/39

RIDADR 

2810

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29124990

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.

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.

P405Store locked up.

P501Dispose of contents/container to..…

2-Chloro-5-thiophenecarboxaldehyde Chemical Properties,Usage,Production

Chemical Properties

clear yellow liquid

Uses

5-Chloro-2-thiophenecarboxaldehyde is used in the evaluation of 2-benzylidene-1-tetralone derivative as antagonists of A1 and A2A adenosine receptors.

Uses

5-Chloro-2-thiophenecarboxaldehyde may be used for synthesis of 2-heteroaryl-α-methyl-5-benzoxazoleacetic acids and N,N′-bis[(E)-(5-chloro-2-thienyl)methylidene]ethane-1,2-diamine

General Description

5-Chloro-2-thiophenecarboxaldehyde is a thiophene derivative.

Synthesis

GENERAL METHOD: 2-chloro-5-methylthiophene (200 mmol) was dissolved in anhydrous DMF (43.86 g, 600 mmol) under anhydrous conditions, cooled in an ice-water bath and stirred. POCl3 (46.00 g, 300 mmol) was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was continued to be stirred at the temperature of the ice-water bath for 30 min, and then warmed up to 100 °C for 5 h. The reaction was carried out at the temperature of the ice-water bath. Upon completion of the reaction, the mixture was cooled to room temperature and carefully poured into ice water (300 mL). The aqueous phase was extracted with dichloromethane (300 mL × 3) and the organic phase was combined. The organic phase was washed sequentially with 5% brine (200 mL), 10% aqueous K2CO3 (200 mL), and 5% brine (200 mL), and then dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure to obtain the crude product. Purification of the crude product by column chromatography afforded the target compound 5-chlorothiophene-2-carbaldehyde (10ha): a colorless oil in 22.00 g (75%) yield.1H-NMR (DMSO-d6, 400 MHz) δ: 9.82 (s, 1H), 7.95 (d, J = 4.0 Hz, 1H), 7.39 (d, J = 4.0 Hz, 1H). The obtained 1H-NMR data are in agreement with literature reports [53].

References

[1] Molecules, 2018, vol. 23, # 2,
[2] Journal of the American Chemical Society, 1953, vol. 75, p. 988