3-IODOTHIOPHENE-2-CARBOXYLIC ACID

3-IODOTHIOPHENE-2-CARBOXYLIC ACID Property

Melting point:

195°C

Boiling point:

340.3±27.0 °C(Predicted)

Density 

2.238±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

3.10±0.10(Predicted)

Appearance

White to off-white Solid

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..…

3-IODOTHIOPHENE-2-CARBOXYLIC ACID Chemical Properties,Usage,Production

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 1777, 1985 DOI: 10.1016/S0040-4039(00)98336-9

Synthesis

Example 1 Preparation of 3-iodothiophene-2-carboxylic acid 1. dissolve thiophene-2-carboxylic acid (12.8 g, 0.1 mol) in THF at -78 °C. 2. n-Butyllithium (88 mL, 2.5 M THF solution, 2.2 eq.) was added slowly dropwise and stirring was continued for 0.5 hr after completion of the drop. 3. THF solution of iodine (28 g, 1.1 eq.) was added slowly with stirring. 4. The reaction mixture was gradually warmed to room temperature and stirred at room temperature until the reaction was complete. 5. The reaction mixture was concentrated to give a crude product. 6. The crude product was dissolved in EtOAc and extracted with 10% aqueous Na2CO3 solution. 7. The aqueous phases were combined and acidified with concentrated hydrochloric acid to pH<2. 8. The acidified aqueous phase was extracted with EtOAc and the organic phases were combined. 9. The organic phase was dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 3-iodothiophene-2-carboxylic acid as a yellow-orange solid (23.5 g, 95% yield). 10. The product was characterized and confirmed by HPLC and mass spectrometry.

References

[1] Patent: WO2005/12311, 2005, A1. Location in patent: Page/Page column 22
[2] Synthetic Communications, 1998, vol. 28, # 13, p. 2467 - 2481
[3] Tetrahedron, 2006, vol. 62, # 41, p. 9554 - 9570
[4] Synlett, 1998, # 1, p. 33 - 34
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 173 - 182