5-Iodo-2-thiophenecarbonitrile

5-Iodo-2-thiophenecarbonitrile Property

Density 

2.14

storage temp. 

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

InChI

InChI=1S/C5H2INS/c6-5-2-1-4(3-7)8-5/h1-2H

InChIKey

DCTRQPYCGCNWBN-UHFFFAOYSA-N

SMILES

C1(C#N)SC(I)=CC=1

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..…

5-Iodo-2-thiophenecarbonitrile Chemical Properties,Usage,Production

Synthesis

Under nitrogen protection, 2-cyanothiophene (1 mmol) was dissolved in anhydrous THF (1.5 mL) in a flame-dried flask. TMPMgCl-LiCl (1.0 M solution of THF, 1.8 mL, 1.8 mmol) was slowly added dropwise at 25 °C and the reaction mixture was stirred for 2 h (for substrate 1a, it is recommended that the metallization time be kept within 1 h). The completion of the metallization reaction was monitored by GC analysis, and an aliquot of the reaction solution was taken and quenched with anhydrous THF solution of iodine (I2) to terminate the reaction. Subsequently, a solution of anhydrous THF (2 mL) with electrophilic reagent (2 mmol) was slowly added dropwise at 0 °C, and the temperature was raised to 25 °C to continue stirring for 1 hour. Upon completion of the reaction, the reaction was quenched with saturated aqueous NaHCO3 solution. Extraction was carried out sequentially with NaHSO3 or NH4Cl solution (5 mL) and ethyl acetate (3 x 15 mL), the organic phases were combined and dried with anhydrous MgSO4. After filtration to remove the desiccant, the solvent was removed by distillation under reduced pressure to give the crude product 5-iodothiophene-2-carbonitrile.

References

[1] Synlett, 2015, vol. 26, # 20, p. 2795 - 2800
[2] Tetrahedron Letters, 1995, vol. 36, # 27, p. 4883 - 4884