| Identification | More | [Name]
3-Thiophenecarbonitrile | [CAS]
1641-09-4 | [Synonyms]
3-CYANOTHIOPHENE
3-THIOPHENECARBONITRILE
BUTTPARK 96\11-31
THIOPHENE-3-CARBONITRILE
Thiophene-3-carbonitrile 97%
3-Cyanothiophene, Thiophene-3-nitrile | [EINECS(EC#)]
216-687-7 | [Molecular Formula]
C5H3NS | [MDL Number]
MFCD00151852 | [Molecular Weight]
109.15 | [MOL File]
1641-09-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless liquid | [Boiling point ]
82 °C10 mm Hg(lit.)
| [density ]
1.2 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.5630(lit.)
| [Fp ]
186 °F
| [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
Liquid | [color ]
Clear colorless | [Specific Gravity]
1.2 | [BRN ]
107104 | [CAS DataBase Reference]
1641-09-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
3276 | [WGK Germany ]
3
| [Hazard Note ]
Harmful | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29341000 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless liquid | [Uses]
3-Thiophenecarbonitrile can be used to synthesize the following:
- 2,4-dinaphthyl-3-cyanothiophene via reaction with iodonaphthalene
- 2,5-bis-tri(n-butyl)tin-3-cyanothiophene, a building block for the synthesis of new alternating (3-alkyl/3-cyano)thiophene copolymers
| [Synthesis Reference(s)]
The Journal of Organic Chemistry, 44, p. 1670, 1979 DOI: 10.1021/jo01324a019
Synthetic Communications, 20, p. 3153, 1990 DOI: 10.1080/00397919008051539 | [Synthesis]
General procedure for the synthesis of 3-cyanothiophene from 3-thiophenecarboxaldehyde: A mixture of 3-thiophenecarboxaldehyde (1.0 mmol), NH2OH-HCl (1.5 mmol), and Cog-C3N4 (20 mg) in H2O/MeOH (1:1, 5 mL) was added to a round-bottomed flask and the reaction was stirred for 14-20 h at room temperature under visible-light irradiation. The reaction progress was monitored by TLC. After completion of the reaction, the catalyst was removed by filtration and the filtrate was extracted by adding EtOAc (10 mL) to the filtrate. The organic layer was separated and washed sequentially with brine (2 x 5 mL) and distilled water (1 x 10 mL) and then dried with anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product. The crude product was further purified by fast column chromatography with the eluent ratio of EtOAc/hexane (10:90) to obtain analytically pure 3-cyanothiophene. | [References]
[1] Organic Letters, 2017, vol. 19, # 11, p. 3005 - 3008
[2] Catalysis Communications, 2019, p. 76 - 81
[3] Journal of Polymer Science, Part A: Polymer Chemistry, 2014, vol. 52, # 8, p. 1055 - 1058
[4] Tetrahedron Letters, 2012, vol. 53, # 7, p. 882 - 885
[5] Chemical Communications, 2013, vol. 49, # 54, p. 6030 - 6032 |
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