| Identification | More | [Name]
2-IODOPHENYLACETONITRILE | [CAS]
40400-15-5 | [Synonyms]
2-IODOBENZYL CYANIDE
2-IODOPHENYLACETONITRILE
O-IODOPHENYLACETONITRILE
2-Iodophenylacetonitrile,96%
2-Iodobenzeneacetonitrile | [Molecular Formula]
C8H6IN | [MDL Number]
MFCD00040888 | [Molecular Weight]
243.04 | [MOL File]
40400-15-5.mol |
| Chemical Properties | Back Directory | [Boiling point ]
113-120 °C0.5 mm Hg(lit.) | [density ]
1.75 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.618(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [Appearance]
White to light yellow Solid | [Sensitive ]
Light Sensitive | [BRN ]
2083106 | [CAS DataBase Reference]
40400-15-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [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 ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
3276 | [WGK Germany ]
3
| [HazardClass ]
6.1 | [PackingGroup ]
III |
| Hazard Information | Back Directory | [Uses]
2-Iodophenylacetonitrile may be used in the preparation of:
- 2?-aminobiphen-2-ylacetonitrile
- ethyl (2-iodophenyl)iminoacetate hydrochloride
- 3,4-disubstituted 2-naphthalenamines
It may also be used in the preparation of the following nitriles:
- 2-(2-iodophenyl)-2-methylpropanenitrile
- 1-(2-iodophenyl)cyclopentanecarbonitrile
- 5-bromo-2-(2-iodophenyl)pentanenitrile
- 2-(2-iodophenyl)-2-propylpentanenitrile
- 1-(2-iodophenyl)cyclohexanecarbonitrile
- 1-(2-Iodophenyl)cyclopropanecarbonitrile
| [General Description]
2-Iodophenylacetonitrile is a 2-aryl substituted nitrile. It reacts with lactams to form ring-fused isoquinolinones via palladium-catalyzed carboxamidation in tandem with aldol condensation. | [Synthesis]
Distilled dichloromethane (5 mL) was added to a 25 mL reaction tube under nitrogen protection. Subsequently, 161 mg (0.5 mmol) of iodobenzene diacetate was added. Next, 180 μL of trimethylsilyl trifluoromethanesulfonate (TMSOTf, 1.0 mmol) was added. The reaction mixture was stirred at room temperature for 5 min. After that, 198 mg (0.6 mmol) of 2-(tributylstannyl)acetonitrile was added at -78 °C and stirring was continued for 5 min, and the reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, 3 mL of saturated sodium bicarbonate solution was added to quench the reaction. The reaction was slowly warmed to room temperature and then extracted with dichloromethane (3 mL x 3). The organic phases were combined and dried over anhydrous sodium sulfate. It was subsequently concentrated under reduced pressure. Purification by column chromatography (Rf = 0.19, unfolding agent: petroleum ether/ethyl acetate = 40/1, v/v) afforded the target product 2-iodophenylacetonitrile as a white solid in 86% yield. | [References]
[1] Angewandte Chemie - International Edition, 2018, vol. 57, # 29, p. 9078 - 9082
[2] Angew. Chem., 2018, vol. 130, # 29, p. 9216 - 9220,5
[3] Patent: CN108409602, 2018, A. Location in patent: Paragraph 0022; 0023; 0024 |
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