| Identification | More | [Name]
4-IODOPHENYLACETONITRILE | [CAS]
51628-12-7 | [Synonyms]
4-IODOBENZYL CYANIDE
4-IODOPHENYLACETONITRILE
4-Iodophenylacetonitrile 4-Iodobenzyl Cyanide p-Iodobenzyl Cyanide
p-IodobenzylCyanide | [EINECS(EC#)]
626-811-5 | [Molecular Formula]
C8H6IN | [MDL Number]
MFCD00060306 | [Molecular Weight]
243.04 | [MOL File]
51628-12-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
53-57 °C(lit.) | [Boiling point ]
152°C/ 3mm | [density ]
1.764±0.06 g/cm3(Predicted) | [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [color ]
White to Light yellow | [Water Solubility ]
Insoluble in water | [Sensitive ]
Light Sensitive | [BRN ]
1934479 | [InChI]
1S/C8H6IN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5H2 | [InChIKey]
PNXWQTYSBFGIFD-UHFFFAOYSA-N | [SMILES]
Ic1ccc(CC#N)cc1 | [CAS DataBase Reference]
51628-12-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R43:May cause sensitization by skin contact. | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
3276 | [WGK Germany ]
3
| [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29269090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Skin Sens. 1 |
| Hazard Information | Back Directory | [Uses]
4-Iodophenylacetonitrile is used as an intermediate in organic syntheses and in pharmaceuticals. | [Synthesis]
The general procedure for the synthesis of 4-iodophenylacetonitrile using 4-iodotoluene as starting material was as follows: referring to the operation of Example 3, a mixture of 4.36 g (20.0 mmol) of p-iodotoluene (Tokyo Kasei), 3.92 g (22.0 mmol) of N-bromosuccinimide (Tokyo Kasei) and 60 mL of carbon tetrachloride (Wako Junyaku Kogyo) was refluxed under incandescent lamp for 4 h. 2.67 g (yield: 45.0%) of 4-iodobenzyl bromide was obtained and the product was a white crystal. Subsequently, 0.49 g (10.0 mmol) of sodium cyanide (Kokusan Kagaku) was dissolved in 10 mL of dimethyl sulfoxide (Aldrich) at 50 °C, 1.48 g (5.0 mmol) of the 4-iodobenzyl bromide prepared as described above was added, and the mixture was stirred for 3 h at room temperature. After the reaction was completed, the reaction mixture was dissolved in water, extracted with hexane, and the hexane was removed by evaporation to give 0.84 g (yield: 68.9%) of 4-iodobenzylacetonitrile, the product was white crystal. | [References]
[1] Patent: US5574062, 1996, A
[2] Patent: US5574062, 1996, A
[3] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1114 - 1126 |
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