| Identification | Back Directory | [Name]
BENZYL ISOCYANIDE | [CAS]
10340-91-7 | [Synonyms]
HANSA ISN-0155
BENZYL ISOCYANIDE
BENZYL ISONITRILE
BIO-FARMA BF000644
Benzyl carbylamine
Benzyl lsocyanide
Benzyl isocyanide,98%
(IsocyanoMethyl)benzene
Phenylmethyl isocyanide
Benzyl isocyanide, 98% 1GR
(isocyanoMethyl)cyclohexane | [EINECS(EC#)]
233-738-9 | [Molecular Formula]
C8H7N | [MDL Number]
MFCD00000004 | [MOL File]
10340-91-7.mol | [Molecular Weight]
117.15 |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to yellowish liquid | [Boiling point ]
105-106 °C75 mm Hg(lit.)
| [density ]
0.962 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.521(lit.)
| [Fp ]
175 °F
| [storage temp. ]
?20°C | [form ]
clear liquid | [pka]
27.4 | [color ]
Colorless to Red to Green |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to yellowish liquid | [Uses]
Benzyl Isocyanide is used in the preparation of arylamide compounds. also used as a catalyst in the cycloaddition of norbornenes with internal and terminal acetylenes. | [Application]
Benzyl isocyanide forms phosphaalkene-containing complexes. Benzyl isocyanide was used in the synthesis of Ru(II) complexes containing hydrazine and benzyl isocyanide ligands. It was used in a three-component coupling process leading to O- and N-arylamides. | [Synthesis]
Synthesis of benzyl isocyanide
In a 500-mL, round-bottomed flask equipped with a magnetic stirring bar and a pressure-equalizing funnel are placed 5-benzylaminotetrazole (10.5 g, 60 mmol), 100 mL of 10% sodium hydroxide solution, and 70 mL of dichloromethane. The mixture is cooled to 0°C and a solution of NaOBr in water (165 mL, 65 mmol) (Note 2) is added with vigorous stirring over a 15-min period (Note 3). The dichloromethane layer is separated and the aqueous phase extracted with five 50-mL portions of dichloromethane. The combined dichloromethane extracts are dried over anhydrous MgSO4, the drying agent is removed by filtration, and the dichloromethane is removed by simple distillation. The pressure is then reduced to ~20 mm with an aspirator and benzyl isocyanide is distilled at 98–100°C; yield: 5.91 g (84%) (Note 4) and (Note 5).
Organic Syntheses, Coll. Vol. 7, p. 27, 1990
http://www.orgsyn.org |
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