PRODUCT Properties
| Melting point: | 148-150 °C |
| Boiling point: | 91 °C(lit.) |
| Density | 0.735 g/mL at 25 °C(lit.) |
| refractive index | n |
| Flash point: | -2 °C |
| storage temp. | Inert atmosphere,2-8°C |
| solubility | Soluble in organic solvents such as ethanol, methanol, ether, toluene and dichloromethane. |
| form | liquid |
| color | colorless |
| Specific Gravity | 0.735 |
| BRN | 1903156 |
| Exposure limits | NIOSH: IDLH 25 mg/m3 |
| Stability: | store cold |
| InChI | InChI=1S/C5H9N/c1-5(2,3)6-4/h1-3H3 |
| InChIKey | FAGLEPBREOXSAC-UHFFFAOYSA-N |
| SMILES | C(C)(C)(C)[N+]#[C-] |
| CAS DataBase Reference | 7188-38-7(CAS DataBase Reference) |
Description and Uses
tert-Butyl isocyanide is a key regent for synthesizing many heterocycles and can undergo many cyclization reactions1. It is a colorless liquid, with a strong smell, bench-stable, and soluble in most organic solvents, including methanol, ethanol, ether, toluene, and dichloromethane. Many combinations of 5-member heterocycles with C, N, S, and O atoms, and even boron-containing cycles can be done via [4+1] cycloaddition. Except for heterocyclization, the reagent can be used as a mild esterification reagent, especially in the chemistry of β-lactam antibiotics, penicillins, and cephalosporins. The Passerini reaction with α-geminal polyhalogenated aldehydes allows easy esterification of such intricate substrates.
tert-Butyl isocyanide is used in a tin-free procedure for alkyl radical reactions in the presence of a free-radical initiator. It is a useful intermediate in multicomponent reactions. It is also used in the synthesis of coumarines, 4H-chromenes, isoxazolines and to trap 2-cyclopropylidene-1,3-diones.
Safety
| Symbol(GHS) |   GHS02,GHS06 |
| Signal word | Danger |
| Hazard statements | H225-H330 |
| Precautionary statements | P210-P304+P340+P310 |
| Hazard Codes | F,T |
| Risk Statements | 11-23-2017/11/23 |
| Safety Statements | 16-45 |
| RIDADR | UN 1993 3/PG 2 |
| WGK Germany | 3 |
| RTECS | EQ7102500 |
| HazardClass | 3 |
| PackingGroup | II |
| HS Code | 29299090 |
