| Identification | More | [Name]
TERT-BUTYL ISOCYANIDE | [CAS]
7188-38-7 | [Synonyms]
2-ISOCYANO-2-METHYL-PROPANE
T-BUTYLISOCYANIDE
TERT-BUTYL ISOCYANIDE
TERT-BUTYL ISONITRILE
(CH3)3CNC
2-isocyano-2-methyl-propan
2-Methyl-2-isocyanopropane
Propane, 2-isocyano-2-methyl-
Propane,2-isocyano-2-methyl-
TBIN
2-methylpropyl isocyanide
t-Butylisocyanide,min.98%
t-Butylisocyanide, min. 98% | [EINECS(EC#)]
230-553-5 | [Molecular Formula]
C5H9N | [MDL Number]
MFCD00000002 | [Molecular Weight]
83.13 | [MOL File]
7188-38-7.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless liquid | [Melting point ]
148-150 °C | [Boiling point ]
91 °C(lit.)
| [density ]
0.735 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.376(lit.)
| [Fp ]
-2 °C
| [storage temp. ]
Flammables area | [solubility ]
Soluble in organic solvents such as ethanol, methanol, ether, toluene and dichloromethane. | [form ]
liquid | [color ]
colorless | [Specific Gravity]
0.735 | [Detection Methods]
GC | [BRN ]
1903156 | [Exposure limits]
NIOSH: IDLH 25 mg/m3 | [Stability:]
store cold | [CAS DataBase Reference]
7188-38-7(CAS DataBase Reference) | [Storage Precautions]
Moisture sensitive |
| Questions And Answer(Q&A) | Back Directory | [Preparation]
CAUTION: Use a well-ventilated hood and observe all precautions when using hydrogen cyanide.
To a 1-1, stainless steel Hoke pressure cylinder in a well-ventilated hood is added 196 gm (3.5 moles) of isobutene, 95 gm (3.5 moles) of hydrogen cyanide, and 100 gm (0.7 mole) or cuprous bromide. The cylinder is closed, shaken for 15 hr at 70°C, cooled to room temperature, and vented cautiously in the hood, and the viscous residue is poured slowly into aqueous potassium cyanide (260 gm in 100 ml of water) to decompose the cuprous complex, liberating an organic layer. The organic layer is separated, dried, and distilled under reduced pressure to afford 97 gm, b.p. 60-63°C (314 mm Hg), ng 1.3749, IR 2143 s, 1472 m, 1368 m, 1230 m, 1208 m, 855 w c m - 1; yield, 33% based on starting isobutylene; 16% based on CuBr.
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| Safety Data | Back Directory | [Hazard Codes ]
F,T | [Risk Statements ]
R11:Highly Flammable.
R23:Toxic by inhalation. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 1993 3/PG 2
| [WGK Germany ]
3
| [RTECS ]
EQ7102500
| [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29299090 |
| Hazard Information | Back Directory | [Description]
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. | [Chemical Properties]
clear colorless liquid | [Uses]
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. | [General Description]
Carbon dative bond formation by tert-butyl isocyanide on the germanium (100) surface has been reported. It also forms complexes with metals and inserts into metal-carbon bonds to form iminoacyls. |
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