2-Methylpropylisocyanid

2-ISOCYANO-2-METHYL-PROPANE · T-BUTYLISOCYANIDE · TBIN · TERT-BUTYL ISONITRILE · Propane, 2-isocyano-2-methyl- · 2-methylpropyl isocyanide · (CH3)3CNC · tert-Butyl isocyanide

https://huagongshe.com/de/chemical/23577

Molekülstruktur von 2-Methylpropylisocyanid

Identifikatoren & physikalische Daten

CAS No.	7188-38-7
Summenformel	C5H9N
Durchschnittliche Molmasse	83,13 g/mol
Monoisotopische Masse	83,07349929 g/mol
SMILES	[C-]#[N+]C(C)(C)C
InChIKey	FAGLEPBREOXSAC-UHFFFAOYSA-N
PubChem CID	23577
ChEBI	CHEBI:235305
EC No.	230-553-5
DTXSID	DTXSID60222145
Lokaler Name	2-Methylpropylisocyanid

Chemische & physikalische Eigenschaften

XLogP	0,9
Polarare Oberfläche (TPSA)	4,4
H-Brücken-Donoren	0
H-Brücken-Akzeptoren	1
Frei drehbare Bindungen	0
Schwere Atome	6
Formalladung	0
Komplexität	77
Schmelzpunkt	148-150 °C
Siedepunkt	91 °C(lit.)
Dichte	0.735 g/mL at 25 °C(lit.)
Brechungsindex	n20/D 1.376(lit.)
Flammpunkt	-2 °C
Lagerbedingungen	Inert atmosphere,2-8°C
Löslichkeit	Soluble in organic solvents such as ethanol, methanol, ether, toluene and dichloromethane.
Aggregatzustand	liquid
Wichte	0.735
Farbe	colorless
BRN	1903156
Stabilität	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 Datenbank	7188-38-7(CAS DataBase Reference)

Sicherheit & Vorschriften

Wassergefährdungsklasse (WGK)	3
UN-Transportnummer	UN 1993 3/PG 2
Zollcode	29299090
RTECS-Nr.	EQ7102500
R-Sätze (R)	11-23-2017/11/23
Gefahrensymbole	F,T
Sicherheitshinweise (S)	16-45
Gefahrenklasse	3Acute Tox. 2 InhalationFlam. Liq. 2
Verpackungsgruppe	II
Lagerklasse	3 - Flammable liquids

Anwendungen & Verwendung

Beschreibung

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.

Verwenden

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.

Herstellung & Synthese

synthetische

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 g tert-Butyl isocyanide, 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.