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Sigma-Aldrich

tert-Butyl isocyanide

98%

Synonym(s):

1,1-Dimethylethyl isocyanide, 1-tert-Butylisonitrile, 2-Isocyano-2-methylpropane, t-Butylisonitrile, tert-Butylisonitrile

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About This Item

Linear Formula:
(CH3)3CNC
CAS Number:
7188-38-7
Molecular Weight:
83.13
Beilstein:
1903156
EC Number:
230-553-5
MDL number:
MFCD00000002
UNSPSC Code:
12352100
PubChem Substance ID:
24855763
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.376 (lit.)

bp

91 °C (lit.)

density

0.735 g/mL at 25 °C (lit.)

SMILES string

CC(C)(C)[N+]#[C-]

InChI

1S/C5H9N/c1-5(2,3)6-4/h1-3H3

InChI key

FAGLEPBREOXSAC-UHFFFAOYSA-N

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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.

Application

tert-Butyl isocyanide was used in the synthesis of coumarines, 4H-chromenes and isoxazolines. It was also used to trap 2-cyclopropylidene-1,3-diones.

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Statements

H225,H330

Hazard Classifications

Acute Tox. 2 Inhalation - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

28.4 °F - closed cup

Flash Point(C)

-2 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Journal of the Chemical Society. Chemical Communications, 189-189 (1987)
Organometallics, 12, 2414-2414 (1993)
Graham A Bowmaker et al.
Dalton transactions (Cambridge, England : 2003), (13)(13), 1710-1720 (2008-03-21)
Single-crystal structural characterizations confirm the existence of the unusual 1 : 4 copper(I) halide : unidentate ligand adducts [Cu(CNt-Bu)4]X for X = Cl, Br (two forms), I (the chloride and one form of the bromide being solvated) with crystal packing
Habib Nasri et al.
Inorganic chemistry, 43(9), 2932-2942 (2004-04-27)
The addition of the strongly pi-bonding ligands CO or tert-butyl isocyanide to the low-spin five-coordinate iron(II) nitrite species [Fe(TpivPP)(NO2)]- (TpivPP = picket fence porphyrin) gives two new six-coordinate species [Fe(TpivPP)(NO2)(CO)]- and [Fe(TpivPP)(NO2)(t-BuNC)]-. These species have been characterized by single-crystal structure
Synthesis of coumarines and 4H-chromenes through the reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in presence of 2-hydroxybenzaldehydes.
Yavari I, et al.
Synthesis, 5, 679-682 (2004)
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