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553344

Sigma-Aldrich

Isopropyl isocyanide

97%

Synonym(s):

2-Isocyanopropane, 2-Propyl isonitrile, Isopropyl isonitrile

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About This Item

Linear Formula:
(CH3)2CHNC
CAS Number:
598-45-8
Molecular Weight:
69.11
MDL number:
MFCD00015503
UNSPSC Code:
12352100
PubChem Substance ID:
24879320
NACRES:
NA.22

Assay

97%

refractive index

n20/D 1.371 (lit.)

bp

75 °C (lit.)

density

0.733 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C4H7N/c1-4(2)5-3/h4H,1-2H3

InChI key

MJZUMMKYWBNKIP-UHFFFAOYSA-N

General description

Isopropyl isocyanide is an alkyl isocyanide.

Application

Isopropyl isocyanide may be used in the preparation of:
  • Ugi ligand A2C11I1, which is employed in the solid-phase Ugi synthesis.
  • Pentafluorophenyl (PFP) functional monomers, via Passerini reaction.
  • Dinuclear copper complex [Cu2(μ-PiPr2bipy)2{μ-CNCH(CH3)2}](PF6)2 [PiPr2bipy = 6-(diisopropylphosphanyl)-2,2′-bipyridine].
  • (3E)-(Imino)thiaisoindoline 1,1-dioxide derivative.
  • N,N′-diisopropylcarbodiimide (DIC) analog via reaction with propan-2-amine.
  • 1-t-butyl-2-isopropyldiaziridinone via reaction with 2-methyl-2-nitrosopropane
  • isopropyl isocyanate via reaction with ozone
  • 1-phthalimidoazetidines via [1+3]cycloaddition reaction with 1-pththalimidoaziridines

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Statements

H225,H301 + H311 + H331

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

69.1 °F - closed cup

Flash Point(C)

20.6 °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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A Series of Dinuclear Copper Complexes Bridged by Phosphanylbipyridine Ligands: Synthesis, Structural Characterization and Electrochemistry.
Lilio AM, et al.
European Journal of Organic Chemistry, 22-23, 4016-4023 (2013)
Palladium-Catalyzed C C Coupling of Aryl Halides with Isocyanides: An Alternative Method for the Stereoselective Synthesis of (3E)-(Imino) isoindolin-1-ones and (3E)-(Imino) thiaisoindoline 1, 1-Dioxides.
Liu B, et al.
Advanced Synthesis & Catalysis, 354(11-12), 2288-2300 (2012)
Synthesis of Carbodiimides by I2/CHP-Mediated Cross-Coupling Reaction of Isocyanides with Amines under Metal-Free Conditions.
Zhu TH, et al.
Organic Letters, 17(8), 1974-1977 (2015)
Thiol-reactive functional poly (meth) acrylates: multicomponent monomer synthesis, RAFT (co) polymerization and highly efficient thiol-para-fluoro postpolymerization modification.
Noy JM, et al.
Polym. Chem., 6(3), 436-447 (2015)
Diaziridinones. IV. Formation by condensation of alkyl isocyanide with nitrosoalkane. Evidence for a carbodiimide N-oxide
Greene DF and Pazos FJ
The Journal of Organic Chemistry, 34(8), 2269-2274 (1969)
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