I-PROPYLISOCYANIDE Property

Boiling point:

75 °C(lit.)

Density 

0.733 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.371(lit.)

Flash point:

69 °F

storage temp. 

2-8°C

form 

liquid

Specific Gravity

0.7596

color 

colorless

Stability:

store cold

Safety

Hazard Codes 

F,T

Risk Statements 

11-23/24/25

Safety Statements 

16-23-26-33-36/37/39-45

RIDADR 

UN 1992 3/PG 2

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

I-PROPYLISOCYANIDE Chemical Properties,Usage,Production

Uses

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

Preparation

To a flask containing 100 ml (0.85 mole) of distilled quinoline is added with stirring 41 gm (0.214 mole) of /7-toluenesulfonyl chloride (see Note), and the solution is warmed to 75°C. Then 18.4 gm (0.212 mole) of isopropylformamide is added and the pressure of the system is reduced to 70 mm Hg. The isopropylisonitrile as it forms distills into a liquid nitrogencooled receiver. (Dry ice is not as effective but may be used.) The product is redistilled to afford 4.2 gm (30%), b.p. 88-89°C (735 mm Hg).

General Description

Isopropyl isocyanide is an alkyl isocyanide.