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CYCLOHEXYL ISOCYANIDE

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CYCLOHEXYL ISOCYANIDE Basic information

Product Name:
CYCLOHEXYL ISOCYANIDE
Synonyms:
  • Cyclohexane, isocyano-
  • Cyclohexaneisonitrile
  • BIO-FARMA BF001328
  • ISOCYANOCYCLOHEXANE
  • HANSA ISN-0519
  • CYCLOHEXYL ISOCYANIDE
  • CYCLOHEXYL ISONITRILE
  • Cyclohexyl #niso-cyanide
CAS:
931-53-3
MF:
C7H11N
MW:
109.17
EINECS:
213-238-7
Product Categories:
  • ISONITRITE
Mol File:
931-53-3.mol
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CYCLOHEXYL ISOCYANIDE Chemical Properties

Melting point:
6.45°C
Boiling point:
173-176 °C
Density 
0.878 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.45(lit.)
Flash point:
170 °F
storage temp. 
Store at +2°C to +8°C.
form 
Liquid
color 
Clear colorless to slightly brown
BRN 
3662332
Stability:
Stable. Incompatible with strong acids, strong bases, strong reducing agents, strong oxidizing agents. Flammable.
CAS DataBase Reference
931-53-3(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn,T
Risk Statements 
20/21/22-23/24/25
Safety Statements 
36/37-45-24/25
RIDADR 
UN 2810 6.1/PG 2
WGK Germany 
3
10-13-21
HazardClass 
6.1
PackingGroup 
III
HS Code 
29299090

MSDS

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CYCLOHEXYL ISOCYANIDE Usage And Synthesis

Chemical Properties

colourless liquid

Uses

Cyclohexyl Isocyanide can be used as novel arginase inhibitors to treat diseases.

Definition

ChEBI: Cyclohexyl isocyanide is an isocyanide having a cyclohexyl group attached to nitrogen. It is a conjugate base of a cyclohexyl isocyanide(1+).

Preparation

CAUTION: Use a well-ventilated hood and take all precautions before using phosgene.
To a flask equipped as in Preparation 3-1 is added 1.27 kg (10.0 moles) of N-cyclohexylformamide, 3.20 liters of triethylamine, and 4.50 liters of methylene chloride. The solution is stirred while phosgene is rapidly added (300-400 gm/hr) to cause vigorous refluxing. Refluxing ceases after 1.04 kg (10.2 moles) of phosgene have been added and the addition is stopped. The reaction mixture is cooled to 22-25°C, 400 gm (23.5 moles) of ammonia gas added over a period of 1-2 hr, the mixture filtered then concentrated under reduced pressure, and the residue distilled to afford 955 gm (88%), b.p. 67-72°C (14 mm Hg).

General Description

Cyclohexyl isocyanide reacts with dimethyl acetylenedicarboxylate to give a mixture of cyclopenta[b]pyridine derivatives, azaspirononatriene derivative and the azabicyclononatriene. It reacts with dialkyl acetylenedicarboxylates to form 1:1 intermediate which on facile addition to 1-benzylisatin and tryptantrin yields highly functionalized novel unsaturated γ-spiroiminolactones.

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