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)

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

F 

10-13-21

HazardClass 

6.1

PackingGroup 

III

HS Code 

29299090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

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.

References

[1] Khalili, Gholamhossein. “ChemInform Abstract: A Diastereoselective Synthesis of (Z)-3-[(Aryl)(hydroxyimino)methyl] -2-cyclohexyl-1-(cyclohexylamino)imidazo[5,1-a]isoquinolinium Chlorides from Isoquinoline, Chlorooximes, and Cyclohexyl Isocyanide.” ChemInform 47 25 (2016).
[2] M. Anary‐Abbasinejad, M. Heidari, N. Shams. “One-pot synthesis of highly functionalised 1H-pyrazoles from arylcarbohydrazides, cyclohexyl isocyanide, and acetylene diesters.” Arkivoc 2012 1 (2012).
[3] Anary‐Abbasinejad, M. M. Jaafari and Mahdiyeh Talebizadeh. “One-pot Four-component Reaction between Arylamines, Arylglyoxals, Cyclohexyl Isocyanide, and Acetylene Diesters: An Efficient Synthesis of 2H-iminopyran Derivatives.” 2019. 0.
[4] Alireza Hassanabadi. “ChemInform Abstract: Use of Cyclohexyl Isocyanide in the Esterification of N-Benzoyl α-Amino Acid Derivatives.” ChemInform 43 3 (2011).
[5] A. Hassanabadi. “The use of cyclohexyl isocyanide in the esterification of N -benzoyl α-amino acids derivatives.” Journal of Chemical Research-s 18 1 (2011): 468–470.

CYCLOHEXYL ISOCYANIDE(931-53-3)Related Product Information

• 3,4-Diaminobenzoic acid
• Dimedone
• Benzyl isocyanide
• Benzeneacetonitrile
• Benzyl chloride
• Benzyl isocyanate
• CYCLOHEXYL ISOCYANIDE
• 1-ADAMANTANEISOCYANIDE
• 4-(N-T-BUTOXYCARBONYLAMINO)CYCLOHEXYLISOCYANIDE
• 2-(1'-ISOCYANOCYCLOHEXYL) ACETIC ACID METHYL ESTER
• ETHYL 1-ISOCYANOCYCLOHEXANECARBOXYLATE
• TRANS-ETHYL-2-ISOCYANO-CYCLOHEXYLCARBOXYLATE
• (S,S)-1,2-DIISOCYANOCYCLO-HEXANE
• 1,2-DIISOCYANOCYCLOHEXANE
• Cyclohexanecarboxylic acid, 1-isocyano-, methyl ester (9CI)
• CIS-ETHYL-2-ISOCYANOCYCLO-HEXYLCARBOXYLATE
• BIO-FARMA BF001930
• Cyclohexane, 1,4-diisocyano- (9CI)