57576-15-5

Basic information

• Product Name: 2,6,6-trimethyl-1-cyclohexene-1-acetonitrile
• Synonyms: 2,6,6-trimethyl-1-cyclohexene-1-acetonitrile;1-Cyclohexene-1-acetonitrile, 2,6,6-trimethyl-;Einecs 260-822-2
• CAS NO: 57576-15-5
• Molecular Formula: C₁₁H₁₇N
• Molecular Weight: 163.25938
• EINECS: 260-822-2
• Mol File: 57576-15-5.mol

Chemical Properties

• Boiling Point: 234.6°C at 760 mmHg
• Flash Point: 101.6°C
• Appearance: /
• Density: 0.882g/cm³
• Vapor Pressure: 0.0525mmHg at 25°C
• Refractive Index: 1.458
• CAS DataBase Reference: 2,6,6-trimethyl-1-cyclohexene-1-acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6,6-trimethyl-1-cyclohexene-1-acetonitrile(57576-15-5)
• EPA Substance Registry System: 2,6,6-trimethyl-1-cyclohexene-1-acetonitrile(57576-15-5)

Safety Data

• Hazardous Substances Data: 57576-15-5(Hazardous Substances Data)

Usage

Physical state

Colorless liquid

Odor

Fruity

Common uses

Flavor and fragrance ingredient in perfumes, soaps, personal care products, and food industry

Potential applications

Pharmaceutical and agricultural industries

Safety precautions

Can be harmful if ingested or inhaled, may cause skin and eye irritation

InChI:InChI=1/C11H17N/c1-9-5-4-7-11(2,3)10(9)6-8-12/h4-7H2,1-3H3

Upstream product

• 79857-84-4 (3E)-8-hydroxy-4,8-dimethyl-3-nonenenitrile 
• 59633-88-4 2-(bromomethyl)-1,3,3-trimethylcyclohex-1-ene 
• 143-33-9 sodium cyanide 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 472-20-8 β-cyclogeraniol 
• 57576-16-6 (3E)-7-bromo-8-hydroxy-4,8-dimethyl-3-nonenenitrile 
• 472-66-2 (2,6,6-trimethyl-1-cyclohexen-1-yl)acetaldehyde 

Downstream Products

• 472-68-4 (2,6,6-trimethylcyclohex-1-enyl)acetic acid 
• 514-62-5 (+/-)-ferruginol 
• 3772-54-1 (+/-)-nimbiol methyl ether 
• 113332-25-5 (+/-)-nimbidiol 

Relevant articles and documents

An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitriles mediated by propylphosphonic anhydride (T3P)

An efficient method for the Beckmann rearrangement of ketoximes to amides mediated by a catalytic amount (15 mol %) of propylphosphonic anhydride (T3P) is described. Aldoximes underwent second order Beckmann rearrangement to provide the corresponding nitriles in excellent yields on reacting with T3P (15 mol %) at room temperature. The main advantages of this environmentally friendly protocol include procedural simplicity, and particularly ease of isolation of the products.

Propylphosphonic anhydride (T3P): A remarkably efficient reagent for the one-pot transformation of aromatic, heteroaromatic, and aliphatic aldehydes to nitriles

Propylphosphonic anhydride has been demonstrated to be an efficient reagent for the transformation of aromatic, heteroaromatic, and aliphatic aldehydes to respective nitriles in excellent yields. This procedure offers simple and one-pot access to nitriles and highlights the synthetic utility of T3P as a versatile reagent in organic chemistry. Georg Thieme Verlag Stuttgart - New York.

Novel domino reactions for diterpene synthesis

New types of concerted domino acylation-cycloalkylation/alkylation- cycloacylation reactions have been described. These processes promoted by methanesulfonic acid-phosphorus pentoxide and concentrated H2SO 4, respectively, provide efficient, elegant, and expeditious routes for biologically active naturally occurring diterpenoids, namely (±)-ferruginol (1), (±)-nimbidiol (2), (±)-nimbiol (3), (±)-totarol (4), and ar-abietatriene (5).

CATIONIC CYCLIZATION OF GERANONITRILE AND RELATED COMPOUNDS VIA THEIR BROMOHYDRINS: APPLICATION TO THE SYNTHESIS OF (+/-)-SNYDEROLS

Cationic cyclization of bromohydrins of geranonitrile and homogeranonitrile in the presence of boron trifluoride complexes proceeded smoothly, giving mixtures of bromo cyclic olefins in satisfactory yields.This cyclization method was applied to the synthesis of (+/-)-snyderols.