51566-62-2

Basic information

• Product Name: Citronellyl nitrile
• Synonyms: 3,7-Dimethyl-6-octene-1-nitrile;3,7-dimethyl-6-octenenitril;Agrunitrile;Baranylnitrile;Citronellonitrile;Citrylone;CITRONELLYL NITRILE;CITRONALVA
• CAS NO: 51566-62-2
• Molecular Formula: C₁₀H₁₇N
• Molecular Weight: 151.25
• EINECS: 257-288-8
• Mol File: 51566-62-2.mol

Chemical Properties

• Boiling Point: 248.1 °C at 760 mmHg
• Flash Point: 109.7 °C
• Appearance: /
• Density: 0.836 g/cm³
• Vapor Pressure: 0.0247mmHg at 25°C
• Refractive Index: 1.445
• Water Solubility: 119mg/L at 20℃
• CAS DataBase Reference: Citronellyl nitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Citronellyl nitrile(51566-62-2)
• EPA Substance Registry System: Citronellyl nitrile(51566-62-2)

Safety Data

• Hazardous Substances Data: 51566-62-2(Hazardous Substances Data)

Usage

Uses

Used in the Coatings Industry:
Citronellyl nitrile is used as a component in the preparation method of Cyano-modified organic Silicon synthetic leather coating. Its incorporation enhances the properties of the coating, providing improved durability, flexibility, and resistance to various environmental factors.
The specific application reason for Citronellyl nitrile in this context is its ability to improve the performance characteristics of the synthetic leather coating, making it a valuable addition to the coatings industry.

Flammability and Explosibility

Nonflammable

Trade name

Citronellylnitrile (BASF).

InChI:InChI=1/C10H17N/c1-9(2)5-4-6-10(3)7-8-11/h5,10H,4,6-7H2,1-3H3

Upstream product

• 502-47-6 racemic citronellic acid 
• 106-23-0 3,7-dimethyl-oct-6-enal 
• 106-22-9 Citronellol 
• 5146-66-7 geranonitrile 
• 73127-86-3 3,7-dimethyloct-6-enamide 
• 5585-39-7 (E)-3,7-dimethylocta-2,6-dienenitrile 
• 135500-74-2 rac-E-3,7-dimethyloct-6-enaldehyde oxime 
• 22457-25-6 rac-3,7-dimethyloct-6-enenitrile oxime 

Relevant articles and documents

Preparation method of citronella and catalyst adopted by method

The method comprises the following steps: carrying out selective hydrogenation reaction on limonene under the action of a hydrogenation catalyst; and after the reaction is finished, the citronellal is obtained. In the synthesis process MOFs, the adopted hydrogenation catalyst is introduced into a metal site with catalytic activity, so MOFs materials have a specific catalytic capacity, the catalytic effect of the catalyst is improved, the conversion rate and selectivity are improved, and the obtained product has better fragrance. The invention also discloses a hydrogenation catalyst for the preparation method.

A convenient reagent for the conversion of aldoximes into nitriles and isonitriles

For the dehydroxylation of aldoximes with 4-nitro-1-((trifluoromethyl)sulfonyl)-imidazole (NTSI), slight modifications of reaction conditions resulted in significantly different reaction paths to provide either nitriles or isonitriles. The challenging conversion of aldoximes into isonitriles was achieved under mild conditions.

Preparation method of citronellyl cyanide

The invention discloses a preparation method of citronellyl cyanide, which comprises the following steps: under the action of an In-MOF catalyst, carrying out Mom rearrangement reaction on citronellylacid and aliphatic nitrile to obtain citronellyl cyanide. Under mild reaction conditions, the In-MOF catalyst is utilized to catalyze citronellyl acid to prepare citronellyl cyanide at high yield, and the method has the advantages of simpler reaction process, lower reaction cost, favorable environment friendliness and favorable industrial prospects.

Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO

A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.

Cyanide-Free and Broadly Applicable Enantioselective Synthetic Platform for Chiral Nitriles through a Biocatalytic Approach

A cyanide-free platform technology for the synthesis of chiral nitriles by biocatalytic enantioselective dehydration of a wide range of aldoximes is reported. The nitriles were obtained with high enantiomeric excess of >90 % ee (and up to 99 % ee) in many cases, and a “privileged substrate structure” with respect to high enantioselectivity was identified. Furthermore, a surprising phenomenon was observed for the enantiospecificity that is usually not observed in enzyme catalysis. Depending on whether the E or Z isomer of the racemic aldoxime substrate was employed, one or the other enantiomer of the corresponding nitrile was formed preferentially with the same enzyme.

Perfluoroalkanosulfonyl fluoride: A useful reagent for dehydration of aldoximes to nitriles

The reaction of a variety of aldoximes with perfluoroalkanosulfonyl fluoride in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dichloromethane smoothly generated the corresponding nitriles in 70%-95% yields.

Tin or gallium-catalyzed cyanide-transition metal-free synthesis of nitriles from aldehydes or oximes

Tin or gallium chloride catalyzed transformation of oximes or aldehydes to nitriles is described. Various nitriles were obtained in up to 99% of yields. The gram-scale reaction or the optically active dinitrile was also available. This synthetically useful method has avoided toxic organic or inorganic cyanides as well as transition or noble metal catalysts.

Postsynthesis-Treated Iron-Based Metal-Organic Frameworks as Selective Catalysts for the Sustainable Synthesis of Nitriles

The dehydration of aldoximes to the corresponding nitriles can be performed with excellent activity and selectivity by using iron trimesate as a homogeneous catalyst. Iron trimesate has been heterogenized by synthesizing metal-organic frameworks (MOFs) from iron trimesate, that is, Fe(BTC), and MIL-100 (Fe). These materials were active and selective aldoxime dehydration catalysts, and postsynthesis-treated MIL-100 (Fe) produced the desired nitriles with 100 conversion and selectivities >90 under mild reaction conditions and in short reaction times. X-ray photoelectron spectroscopy showed the presence of different Fe species in the catalyst, and in situ IR spectroscopy combined with catalytic results indicates that the catalytic activity is associated with Fe framework species. The postsynthesis-treated MIL-100 (Fe)-NH4F can be recycled several times and has an excellent reaction scope, which gives better catalytic results than other solid acid or base catalysts.

METHOD FOR PRODUCING NITRILE

The present invention provides a method for producing a nitrile represented by general formula (1) (in the formula, R denotes an optionally substituted alkyl group, alkenyl group, dienyl group, aralkyl group or aryl group having a total of 3-20 carbon atoms), and the method includes heating an aldoxime represented by general formula (2) (in the formula, R denotes the same groups as those mentioned above) at 80-250°C in the presence of an alkali metal or alkaline earth metal salt of phosphoric acid (catalyst A) and distilling off water generated as the reaction progresses to outside the reaction system.

Direct Synthesis of Nitriles from Aldehydes Using an O-Benzoyl Hydroxylamine (BHA) as the Nitrogen Source

The direct synthesis of nitriles from commercially available or easily prepared aldehydes has been achieved. O-(4-CF3-benzoyl)-hydroxylamine (CF3-BHA) was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes, which can be converted to a nitrile with the assistance of a Bronsted acid. Several aliphatic, aromatic, and α,β-unsaturated nitriles that contain different functional groups were prepared in high yields (up to 94% yield). This method has notable advantages, such as simple and mild conditions, high yields, and good functional group tolerance.