5146-66-7

Basic information

• Product Name: 3,7-Dimethyl-2,6-octadienenitrile
• Synonyms: 3,7-DIMETHYL-OCTA-2,6-DIENENITRILE;3,7-DIMETHYL-2,6-OCTADIENENITRILE;3,7-DIMETHYL-2,6-OCTADIENE-1-NITRILE;2,6-DIMETHYL-1,5-HEPTADIENYL CYANIDE;LRT8;CITRALVA;GERANONITRILE;GERANYL NITRILE
• CAS NO: 5146-66-7
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.23
• EINECS: 225-918-0
• Product Categories: Acyclic Monoterpenes;Biochemistry;Terpenes;Alphabetical Listings;C-D;Flavors and Fragrances;C10 to C27;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 5146-66-7.mol

Chemical Properties

• Boiling Point: 110 °C1.3 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear yellow liquid
• Density: 0.853 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.025mmHg at 25°C
• Refractive Index: n20/D 1.475(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: SLIGHTLY SOLUBLE
• CAS DataBase Reference: 3,7-Dimethyl-2,6-octadienenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3,7-Dimethyl-2,6-octadienenitrile(5146-66-7)
• EPA Substance Registry System: 3,7-Dimethyl-2,6-octadienenitrile(5146-66-7)

Safety Data

• Hazard Codes: Xn,N
• Statements: 51/53-68-20/21
• Safety Statements: 36/37-61-23
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 1
• RTECS: RG5370000
• Hazardous Substances Data: 5146-66-7(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
3,7-Dimethyl-2,6-octadienenitrile is used as a fragrance ingredient for its fruity odor quality, adding a pleasant and distinctive scent to various products.
Used in Pharmaceutical Industry:
3,7-Dimethyl-2,6-octadienenitrile is used as a cyclase stimulator for its potent stimulating effect on cyclase enzymes, which can have potential applications in the development of drugs targeting specific biological processes.
Used in Flavor Industry:
3,7-Dimethyl-2,6-octadienenitrile is used as a flavoring agent for its fruity odor, enhancing the taste and aroma of various food and beverage products.
Used in Chemical Research:
3,7-Dimethyl-2,6-octadienenitrile is used as a chemical intermediate in the synthesis of other compounds, contributing to the development of new materials and products in the chemical industry.

Preparation

From geranialoxime with acetic anhydride (Arctander. 1969).

Flammability and Explosibility

Nonflammable

Metabolism

The toxicity of organic cyanides appears to depend, in almost every case, on whether they can be metabolized in the body to the free cyanide ion, CN~, and on the rate and extent of this conversion and the rate of detoxication of cyanide to thiocyanate. Alkyl cyanides appear to be metabolized in the body chiefly by formation of hydrogen cyanide plus the acid with one less carbon atom (Williams, 1959).

InChI:InChI=1/C10H15N/c1-9(2)5-4-6-10(3)7-8-11/h5,7H,4,6H2,1-3H3/b10-7+

Upstream product

• 13372-77-5 3,7-dimethylocta-2,6-dienal oxime 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 372-09-8 cyanoacetic acid 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 35278-77-4 geranylamine 
• 624-15-7 geraniol 
• 870-63-3 prenyl bromide 
• 23089-87-4 5-methyl-4-hexenenitrile 
• 75-05-8 acetonitrile 

Downstream Products

• 63089-69-0 (1,5-Dimethyl-hex-4-enylidene)-cyclohexane 
• 51566-62-2 citronellylnitrile 
• 57524-14-8 2,2,6-trimethyl-1-cyclohexenylcarbonitrile 
• 57524-13-7 2,6,6-trimethyl-2-cyclohexenecarbonitrile 
• 140848-05-1 2-cyano-1,1-dimethyl-3-methylenecyclohexane 
• 4630-06-2 6-methylhept-5-en-2-ol 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 459-80-3 geranic acid 
• 6246-48-6 geranylamine 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 53339-59-6 3,7-dimethyl-6-octenylamine 
• 7542-45-2 3,3'-dihydroxy-β,β-carotene-4,4'-dione 
• 29538-78-1 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4-pentadienol 
• 56830-39-8 2,4,4-Trimethylcyclohex-2-en-1-one-3-carbonitrile 

Relevant articles and documents

Atomically Dispersed Ru on Manganese Oxide Catalyst Boosts Oxidative Cyanation

There is a strong incentive for environmentally benign and sustainable production of organic nitriles to avoid the use of toxic cyanides. Here we report that manganese oxide nanorod-supported single-site Ru catalysts are active, selective, and stable for oxidative cyanation of various alcohols to give the corresponding nitriles with molecular oxygen and ammonia as the reactants. The very low amount of Ru (0.1 wt %) with atomic dispersion boosts the catalytic performance of manganese oxides. Experimental and theoretical results show how the Ru sites enhance the ammonia resistance of the catalyst, bolstering its performance in alcohol dehydrogenation and oxygen activation, the key steps in the oxidative cyanation. This investigation demonstrates the high efficiency of a single-site Ru catalyst for nitrile production.

COMPOUNDS AND METHODS OF TREATING OCULAR DISORDERS

A method of treating an ocular disorder in a subject associated with increased all-trans-retinal in an ocular tissue includes administering to the subject a therapeutically effective amount of a primary amine compound of formula (I); and pharmaceutically acceptable salts thereof.

Synthesis of nitriles from amines using nanoscale Co3O4-based catalysts via sustainable aerobic oxidation

The selective oxidation of amines for the benign synthesis of nitriles under mild conditions is described. Key to success for this transformation is the application of reusable cobalt oxide-based nanocatalysts. The resulting nitriles constitute key precursors and central intermediates in organic synthesis.

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.

"Nanorust"-catalyzed benign oxidation of amines for selective synthesis of nitriles

Organic nitriles constitute key precursors and central intermediates in organic synthesis. In addition, nitriles represent a versatile motif found in numerous medicinally and biologically important compounds. Generally, these nitriles are synthesized by traditional cyanation procedures using toxic cyanides. Herein, we report the selective and environmentally benign oxidative conversion of primary amines for the synthesis of structurally diverse aromatic, aliphatic and heterocyclic nitriles using a reusable "nanorust" (nanoscale Fe2O3)-based catalysts applying molecular oxygen.

One-pot oxidative conversion of alcohols into nitriles by using a TEMPO/PhI(OAc)2/NH4OAc system

A direct conversion of alcohols into nitriles with 2,2,6,6- tetramethylpiperidine-1-oxyl (TEMPO), iodosobenzene diacetate, and ammonium acetate as a nitrogen source is reported. This transformation, which proceeds through an oxidation-imination-aldimine oxidation sequence in situ, has been applied to a range of aliphatic, benzylic, heteroaromatic, allylic, and propargyl alcohols. Highly chemoselective ammoxidation of primary alcohols in the presence of secondary alcohols was also achieved. Georg Thieme Verlag Stuttgart New York.

Acetohydroxamic acid: A new reagent for efficient synthesis of nitriles directly from aldehydes using Bi(OTf)3 as the catalyst

An efficient method for the preparation of nitriles directly from aldehydes by reaction with AHA using Bi(OTf)3 as the catalyst is described. Bi(OTf)3 is shown to be an efficient catalyst also for the conversion of aldoximes into nitriles.

S,S-dimethyl dithiocarbonate: A useful reagent for efficient conversion of aldoximes to nitriles

Dimethyl dithiocarbonate (DMDTC) has been shown to be an efficient dehydrating agent for a range of oximes derived from aliphatic, aromatic and heteroaromatic aldehydes yielding the corresponding nitriles in high yields.

Two-carbons homologation of methyl ketones examplified for the synthesis of citral from 6-methyl-5-hepten-2-one

New facile syntheses of 3,7-dimethyl-octadien-2,6-al (citral) from homologation of 6-methyl-5-hepten-2-one are reported.

A simple and highly efficient one-pot chemoselective synthesis of nitriles from aldehydes: Mechanistic insight and selectivity control through modulation of electronic and steric factors

Aldehydes are converted into nitriles in a one-pot reaction by treatment with H2NOH·HCl in dipolar aprotic solvents under heating. Amongst various solvents NMP offers the best results. No competitive ether cleavage (e.g. methoxy, benzyloxy) or aromatic nucleophilic substitution (e.g. nitro or chloro) takes place for substrates beating such functionalities. Electronic and steric factors around the aldehyde carbon affect the rate of nitrile formation. Excellent to moderate selectivity is observed during intermolecular competition between pair of aldehydes with varying electronic and steric requirements.