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
• Article Data: 13

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

Chemical Properties

CLEAR YELLOW LIQUID

Occurrence

Has apparently not been reported to occur in nature.

Uses

Geranyl Nitrite, is a substituted terpenoid odorant with a fruity odor quality. It is one of the most potent cyclase stimulators.

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

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

Downstream Products

• 63089-69-0 (1,5-Dimethyl-hex-4-enylidene)-cyclohexane 
• 57524-14-8 2,2,6-trimethyl-1-cyclohexenylcarbonitrile 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 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 
• 145106-79-2 3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbonitrile 
• 94669-81-5 (E)-6-Hydroxy-3-(5-hydroxy-3-methyl-1,3-pentadienyl)-2,4,4-trimethyl-2-cyclohexen-1-on 
• 264279-20-1 2,3-epoxy-2,6,6-trimethyl-1-cyclohexanecarbonitrile 
• 80736-89-6 (2E,4E)-1-bromo-3-methyl-5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4-pentadiene 
• 35278-77-4 geranylamine 
• 7584-74-9 C₂₀H₂₈O₂ 

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.

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.