49576-57-0

Basic information

• Product Name: (E)-2-methyloct-2-enal
• Synonyms: (E)-2-methyloct-2-enal;2-Octenal, 2-methyl-, (2E)-;2-METHYL-2-OCTENAL;2-Octenal, 2-methyl-, (E)-;Einecs 256-386-8;Fema no. 3711
• CAS NO: 49576-57-0
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140.22274
• EINECS: 256-386-8
• Mol File: 49576-57-0.mol

Chemical Properties

• Boiling Point: 203.9°Cat760mmHg
• Flash Point: 59.1°C
• Appearance: /
• Density: 0.835g/cm³
• Vapor Pressure: 0.271mmHg at 25°C
• Refractive Index: 1.435
• CAS DataBase Reference: (E)-2-methyloct-2-enal(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-methyloct-2-enal(49576-57-0)
• EPA Substance Registry System: (E)-2-methyloct-2-enal(49576-57-0)

Safety Data

• Hazardous Substances Data: 49576-57-0(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
(E)-2-methyloct-2-enal is used as a flavoring agent for its fruity green aroma, adding a unique and appealing scent to various food products. It is particularly useful in the creation of artificial fruit flavors, where it can mimic the natural aroma of certain fruits.
Used in Perfumery:
In the perfumery industry, (E)-2-methyloct-2-enal is used as a fragrance ingredient to provide a fresh, green, and fruity note to perfumes and colognes. Its distinct aroma can enhance the overall scent profile of a fragrance, making it a valuable addition to the perfumer's palette.
Used in Aromatherapy:
(E)-2-methyloct-2-enal can also be used in aromatherapy for its pleasant and uplifting scent. The fruity green aroma can help create a relaxing and refreshing atmosphere, which may be beneficial for promoting mental well-being and reducing stress.
Used in the Cosmetic Industry:
In the cosmetic industry, (E)-2-methyloct-2-enal can be used as a component in the formulation of personal care products, such as lotions, creams, and shampoos. Its fruity green aroma can add a pleasant scent to these products, making them more appealing to consumers.

InChI:InChI=1/C9H16O/c1-3-4-5-6-7-9(2)8-10/h7-8H,3-6H2,1-2H3/b9-7+

Upstream product

• 64-18-6 formic acid 
• 2809-67-8 oct-2-yne 
• 80322-07-2 1,1-Diethoxy-2-methyl-octan-3-ol 
• 66-25-1 hexanal 
• 54827-24-6 2-diethoxymethyl-oct-1-en-3-ol 
• 201230-82-2 carbon monoxide 
• 110-53-2 1-Bromopentane 
• 42588-57-8 3-ethoxymethacrolein 
• 169215-11-6 2-methyl-1-nitrooctene 
• 80322-08-3 acetoxy-3 diethoxy-1,1 methyl-2 octane 
• 88903-12-2 (Z)-1-tert-Butylsulfanyl-3-methoxy-2-methyl-oct-1-ene 
• 33965-55-8 (2E)-2-methyl-2-octen-1-ol 
• 2146-67-0 (dichloromethyl)lithium 
• 111-13-7 hexyl-methyl-ketone 

Downstream Products

• 49576-58-1 2-methyl-oct-2-enal-(2,4-dinitro-phenylhydrazone) 

Relevant articles and documents

Rhodium-Catalyzed Regioselective Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes Using Formic Acid

A rhodium-catalyzed hydroformylation of alkynes with formic acid was developed. The method provides α,β-unsaturated aldehydes in high yield and E-selectivity without the need to handle toxic CO gas.

Organoselenium-Catalyzed Regioselective C?H Pyridination of 1,3-Dienes and Alkenes

An efficient approach for organoselenium-catalyzed regioselective C?H pyridination of 1,3-dienes to form pyridinium salts has been developed. This method was also successfully applied to direct C?H pyridination of alkenes. Fluoropyridinium reagents, or initially loaded pyridine derivatives, acted as pyridine sources in the pyridination reactions. The obtained pyridinium salts could be further converted under different conditions. This work is the first example of catalytic C-2 direct C?H functionalization of 1,3-dienes and the first case of organoselenium-catalyzed C?H pyridination.

The role of imine-enamine tautomerism in effecting cross-aldol condensations

An indirect method to effect cross-aldol coupling of two nonequivalent enolizable aldehydes is reported that involves initial conversion of one aldehyde to an imine derivative possessing an N-3° alkyl substituent. In sharp contrast to the related couplings (e.g., the use of α-lithiated imines at low temperature), condensation between the imine and several representative aldehydes occurs readily at ambient temperature in the presence of a catalytic amount of cobalt(II) chloride.

Rhodium-katalysierte Hydroformylierung innerer Alkine zu α,β-ungesaettigten Aldehyden

Keywords: Alkine; Hydroformylierungen; Katalyse; Alkene; Rhodiumverbindungen

Selective Isomerization of Glycidates and Their Analogues with Triphenylsilyl Perchlorate or Electrogenerated Acid

Isomerization of glycidic esters and nitriles to the corresponding 2-hydroxy-3-alkenoates and their nitrile derivatives occurred on treatment with triphenylsilyl perchlorate or electrogenerated acid (EG acid).The cyanohydrin moiety of the nitriles 4 was transformed to a formyl group, giving the corresponding enals on treatment with weak base.

Facile Synthesis of Allylic Nitro Compounds by N,N-dimethylethylenediamine-Catalyzed Condensation of Aliphatic and Alicyclic Ketones with Primary Nitroalkanes

Aliphatic as well as alicyclic ketones condense with primary nitroalkanes in the presence of N,N-dimethylethylenediamine (1) to give allylic nitro compounds selectively in good to excellent yields without forming α-nitro olefins.Condensation of 2-alkanones and 2-methylcyclopentanone with nitromethane produces the products of thermodynamic control, while the product of kinetic control is obtained from 2-methylcyclohexanone.Propiophenone, an aromatic ketone, reacted with nitromethane in a way analogous to aliphatic ketones to give the corresponding allylic nitro product.A reaction mechanism to account for the exclusive formation of allylic nitro compounds is proposed.Some allylic nitro compounds thus obtained are converted into α,β-unsaturated aldehydes and ketones by treatment with sodium methoxide and then TiCl3 in buffered solution.

REACTIVITY OF THE 1-t.BUTYLTHIO-3-METHOXY-1-ALKENES TOWARDS METALATING AGENTS, I. REGIOSELECTIVE DEPROTONATION AT EITHER ONE OF THE TWO OLEFINIC SITES OF THE Z-ISOMERS

THF solutions of the title Z-isomers (with the exception of the propenyl compound) at -78 degC produce either(i) the 1-metalated derivatives when treated with potassium t.butoxide and n.butyllithium or (ii) the 2-lithiated derivatives when sec.butyllithium is the metalating agent.Both metalated derivatives become new equivalents of the hypothetical anions I and II respectively.

4-(Dimethylamino)pyridinium Chlorochromate, a New Selective Reagent for the Oxidation of Allylic and Benzylic Alcohols

4-(Dimethylamino)pyridinium chlorochromate (3) is a mild selective reagent for the oxidation of complex allylic and benzylic alcohols to the corresponding carbonyl compounds.

Aldolisation dirigee avec l'acroleine. Methode de synthese stereoselective de doubles liaisons trisubstituees fonctionnalisees. Application a la synthese du (+/-)-Z-chloronuciferal et du (+/-)-E-nuciferol

To direct the aldolisation reaction in such a way that an aldehyde reacts upon the electrophilic carbonyl group of a ketone or of another aldehyde, it is necessary to mask the aldehyde and to transform it into a nucleophile.The present article presents an approach to this problem concerning unsaturated aldehydes and describes the condensation between the α-carbanion of acrolein and several carbonyl compounds. Aldol condensation at -70 degC, between 1,1-diethoxy-2-lithio-2-propene and several aldehydes leads to β-hydroxy-α-methylene acetals.These secondary allylic alcohols are stereoselectively transformed into trisubstituted functionalised olefinic compounds (Z-α-chlormethyl-α,β-unsaturated aldehydes and E-α-methyl-α,β-unsaturated primary alcohols). This method is illustrated by the syntheses of (+/-)-Z-chloronuciferal and (+/-)-E-nuciferol.