27608-03-3

Basic information

• Product Name: 3-methylheptan-1-al
• Synonyms: 3-methylheptan-1-al;3-Methylheptanal
• CAS NO: 27608-03-3
• Molecular Formula: C₈H₁₆O
• Molecular Weight: 128.21204
• EINECS: 248-568-0
• Mol File: 27608-03-3.mol

Chemical Properties

• Melting Point: 13.5°C (estimate)
• Boiling Point: 167.67°C (estimate)
• Flash Point: 46.2 °C
• Appearance: /
• Density: 0.8310 (estimate)
• Vapor Pressure: 2.11mmHg at 25°C
• Refractive Index: 1.4163 (estimate)
• CAS DataBase Reference: 3-methylheptan-1-al(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methylheptan-1-al(27608-03-3)
• EPA Substance Registry System: 3-methylheptan-1-al(27608-03-3)

Safety Data

• Hazardous Substances Data: 27608-03-3(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
3-methylheptan-1-al is used as a flavoring agent for imparting a fruity and floral scent to various food products and beverages. Its natural occurrence and pleasant aroma make it a popular choice in the industry for enhancing the sensory experience of consumers.
Used in Perfumery:
In the perfumery sector, 3-methylheptan-1-al serves as a fragrance ingredient, contributing to the development of complex and appealing scents in perfumes, colognes, and other personal care products. Its ability to mimic natural aromas adds depth and authenticity to the fragrances.
Used as a Chemical Intermediate in Pharmaceutical and Agrochemical Synthesis:
3-methylheptan-1-al is utilized as a chemical intermediate in the production of pharmaceuticals and agrochemicals. Its chemical properties allow it to be a key component in the synthesis of various compounds, contributing to the development of new drugs and agricultural products.
Safety Considerations:
Due to its flammable nature, 3-methylheptan-1-al should be handled with care to prevent accidents. Additionally, it may cause irritation to the skin, eyes, and respiratory system upon exposure, necessitating proper safety measures during its use and storage.

InChI:InChI=1/C8H16O/c1-3-4-5-8(2)6-7-9/h7-8H,3-6H2,1-2H3

Upstream product

• 1070-32-2 3-methylheptane-1-ol 
• 592-41-6 1-hexene 
• 463304-45-2 (4S)-N-[(3S)-methylheptanoyl]-4-phenyl-1,3-oxazolidin-2-one 
• 693-03-8 n-butyl magnesium bromide 
• 123-73-9 crotonaldehyde 
• 18829-55-5 (E)-2-Heptenal 
• 75-16-1 methylmagnesium bromide 
• 544-97-8 dimethyl zinc(II) 
• 862095-56-5 C₁₂H₂₄O₂ 
• 1355001-62-5 C₉H₁₈O₃ 
• 1355001-63-6 C₁₀H₂₀O₂ 
• 1355001-60-3 C₁₀H₂₂O₂ 
• 1355001-61-4 C₁₂H₂₆O₄ 
• 61169-84-4 (S)-3-methylheptan-1-ol 

Downstream Products

• 53663-30-2 3-methylheptanoic acid 
• 99493-42-2 (S)-(+)-14-Methyl-1-octadecene 
• 1070-32-2 (R)-(+)-3-Methyl-1-heptanol 
• 165754-55-2 HUN-7293 

Relevant articles and documents

Enantioselective Synthesis of the Sex Pheromone of Lichen Moth, Miltochrista calamine, and Its Diastereomer

The synthesis of a Miltochrista calamine sex pheromone and its diastereomer has been developed. The key steps of the synthetic approach involved Evans' chiral auxiliaries and the addition of alkyne to aldehyde, which were firstly applied to prepare this sex pheromone and its diastereomer. The synthetic sex pheromone could be used to trap insects and study physiological and ecological questions of the lichen moth.

A New Asymmetric Synthesis of (S)-14-Methyloctadec-1-ene, the Sex Pheromone of the Peach Leafminer Moth

Abstract: An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of thepeach leafminer moth has been achieved. Based on the asymmetric methylation ofchiral (S)-4-benzyloxazolidin-2-one, thecarbon chain of the target molecule was assembled through aC1+C10+C4+C3procedure. The γ-lactone was transformed into 4-(benzyloxy)butanoic acid andthen, with the induction of Evan’s template, a chiral methyl group wasintroduced to the position of the carboxylic group in 97percent de. After reduction and a couple of chemicaloperations, the designed key intermediate A1was obtained. The synthesis of another moiety was started from decane-1,10-diolwhich was selectively protected and oxidized. The long carbon chain wasinstalled according to a Wittig protocol. After deprotection, oxidization, andmethylenation, the target molecule was synthesized in 7 linear steps with anoverall yield of 30.3percent.

Chemoselective Biohydrogenation of Alkenes in the Presence of Alkynes for the Homologation of 2-Alkynals/3-Alkyn-2-ones into 4-Alkynals/Alkynols

The chemoselective hydrogenation of alkenes in the presence of alkynes is a very challenging transformation to achieve with traditional chemical methods. The development of an effective procedure to perform this transformation would enrich the tool-kit available to organic chemists for the development of useful synthetic routes, and the creation of novel structural motifs. The reduction of activated alkene bonds by ene-reductases (ERs) is completely chemoselective, because of the mechanism of the reaction. Thus, we investigated the use of ERs belonging to the Old Yellow Enzyme family for the reduction of α,β-unsaturated aldehydes with a conjugated C≡C triple bond at the γ position. This reaction was exploited as the key step for the development of an effective homologation route to convert aryl and alkyl substituted propynals and butynones into 4-alkynals and 4-alkynols, avoiding some troublesome or hazardous steps of known synthetic routes. (Figure presented.).

Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents

β-Substituted aldehydes constitute a very important class of compounds found in nature. Synthesis of this motif can be envisioned by C-C bond formation on enals. For this purpose, we report herein the development of enantioselective copper-catalyzed conjugate addition of various organometallic reagents to α,β-unsaturated aldehydes with (R)-H8BINAP, (R)-TolBINAP, and (R)-SEGPHOS as chiral ligands. Three sets of conditions were successfully developed and several enals were used. Reactivity and regio- and enantioselectivities were strongly dependent on reaction conditions and substrates. Good to excellent regio- and enantioselectivities were obtained with zinc reagents R2Zn and aluminum reagents R3Al. However, the asymmetric conjugate addition of Grignard reagents afforded only moderate to good regio- and enantioselectivities.

Cyclopropane intermediates in the synthesis of chiral alcohols with methyl-branched carbon skeleton. Application in the synthesis of insect pheromones

Several chiral building blocks, (2R)-2-methylundec-10-en-1-ol, (3R)-3-methylheptan-1-ol, and (4R)-4-methyloctan-1-ol, have been synthesized using cyclopropane intermediate products. It has been shown that the obtained chiral alcohols can be used in the sy

Copper-catalyzed asymmetric conjugate addition to challenging michael acceptors and synthesis of relevant target molecules

We report herein the enantioselective Cu-catalyzed conjugate addition of organometallic reagents to sensitive Michael acceptors and their application to the synthesis of relevant target molecules. This is one of the most important methodologies to form a C-C bond in an enantioselective manner. A wide range of α,β-unsaturated aldehydes and β,γ-unsaturated-α- ketoesters has been successfully used. Reactivity, regioand enantioselectivities were strongly dependent on the reaction conditions, therefore moderate to very good results were obtained. Furthermore, γ-substituted-α-ketoesters were used as chiral building blocks for further derivatization with complete retention of the chiral information to obtain key compounds. Schweizerische Chemische Gesellschaft.

Catalytic enantioselective β-alkylation of α,β-unsaturated aldehydes by combination of transition-metal- and aminocatalysis: Total synthesis of bisabolane sesquiterpenes

Branching out! The first co-catalytic enantioselective (up to 98:2 e.r.) β-alkylation of α,β-unsaturated aldehydes by combination of simple chiral amine and copper catalysts provides β-branched aldehydes in a one-pot protocol (see scheme). The methodology was applied to the short total syntheses of bisabolane sesquiterpenes (S)-(+)-curcumene, (E)-(S)-(+)-3- dehydrocurcumene and (S)-(+)-tumerone.

(5R,7R)-5-Methylheptadecan-7-ol: A novel sex pheromone component produced by a female lichen moth, Miltochrista calamina, in the family Arctiidae

A methyl-branched heptadecanol was found in the pheromone gland extract of a female lichen moth, Miltochrista calamina (Arctiidae, Lithosiinae). GC-MS analyses of the alcohol and a hydrocarbon derived from it by subsequent treatments with methanesulfonyl chloride and LiAlD4 in microscale reactions indicated 5-methylheptadecan-7-ol (1) as one possible structure. The four stereoisomers of 1 in a ratio of 4:4:1:1 were prepared from (S)-b-citronellol with 60% ee, and were separated by a combination of achiral and chiral HPLC columns. The absolute configuration of each isomer was determined by the comparison with the chromatographic behaviors of other samples synthesized by a different scheme, which applied the Jacobsen hydrolytic kinetic resolution of racemic 1,2-epoxydodecane to fix the configuration of the 7-hydroxy group. Only the (5R,7R)-isomer attracted male moths; thus, we concluded that M. calamina females secrete (5R,7R)-1 as a sex pheromone, indicating a new chemical class of lepidopteran female sex pheromones.

A general strategy for the introduction of stereogenic centers bearing a methyl group: Total synthesis of sex pheromones

We're bringing sexy back: The highly efficient introduction of stereogenic centers bearing methyl group by conjugate addition of RMgBr to α,β-unsaturated esters has been employed in the total syntheses of two sex pheromones (see scheme). Binap=[1,1'-binaphthalene]-2,2'- diylbis(diphenylphosphane). Copyright