10032-05-0

Basic information

• Product Name: HEPTANAL DIMETHYL ACETAL
• Synonyms: HEPTANAL DIMETHYL ACETAL;FEMA 2541;1,1-DIMETHOXYHEPTANE;1,1-dimethoxy-heptan;Heptane, 1,1-dimethoxy-;n-Heptanal dimethyl acetal;heptaldehyde dimethyl acetal
• CAS NO: 10032-05-0
• Molecular Formula: C₉H₂₀O₂
• Molecular Weight: 160.25
• EINECS: 233-103-6
• Mol File: 10032-05-0.mol

Chemical Properties

• Boiling Point: 183 °C760 mm Hg(lit.)
• Flash Point: 136 °F
• Appearance: COA
• Density: 0.832 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.51mmHg at 25°C
• Refractive Index: n20/D 1.4105(lit.)
• BRN: 1698661
• CAS DataBase Reference: HEPTANAL DIMETHYL ACETAL(CAS DataBase Reference)
• NIST Chemistry Reference: HEPTANAL DIMETHYL ACETAL(10032-05-0)
• EPA Substance Registry System: HEPTANAL DIMETHYL ACETAL(10032-05-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 23-24/25
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 2
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 10032-05-0(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
Heptanal dimethyl acetal is used as a flavoring agent for its pleasant odor reminiscent of walnut and cognac. It adds a unique and desirable taste to various food and beverage products, enhancing their overall flavor profile.
Used in Perfumery:
In the perfumery industry, heptanal dimethyl acetal is used as a fragrance ingredient. Its distinct walnut and cognac-like aroma adds depth and complexity to perfume compositions, creating a more appealing and long-lasting scent.
Used in Cosmetics:
Heptanal dimethyl acetal is also utilized in the cosmetics industry, where it serves as a key ingredient in the formulation of various personal care products. Its pleasant odor enhances the sensory experience of these products, making them more enjoyable for consumers to use.
Used in the Pharmaceutical Industry:
In the pharmaceutical industry, heptanal dimethyl acetal may be used as a component in the development of drugs that target specific taste receptors. Its unique taste characteristics could potentially be harnessed to create medications that help alleviate certain taste-related conditions or to develop novel drug delivery systems that improve patient compliance through enhanced taste and aroma.

Preparation

From heptyl aldehyde and HCl in methanol solution; from heptyl aldehyde and methanol in the presence of Twitchell’s reagent.

InChI:InChI=1/C9H20O2/c1-4-5-6-7-8-9(10-2)11-3/h9H,4-8H2,1-3H3

Upstream product

• 67-56-1 methanol 
• 111-71-7 heptanal 
• 66222-32-0 1-chloro-1-methoxy-heptane 
• 6008-84-0 2-hexyl-1,3-dithiolane 
• 71715-68-9 2-phenylsulfanyl-octanoic acid 
• 53799-82-9 dimethyl-dithiocarbamic acid 1-methylsulfanyl-heptyl ester 
• 149-73-5 trimethyl orthoformate 
• 40416-74-8 1-Hydroperoxy-1-methoxypentan 
• 111-66-0 oct-1-ene 
• 343217-90-3 3,5-dihexyl-1,2,4-trioxolan 
• 592-41-6 1-hexene 
• 201230-82-2 carbon monoxide 
• 681-84-5 tetramethylorthosilicate 
• 65644-37-3 2-hydroxyoctanal dimethyl acetal 

Downstream Products

• 10508-93-7 <1-Methoxy-heptyl>-<α-phenyl-isopropyl>-peroxid 
• 1825-61-2 Trimethylmethoxysilane 
• 111-71-7 heptanal 
• 106-70-7 methyl hexanoate 
• 142836-44-0 2-chloroheptanal dimethyl acetal 
• 106-73-0 methyl heptanoate 
• 3021-89-4 (E)-2-n-pentyl-2-n-nonenal 
• 78605-96-6 jasminaldehyde 
• 951402-70-3 1-methoxy-2-pentyl-1H-indene 
• 10201-58-8 (E)-1-heptenylbenzene 
• 111-14-8 oenanthic acid 
• 1227489-38-4 (Z)-N-(3-methoxy-2-phenylnonylidene)-2-methylpropan-2-amine oxide 
• 132904-11-1 (E)-3-Phenyl-N-(1-[1,2,4]triazol-1-yl-heptyl)-acrylamide 
• 132904-12-2 2-Ethoxy-N-(1-[1,2,4]triazol-1-yl-heptyl)-benzamide 

Relevant articles and documents

A novel application of terminal alkynes as the homogeneous catalysts for acetalization and esterification

The theoretical study focused on the possible use of low-molecular-weight mono-as well as multifunctional terminal alkynes as catalysts for two reactions, which are known to be typically acid catalyzed - acetalization and esterification, is presented in this study. Multifunctional terminal alkynes [(diethynylbenzenes, triethynylbenzene, and tetrakis(4-ethynylphenyl)methane]were significantly more active than the monofunctional ones (cyclopropylacetylene, phenylacetylene, 3-cyclohexylprop-1-yne, 1-ethynyl-2-fluorobenzene, 1-ethynyl-4-fluorobenzene, 4-ethynyltoluene, 4-tert-butylphenylacetylene, and 2-ethynyl-α,α,α-trifluorotoluene), this fact can be partly explained by the higher amount of ethynyl groups per alkyne molecule. We confirmed that terminal ethynyl groups in low-molecular-weight alkynes can successfully act as acid catalytic centers for acetalization as well as for esterification.

Hyper-Cross-Linked Polyacetylene-Type Microporous Networks Decorated with Terminal Ethynyl Groups as Heterogeneous Acid Catalysts for Acetalization and Esterification Reactions

Heterogeneous catalysts based on materials with permanent porosity are of great interest owing to their high specific surface area, easy separation, recovery, and recycling ability. Additionally, porous polymer catalysts (PPCs) allow us to tune catalytic activity by introducing various functional centres. This study reports the preparation of PPCs with a permanent micro/mesoporous texture and a specific surface area SBET of up to 1000 m2 g?1 active in acid-catalyzed reactions, namely aldehyde and ketone acetalization and carboxylic acid esterification. These PPC-type conjugated hyper-cross-linked polyarylacetylene networks were prepared by chain-growth homopolymerization of 1,4-diethynylbenzene, 1,3,5-triethynylbenzene and tetrakis(4-ethynylphenyl)methane. However, only some ethynyl groups of the monomers (from 58 to 80 %) were polymerized into the polyacetylene network segments while the other ethynyl groups remained unreacted. Depending on the number of ethynyl groups per monomer molecule and the covalent structure of the monomer, PPCs were decorated with unreacted ethynyl groups from 3.2 to 6.7 mmol g?1. The hydrogen atoms of the unreacted ethynyl groups served as acid catalytic centres of the aforementioned organic reactions. To the best of our knowledge, this is first study describing the high activity of hydrogen atoms of ethynyl groups in acid-catalyzed reactions.

Low pressure hydroformylation in the presence of alcohol promoters

Active carbon supported cobalt catalyst was studied for the hydroformylation of 1-hexene in the presence of alcohol solvents at low pressure. The influence of various solvents on the hydroformylation and the CO conversion vs time on stream were investigated in detail. It was found that the heterogeneous catalyst shows excellent activity only in the alcohol solvents.

AN EFFICIENT SbCl3-METAL SYSTEM FOR ALLYLATION, REDUCTION AND ACETALIZATION OF ALDEHYDES

SbCl3-Fe or SbCl3-Al could induce allylation of aldehydes with allylic halides at room temperature to give high yields of the corresponding homoallylic alcohols with high regio- and chemoselectivity.SbCl3-Al or SbCl3-Zn in DMF-H2O was found to be an efficient reduction system for conversion of aldehydes to alcohols at room temperature in excellent yields.While alcohol was used as solvent instead of DMF-H2O, the acetalization product was obtained in almost quantitative yield.Catalytic amount of SbCl3 was effective for this purpose.This acetalization method could also be applied to ketone.

A simple one-pot procedure for the conversion of aldehydes to methyl esters

Several methyl esters were obtained by an efficient and simple one-pot procedure from the corresponding aldehydes in high yields. This procedure involves dimethyl acetal formation from aldehydes and subsequent oxidation.

A simple and versatile method for the synthesis of acetals from aldehydes and ketones using bismuth triflate

Acetals are obtained in good yields by treatment of aldehydes and ketones with trialkyl orthoformate and the corresponding alcohol in the presence of 0.1 mol % Bi(OTf)3·4H2O. A simple procedure for the formation of acetals of diaryl ketones has also been developed. The conversion of carbonyl compounds to the corresponding 1,3-dioxolane using ethylene glycol is also catalyzed by Bi(OTf)3· 4H2O (1 mol %). Two methods, both of which avoid the use of benzene, have been developed.

A convenient and highly efficient method for the protection of aldehydes using very low loading hydrous ruthenium(III) trichloride as catalyst

A convenient method for the chemoselective protections of both aliphatic and aromatic aldehydes has been developed. Ruthenium(III) trichloride (0.1 mol %) has found to be an highly efficient catalyst in the acetalizations of aldehydes with various simple alcohols such as methanol, ethanol, or diols such as 1,2-ethylanediol and 1,3-propanediol under mild reaction conditions.

Use of delaminated zeolites (ITQ-2) and mesoporous molecular sieves in the production of fine chemicals: Preparation of dimethylacetals and tetrahydropyranylation of alcohols and phenols

The combination of zeolitic acidities, easy reactant accessibility, and fast desorption-diffusion of products are determinant issues for designing successful catalysts for acid-catalyzed reactions in the field of fine chemicals production. Protection of aldehydes by formation of the corresponding dimethyl acetals and of alcohols and phenols by formation of the corresponding tetrahydropyranyl ethers were performed using ITQ-2 zeolite as acid catalyst. Its catalytic activity for these reactions was compared with those obtained with MCM-22, Beta zeolites, and the mesoporous aluminosilicate MCM-41, all with similar Si/Al ratios. When the reactions involved bulky reactants, ITQ-2 showed, in all cases, the highest activity as a consequence of the combination of its delaminated structure and the presence of strong acid sites. The zeolitic nature of the acid sites present in the delaminated ITQ-2 zeolite made the acid sites more stable than those present in the short range amorphous MCM-41 molecular sieve, providing the former catalyst better activity and thermal regenerability. ITQ-2 and MCM-41 are active and selective catalysts for acetalization reactions involving reactants as large as diphenylacetaldehyde and cholesterol.

Metal organic frameworks as solid acid catalysts for acetalization of aldehydes with methanol

Room temperature acetalization of aldehydes with methanol has been carried out using metal organic frameworks (MOFs) as solid heterogeneous catalysts. Of the MOFs tested, a copper-containing MOF [Cu3(BTC)2] (BTC=1,3,5-benzenetricarboxylate) showed better catalytic activity than an iron-containing MOF [Fe(BTC)] and an aluminium containing MOF [Al 2(BDC)3] (BDC=1,4-benzenedicarboxylate). The protocol was validated for a series of aromatic and aliphatic aldehydes and used to protect various aldehydes into commercially important acetals in good yields without the need of water removal. In addition, the reusability and heterogeneity of this catalytic system was demonstrated. The structural stability of MOF was further studied by characterization with powder X-ray diffraction, Brunauer-Emmett- Teller surface area measurements and Fourier-transformed infrared spectroscopic analysis of a deactivated catalyst used to convert a large amount of benzaldehyde. The performance of copper MOF as acetalization catalyst compares favourably with those of other conventional homogeneous and heterogeneous catalysts such as zinc chloride, zeolite and clay. Copyright

Chemoselective protection of aldehydes in the presence of ketones using rupvp complex as a heterogeneous catalyst

Ruthenium(III)-polyvinyl pyridine (RuPVP) complex was prepared by refluxing a methanolic solution of polyvinyl pyridine and trihydrated ruthenium trichloride. RuPVP catalyst was characterized by Fourier transform-infrared and diffential scanning calorimetry-thermogravimetry (TG). The catalyst was used for chemoselective protection of aldehydes in the presence of a ketonic carbonyl group.