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1,1-Dimethoxyethane, also known as acetaldehyde dimethyl acetal, is an aliphatic hydrocarbon with a sharp ethereal, fruity, and green note. It is a clear colorless liquid that is less dense than water and has a flash point between 0-73°F. It is mildly toxic by ingestion and inhalation and can severely irritate the skin and eyes. 1,1-Dimethoxyethane is used to make other chemicals and is found in various natural sources such as raspberry, blackberry, strawberry, peas, fresh figs, hop oil, coffee, cognac, white wine, and tea.

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  • 534-15-6 Structure
  • Basic information

    1. Product Name: 1,1-Dimethoxyethane
    2. Synonyms: Ethane,1,1-dimethoxy-;methylformyl;FEMA 3426;ETHYLIDENE DIMETHYL ETHER;DIMETHYL ACETAL;AKOS BBS-00004400;ACETALDEHYDE DIMETHYL ACETAL;1,1-DIMETHOXYETHANE
    3. CAS NO:534-15-6
    4. Molecular Formula: C4H10O2
    5. Molecular Weight: 90.12
    6. EINECS: 208-589-8
    7. Product Categories: aldehyde Flavor
    8. Mol File: 534-15-6.mol
  • Chemical Properties

    1. Melting Point: -113 °C
    2. Boiling Point: 64 °C(lit.)
    3. Flash Point: 1 °F
    4. Appearance: /
    5. Density: 0.852 g/mL at 25 °C(lit.)
    6. Vapor Density: 3.1 (vs air)
    7. Vapor Pressure: 187mmHg at 25°C
    8. Refractive Index: n20/D 1.367(lit.)
    9. Storage Temp.: Flammables area
    10. Solubility: Chloroform (Sparingly)
    11. Water Solubility: Soluble
    12. Sensitive: Moisture Sensitive
    13. Merck: 14,3226
    14. BRN: 1697039
    15. CAS DataBase Reference: 1,1-Dimethoxyethane(CAS DataBase Reference)
    16. NIST Chemistry Reference: 1,1-Dimethoxyethane(534-15-6)
    17. EPA Substance Registry System: 1,1-Dimethoxyethane(534-15-6)
  • Safety Data

    1. Hazard Codes: F
    2. Statements: 11
    3. Safety Statements: 9-16-33
    4. RIDADR: UN 2377 3/PG 2
    5. WGK Germany: 2
    6. RTECS: AB2825000
    7. F: 10-21
    8. TSCA: Yes
    9. HazardClass: 3
    10. PackingGroup: II
    11. Hazardous Substances Data: 534-15-6(Hazardous Substances Data)

534-15-6 Usage

Uses

1. Used in Pharmaceutical Synthesis:
1,1-Dimethoxyethane is used as a reagent in the synthesis of tricyclic and tetracyclic 1,5-benzodiazepine derivatives, specifically as nevirapine analogues. These analogues have potential applications in the development of new pharmaceutical compounds.
2. Used in Steganol Preparation:
Acetaldehyde dimethyl acetal, another name for 1,1-Dimethoxyethane, may be used in the preparation of glucoside derivatives of steganol. This application is relevant in the field of organic chemistry and pharmaceuticals.
3. Used as a Polymer Solvent:
1,1-Dimethoxyethane can be used as a polymer solvent for the encapsulation of water-soluble model proteins, such as bovine serum albumin, into biodegradable poly(D,L-lactic acid). This application is significant in the field of drug delivery and biomaterials.
4. Used in Mering's Mixture:
As a component of Mering's mixture, which consists of 2 volumes of dimethylacetal and 1 volume of chloroform, 1,1-Dimethoxyethane is utilized in various chemical procedures and laboratory settings.
5. Used in Flavoring Agent:
1,1-Dimethoxyethane is used as a flavoring agent in the food industry due to its sharp ethereal, fruity, and green note. This application takes advantage of its natural occurrence in various fruits and beverages.
6. Used in Diol Protection and Condensation Reactions:
In the field of organic chemistry, 1,1-Dimethoxyethane is also used as a reagent for diol protection and condensation reactions, which are essential steps in the synthesis of complex organic molecules.

Preparation

To a flask equipped with a mechanical stirrer, condenser, and gas addition tube and containing 10 gm of a 6 3% solution of boron trifluoride in methanol is added 1.0 gm of mercuric oxide and 200 gm (6.25 moles) of methanol. Then 70 gm (3.13 moles) of acetylene is added with vigorous stirring at room temperature. After the reaction the catalyst is neutralized with aqueous potassium carbonate, the product is extracted into ether, dried, and distilled to afford 104 gm (37%), b.p. 64°-65°C.

Preparation

From acetaldehyde and methanol.

Reference

Evaluation of Certain Food Additives and Contaminants: Fifty-seventh report of the Joint FAO/WHO Expert Committee on Food Additives, 2001, ISBN 92-4-120909-7 M. J. Taschner, Encyclopedia of Reagents for Organic Synthesis, 2001, ISBN 9780471936237

Air & Water Reactions

Highly flammable. May form unstable peroxides when exposed to oxygen. These products can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid. Slightly soluble in water.

Reactivity Profile

1,1-Dimethoxyethane may react violently with strong oxidizing agents. Can act as a weak base to form salts with strong acids and addition complexes with Lewis acids. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Mildly toxic by inhalation, ingestion, and skin contact. A skin and eye irritant. A very dangerous fire hazard when exposed to heat, flame, or oxiduzers. When exposed to heat or flame it can react vigorously with oxidizing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS.

Purification Methods

Distil the dimethyl acetal through a fractionating column and fraction boiling at 63.8o/751mm is collected. It forms an azeotrope with MeOH. Alternatively purify it as for acetal above. It has been purified by GLC. [Beilstein 1 IV 3103.]

Check Digit Verification of cas no

The CAS Registry Mumber 534-15-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 4 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 534-15:
(5*5)+(4*3)+(3*4)+(2*1)+(1*5)=56
56 % 10 = 6
So 534-15-6 is a valid CAS Registry Number.

534-15-6 Well-known Company Product Price

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  • Aldrich

  • (385395)  Acetaldehydedimethylacetal  95%

  • 534-15-6

  • 385395-25ML

  • CNY

  • Detail
  • Aldrich

  • (385395)  Acetaldehydedimethylacetal  95%

  • 534-15-6

  • 385395-100ML

  • 807.30CNY

  • Detail

534-15-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,1-Dimethoxyethane

1.2 Other means of identification

Product number -
Other names Ethylidene Dimethyl Ether

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:534-15-6 SDS

534-15-6Relevant articles and documents

Kinetics and Mechanistic Study of the Methanol Homologation with Cobalt-Ruthenium mixed Catalyst

Watanabe, Kazuhiro,Kudo, Kiyoshi,Sugita, Nobuyuki

, p. 2029 - 2037 (1985)

The role of each catalyst was examined in detail in the methanol homologation with cobalt-ruthenium miwed catalyst.Cobalt catalyst showed much higher activity for the hydrocarbonylation of methanol than ruthenium.On the other hand, the hydrogenation of acetaldehyde proceeded much more rapidly by ruthenium catalyst.The rate of methanol homologation in 1,4-dioxane with cobalt-ruthenium mixed catalyst system was found to be of the first order with respect to the partial pressure of CO.The in situ IR spectra indicated that (1-) was an active species for the hydrocarbonylation of methanol and that existed under the reaction conditions.On the basis of both the kinetic studies and in situ IR spectral observations, the reaction mechanism of methanol homologation was fully discussed.

High activity cobalt based catalysts for the carbonylation of methanol

Marr, Andrew C.,Ditzel, Evert J.,Benyei, Attila C.,Lightfoot,Cole-Hamilton, David J.

, p. 1379 - 1380 (1999)

[Cp(*)Co(CO)2] in the presence of PEt3 and Mel catalyses the carbonylation of methanol with initial rates up to 44 mol dm-3 h-1 before decaying to a second catalytic phase with rates of 3 mol dm-3 h-1; [CoI(CO)2(PEt3)2], which is trigonal bipyramidal with axial PEt3 ligands, has been isolated from the final reaction solution.

FLASH VACUUM THERMOLYSIS OF 2-BROMOETHANOL. FORMATION OF &α-BROMOETHYLETHERS VIA 1-BROMOETHANOL.

Jenneskens, Leonardus W.,Wiersum, Ulfert E.,Ripoll, Jean-Louis

, p. 6489 - 6492 (1988)

Flash Vacuum Thermolysis of 2-bromoethanol (2) leads to the quantitative formation of 1-bromo-1-(1-bromoethoxy)ethane (5, di-α-bromoethylether).Low temperature IR spectroscopy shows that 5 arises from the dimerization of 1-bromoethanol (3), which is observed below -100 deg C as the primary product.

Gas-Phase NMR Studies of Chemical Equilibria. 1. Methodology

Harris, Robin K.,Rao, Renee C.

, p. 580 - 586 (1983)

Methods for obtaining 1H NMR spectra of gases are discussed.Particular attention is paid to the nature of the tube and to the use of 'second sample' field/frequency locking.The question of the chemical shift reference is examined, and some results for tetramethylsilane gas are presented.Representative spectra are shown for three types of organic equilibria in the gas phase: keto-enol tautomerism, addition of methanol to acetaldehyde and Z-E isomerism of acetaldoxime.

Functional methacryloyoxy acetals: II. Electophilic addition of alcohols to vinyloxyalkyl methacrylates

Gorelova,Oparina,Parshina,Gusarova,Trofimov

, p. 1683 - 1687 (2001)

Alcohols of various structures, in particular, ethylene, acetylene, fluorocontaining alcohols, add regio-and chemoselectively to the vinyloxy group of vinyloxyalkyl methacrylates at 20-40°C in the presence of catalytic quantities of trifluoroacetic acid a

Tetrachloromethane Hydrodechlorination over Palladium-Containing Nanodiamonds

Belkina, E. G.,Gruzdev, M. S.,Kalmykov, P. A.,Klyuev, M. V.,Lysenok, A. A.,Magdalinova, N. A.

, p. 1148 - 1153 (2020/10/14)

Abstract: Using nanodiamonds of the UDD-STP brand 1 wt % palladium-containing nanodiamonds are obtained and tested as catalysts of tetrachloromethane hydrodechlorination under mild conditions (solvents, ethanol and methanol; Т = 298–318 K; PH2 = 0.1 MPa). The catalytic properties of the obtained material and a palladium-containing analog based on activated carbon are compared. It is shown that the hydrodechlorination reaction occurs in a stepwise manner via two pathways: to form products with a smaller content of chlorine, for example, chloroform, and to yield oxygen-containing products, for example, diethyl carbonate. The qualitative and quantitative compositions of reaction products are determined by gas chromatography/mass spectrometry.

Catalytic Hydromethoxylation of Acetylene over Pre-Activated K2PdCl4

Khazipov, O. V.,Krasnyakova, T. V.,Mitchenko, S. A.,Nikitenko, D. V.

, p. 879 - 885 (2020/12/30)

Abstract: The catalytic addition of methanol to the triple bond of acetylene occurred on the surface of mechanically pre-activated K2PdCl4 and formed dimethylacetal and the vinyl chloride by-product. The addition of alcohol occurs regioselectively in accordance with the Markovnikov rule. The stereoselectivity of acetylene hydrochlorination corresponds to the trans-addition of H and Cl to the C≡C triple bond of acetylene. The effective activation energies of reaction routes were determined. A possible mechanism of formation of H3C–CH(OCH3)2 and H2C=CHCl was proposed.

Photocatalytic decarboxylation of lactic acid by Pt/TiO2

Liu, Kaituo,Litke, Anton,Su, Yaqiong,Van Campenhout, Bart G.,Pidko, Evgeny A.,Hensen, Emiel J. M.

, p. 11634 - 11637 (2016/10/04)

A photocatalytic route for the conversion of lactic acid to acetaldehyde in water is demonstrated. Direct UV photolysis of lactic acid yields CO2 and ethanol via a radical mechanism. Pt/TiO2 considerably increases the rate of lactic acid decarboxylation with acetaldehyde, H2 and CO2 as the main products. A concerted photodecarboxylation/dehydrogenation mechanism is proposed.

A catalytic conversion method for preparing pyruvate ester of lactic acid (by machine translation)

-

Paragraph 0017, (2016/10/10)

A method for preparing pyruvate through catalytic conversion of lactic acid is provided; according to the method, with oxygen or air as an oxidant, alcohol as a solvent, and molybdovanadophosphoric heteropoly acid and/or tungstovanadophosphoric heteropoly acid as a catalyst, and by coupling of a catalytic oxidation reaction and an esterification reaction, lactic acid is converted into pyruvate by one step. The method directly adopts oxygen or air as the oxidant and is green and safe; the used raw material lactic acid is obtained directly from conversion of biomass resources, moreover, the reaction conditions are mild, and the method has important application prospects.

Conversion of alcohols to longer chain aldehydes or alcohols

-

Page/Page column 34-36, (2016/04/20)

Processes are provided for contacting at least one Cn alcohol equivalent having n carbon atoms and at least one Cn+1 alcohol equivalent having (n+1) carbon atoms with a Guerbet catalyst to form a product composition comprising a product compound having the structure: wherein: C is a carbon atom; H is a hydrogen atom; Q is an alcohol or aldehyde group having one carbon; R is a linear alkyl group having n carbon atoms; and T is an alkyl group having (n?1) carbon atoms, except that when n=1, T is methyl.

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