1,1-Dimethoxyethane Property

Melting point:

-113 °C

Boiling point:

64 °C(lit.)

Density 

0.852 g/mL at 25 °C(lit.)

vapor density 

3.1 (vs air)

vapor pressure 

200 hPa (20 °C)

FEMA 

3426 | 1,1-DIMETHOXYETHANE

refractive index 

n20/D 1.367(lit.)

Flash point:

1 °F

storage temp. 

Store below +30°C.

solubility 

Chloroform (Sparingly)

form 

Oil

color 

Colourless

Odor

at 1.00 % in propylene glycol. sharp sweet alcohol ether green new mown hay

Odor Type

ethereal

Water Solubility 

Soluble

Sensitive 

Moisture Sensitive

Merck 

14,3226

JECFA Number

940

BRN 

1697039

Dielectric constant

3.4900000000000002

LogP

0.63 at 25℃

CAS DataBase Reference

534-15-6(CAS DataBase Reference)

NIST Chemistry Reference

Ethane, 1,1-dimethoxy-(534-15-6)

EPA Substance Registry System

1,1-Dimethoxyethane (534-15-6)

Safety

Hazard Codes 

F

Risk Statements 

11

Safety Statements 

9-16-33

RIDADR 

UN 2377 3/PG 2

WGK Germany 

2

RTECS 

AB2825000

F 

10-21

TSCA 

Yes

HS Code 

2911 00 00

HazardClass 

3

PackingGroup 

II

Hazardous Substances Data

534-15-6(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 6.5 g/kg; LC (in air) in rats: 16000 ppm (Smyth)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

1,1-Dimethoxyethane Chemical Properties,Usage,Production

Description

1,1-Dimethoxyethane is an aliphatic hydrocarbon which is found in figs, leek, and black tea. It gives a sharp ethereal, fruity and green note. It is used as a flavoring agent in food. 1,1-Dimethoxyethane is also used as a reagent for the diol protection and condensation reactions.

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.

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

Chemical Properties

1,1-Dimethoxybenzene is a clear colorless liquid with a sharp, sweet, alcohol, ether, green, new-mown-hay odor. It can miscible with water, alcohol, ether and chloroform.

Occurrence

Reported found in raspberry, blackberry, strawberry, peas, fresh figs, hop oil, coffee, cognac, white wine and tea.

Uses

1,1-Dimethoxyethane is used as a reagent in the synthesis of tricyclic and tetracyclic 1,5-benzodiazepine derivatives as nevirapine analogues. It can also be used as Mering's mixture which is 2 vol dimethylacetal and 1 vol chloroform.

Uses

Acetaldehyde dimethyl acetal may be used in the preparation of glucoside derivatives of steganol. It may be used as polymer solvent for the encapsulation of water-soluble model protein, bovine serum albumin into biodegradable poly(D,L-lactic acid.

Definition

ChEBI: 1,1-dimethoxyethane is an acetal that is dimethoxymethane substituted by a methyl group at position 1. It has a role as a flavouring agent and a plant metabolite. It is an acetal and a diether. It is functionally related to a dimethoxymethane.

Preparation

From acetaldehyde and methanol.

General Description

A liquid with a sharp odor. Less dense than water. Flash point between 0-73°F. Mildly toxic by ingestion and inhalation. Severely irritates the skin and eyes. Used to make other chemicals.

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.]