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109-87-5

Basic Information
CAS No.: 109-87-5
Name: Dimethoxymethane
Article Data: 229
Molecular Structure:
Molecular Structure of 109-87-5 (Dimethoxymethane)
Formula: C3H8O2
Molecular Weight: 76.0953
Synonyms: 2,4-Dioxapentane;Anesthenyl;Bis(methoxy)methane;Dimethoxymethane;Dimethyl formal;Formal;Formaldehyde dimethyl acetal;Formaldehyde methyl ketal;Methoxymethyl methylether;Methylal;Methylene dimethyl ether;
EINECS: 203-714-2
Density: 0.86 g/cm3
Melting Point: -105 °C
Boiling Point: 45.238 °C at 760 mmHg
Flash Point: -18 °C
Solubility: 32.3 g/100 mL (16 °C) in water
Appearance: colorless transparent liquid
Hazard Symbols: FlammableF,IrritantXi
Risk Codes: 11-19-36-36/37/38
Safety: 16-26-33-7/9-37/39
Transport Information: UN 1234 3/PG 2
PSA: 18.46000
LogP: 0.23670
Synthetic route
67-56-1

methanol

50-00-0

formaldehyd

A

109-87-5

Dimethoxymethane

B

107-31-3

Methyl formate

Conditions
ConditionsYield
In water at 46 - 100℃; Acidic ion exchange resin;A 98.2%
B 0.6%
Katapak-catalyst In water at 46 - 100℃; Product distribution / selectivity;
67-56-1

methanol

50-00-0

formaldehyd

109-87-5

Dimethoxymethane

Conditions
ConditionsYield
With sulfuric acid for 5h; Reagent/catalyst; Reflux;96%
ion exchange resin with sulphonic acid groups In water at 70℃; for 0.2h; Industry scale;95.9%
ion-exchange resines In water Product distribution; continuous apparatus (rectification of the formed methylal);
22106-70-3

1-(methoxymethyl)-2-pyrrolidinone

107-30-2

chloromethyl methyl ether

A

31282-95-8

1-(chloromethyl)pyrrolidin-2-one

B

109-87-5

Dimethoxymethane

Conditions
ConditionsYield
Heating;A 96%
B n/a
1112-39-6

dimethyldimethoxysilan

14879-83-5

2,2-dimethyl-[1,3,2]dioxasilinane

A

109-87-5

Dimethoxymethane

B

77181-39-6

2,2,4,4,6-Pentamethyl-1,3-dioxa-2-silacyclohexane

Conditions
ConditionsYield
With tin(IV) chloride at 65℃; Product distribution; other reaction conditions; also with 1,3-dioxane and 4,4-dimethyl-1,3-dioxane;A n/a
B 94%
67-56-1

methanol

536-74-3

phenylacetylene

A

93-58-3

benzoic acid methyl ester

B

109-87-5

Dimethoxymethane

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene at 60℃; for 15h; Time; Reagent/catalyst; Concentration; Temperature; Sealed tube;A 82%
B n/a
115-10-6

Dimethyl ether

A

67-56-1

methanol

B

50-00-0

formaldehyd

C

109-87-5

Dimethoxymethane

D

107-31-3

Methyl formate

Conditions
ConditionsYield
With nitrogen; oxygen at 239.84℃; Conversion of starting material;A 19.4%
B 79%
C 0.1%
D 1.6%
With nitrogen; oxygen at 199.84 - 259.84℃; Rate constant;A 17.3%
B 69.2%
C 0%
D 1.6%
With nitrogen; oxygen at 239.84℃; Conversion of starting material;A 22.4%
B 60.1%
C 0%
D 5%
67-56-1

methanol

75-09-2

dichloromethane

201230-82-2

carbon monoxide

A

109-87-5

Dimethoxymethane

B

79-20-9

acetic acid methyl ester

C

6290-49-9

methyl methoxyacetate

D

108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
With Methyl formate; sodium methylate; Co2(CO)6{P(C4H9-n)3}2 at 80℃; under 11250.9 Torr; for 15h; electrolysis;A 8%
B n/a
C 3%
D 74.5%
With Methyl formate; sodium methylate; Co2(CO)6{P(C4H9-n)3}2 at 80℃; under 11250.9 Torr; for 15h; Product distribution; Mechanism; electrolysis, var. of catalyst, its reduction method, ratio;A 8%
B n/a
C 3%
D 74.5%
With sodium hydroxide; carbon-doped cobalt at 80℃; under 23560 Torr; for 1h;A 1.2 % Chromat.
B 7.5 % Chromat.
C 1.9 % Chromat.
D 28.8 % Chromat.
2949-92-0

methanethiosulfonic acid S-methyl ester

A

64-18-6

formic acid

B

75-75-2

methanesulfonic acid

C

109-87-5

Dimethoxymethane

D

107-31-3

Methyl formate

Conditions
ConditionsYield
With oxygen In methanol Irradiation;A n/a
B 72%
C n/a
D n/a
23433-02-5

4-octyl-1,3-dioxane

A

109-87-5

Dimethoxymethane

B

6071-32-5

undecane-1,3-diol

Conditions
ConditionsYield
With methanol; sulfuric acid Heating;A n/a
B 70%
67-56-1

methanol

74-95-3

1,2-dibromomethane

109-87-5

Dimethoxymethane

Conditions
ConditionsYield
With 4-vinylpyridine at 125℃; under 6000.6 Torr; for 2h;58%
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  • 109-87-5          C3H8O2                Dimethoxymethane

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    Product Name: Dimethoxymethane Molecular Formula: C3H8O2 Molecular Weight: 76.09 Moisture: ≤0.30%Appearance:Colorless transparent liquid Package:160 kilograms/barrels

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Standards and Recommendations

OSHA PEL: TWA 1000 ppm
ACGIH TLV: TWA 1000 ppm
DFG MAK: 1000 ppm (3200 mg/m3)
DOT Classification:  3; Label: Flammable Liquid

Analytical Methods

For occupational chemical analysis use NIOSH: Methylal, 1611.

Specification

The Dimethoxymethane , with cas registry number of 109-87-5, is a clear colorless flammable liquid with a chloroform-like odor and a pungent taste. Its IUPAC name and systematic name are called the same which is dimethoxymethane . The superlist names about this chemical include Dimethoxymethane ; Methane, dimethoxy- ; Methylal ; Methylal [UN1234] [Flammable liquid] ; UN1234 . This compound is soluble in three parts water and miscible with most common organic solvents. It is sensitive to moisture. May form explosive peroxides upon exposure to air. It is incompatible with strong oxidizing agents, strong acids. It should be stored at temp. 2-8°C.

Physical properties about Dimethoxymethane are: 
(1) # of Rule of 5 Violations: 0 ; (2) ACD/BCF (pH 5.5): 1 ; (3) ACD/BCF (pH 7.4): 1 ; (4) ACD/KOC (pH 5.5): 17.09 ; (5) ACD/KOC (pH 7.4): 17.09 ; (6) #H bond acceptors: 2 ; (7) #H bond donors: 0 ; (8) #Freely Rotating Bonds: 2 ; (9) Polar Surface Area: 18.46 Å2 ; (10) Index of Refraction: 1.348 ; (11) Molar Refractivity: 19.43 cm3 ; (12) Molar Volume: 90.7 cm3 ; (13) Surface Tension: 19.5 dyne/cm ; (14) Density: 0.838 g/cm3 ; (15) Enthalpy of Vaporization: 27.72 kJ/mol ; (16) Boiling Point: 45.2 °C at 760 mmHg ; (17) Vapour Pressure: 365 mmHg at 25°C ; (18) Refractive index: n20/D 1.354.

Preparation of Dimethoxymethane: 
there are two simple ways. One is it is prepared by oxidation of methanol . The other way is by the reaction of formaldehyde with methanol.

Uses information of Dimethoxymethane:
This chemical mainly used in organic synthesis. Here is an example, it can be used to prepared 1,3-dithia-5-cycloheptene with but-2c-ene-1,4-dithiol .

This reaction just needs a reagent boron trifluoride . The yield is about 37%.

Safety information of Dimethoxymethane:
When you are using this chemical, please be cautious about it as the following:
Moderately toxic by subcutaneous route. Mildly toxic by ingestion and inhalation. Can cause injury to lungs, liver, kidneys, and the heart. A narcotic and anesthetic in high concentrations. A very dangerous fire hazard when exposed to heat, flame, or oxidizers. Moderately explosive when exposed to heat or flame. May ignite or explode when heated with oxygen. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

You can still convert the following datas into molecular structure:
(1) SMILES:COCOC;
(2) InChI:InChI=1/C3H8O2/c1-4-3-5-2/h3H2,1-2H3;
(3) InChIKey:NKDDWNXOKDWJAK-UHFFFAOYAE

The toxicity data of Dimethoxymethane is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LC50 inhalation 57gm/m3/7H (57000mg/m3)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 259, 1986.
rabbit LD skin > 16mL/kg (16mL/kg) SENSE ORGANS AND SPECIAL SENSES: IRITIS: EYE

LIVER: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
National Technical Information Service. Vol. OTS0536049,
rabbit LD50 oral 5708mg/kg (5708mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 29, Pg. 730, 1932.
rat LC50 inhalation 15000ppm (15000ppm)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 73, 1974.
rat LDLo intraperitoneal 5gm/kg (5000mg/kg)   National Technical Information Service. Vol. OTS0524346,