Dimethoxymethane

HCID 8020CAS 109-87-5

Basic information

Standard SMILES
COCOC
InChIKey
NKDDWNXOKDWJAK-UHFFFAOYSA-N
Molecular formula
C3H8O2
Average molar mass
76.09 g/mol
Monoisotopic mass
76.0524295

Overview

Methylal appears as a clear colorless liquid with a chloroform-like odor. Flash point 0 °F. Boiling point 42.3 °C. Density 0.864 g / cm3 at 68 °F (20 °C). Vapors heavier than air.

Names & identifiers

Preferred name
Dimethoxymethane
IUPAC
dimethoxymethane
English name
Dimethoxymethane
Molecular formula
C3H8O2
Molecular weight
76.09

Names & synonyms

Dimethoxymethane109-87-5METHYLALFormalMethane, dimethoxy-Formaldehyde dimethyl acetalDimethyl formalAnesthenyl2,4-DioxapentaneMethylene dimethyl etherBis(methoxy)methaneMethoxymethyl methyl ether
Show more names
1,1-DIMETHOXYMETHANEMethylaMethyl formalDIMETHYLFORMALFORMALDEHYDE DIMETHYLmethanal,dimethylacetal
Formaldehyde methyl ketalMetylalFormaldehyde dimethylacetal7H1M4G2NUEDTXSID1025564CHEBI:48341RefChem:134194DTXCID905564

Database identifiers

CAS
109-87-5
PubChem CID
8020
DTXSID
DTXSID1025564
ChEMBL
CHEMBL15537
ChEBI
CHEBI:48341
UNII
7H1M4G2NUE
EC Number
203-714-2
Nikkaji
J3.250F

Properties

Computed structural properties

XLogP
0.2
Topological polar surface area
18.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
5

Experimental & physicochemical properties

Chemical Classes · 3 items

Other Classes -> Acetals

Flammable agents - 3rd degree

Volatile Organic Compound (VOC)

CosmeticsSolvent
SpringerMaterials PropertiesSchoenflies notation
LogP · 2 items

log Kow= 0.0

0.18

Odor · 2 items

CHLOROFORM ODOR

Chloroform-like odor.

TastePUNGENT TASTE

Physicochemical properties

Melting point
-105 °C · -105 °C
Boiling point
41 · 41-43 °C
Density
0.86 g/mL · 0.860 g/mL at 20 °C(lit.)
vapor density
2.6 · 2.6 (vs air)
vapor pressure
6.38 psi · 6.38 psi ( 20 °C)
refractive index
20 · n20/D 1.354

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 1.2% (5 of 433) of reports.

Danger

H225 (98.8%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 433 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Hazard information

Regulatory Information · 6 items

Chemical: Methane, dimethoxy-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Methane, dimethoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methane, dimethoxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 27-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/5159

Methane, dimethoxy-: HSNO Approval: HSR001047 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelFlammable Liquid
Fire Hazards · 3 items

FLAMMABLE. Irritating gases may be produced when heated. Containers may explode in fire. Flashback along vapor trail may occur. Vapor may explode if ignited in an enclosed area. Irritating formaldehyde gas may be present in smoke. (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Heating will cause rise in pressure with risk of bursting. Vapour/air mixtures are explosive. Risk of fire and explosion on contact with strong oxidizing agents or strong bases.

Fire PotentialDANGEROUS, WHEN EXPOSED TO HEAT, FLAME, OXIDIZERS
Health Hazards · 2 items

VAPOR: Irritating to eyes, nose and throat. Harmful if inhaled. LIQUID: Irritating to skin and eyes. Harmful if swallowed. (USCG, 1999)

· Inhalation or contact with material may irritate or burn skin and eyes.

Hazards SummaryAnimal inhalation studies: anesthesia and damage to the liver and other organs; [ACGIH] A skin, eye, and respiratory tract irritant; Inhalation of high concentrations can cause CNS depression; [ICSC]

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

Use water spray, dry powder, carbon dioxide, alcohol-resistant foam. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3 items

Excerpt from NIOSH Pocket Guide for Methylal:

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from strong oxidants and strong bases. Cool. Keep in the dark. Well closed. Store only if stabilized. Store in an area without drain or sewer access.
Exposure Control and Personal Protection · 2 items

· Wear positive pressure self-contained breathing apparatus (SCBA).

500.0 [ppm]

Toxicology

Body Burden · 1 item

In the EPA National Human Adipose Survey for fiscal year 1982, 46 composite samples categorized broadly by region and age group were analyzed for pollutants(1). Methylal was identified in one sample from the northeast US in the >45 age group.

Target OrgansEyes, skin, respiratory system, central nervous system
Environmental Fate · 3 items

TERRESTRIAL FATE: If released on land, methylal would volatilize rapidly due to its high vapor pressure and Henry's Law constant and low adsorptivity to soil. It would also exhibit high mobility in soil. The importance of biodegradation in soil is unknown. (SRC)

AQUATIC FATE: If released to water, methylal will be primarily lost through volatilization. Its half-life in a model river is estimated from a calculated Henry's Law constant to be 7.2 hr(1-3). Adsorption to sediment and particulate matter in the water column, and bioconcentration should not be important. The importance of biodegradation in water is unknown. Hydrolysis is fairly slow(SRC).

ATMOSPHERIC FATE: The atmosphere is the sink for methylal. In the atmosphere, methylal will degrade by reaction with photochemically-produced hydroxyl radicals. The half-life for this reaction is estimated to be 2.3 days(1). Methylal is highly soluble in water, 2.44X10+5 ppm(2), and would be washed out by rain. However, methylal thus remove would be recycled back into the atmosphere. (SRC)

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure Routes · 2 items

The substance can be absorbed into the body by inhalation of its vapour.

inhalation, ingestion, skin and/or eye contact

Signs and Symptoms · 5 items

Cough. Dizziness. Drowsiness. Headache. Sore throat. Unconsciousness.

Dry skin.

Redness. Pain.

Abdominal pain. Nausea. Vomiting. Further see Inhalation.

irritation eyes, skin, upper respiratory system; anesthesia

Regulatory information

TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Methane, dimethoxy- is included on this list.

Safety data

F
21
OEB
A
OEL
TWA: 1000 ppm (3100 mg/m3)
PPE
Eyeshields, Faceshields, Gloves
wgk
1
IDLA
2,200 ppm [10% LEL]

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Methylal (dimethoxymethane) ... was metabolised by rats to methanol and dimethyl ether in equimolar ratio, regardless of the route of administration. Symptoms of methylal poisoning and the typical damage to the retina and optic nerve are the same as those seen in methanol poisoning. Inhalation experiments showed that the blood methanol concentration is proportional to the concentration of methylal in the air.

Uses & manufacturing

Uses · 6 items

Used as a solvent for adhesives and coatings, a fuel, and an intermediate for other organic compounds; [ACGIH] Has been used as an anesthetic; [HSDB]

Painting (Solvents) [Category: Paint]

IN PERFUMERY; MFR ARTIFICIAL RESINS; REACTION MEDIUM FOR GRIGNARD & REPPE REACTIONS

EXTERNALLY AS OINTMENT AND INTERNALLY AS AN ANAESTHETIC AND HYPNOTIC

SPECIAL PURPOSES FUEL; SOLVENT FOR ADHESIVES & COATINGS; IN ORG SYNTHESES

In methacrylate mfg

U.S. Production2023: 1,000,000 - <2,500,000 lb
Consumer UsesSolvent
Industry UsesIntermediate
Methods of Manufacturing... BY CATALYTIC VAPOR-PHASE OXIDN OF METHANOL IN PRESENCE OF SMALL AMT OF HYDROCHLORIC ACID; FROM METHANOL & FORMALDEHYDE. FROM PARAFORMALDEHYDE + METHANOL IN PRESENCE OF CALCIUM CHLORIDE + HYDROCHLORIC ACID.
Household ProductsInformation on 10 consumer products that contain Dimethoxymethane in the following categories is provided:
Applications · 3 items

DescriptionMethylal is a colorless liquid with a pungent odor. Molecular weight= 76.11; Specific gravity (H2O:1)= 0.86;Boiling point=43.9℃; Freezing/Melting point=105℃; Vapor pressure 330 mmHg at 20℃; Flash point=32℃; Autoignition temperature=237℃. Explosive limits: LEL= 2.2%; UEL= 13.8%. Hazard Identification (based on NFPA-704 M Rating System): Health 2, Flammability 3, Reactivity 2. Soluble in water; solubility= 33%.

UsesDimethoxymethane (Methylal) is a valuable extraction solvent for pharmaceutical products and a stable, inexpensive solvent for Grignard reactions. Methylal is stable under alkaline and mild acidic conditions. Its dissolving ability is stronger than ether, acetone, and methanol and azeotrope can dissolve nitrocellulose with high nitrogen content. Dimethoxymethane is mainly used in the production of anion-exchange resins, and also as solvents and special fuels.

General DescriptionDimethoxymethane (DMM, methylal) is a biodegradable dimethyl acetal. It can be synthesized by acid catalyzed condensation of formaldehyde with methanol. It is amphiphilic in nature with low viscosity, surface tension and boiling point. It is a flammable, highly volatile solvent with good dissolving power. DMM is considered as a potential alternative fuel and fuel additive due to its high oxygen content and its ability to enhance the combustion characteristics of diesel and petrol. Its thermal diffusivity has been determined by photoacoustic method. Analysis of the molecular structure of DMM by electron diffraction technique shows that it has C2 symmetry with a gauche-gauche conformation.

Preparation methods · 1 item

PreparationDimethoxymethane synthesis is based on the liquid-phase acetalization reaction of methanol and formaldehyde. It can be manufactured by oxidation of methanol or by the reaction of formaldehyde with methanol. In aqueous acid, it is hydrolyzed back to formaldehyde and methanol. Reaction mechanisms and catalysis in the one-step synthesis of methylal via methanol oxidationNovel Porous Iron Molybdate Catalysts for Synthesis of Dimethoxymethane from Methanol: Metal Organic Frameworks as Precursors

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海犇特化工有限公司13761726461 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
聊城作之杭化工有限公司19163518031; 19163518031

Additional notes

DefinitionChEBI: Dimethoxymethane is an acetal that is the dimethyl acetal derivative of formaldehyde. It is an acetal and a diether. It derives from a methanediol.

Related reactions

182 records

Linked notes

Loading…