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Dimethoxymethan

Dimethoxymethane

HCID 8020
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Grundinformationen

CAS
109-87-5
Standard-SMILES
COCOC
InChIKey
NKDDWNXOKDWJAK-UHFFFAOYSA-N
Summenformel
C3H8O2
Durchschnittliche Molmasse
76,09 g/mol
Monoisotopische Masse
76,0524295

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Dimethoxymethane
IUPAC
dimethoxymethane
Lokaler Name
Dimethoxymethan
Englischer Name
Dimethoxymethane
Summenformel
C3H8O2
Molmasse
76.09

Namen und Synonyme

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
0,2
Polarare Oberfläche (TPSA)
18,5 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
2
Schwere Atome
5
Formalladung
0
Komplexität
12,4

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 3 Einträge

Other Classes -> Acetals

Flammable agents - 3rd degree

Volatile Organic Compound (VOC)

CosmeticsSolvent
SpringerMaterials PropertiesSchoenflies notation
LogP · 2 Einträge

log Kow= 0.0

0.18

Odor · 2 Einträge

CHLOROFORM ODOR

Chloroform-like odor.

TastePUNGENT TASTE
Density · 6 Einträge

0.861 at 68 °F (USCG, 1999) - Less dense than water; will float

0.8593 @ 20 °C/4 °C

0.86 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.7

0.86

0.8593 @ 20°C

Flavoring AgentsEU Flavoring substances
Color/Form

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

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

Gefahrenhinweise

Regulatory Information · 6 Einträge

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 Einträge

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)

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

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.

Verwendung und Herstellung

Uses · 6 Einträge

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:
Use ClassificationCosmetics -> Solvent
General Manufacturing Information

Zugehörige Reaktionen

182
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 1455
HRID 1455als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 18437
HRID 18437als Lösungsmitteluspto-grants-2010_06
Reaktionsgleichung von HRID 21512
HRID 21512als Eduktuspto-grants-1995_06
Reaktionsgleichung von HRID 24289
HRID 24289als Eduktuspto-grants-2005_02
Reaktionsgleichung von HRID 25918
HRID 25918als Eduktuspto-grants-1979_04
Reaktionsgleichung von HRID 49005
HRID 49005als Eduktuspto-grants-2004_03
Reaktionsgleichung von HRID 67054
HRID 67054als Eduktuspto-grants-1982_08
Reaktionsgleichung von HRID 89508
HRID 89508als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
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· 2 Einträge

COLORLESS, CLEAR LIQUID

Colorless solid.

Solubility · 6 Einträge

33 % (NIOSH, 2024)

MISCIBLE WITH ALCOHOL, ETHER, OILS; SOL IN 3 PARTS WATER

SOL IN ALL ACETONE, AND BENZENE

Water solubility: 330,000 mg/l

Solubility in water, g/100ml at 20 °C: 28.5 (good)

33%

Flash Point · 6 Einträge

0 °F (USCG, 1999)

-32 °C

-26 °F (-32 °C) (OPEN CUP)

-31 °C c.c.

-26 °F (open cup)

(oc) -26 °F

Boiling Point · 6 Einträge

108 °F at 760 mmHg (USCG, 1999)

41.6 °C @ 760 MM HG

42 °C

111 °F

42 °C @760 [mm Hg]

111 °F

Physikochemische Eigenschaften

Schmelzpunkt
-105 °C · -105 °C
Siedepunkt
41 · 41-43 °C
Dichte
0.86 g/mL · 0.860 g/mL at 20 °C(lit.)
Dampfdichte
2.6 · 2.6 (vs air)
Dampfdruck
6.38 psi · 6.38 psi ( 20 °C)
Brechungsindex
20 · n20/D 1.354
Flammpunkt
-18 °C · -18 °C
storage temp.
20 °C · Store at <= 20°C.
Löslichkeit
32.3 g/100 · 32.3 g/100 mL (16°C)
Aggregatzustand
Liquid
pka
3.1 · 3.1[at 20 ℃]
Farbe
Clear colorless
Geruch (Odor)
Mild, ethereal; chloroform-like.
PH
pH (12.5vol % , 25℃) : 4.5~6.6
Explosionsgrenze
1.6 · 1.6-17.6%(V)
Wasserlöslichkeit
32.3 g/100 · 32.3 g/100 mL (16 ºC)
Spezifische Wärmekapazität
2.13 J/ · Cp(liquid): 2.13 J/(g·K), at 25℃
Merck
14 · 14,6012
BRN
1697025 · 1697025
Henry's Law Constant
(x 10-4 atmm3/mol): 1.73 at 25 °C (Hine and Mookerjee, 1975)
Dielectric constant
2.7 · 2.7(20℃)
Stabilität
Stable. Extremely flammable. Readily forms explosive mixtures with air. Note low flash point and wide explosive limits. Incompatible with strong oxidizing agents, strong acids. May form explosive peroxides upon exposure to air.
Kosmetik-Inhaltsstoffe Funktionen
SOLVENT
InChI
1S/C3H8O2/c1-4-3-5-2/h3H2,1-2H3
InChIKey
NKDDWNXOKDWJAK-UHFFFAOYSA-N
SMILES
COCOC
LogP
0 · 0
CAS Datenbank
109 · 109-87-5(CAS DataBase Reference)
NIST chemische Informationen
Methane, dimethoxy-(109-87-5)
EPA chemische Informationen
Dimethoxymethane (109-87-5)

· 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 Einträge

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]
DOT ID and Guide · 2 Einträge

1234 127

1234 127

Reactive GroupAcetals, Ketals, Hemiacetals, and Hemiketals
UN ClassificationUN Hazard Class: 3; UN Pack Group: II
TSCA Requirements · 1 Eintrag

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.

Reactivity AlertsHighly Flammable
OSHA Standards8 hr Time-Weighted avg: 1,000 ppm (3,100 mg/cu m)

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

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 Einträge

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 Einträge

· 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 Einträge

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 Einträge

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

500.0 [ppm]

Fire Fighting Procedures · 2 Einträge

TO FIGHT FIRE: FOAM, CARBON DIOXIDE, DRY CHEMICAL ...

Water may be ineffective. Alcohol foam.

Cleanup Methods · 1 Eintrag

1. REMOVE ALL IGNITION SOURCES. 2. VENTILATE AREA OF SPILL OR LEAK. 3. FOR SMALL QUANTITIES, ABSORB ON PAPER TOWELS. EVAPORATE IN SAFE PLACE (SUCH AS FUME HOOD). ALLOW SUFFICIENT TIME TO COMPLETELY CLEAR HOOD DUCTWORK. BURN PAPER IN SUITABLE LOCATION AWAY FROM COMBUSTIBLE MATERIALS. 3. LARGE QUANTITIES CAN BE COLLECTED, DISSOLVED IN ALC OF GREATER MOLECULAR WT THAN BUTYL ALC, & ATOMIZED IN SUITABLE COMBUSTION CHAMBER. METHYLAL SHOULD NOT BE ALLOWED TO ENTER CONFINED SPACE, SUCH AS SEWER, BECAUSE OF THE POSSIBILITY OF AN EXPLOSION.

Nonfire Spill ResponseExcerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:
Disposal Methods... MAY BE DISPOSED OF BY DISSOLVING IN ALCOHOL OF GREATER MOLECULAR WEIGHT THAN BUTYL ALCOHOL & ATOMIZING IN SUITABLE COMBUSTION CHAMBER.
Spillage Disposal · 1 Eintrag

Consult an expert! Personal protection: filter respirator for organic vapours of low boiling point adapted to the airborne concentration of the substance. Remove all ignition sources. Cover the spilled material with sand or other non-combustible material. Collect leaking liquid in covered containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Preventive Measures · 5 Einträge

SRP: The scientific literature supports the wearing of contact lenses in industrial environments, as part of a program to protect the eye against chemical compounds and minerals causing eye irritation. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases contact lenses should not be worn.

SAFE-HANDLING PRECAUTIONS SHOULD INCL USE OF ADEQUATE VENTILATION TO BE CERTAIN THAT AVG CONCN ARE WELL BELOW 1000 PPM, & AVOIDANCE OF EXCESSIVE OR PROLONGED SKIN CONTACT. METHYLAL SHOULD BE HANDLED WITH DUE REGARD FOR ITS FLAMMABLE PROPERTIES.

To prevent injury from occurring as a result of contact with an aldehyde in the form of liquid or vapor, the process in which the substance is present should, if possible be conducted in enclosed plant. If openings are necessary for the purposes of manipulation, vapor should be prevented from escaping into the workroom by the application of exhaust ventilation to the plant or enclosure. When the process cannot be enclosed, exhaust ventilation hoods should be fitted to trap and extract escaping vapor before it can diffuse into the workroom atmosphere. /Aldehydes and ketals/

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet should be immediately removed due to its flammability hazard.

Toxikologische Informationen

Body Burden · 1 Eintrag

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 Einträge

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 Einträge

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

inhalation, ingestion, skin and/or eye contact

Signs and Symptoms · 5 Einträge

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

Effluent Concentrations · 1 Eintrag

In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, methylal was identified in discharges of the following industrial category (positive occurrences; median concn in ppb): leather tanning (1; 1637.5), plastics and synthetics (3; 30.8), organic chemicals (6; 45.6), publicly owned treatment works (3; 5.0)(1). The highest effluent concn was 1637 ppb in the leather tanning industry(1). Detected in effluent concentrates from the advanced treatment plant in Orange County, CA, but not in that of five other communities(2).

ICSC Environmental DataEnvironmental effects of the substance have been adequately investigated, but no significant effects have been found.
Soil Adsorption/MobilityThe Koc for methylal estimated from its water solubility, 2.44X10+5 ppm(1), by a recommended regression equation is 5(2). Therefore methylal would be very mobile in soil(3).
Human Toxicity Excerpts · 2 Einträge

... PROPERTIES OF SIMPLE UNSUBSTITUTED ACETALS ARE CHARACTERIZED BY ETHER-LIKE ANESTHETIC ACTION, & BY RELATIVELY LOW DEGREE OF PRIMARY IRRITATION COMPARED TO PARENT ALDEHYDE. /ACETALS/

INHALATION CAUSES IRRITATION OF RESP SYSTEM & DEPRESSION OF CNS. LIQ CAUSES IRRITATION OF EYES & WILL IRRITATE SKIN IF ALLOWED TO REMAIN.

Artificial Pollution Sources · 2 Einträge

Methylal used as a solvent and reagent in organic synthesis(2) may be released to the environment in waste water and as fugitive emissions relating to its manufacture and use. Mean vapor emission rates of methylal measured at two locations at an industrial waste water treatment facility in December were 28.6 and 14.7 mg/min sq-m, at which time the ambient and liquid surface temperatures were 6 and 15 °C, respectively(1).

METHYLAL WAS ONE OF THE COMPONENTS IN WASTE WATER FROM A UREA-FORMALDEHYDE GLUE PLANT.

Environmental Biodegradation · 1 Eintrag

A reduction in BOD in 8 hr was obtained in one study in which well acclimated sewage seed was incubated with 333 ppm of methylal(1). However this reduction was small compared with the theoretical oxygen demand and toxicity resulted in an initial increase in BOD.

Regulatorische Informationen

TSCA Requirements · 1 Eintrag

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.

Sicherheitsdaten

F
21
OEB
A
OEL
TWA: 1000 ppm (3100 mg/m3)
wgk
1
IDLA
2,200 ppm [10% LEL]
tsca
TSCA listed
ridadr
UN 1234
hs_code
2911 00 00
RTECS-Nr.
PA8750000
risk_code
11-19-36-36/37/38
Toxizität
LD50 orally in Rabbit: 6653 mg/kg
hazard_code
F,Xi
safety_code
16-26-33-7/9-37/39
hazard_class
3
packing_group
II
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
109-87-5(Hazardous Substances Data)
Hazard Classifications
Flam. Liq. 2
Selbstentzündungstemperatur
459 °F
· 2 Einträge

Plastics Material and Resin Manufacturing

Methane, dimethoxy-: ACTIVE

Anwendungen · 1 Eintrag

VerwendenDimethoxymethane (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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

WasserstoffperoxidNatriumParaformaldehydeGlycinMethanolMethylformiat1-Propene, 2-chloro-3,3-dimethoxy-Methoxymethanol

Nachgelagerte Produkte

DirithromycinAcetamipridFormaldehydα-Brom-4-nitro-o-kresol1,3-Dithian1-Phenylprop-2-in-1-ol1,3-Dioxolan-4-ylmethanolDimethylsulfit2,3-Dihydrothiophene1,1-DIMETHOXYCYCLOHEXANE7-Chlor-p-cymol7-AMCA4-(Chlormethyl)biphenyl6-Methyleneandrost-4-ene-3,17-dione(Methoxymethyl)diphenylphosphinoxid

Ergänzende Hinweise

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.