ホルムアルデヒドジメチルアセタール

Dimethoxymethane

HCID 8020CAS 109-87-5

基本情報

標準SMILES
COCOC
InChIKey
NKDDWNXOKDWJAK-UHFFFAOYSA-N
分子式
C3H8O2
平均分子量
76.09 g/mol
単同位体質量
76.0524295

概要

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.

名称と識別子

優先名称
Dimethoxymethane
IUPAC
dimethoxymethane
現地名
ホルムアルデヒドジメチルアセタール
英語名
Dimethoxymethane
分子式
C3H8O2
分子量
76.09

名称と別名

Dimethoxymethane109-87-5METHYLALFormalMethane, dimethoxy-Formaldehyde dimethyl acetalDimethyl formalAnesthenyl2,4-DioxapentaneMethylene dimethyl etherBis(methoxy)methaneMethoxymethyl methyl ether
名称をさらに表示
ジメトキシメタンホルムアルデヒドメチルケタールジメチルホルマールアネステニルメチレングリコールジメチルエーテルメトキシメチルメチルエーテルメチラールメチレンジメチルエーテル2,4-ジオキサペンタンホルマールメチラルメチラ-ルメチラ?ルホルムアルデヒド=ジメチルアセタ-ルホルムアルデヒドジメチルアセタール1,1-DIMETHOXYMETHANEMethylaMethyl formalDIMETHYLFORMALFORMALDEHYDE DIMETHYLmethanal,dimethylacetal
Formaldehyde methyl ketalMetylalFormaldehyde dimethylacetal7H1M4G2NUEDTXSID1025564CHEBI:48341RefChem:134194DTXCID905564

データベース識別子

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

物性

構造計算による物性

XLogP
0.2
極性表面積
18.5 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
2
重原子数
5

実験および物理化学的性質

Chemical Classes · 3 件

Other Classes -> Acetals

Flammable agents - 3rd degree

Volatile Organic Compound (VOC)

CosmeticsSolvent
SpringerMaterials PropertiesSchoenflies notation
LogP · 2 件

log Kow= 0.0

0.18

Odor · 2 件

CHLOROFORM ODOR

Chloroform-like odor.

TastePUNGENT TASTE

物理化学的性質

融点
-105 °C · -105 °C
沸点
41 · 41-43 °C
比重(密度)
0.86 g/mL · 0.860 g/mL at 20 °C(lit.)
蒸気密度
2.6 · 2.6 (vs air)
蒸気圧
6.38 psi · 6.38 psi ( 20 °C)
屈折率
20 · n20/D 1.354
化学的性質 · 1 件

化学的特性Dimethoxymethane, also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power. It is stable in the presence of alkalis and mild acids, and to high temperatures and pressures. It differs from other ethers in that it forms only minute omounts of peroxides. It will dissolve such synthetic resins as nitrocellulose, cellulose acetate and propionate, ethyl cellulose, vinyl, "Epons" and polystyrene, and also many of the natural gums and waxes. Methylal as a latent solvent is activated by the addition of esters, ketones or alcohols. Its evaporation rate, twice that of acetone, places this ether in a class with such solvents as acetone, methyl acetate and ethyl acetate in resin formulations.

安全と法規制

GHS分類

GHS Classification · 6 件

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

危険有害性情報

Regulatory Information · 6 件

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 件

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 件

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]

安全と保護具

Fire Fighting · 2 件

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 件

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 件

· 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 件

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 件

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

500.0 [ppm]

毒性情報

Body Burden · 1 件

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 件

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 件

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

inhalation, ingestion, skin and/or eye contact

Signs and Symptoms · 5 件

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

法規制情報

TSCA Requirements · 1 件

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.

安全データ

F
21
OEB
A
OEL
TWA: 1000 ppm (3100 mg/m3)
wgk
1
IDLA
2,200 ppm [10% LEL]
tsca
TSCA listed

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

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.

用途と製造

Uses · 6 件

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:
応用分野 · 4 件

解説ホルムアルデヒドジメチルアセタール,無色の液体.融点-105 ℃,沸点41~42 ℃.d420"0.8593.nD18"1.3589.揮発性.ほとんどの有機溶媒に可溶.クロロホルムに似た臭気を有する.ヨウ化水素と反応してヨウ化メチルとホルムアルデヒドになる.溶剤,香料,有機合成などに用いられる.肝臓や腎臓障害の原因になるほか,高濃度では催眠性がある.森北出版「化学辞典(第2版)

用途有機合成原料、溶剤

使用Dimethoxymethane (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.

一般的な説明Dimethoxymethane (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.

調製方法 · 1 件

純化方法It is a volatile flammable liquid which is soluble in three parts of H2O, and is readily hydrolysed by acids. Purify it by shaking with an equal volume of 20% aqueous NaOH, stand for 20minutes, dry over fused CaCl2, filter and fractionally distil it through an efficient column. Store it over molecular sieves. [Buchler et al. Org Synth Coll Vol III 469 1955, Rambaud & Besserre Bull Soc Chim Fr 45 1955, IR: Wilmshurst Can J Chem 36 285 1958, Beilstein 1 IV 3026.]

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補足説明

定義本品は、次の化学式で表されるエーテルである。

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

関連反応

182 件

関連ノート

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