1,4-Dimethoxybenzene

HCID 9016CAS 150-78-7

基本情報

標準SMILES
COc1ccc(OC)cc1
InChIKey
OHBQPCCCRFSCAX-UHFFFAOYSA-N
分子式
C8H10O2
平均分子量
138.16 g/mol
単同位体質量
138.06807956

概要

1,4-dimethoxybenzene appears as colorless crystals. (NTP, 1992)

名称と識別子

優先名称
1,4-Dimethoxybenzene
IUPAC
1,4-dimethoxybenzene
現地名
1,4-ジメトキシベンゼン
英語名
1,4-Dimethoxybenzene
分子式
C8H10O2
分子量
138.16

名称と別名

1,4-Dimethoxybenzene150-78-7p-Dimethoxybenzenep-MethoxyanisoleHYDROQUINONE DIMETHYL ETHERBenzene, 1,4-dimethoxy-Benzene, p-dimethoxy-4-MethoxyanisoleQuinol dimethyl ether1,4-DimethoxybenzolDimethylhydroquinone etherDimethyl ether hydroquinone
名称をさらに表示
1,4-ジメトキシベンゼンP-ジメトキシベンゼンヒドロキノンジメチルエーテルpジメトキシベンゼン2,5-ジメトキシベンゼンメチル4-メトキシフェニルエーテル4-メトキシアニソールdimethoxybenzeneDIMETHYLHYDROQUINONEFEMA 23861,4-dimethoxy-benzen4-DiMethoxybenzene1,4-dimethoxybezene
USAF AN-9Dimethyl hydroquinoneHydroquinone, dimethyl etherMethyl p-methoxyphenyl etherDimethylether hydrochinonuFEMA No. 2386para-dimethoxybenzeneDTXSID0022014

データベース識別子

CAS
150-78-7
PubChem CID
9016
DTXSID
DTXSID0022014
ChEMBL
CHEMBL1668604
ChEBI
CHEBI:179261
UNII
24WC6T6X0G
EC Number
205-771-9
Nikkaji
J5.858K

物性

構造計算による物性

XLogP
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
10

実験および物理化学的性質

Chemical ClassesOther Classes -> Ethers, Other
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (p-Dimethoxybenzene) -> IFRA transparency List
LogP · 3 件

log Kow = 2.03

2.04

2.04

Odor · 2 件

SWEET CLOVER ODOR

SWEET, NUT-LIKE AROMA

TasteOILY, PHENOLIC TASTE

物理化学的性質

融点
54 · 54-56 °C(lit.)
沸点
213 °C · 213 °C(lit.)
比重(密度)
1.053 g/mL · 1.053 g/mL at 25 °C(lit.)
蒸気密度
4.8 · 4.8 (vs air)
蒸気圧
1 mm · <1 mm Hg ( 20 °C)
屈折率
1.5231 · 1.5231 (estimate)

化学的性質

化学的特性white crystals or powder

安全と法規制

GHS分類

GHS Classification · 3 件

This chemical does not meet GHS hazard criteria for 97.5% (1792 of 1838) of all reports.

Not Classified

Aggregated GHS information provided per 1838 reports by companies from 7 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 4 件

Chemical: Benzene, 1,4-dimethoxy-

Commission Regulation (EC) No 1565/2000 (Repealed by Com.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

Status: Active Update: 12-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/2003

Benzene, 1,4-dimethoxy-: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsCombustible. Finely dispersed particles form explosive mixtures in air.
Hazards Summary · 1 件

Moderate skin irritant; Acts as general anesthetic in lethal-dose feeding studies of rats; [RTECS] Safe as a flavoring agent in food; [JECFA] Emergency treatment: see Hydroquinone and Quinone. [HSDB] No listed effects of short-term or long-term exposure; Insufficient data are available on the effect of this substance on human health, therefore utmost care must be taken. [ICSC] An irritant; [MSDSonline]

Reactive GroupEthers
Special ReportsOPDYKE DL J; FOOD COSMET TOXICOL 16 (1): 715 (1978). REVIEW WITH 18 REFERENCES ON DIMETHYLHYDROQUINONE INCLUDING TOXICITY, IRRITATION, SENSITIZATION, DEPIGMENTATION, METAB & PHARMACOLOGY.
Reactivity Profile1,4-DIMETHOXYBENZENE is an ether. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.

安全と保護具

Fire FightingUse water spray, powder, alcohol-resistant foam, carbon dioxide.
First Aid Measures · 4 件

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

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

Rinse mouth.

First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from strong oxidants.
Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

毒性情報

Ecotoxicity ValuesLC50 Pimephales promelas (fathead minnow) 117 mg/l 96 hr flow-through bioassay, wt 0.12 g, water hardness 45.5 mg/l calcium carbonate , temp: 25 + or - 1 °C, pH 7.5, dissolved oxygen greater than 60% of saturation
Environmental Fate · 3 件

TERRESTRIAL FATE: An estimated Koc of 300(1,SRC), calculated from an experimental log Kow of 2.03(2,SRC), suggests that hydroquinone dimethyl ether will have moderate mobility in soil(SRC), based upon a recommended classification scheme(3). Hydroquinone dimethyl ether may volatilize from moist soil surfaces based on an estimated Henry's Law constant of 3.5X10-3 atm-cu m/mole(4,SRC). It may volatilize from dry soil surfaces based on an estimated vapor pressure of 8.7X10-2 mm Hg(5,SRC). Incomplete information is available regarding the biodegradation potential of hydroquinone dimethyl ether; however, this compound was completely biodegraded within eight days under aerobic conditions using a mixed soil population(6); another soil isolate was unable to biodegrade this compound(7).

AQUATIC FATE: Hydroquinone dimethyl ether is expected to volatilize from water surfaces based on an estimated Henry's Law constant of 3.54X10-3 atm-cu m/mole(1,SRC). The volatilization half-life from a model river was estimated as 4 hours and from a model lake, 5 days(2,SRC) Photooxidation half-lives of 60 hours for continuous sunlight on the water's surface and 150 hours of continous sunlight at a 1 meter depth was measured for hydroquinone dimethyl ether in natural water(3). An estimated BCF value of 20(2,SRC), calculated from an experimental log Kow(4), indicates that hydroquinone dimethyl ether should not bioconcentrate in aquatic organisms(2,SRC). Incomplete information is available regarding the biodegradation potential of hydroquinone dimethyl ether, however, this compound was completely biodegraded within eight days under aerobic conditions using a mixed soil population(5); another soil isolate was unable to biodegrade this compound(6).

ATMOSPHERIC FATE: Based on an estimated vapor pressure of 8.7X10-2 mm Hg at 25 °C(1,SRC), hydroquinone dimethyl ether will exist mainly in the vapor phase(2,SRC). Hydroquinone dimethyl ether will degrade in the vapor phase by reaction with photochemically produced hydroxyl radicals (5X10+5 hydroxyl radicals per cu cm) with an estimated half-life of about 19 hours(3,SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by inhalation.
Toxicity Summary · 1 件

IDENTIFICATION AND USE: Hydroquinone dimethyl ether exists as white flakes or leaflets. It has a sweet clover or nut like odor and has an oily phenolic taste. It is slightly soluble in water; very soluble in ether, benzene, alcohol and acetone. It is used as a flavoring agent, weathering agent in paints and plastics, and as a fixative in perfumes, also used in dyes; resin intermediates, and in cosmetics, and flavoring agent. HUMAN EXPOSURE AND TOXICITY: Chronic neurotoxic effects include vision disturbances. Exposure to this chemical could result from industrial handling. ANIMAL STUDIES: In female rats fed a diet containing this chemical at a concentration of 2% or greater produced questionable results on growth. In dogs fed hydroquinone ethers only minor body weight loss was noted. A solution in olive oil containing this chemical caused a slight or moderate irritation to Guinea pig skin.

Effluent ConcentrationsHydroquinone dimethyl ether was detected in one occurrence in the wastewater from a petroleum refining company at unreported concentrations(1).

安全データ

wgk
1
tsca
TSCA listed
rtecs
CZ6650000
hs_code
29093090
risk_code
36/37/38
化審法
(3)-582

化学と産業

薬理情報

Metabolism/Metabolites1,4-DIMETHOXYBENZENE GIVES P-METHOXYPHENOL IN RABBIT. /FROM TABLE/
Cellular LocationsCytoplasm

用途と製造

Uses · 4 件

Used as a weathering agent in paints and plastics, a fixative in perfumes, and a flavoring additive; Also used in dyes, as a resin intermediate, and in cosmetics and suntan creams; [Hawley]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

WEATHERING AGENT IN PAINTS & PLASTICS; FIXATIVE IN PERFUMES; DYES; RESIN INT; COSMETICS; FLAVORING

HYDROQUINONE DIMETHYL ETHER IS USED AS INT IN MFR OF CERTAIN NAPHTHOL DYES & AS WEATHERING AGENT FOR PAINTS & PLASTICS. BECAUSE OF ITS FRAGRANT ODOR, IS ALSO USED...IN SOAP PERFUMES, LOTIONS, & CREAMS.

U.S. Imports · 2 件

(1977) 5.75X10+5 GRAMS (PRINCPL CUSTMS DISTS)

(1979) 2.77X10+7 GRAMS (PRINCPL CUSTMS DISTS)

U.S. Production · 2 件

(1977) PROBABLY GREATER THAN 4.54X10+6 GRAMS

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

Methods of ManufacturingMETHYLATION OF HYDROQUINONE USING DIMETHYLSULFATE & ALKALI
Use Classification · 4 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 2 件

Benzene, 1,4-dimethoxy-: ACTIVE

FEMA NO 2386; REPORTED USES: NON-ALCOHOLIC BEVERAGES, 8.1 PPM; ICE CREAM, ICES, ETC, 5.0 PPM; CANDY, 4.7 PPM; BAKED GOODS, 5.8 PPM. /FROM TABLE/

応用分野 · 4 件

用途有機合成原料、香料材料。

天然物の起源Reported found in hyacinth (Hyacinthus orientalis L.) essential oil, Rhodophyllus icterius, papaya, peppermint oil, green tea, cherimoya and cooked shrimp

使用1,4-Dimethoxybenzene is used as Pharmaceutical Intermediate. It is used in some paints and as a diazo dye. It is also used in perfumes and flavors in order to its floral odor. In addition, it is used on greasy skin, and with sulfur to treat acne, or as a dandruff treatment.

一般的な説明Colorless crystals.

調製方法

製造方法By methylation of hydroquinone using dimethyl sulfate and alkali.

純化方法Steam distil 1,4-dimethoxybenzene, then crystallise it from hexane or *benzene, and from MeOH or EtOH, but these are wasteful due to high solubilities. Dry it under vacuum. It also sublimes under vacuum. [Beilstein 6 IV 5718.]

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関連反応

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