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1,4-Dimethoxybenzene

HCID 9016
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
150-78-7
Standard SMILES
COc1ccc(OC)cc1
InChIKey
OHBQPCCCRFSCAX-UHFFFAOYSA-N
Molecular formula
C8H10O2
Average molar mass
138.16 g/mol
Monoisotopic mass
138.06807956

Overview

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

Names & identifiers

Preferred name
1,4-Dimethoxybenzene
IUPAC
1,4-dimethoxybenzene
English name
1,4-Dimethoxybenzene
Molecular formula
C8H10O2
Molecular weight
138.16

Names & synonyms

1,4-Dimethoxybenzene150-78-7p-Dimethoxybenzenep-MethoxyanisoleHYDROQUINONE DIMETHYL ETHERBenzene, 1,4-dimethoxy-Benzene, p-dimethoxy-4-MethoxyanisoleQuinol dimethyl ether1,4-DimethoxybenzolDimethylhydroquinone etherDimethyl ether hydroquinone
Show more names
dimethoxybenzeneDIMETHYLHYDROQUINONEFEMA 23861,4-dimethoxy-benzen4-DiMethoxybenzene1,4-dimethoxybezene
USAF AN-9Dimethyl hydroquinoneHydroquinone, dimethyl etherMethyl p-methoxyphenyl etherDimethylether hydrochinonuFEMA No. 2386para-dimethoxybenzeneDTXSID0022014

Database identifiers

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

Properties

Computed structural properties

XLogP
2
Topological polar surface area
18.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
10
Formal charge
0
Complexity
73.3

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Ethers, Other
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (p-Dimethoxybenzene) -> IFRA transparency List
LogP · 4 items

log Kow = 2.03

2.04

2.04

2.03

Odor · 2 items

SWEET CLOVER ODOR

SWEET, NUT-LIKE AROMA

TasteOILY, PHENOLIC TASTE
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 2 items

1.053 at 131 °F (NTP, 1992) - Denser than water; will sink

1.0526 @ 55 °C/55 °C

Flavoring AgentsEU Flavoring substances
Viscosity1.04 CENTIPOISE @ 65 °C

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 3 items

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.

Hazard information

Regulatory Information · 4 items

Chemical: Benzene, 1,4-dimethoxy-

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

REACH registered substance: 1,4-dimethoxybenzene (EC: 205-771-9)

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 item

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.

Chemistry & industry

Pharmacology

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

Uses & manufacturing

Uses · 4 items

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 items

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

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

U.S. Production · 2 items

(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 items

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 items

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/

Related reactions

59 records
New reaction record
HRID 25913 reaction equation
HRID 25913As reactantuspto-grants-1979_04
HRID 217582 reaction equation
HRID 217582As reactantuspto-grants-2012_06
HRID 223557 reaction equation
HRID 223557As reactantuspto-grants-1982_10
HRID 239613 reaction equation
HRID 239613As reactantuspto-grants-2014_02
HRID 294317 reaction equation
HRID 294317As reactantTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 309820 reaction equation
HRID 309820As reactantTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 347395 reaction equation
HRID 347395As reactantuspto-grants-2007_02
HRID 370880 reaction equation
HRID 370880As reactantuspto-grants-1985_07
Page 1 of 8

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Color/Form · 2 items

LEAFLETS FROM WATER

WHITE FLAKES

Solubility · 6 items

Slightly soluble (NTP, 1992)

SLIGHTLY SOL IN WATER; VERY SOL IN ETHER, BENZENE

1:10 IN 95% ALCOHOL

SOL IN ACETONE

Solubility in water: none

Slightly soluble in water

Physicochemical properties

Melting point
54 · 54-56 °C(lit.)
Boiling point
213 °C · 213 °C(lit.)
Density
1.053 g/mL · 1.053 g/mL at 25 °C(lit.)
vapor density
4.8 · 4.8 (vs air)
vapor pressure
1 mm · <1 mm Hg ( 20 °C)
refractive index
1.5231 · 1.5231 (estimate)
FEMA
2386 · 2386 | P-DIMETHOXYBENZENE
FLAVIS Number
4.034 · 04.034 | 1,4-Dimethoxybenzene
Flash point
98 °C · 98 °C
storage temp.
Sealed in dry,Room Temperature
solubility
0.1 g/mL, · dioxane: 0.1 g/mL, clear
form
Crystalline Powder, Crystals, or Flakes
color
White
Specific Gravity
1.053 · 1.053
Odor
1 % · at 1.00 % in dipropylene glycol. sweet green new mown hay fennel
PH
7 · 7 (H2O, 20℃)(saturated solution)
explosive limit
1.2 · 1.2-5.6%(V)
Odor Type
green
biological source
synthetic
Water Solubility
0.8 g/l · 0.8 g/l (20 ºC)
Sensitive
Light Sensitive
JECFA Number
1250 · 1250
BRN
774605 · 774605
Henry's Law Constant
2.8 · 2.8×10-3 mol/(m3Pa) at 25℃, HSDB (2015)
Dielectric constant
4.5 · 4.5(23℃)
Stability
Stable. Combustible. Incompatible with strong oxidizing agents.
Major Application
cleaning productscosmeticsfood and beveragespersonal care
Cosmetics Ingredients Functions
PERFUMING
InChI
1S/C8H10O2/c1-9-7-3-5-8(10-2)6-4-7/h3-6H,1-2H3
InChIKey
OHBQPCCCRFSCAX-UHFFFAOYSA-N
SMILES
COc1ccc(OC)cc1
LogP
2.08 at · 2.08 at 20℃
CAS DataBase Reference
150 · 150-78-7(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
P-DIMETHOXYBENZENE
EWG's Food Scores
1 · 1
FDA UNII
24 WC6T6X0G · 24WC6T6X0G
NIST Chemistry Reference
1 · Benzene, 1,4-dimethoxy-(150-78-7)
EPA Substance Registry System
p-Dimethoxybenzene (150-78-7)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319
Precautionary statements
280 g-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 · P280g-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36-24/25
WGK Germany
1 · 1
RTECS
6650000 · CZ6650000
Autoignition Temperature
1463 °F · 1463 °F
TSCA
TSCA listed
HS Code
29093090 · 29093090
Storage Class
11 · 11 - Combustible Solids
Hazardous Substances Data
150 · 150-78-7(Hazardous Substances Data)
REACH Registrations
Active
Chemical DangersReacts with strong oxidants.
Physical DangersDust explosion possible if in powder or granular form, mixed with air.
Air and Water ReactionsSlightly water soluble (NTP, 1992).
Hazard Classes and CategoriesNot Classified
Explosive Limits and PotentialExplosive limits , vol% in air: 1.2-5.6

Safety & protection

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

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 item

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 item

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 item

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.

Spillage Disposal · 1 item

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Ventilation. Remove all ignition sources. Sweep spilled substance into covered sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Eye PreventionWear safety spectacles.
Fire PreventionNO open flames. NO contact with combustible substances. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
Skin PreventionProtective gloves.
Ingestion PreventionDo not eat, drink, or smoke during work.

Toxicology

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 items

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 item

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).
Soil Adsorption/Mobility · 1 item

Based on an experimental log Kow of 2.03(1), the Koc of hydroquinone dimethyl ether is estimated as approximately 300 using a regression-derived equation(2,SRC). According to a suggested classification scheme(3), this estimated Koc value suggests that hydroquinone dimethyl ether will have moderate mobility in soil(SRC).

Natural Pollution SourcesREPORTED FOUND IN HYACINTH (HYACINTHUS ORIENTALIS L) ESSENTIAL OIL & IN RHODOPHYLLUS ICTERIUS.
Human Toxicity Excerpts · 2 items

Cell lines Raji and K 562, lacking tyrosinase, and two melanotic human melanoma cell lines (IRE 1 and IRE 2), were exposed to concentrations from 5 X 10(-3) M to 10(-51 M of different phenols which are substrates of tyrosinase, ie 1-dopa, dopamine, hydroquinone, tertbutylcatechol, and of phenols which are not substrates of the tyrosinase ie resorcinol butylated hydroxyanisole and hydroquinone dimethyl ether. Cultures were carried out in the presence or in the absence of oxygen radical scavenger enzymes superoxide dismutase catalase and peroxidase. The stability of each substance in culture medium was assayed by high performance liquid chromatography. Results showed that: catechols which are substrates of tyrosinase decompose fully after 24 hr in medium; they are equally toxic for melanona and non-melanoma cell lines; their toxicity is significantly reduced by addition of scavenger enzymes; on the contrary phenols not substrates of tyrosinase are stable in medium and their toxicity is not reduced by scavenger enzynes. Tyrosinase does not play a major role in catechol toxicity in vitro.

Chronic neurotoxic effects include vision disturbances. /From table/ /Quinones/

Artificial Pollution Sources · 1 item

Hydroquinone dimethyl ether's production and subsequent use as a weathering agent in paints and plastics, as a fixative in perfumes and in cosmetics, as an intermediate in the production of dyes and resins, and as a flavoring(1) may result in its release to the environment through various waste streams(SRC).

Environmental Biodegradation · 1 item

Eight days were required to completely degrade hydroquinone dimethyl ether using a mixed soil population, as measured by loss of UV absorbance (indicates ring cleavage)(1). Hydroquinone dimethyl ether, when present as the sole carbon source, was not utilized by a bacterial soil isolate for growth over 30 days(2).

Environmental Bioconcentration · 1 item

An estimated BCF value of 20 was calculated for hydroquinone dimethyl ether(SRC), using an experimental log Kow of 2.03(2) and a recommended regression-derived equation(1). This BCF value suggests that hydroquinone dimethyl ether will not bioconcentrate in aquatic organisms(SRC).

Safety data

wgk
1
tsca
TSCA listed
rtecs
CZ6650000
hs_code
29093090
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36-24/25
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319
REACH Registrations
Active
Autoignition Temperature
1463 °F
Precautionary statements
P280g-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Hazardous Substances Data
150-78-7(Hazardous Substances Data)
Applications · 4 items

OccurrenceReported found in hyacinth (Hyacinthus orientalis L.) essential oil, Rhodophyllus icterius, papaya, peppermint oil, green tea, cherimoya and cooked shrimp

Uses1,4-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.

UsesWeathering agent in paints and plastics, fixative in perfumes, dyes, resin intermediate, cosmetics, especially suntan preparations, flavoring.

General DescriptionColorless crystals.

Preparation methods

PreparationBy methylation of hydroquinone using dimethyl sulfate and alkali.

Upstream & downstream products

Upstream raw materials

HydroquinoneMetaclazepamDimethyl sulfate

Downstream products

Methyl 2-amino-2-(4-hydroxyphenyl)acetatecis-AnetholAcemetacinN-Isopropylacrylamide1-(2,5-Dimethoxyphenyl)-2-oximino-1-propanoneDemosan2,3-Dichloro-5,8-dihydroxy-1,4-naphthoquinoneAstemizole2,5-Dimethoxypropiophenone1,4-Dimethoxy-2-nitrobenzene(2,5-Dimethoxyphenyl)acetic acid1-(2 5-Dimethoxyphenyl)-2-aminopropane&2,5-Dichlorobenzo-1,4-quinone2,5-Dimethoxyaniline2,5-Dihydroxybenzonitrile2,5-dimethoxyterephthalohydrazide2-tert-butyl-1,4-dimethoxybenzene2-Acetoxy-2',5'-methoxybenzophenone(2,5-dimethoxyphenyl)-pyridin-2-ylmethanol

Additional notes

DefinitionChEBI: 1,4-Dimethoxybenzene is a dimethoxybenzene.