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Home > Encyclopedia > 1,4-Dimethoxybenzene

1,4-Dimethoxybenzene

1,4-Dimethoxybenzene structure

1,4-Dimethoxybenzene 

structure
  • CAS No:

    150-78-7

  • Formula:

    C8H10O2

  • Chemical Name:

    1,4-Dimethoxybenzene

  • Synonyms:

    Benzene,1,4-dimethoxy-;Benzene,p-dimethoxy-;1,4-Dimethoxybenzene;p-Dimethoxybenzene;DMB;Hydroquinone dimethyl ether;Quinol dimethyl ether;p-Methoxyanisole;4-Methoxyanisole;Methyl p-methoxyphenyl ether;1,4-Dimethoxybenzol;p-Hydroquinone dimethyl ether;Methyl 4-methoxyphenyl ether;NSC 7483

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

White crystals or powder Hydroquinone Dimethyl Ether occurs in hyacinth oil and has also been identified in tea. It is a white, crystalline solid (mp 57–58°C) with an intensely sweet, somewhat herbal, nut-like odor. Hydroquinone dimethyl ether is prepared by etherification of hydroquinone and is used in soap perfumes. p-Dimethoxybenzene has a bitter taste. Colorless crystals.


1,4-dimethoxybenzene appears as colorless crystals. (NTP, 1992)|Solid|WHITE FLAKES WITH CHARACTERISTIC ODOUR.|White crystals


1,4-dimethoxybenzene appears as colorless crystals. (NTP, 1992)|1,4-Dimethoxybenzene is a dimethoxybenzene.

1,4-Dimethoxybenzene Basic Attributes

138.16400

138.16

205-771-9

24WC6T6X0G

1297

7483

DTXSID0022014

LEAFLETS FROM WATER|WHITE FLAKES

29093090

Characteristics

18.46000

2

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

1.0526 g/cm3 @ Temp: 55 °C

58-60 °C

212.6 °C

98ºC

1.488

H2O: 0.8 g/l (20 ºC)

Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from

<1 mm Hg ( 20 °C)

4.8 (vs air)

vol% in air: 1.2.6

SWEET CLOVER ODOR

OILY, PHENOLIC TASTE

DIELECTRIC CONSTANT: 2.8|1 MG/L= 177 PPM @ 25 °C, 760 MM HG|UV: 476 (Sadtler Research Laboratories Spectral Collection) /Catechol dimethyl ether/

Slightly water soluble (NTP, 1992).

Ethers

1,4-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.

438 °C

Dust explosion possible if in powder or granular form, mixed with air.

Safety Information

NONH for all modes of transport

1

R36/37/38

S24/25

CZ6650000

Xi

Separated from strong oxidants.

Stable. Combustible. Incompatible with strong oxidizing agents.

P261-P305 + P351 + P338

H315-H319-H335

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.

OPDYKE DL J; FOOD COSMET TOXICOL 16 (1): 715 (1978). REVIEW WITH 18 REFERENCES ON DIMETHYLHYDROQUINONE INCLUDING TOXICITY, IRRITATION, SENSITIZATION, DEPIGMENTATION, METAB & PHARMACOLOGY.

Combustible. Finely dispersed particles form explosive mixtures in air.

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Explosive limits , vol% in air: 1.2-5.6

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.

Separated from strong oxidants.

No 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.

NO open flames. NO contact with combustible substances. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

Use ventilation.

Protective gloves.

Wear safety spectacles.

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

Toxicity

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.

REPORTED FOUND IN HYACINTH (HYACINTHUS ORIENTALIS L) ESSENTIAL OIL & IN RHODOPHYLLUS ICTERIUS.

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).

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).

Using pulse radiolysis, a rate constant of 7X10+9 dm cu/mol-sec at pH 6.5 was measured for the reaction of hydroquinone dimethyl ether with OH radicals in aqueous solution(1). Photooxidation half-lives of 60 hours for continuous sunlight on the water's surface and 150 hours for continous sunlight at a 1 meter depth were measured in natural water(2). The rate constant for the vapor-phase reaction of hydroquinone dimethyl ether with photochemically produced hydroxyl radicals has been estimated as 2.0X10-11 cu cm/molecule-sec at 25 °C(3,SRC). The half-life of hydroquinone dimethyl ether is approximately 19 hours based on a hydroxyl radical concentration of 5X10+5(3,SRC).

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).

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).

The Henry's Law constant for hydroquinone dimethyl ether is estimated as 3.5X10-3 atm-cu m/mole(1,SRC). This value indicates that hydroquinone dimethyl ether may volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec) is estimated as approximately 4 hours(2,SRC). The volatilization half-life from a model lake (1 m deep) is estimated as approximately 5 days(2,SRC).

SURFACE WATER: Hydroquinone dimethyl ether was detected in Rhine River water at concentrations of 0.1 ug/l at Lobith and 0.03 ug/l at Maassluis(1).

EXPOSURE TO DUSTS OF THESE HYDROQUINONE ETHERS COULD OCCUR AS RESULT OF INDUSTRIAL HANDLING. /HYDROQUINONE ETHERS/

Drug Information

1,4-DIMETHOXYBENZENE GIVES P-METHOXYPHENOL IN RABBIT. /FROM TABLE/

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


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.

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/

1,4-dimethoxybenzene

The substance can be absorbed into the body by inhalation.

1,4-Dimethoxybenzene Use and Manufacturing

Methods of Manufacturing

METHYLATION OF HYDROQUINONE USING DIMETHYLSULFATE & ALKALI

Uses

1,4-Dimethoxybenzene is an organic compound with the formula C6H4(OCH3)2. It is one of three isomers of dimethoxybenzene. It is a white solid with an intensely sweet floral odor. It is produced by several plant species.

Production

(1977) PROBABLY GREATER THAN 4.54X10+6 GRAMS|(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

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/

EPA Safer Chemical Functional Use Classes -> Fragrances|Safer Chemical Classes -> Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues|Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index

Flavoring Agents

Computed Properties

Molecular Weight:138.16
XLogP3:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:138.068079557
Monoisotopic Mass:138.068079557
Topological Polar Surface Area:18.5
Heavy Atom Count:10
Complexity:73.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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