HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
1,4-Dimethoxybenzol
dimethoxybenzene · DIMETHYLHYDROQUINONE · P-DIMETHOXYBENZENE · FEMA 2386 · 4-Methoxyanisole · HYDROQUINONE DIMETHYL ETHER · 1,4-Dimethoxybenzol · 1,4-dimethoxy-benzen
Identifikatoren & physikalische Daten
| CAS No. | 150-78-7 |
|---|---|
| Summenformel | C8H10O2 |
| Durchschnittliche Molmasse | 138,16 g/mol |
| Monoisotopische Masse | 138,06807956 g/mol |
| SMILES | COc1ccc(OC)cc1 |
| InChIKey | OHBQPCCCRFSCAX-UHFFFAOYSA-N |
| PubChem CID | 9016 |
| ChEMBL | CHEMBL1668604 |
| ChEBI | CHEBI:179261 |
| EC No. | 205-771-9 |
| DTXSID | DTXSID0022014 |
| Lokaler Name | 1,4-Dimethoxybenzol |
Chemische & physikalische Eigenschaften
| XLogP | 2 |
|---|---|
| Polarare Oberfläche (TPSA) | 18,5 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 73,3 |
| Stoffklassen | Other Classes -> Ethers, Other |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Duftstoffe | Fragrance Ingredient (p-Dimethoxybenzene) -> IFRA transparency List |
| LogP (Verteilungskoeffizient) | log Kow = 2.032.04 |
| Geruch | SWEET CLOVER ODORSWEET, NUT-LIKE AROMA |
| Geschmack | OILY, PHENOLIC TASTE |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 1.053 at 131 °F (NTP, 1992) - Denser than waterwill sink1.0526 @ 55 °C/55 °C1.053 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Viscosity | 1.04 CENTIPOISE @ 65 °C |
| Color/Form | LEAFLETS FROM WATERWHITE FLAKES |
| Löslichkeit | Slightly soluble (NTP, 1992)SLIGHTLY SOL IN WATERVERY SOL IN ETHER, BENZENE1:10 IN 95% ALCOHOLSOL IN ACETONESolubility in water: noneSlightly soluble in waterdioxane: 0.1 g/mL, clear0.8 g/l (20 ºC) |
| Schmelzpunkt | 54-56 °C(lit.) |
| Siedepunkt | 213 °C(lit.) |
| Dampfdichte | 4.8 (vs air) |
| Dampfdruck | <1 mm Hg ( 20 °C) |
| Brechungsindex | 1.5231 (estimate) |
| FEMA | 2386 | P-DIMETHOXYBENZENE |
| Flammpunkt | 98 °C |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | Crystalline Powder, Crystals, or Flakes |
| Farbe | White |
| Wichte | 1.053 |
| Geruch | at 1.00 % in dipropylene glycol. sweet green new mown hay fennel |
| pH | 7 (H2O, 20℃)(saturated solution) |
| Explosionsgrenze | 1.2-5.6%(V) |
| Geruchsart | green |
| Biologische Quelle | synthetic |
| JECFA Number | 1250 |
| BRN | 774605 |
| Henry-Konstante | 2.8×10-3 mol/(m3Pa) at 25℃, HSDB (2015) |
| Dielektrizitätskonstante | 4.5(23℃) |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | cleaning productscosmeticsfood and beveragespersonal care |
| Kosmetik-Inhaltsstoffe Funktionen | 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 (Verteilungskoeffizient) | 2.08 at 20℃ |
| CAS Datenbank | 150-78-7(CAS DataBase Reference) |
| NIST chemische Informationen | Benzene, 1,4-dimethoxy-(150-78-7) |
| EPA chemische Informationen | p-Dimethoxybenzene (150-78-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 97.5% (1792 of 1838) of all reports.Not ClassifiedAggregated GHS information provided per 1838 reports by companies from 7 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | 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/2003Benzene, 1,4-dimethoxy-: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Combustible. Finely dispersed particles form explosive mixtures in air. |
| Gefahrenübersicht | Moderate skin irritantActs 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 exposureInsufficient data are available on the effect of this substance on human health, therefore utmost care must be taken. [ICSC] An irritant[MSDSonline] |
| Reaktive Gruppe | Ethers |
| Special Reports | OPDYKE DL JFOOD COSMET TOXICOL 16 (1): 715 (1978). REVIEW WITH 18 REFERENCES ON DIMETHYLHYDROQUINONE INCLUDING TOXICITY, IRRITATION, SENSITIZATION, DEPIGMENTATION, METAB & PHARMACOLOGY. |
| Reactivity Profile | 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. |
| Chemical Dangers | Reacts with strong oxidants. |
| Physical Dangers | Dust explosion possible if in powder or granular form, mixed with air. |
| Air and Water Reactions | Slightly water soluble (NTP, 1992). |
| Hazard Classes and Categories | Not Classified |
| Explosive Limits and Potential | Explosive limits , vol% in air: 1.2-5.6 |
| Brandbekämpfung | Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | 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. |
| Erste Hilfe | 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. |
| Sichere Lagerung | Separated from strong oxidants. |
| Freisetung ohne Brand | 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. |
| Entsorgungsverfahren | 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. |
| Verschüttetes entsorgen | 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 Prevention | Wear safety spectacles. |
| Fire Prevention | NO open flames. NO contact with combustible substances. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust. |
| Inhalation Risk | 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. |
| Skin Prevention | Protective gloves. |
| Ingestion Prevention | Do not eat, drink, or smoke during work. |
| Ökotoxizitätswerte | LC50 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 |
| Umweltverhalten | 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 etherhowever, 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). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Expositionspfade | The substance can be absorbed into the body by inhalation. |
| Toxizitätsübersicht | 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 watervery 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 dyesresin 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 Concentrations | Hydroquinone dimethyl ether was detected in one occurrence in the wastewater from a petroleum refining company at unreported concentrations(1). |
| Soil Adsorption/Mobility | 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 Sources | REPORTED FOUND IN HYACINTH (HYACINTHUS ORIENTALIS L) ESSENTIAL OIL & IN RHODOPHYLLUS ICTERIUS. |
| Human Toxicity Excerpts | 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 mediumthey are equally toxic for melanona and non-melanoma cell linestheir toxicity is significantly reduced by addition of scavenger enzymeson 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 | 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 | 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 | 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). |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29093090 |
| RTECS-Nr. | CZ6650000 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36-24/25 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 150-78-7(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 1463 °F |
Anwendungen & Verwendung
Occurrence
Reported found in hyacinth (Hyacinthus orientalis L.) essential oil, Rhodophyllus icterius, papaya, peppermint oil, green tea, cherimoya and cooked shrimp
Verwenden
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.
Herstellung & Synthese
synthetische
By methylation of hydroquinone using dimethyl sulfate and alkali.