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3,3'-Dimethoxy-benzidin
3,3'-Dimethoxybenzidine · FAST BLUE B BASE · 3,3'-Dimethoxy-[1,1'-biphenyl]-4,4'-diamine · ai3-00864 · c.i.24110 · bluebasenb · bluebnbase · C.I. 24110
Identifikatoren & physikalische Daten
| CAS No. | 119-90-4 |
|---|---|
| Summenformel | C14H16N2O2 |
| Durchschnittliche Molmasse | 244,29 g/mol |
| Monoisotopische Masse | 244,12117775 g/mol |
| SMILES | COc1cc(-c2ccc(N)c(OC)c2)ccc1N |
| InChIKey | JRBJSXQPQWSCCF-UHFFFAOYSA-N |
| PubChem CID | 8411 |
| ChEMBL | CHEMBL398363 |
| ChEBI | CHEBI:82321 |
| EC No. | 204-355-4 |
| DTXSID | DTXSID3025091 |
| Lokaler Name | 3,3'-Dimethoxy-benzidin |
Chemische & physikalische Eigenschaften
| XLogP | 2,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 70,5 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 18 |
| Formalladung | 0 |
| Komplexität | 236 |
| Stoffklassen | Hazardous Air Pollutants (HAPs)Carcinogens |
| Polymers | Nitrogen Compounds -> Amines, Polyaromatic |
| pH | WEAK BASE |
| LogP (Verteilungskoeffizient) | log Kow = 1.81 |
| Color/Form | LEAFLETS OR NEEDLES FROM WATERColorless crystals that turn a violet color on standing. |
| Löslichkeit | less than 0.1 mg/mL at 68 °F (NTP, 1992)Sol in alc, benzene, etherSol in chloroform, acetonePROBABLY SOL IN MOST ORG SOLVENTS AND LIPIDSIn water, 60 mg/l @ 25 °CSolubility in water, g/100ml at 25 °C: 0.006H2O: slightly solubleSoluble in alcohol, benzene, ether, chloroform, acetone, most organic solvents and lipids. Slightly soluble in water. |
| Flammpunkt | 403 °F (NTP, 1992)206 °C206 °C (403 °F) (closed cup)206 °C c.c. |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Decomposition | When heated to decomp it emits toxic fumes of /nitrogen oxides/. |
| Schmelzpunkt | 279 to 280 °F (NTP, 1992)137 °C137.5 °C279 °F137-138 °C(lit.) |
| Dampfdichte | 8.5 (NTP, 1992) - Heavier than airwill sink (Relative to Air)8.43 (air= 1) |
| Dampfdruck | negligible |
| Siedepunkt | 387.21°C (rough estimate) |
| Dichte | 1.1079 (rough estimate) |
| Brechungsindex | 1.6000 (estimate) |
| Lagerbedingungen | Store at RT. |
| pKa (Säurekonstante) | 4.71±0.10(Predicted) |
| Aggregatzustand | Crystalline Powder |
| Farbe | Pink to beige-brown |
| Merck | 14,2991 |
| BRN | 1879884 |
| Henry-Konstante | 2.1×105 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C14H16N2O2/c1-17-13-7-9(3-5-11(13)15)10-4-6-12(16)14(8-10)18-2/h3-8H,15-16H2,1-2H3 |
| InChIKey | JRBJSXQPQWSCCF-UHFFFAOYSA-N |
| SMILES | COc1cc(ccc1N)-c2ccc(N)c(OC)c2 |
| CAS Datenbank | 119-90-4(CAS DataBase Reference) |
| NIST chemische Informationen | Benzidine, 3,3'-dimethoxy-(119-90-4) |
| EPA chemische Informationen | 3,3'-Dimethoxybenzidine (119-90-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: [1,1'-Biphenyl]-4,4'-diamine, 3,3'-dimethoxy-Hazard Traits - CarcinogenicityThe 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.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzidine congeners: Human health tier II assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | This chemical is combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| Brandpotenzial | Combustible when exposed to heat or flame. |
| Gesundheitsgefahren | Excerpt from NIOSH Pocket Guide for o-Dianisidine: |
| Gefahrenübersicht | 3,3'-Dimethoxybenzidine is used as an intermediate in the production of dyes and pigments. No information is available on the acute (short-term), chronic (long-term), reproductive, developmental, or carcinogenic effects of 3,3'-dimethoxybenzidine in humans. Animal studies have reported effects on the liver, kidneys, spleen, and bladder, and endocrine effects, gastritis, intestinal hemorrhage, and weight loss from chronic oral exposure. Increased incidences of tumors in several organs have been reported in rats orally exposed to 3,3'-dimethoxybenzidine or its salt. EPA has classified 3,3'-dimethoxybenzidine as a Group B2, probable human carcinogen.Causes liver injury and tumors in experimental animals[HSDB] No published epidemiology studies on dye workers and cancerCurrently, dye production in closed systems with low risk to workers[NTP] Classified by NIOSH as a carcinogen--reduce exposure to lowest feasible concentration[NIOSH] Symptoms: Irritation skin |
Anwendungen & Verwendung
Verwenden
o-Dianisidine is a starting material for the production of disazo dyes and pigments. Like benzidine and o-tolidine, o-dianisidine forms colors with numerous oxidizing agents, e.g., copper, cobalt, and gold ions. o-Dianisidine is quantitatively determined by titration with nitrite using potassium iodide and starch paper as the indicator. o-Dianisidine can be detected in the urine using potassium 1,2-naphthoquinone4-sulfonate after extraction. A rapid and easy method is based on the color formed with cyanogen bromide. Its detection limit is 0.05 mg/kg. The free o-dianisidine base and the dihydrochloride are marketed in moist forms with a 10-30% water content.
Herstellung & Synthese
synthetische
2-Nitroanisole is reduced (H2-catalyst or iron-formic acid) to o-anisidine or (benzidine-type reaction) to o-dianisidine [119-90-4], both of which are important as dye intermediates.