4-Aminoazobenzol
P-AMINOAZOBENZENE · SOLVENT YELLOW 1 · 4-Aminoazobenzol · 4-(PHENYLDIAZENYL)ANILINE · 4-AMinoazobe · ANILINE YELLOW · AMINOAZOBENZENE · C.I. Solvent Yellow 1
Identifikatoren & physikalische Daten
| CAS No. | 25548-34-9 |
|---|---|
| Summenformel | C12H11N3 |
| Durchschnittliche Molmasse | 197,24 g/mol |
| Monoisotopische Masse | 197,09529735 g/mol |
| SMILES | Nc1ccc(N=Nc2ccccc2)cc1 |
| InChIKey | QPQKUYVSJWQSDY-UHFFFAOYSA-N |
| PubChem CID | 6051 |
| ChEMBL | CHEMBL1429559 |
| ChEBI | CHEBI:233869 |
| EC No. | 200-453-6 |
| DTXSID | DTXSID6024460 |
| Lokaler Name | 4-Aminoazobenzol |
Chemische & physikalische Eigenschaften
| XLogP | 3,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 50,7 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 201 |
| Stoffklassen | Dyes -> Azo DyesCarcinogens |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | log Kow = 3.412.62 |
| Dichte | 1.05 (NTP, 1992) - Denser than waterwill sink1.2828 (rough estimate) |
| Color/Form | Brownish-yellow needles with bluish castOrange monoclinic needles from alcoholYellow to tan crystals |
| Löslichkeit | less than 1 mg/mL at 66 °F (NTP, 1992)Freely sol in alcohol, benzene, chloroform, etherIn water, 32 mg/L at 25 °CChloroform (Slightly), Methanol (Slightly)29.59mg/L(25 ºC) |
| Siedepunkt | greater than 680 °F at 760 mmHg (NTP, 1992)Above 360 °C360 °C @760 [mm Hg]>360 °C(lit.) |
| Decomposition | When heated to decomp, emits toxic fumes of /nitrogen oxides/. |
| Schmelzpunkt | 262 °F (NTP, 1992)128 °C126 °C123-126 °C(lit.) |
| Dampfdruck | 0.0000014 [mmHg]1.40X10-6 mm Hg at 25 °C |
| Physical Description | 4-aminoazobenzene appears as odorless brownish-yellow needles with bluish coating, or an orange powder. (NTP, 1992)Brownish-yellow solid with a bluish tint[Merck Index] Yellow to tan or orange solid[HSDB] Brown-yellow crystals[MSDSonline] |
| Dissociation Constants | pKa = 2.82 (conjugate acid) |
| Brechungsindex | 1.6500 (estimate) |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 2.82(at 25℃) |
| Farbe | Yellow crystals or orange needles with blue case from EtOH |
| Merck | 14,419 |
| BRN | 1913042 |
| Henry-Konstante | 1.1×105 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | cleaning productscosmeticsenvironmentalfood and beveragespersonal care |
| InChI | 1S/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2/b15-14+ |
| InChIKey | QPQKUYVSJWQSDY-CCEZHUSRSA-N |
| SMILES | Nc1ccc(cc1)\N=N/c2ccccc2 |
| CAS Datenbank | 60-09-3(CAS DataBase Reference) |
| NIST chemische Informationen | Benzenamine, 4-(phenylazo)-(60-09-3) |
| EPA chemische Informationen | 4-Aminoazobenzene (60-09-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH350: May cause cancer [Danger Carcinogenicity]P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)H301 (59.3%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P261, P264, P270, P272, P273, P280, P301+P316, P302+P352, P318, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Benzenamine, 4-(2-phenyldiazenyl)-Hazard Traits - CarcinogenicityStatus: Active Update: 09-12-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/4822Substance: 4-aminoazobenzene4-Aminoazobenzene: Does not have an individual approval but may be used under an appropriate group standardThe 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 - Benzenamine, 4-(phenylazo)-: Human health tier II assessment |
| DOT-Kennzeichnung | Class 9 |
| Brandgefahren | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound include methemoglobinemia, cyanosis, bluish discoloration of the lips, earlobes and fingernails, headache, dizziness and skin sensitization. |
| Gefahrenübersicht | A skin sensitizer, based on human patch test studies[HSDB] May cause methemoglobinemia and skin sensitization. May be fatal by inhalation, ingestion, or skin absorption[CAMEO] An eye irritantTargets the liver[MSDSonline] In a series of patients, about 30% of hairdressers with hand dermatitis had positive patch tests to p-Aminoazobenzene. [Kanerva, p. 1748] |
| Reaktive Gruppe | Azo, Diazo, Azido, Hydrazine, and Azide Compounds |
Anwendungen & Verwendung
Beschreibung
Anilingelb N ist zum Färben von Textilien vollkommen ungeeignet. Der Farbstoff wurde früher unter der Bezeichnung Spritgelb zum Färben von Spirituslacken und Fetten. Auch zum Färben von Lebensmitteln wurde Anilingelb N verwendet. Heute ist der Farbstoff ohne technische Bedeutung, da er krebserzeugend wirkt. Anilingelb N war unter folgenden Markenbezeichnungen im Handel: Anilingelb N I.G. Farbenindustrie AGNULL
Beschreibung
This azoic coloring can be reduced in paraphenylenediamine (PPD). It ean be found in some semipermanent hair dyes, and patch tests are frequently positive (about 30%) in hairdressers with hand dermatitis. Because of cross-sensitivity, the detection of sensitization to p-aminoazobenzene may be assumed by a PPD test.
Verwenden
In form of its salts in dyeing; intermediate in manufacture of Acid Yellow, diazo dyes and indulines.
Herstellung & Synthese
synthetische
commonly known as Aniline Yellow. (a) anilinehydrochloride solution added to a anilinediazonium salt, and slowly, until anilinediazonium salt salt disappear so far. Then in contain a small amount of anilinehydrochloride anilinesolution will product (Diazoaminobenzene) 30 ~ 40 ℃ heating 2 ~ 3 hours,acidified to form 4-(Phenyldiazenyl)benzenaminehydrochloride and crystalline precipitates. In order to obtain 4-(Phenyldiazenyl)benzenaminetimes the company, and then 4-(Phenyldiazenyl)benzenamine hydrochloride dissolved in water and mercerized. (B) anilinediazotization and coupling anilino-methanesulfonic acid, sodium hydroxide solution and then with boiled together, hydrolyzed mesylate.