Grundinformationen
- Standard-SMILES
Nc1ccc(-c2ccc(N)c(O)c2)cc1O- InChIKey
ZGDMDBHLKNQPSD-UHFFFAOYSA-N- Summenformel
- C12H12N2O2
- Durchschnittliche Molmasse
- 216,24 g/mol
- Monoisotopische Masse
- 216,08987762
Überblick
3,3'-dihydroxybenzidine appears as colorless crystals. (NTP, 1992)
Namen und Bezeichner
- Bevorzugter Name
- 3,3'-Dihydroxybenzidine
- IUPAC
- 2-amino-5-(4-amino-3-hydroxyphenyl)phenol
- Englischer Name
- 3,3'-Dihydroxybenzidine
- Summenformel
- C12H12N2O2
- Molmasse
- 216.24
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
2373-98-0- PubChem CID
- 16918
- DTXSID
DTXSID5025073- ChEMBL
CHEMBL85811- UNII
- OJ61P3RD7H
- EC Number
- 679-800-2
- Nikkaji
- J36.114C
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,5
- Polarare Oberfläche (TPSA)
- 92,5 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 16
- Formalladung
- 0
- Komplexität
- 213
Experimentelle und physikochemische Eigenschaften
Physical Description
3,3'-dihydroxybenzidine appears as colorless crystals. (NTP, 1992)
Colorless solid; [CAMEO] Powder; [MSDSonline]
Physikochemische Eigenschaften
- Schmelzpunkt
- 292 °C · 292 °C
- Siedepunkt
- 356.65 °C · 356.65°C (rough estimate)
- Dichte
- 1.171 · 1.1710 (rough estimate)
- Brechungsindex
- 1.666 · 1.6660 (estimate)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- Wasserlöslichkeit
- Practically insoluble in water
- Aggregatzustand
- powder to crystal
- pka
- 9.15 · 9.15±0.10(Predicted)
- Farbe
- White to Gray to Brown
- InChI
- InChI=1S/C12H12N2O2/c13-9-3-1-7(5-11(9)15)8-2-4-10(14)12(16)6-8/h1-6,15-16H,13-14H2
- InChIKey
- ZGDMDBHLKNQPSD-UHFFFAOYSA-N
- SMILES
- C1(C2=CC=C(N)C(O)=C2)=CC=C(N)C(O)=C1
- CAS Datenbank
- 2373 · 2373-98-0(CAS DataBase Reference)
- EPA chemische Informationen
- 3 · 3,3-Dihydroxybenzidine (2373-98-0)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H350 (95.2%): May cause cancer [Danger Carcinogenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Reactivity Profile
3,3'-DIHYDROXYBENZIDINE is an aromatic amino. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Sicherheit und Schutzausrüstung
Fire Fighting
This compound is not very flammable but any fire involving this compound may produce dangerous vapors. You should evacuate the area. All firefighters should wear full-body protective clothing and use self-contained breathing apparatuses. You should extinguish any fires involving this chemical with a dry chemical, carbon dioxide, foam, or halon extinguisher. (NTP, 1992)
First Aid
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.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol 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 alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Disposal Methods
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.
Toxikologische Informationen
Non-Human Toxicity Excerpts
ORAL ADMIN OF 3,3'-DIHYDROXYBENZIDINE CAUSED A HIGH INCIDENCE OF HEPATOMA.
Suspected carcinogen with experimental carcinogenic, neoplastigenic, & tumorigenic data.
Probable Routes of Human Exposure
Processes in which dried dye is handled have the greatest potential for employee exposure during the manufacture or repackaging of benzidine-based dyes. ... During use of benzidine-based dyes, the greatest potential for exposure would be expected to be among dye-weighers who handle dry powders. /Benzidine-based dyes/
Antidote and Emergency Treatment
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
Sicherheitsdaten
- hs_code
- 29222990
- RTECS-Nr.
- DV4900000
- risk_code
- 40-45-48-36/37/38
- hazard_code
- T
- safety_code
- 22-53-45-36/37/39-26-6
- Giftige Stoffe Daten
- 2373-98-0(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Various bacteria and yeast normally found in the small and large intestine can reduce the azo bond in /some/ benzidine-based dyes and release benzidine. /Benzidine-based dyes/
Humans as well as other mammals can change (metabolize) /some/ benzidine-based dyes back to benzidine. The major organ in which /some/ benzidine-based dyes are metabolized to benzidine is the liver, but other organs also can do this to a greater or lesser degree. /Benzidine-based dyes/
Absorption, Distribution and Excretion
The average environmental exposure levels of four of the workers /in a dye manufacturing facility/ were 4.3, 5.2, 11.7, and 17.4 mg total particulate/cu m. The corresponding urinary concentrations of benzidine average 52, 11, 10, and 112 ppb, respectively /SRP: from the precursor during manufacturing/. /Benzidine-based dyes/
Verwendung und Herstellung
Uses
Used as an intermediate for C.I. Direct Blue 84, 95, 98, and 166; Not commercially produced in the US; [HSDB]
CHEM INT FOR CI DIRECT BLUE 84, 95, 98, AND 166
U.S. Production
(1975) NOT PRODUCED COMMERCIALLY IN USA
(1977) NOT PRODUCED COMMERCIALLY IN USA
Anwendungen
Beschreibung3,3'-Dihydroxybenzidine is an organic synthesis intermediate used as a raw material for the synthesis of fire-resistant polymers (polyhydroxyamino acids).3,3'-Dihydroxybenzidine is also used in the preparation of hydroxyl-containing polyimides, all of which are synthesised to be soluble in NMP when heated. 3,3'-Dihydroxybenzidine is used in the synthesis of polyimides with hydroxyl groups. The glass transition temperature (Tg) of polyimides ranges from 336-360°C, independent of the structure of the tetracarboxylic dianhydride. The storage modulus of some polyimides does not decrease at elevated temperatures. All polyimides thermally transform into polybenzoxazole when heated to 500°C for 1 hour under vacuum.
Verwenden4,4'-diaminobiphenyl-3,3'-diol is used as organic intermediates.
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