3,3'-Dihydroxybenzidine

HCID 16918CAS 2373-98-0

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

3,3'-DIHYDROXYBENZIDINE2373-98-04,4'-Diamino-3,3'-biphenyldiol3,3'-Dioxybenzidine3,3'-Dihydroxy-4,4'-diaminobiphenyl3,3'-Dwuoksybenzydyna3,3-DihydroxybenzidineBenzidine, 3,3'-dihydroxy-HSDB 4051m,m'-Biphenol, 6,6'-diamino-4,4'-diaminobiphenyl-3,3'-diol3,3'-Biphenyldiol, 4,4'-diamino-
Weitere Namen anzeigen
HAB4,4'-Diamino-[1,1'-biphenyl]-3,3'-diol1’-biphenyl)-3,3’-diol,4,4’-diamino-(2-amino-5-(4-amino-3-hydroxyphenyl)phenolp-HABDihydroxybenzidine3,3’-dioxybenzidineBENZIDINE-3,3'-DIOL-Dihydroxybenzidine3,3'-Dihydroxybenzid
CCRIS 92253,3'-Dwuoksybenzydyna [Polish]OJ61P3RD7H(1,1'-Biphenyl)-3,3'-diol, 4,4'-diamino-BRN 2725972[1,1'-Biphenyl]-3,3'-diol, 4,4'-diamino-(1,1'-Biphenyl)-4,4'-diamine, 3,3'-dihydroxy-DTXSID5025073

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

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Benzidine and Derivatives
DecompositionWhen heated to decomposition, it emits toxic fumes of /nitrogen oxides/.
Melting Point320 °F (NTP, 1992)
Physical Description · 2 Einträge

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

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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

Health HazardsACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992)
Hazards SummaryA suspected carcinogen; [SAX] Emergency treatment: Methemoglobinemia; [HSDB] See Benzidine.
Reactive GroupPhenols and Cresols
Reactivity Profile · 1 Eintrag

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.

Air and Water ReactionsKeep well closed. Protect from air and light. (NTP, 1992)
Hazard Classes and CategoriesCarc. 1B (95.2%)

Sicherheit und Schutzausrüstung

Fire Fighting · 1 Eintrag

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 · 1 Eintrag

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 · 1 Eintrag

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 · 1 Eintrag

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.

Personal Protective Equipment (PPE)MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

Toxikologische Informationen

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Non-Human Toxicity Excerpts · 2 Einträge

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 · 1 Eintrag

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 · 2 Einträge

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 · 2 Einträge

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 · 1 Eintrag

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 · 2 Einträge

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 · 2 Einträge

(1975) NOT PRODUCED COMMERCIALLY IN USA

(1977) NOT PRODUCED COMMERCIALLY IN USA

Methods of ManufacturingBY ACIDIC IRON REDUCTION OF 4,4-DINITRO-3,3'-BIPHENOL
Anwendungen · 2 Einträge

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.

Vor- und nachgelagerte Produkte

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