4,4'-Diacetylbenzidine

  • 4',4'''-biacetanilide
  • N,N'-(1,1'-biphenyl)-4,4'-diylbis-acetamide 4',4'''-biacetanilide
  • N,N'-4,4'-Biphenylylenebisacetamide
  • 4,4'-Diacetamidobiphenyl
  • 4,4'-Diacetylaminobiphenyl
  • Diacetylbenzidine
Formula
C16H16N2O2
Structure
Description
Needles from acetic acid.
Uses
Used to prepare 3,3'-dichlorobenzidine and 3,3'-dinitrobenzidine.

Registry Numbers and Inventories.
CAS
613-35-4
EC (EINECS/ELINCS)
210-338-2
EC Index Number
612-044-00-3
EC Class
Harmful
RTECS
DT2800000
RTECS class
Tumorigen; Mutagen
Beilstein/Gmelin
2217711
Beilstein Reference
4-13-00-00373
Canada DSL/NDSL
NDSL
US TSCA
Listed

Properties.
Formula
C16H16N2O2
Formula mass
268.34
Boiling point, °C
199
Vapor pressure, mmHg
0.15 (25 C)
Density
0.9272 g/cm3 (25 C)
Solubility in water
Very soluble
Refractive index
1.4329
pKa/pKb
5.04 (pKa)
Heat of vaporization
47.9 kJ/mol
Heat of combustion
-8114 kJ/mol

Hazards and Protection.
Storage
Storage should be close to laboratory where material is to be used, so that only small amounts need to be carried. Carcinogens should be kept in only one section of storage area, explosion-proof refrigerator or freezer as required. The area should be appropriately labeled. An inventory should be kept showing the quantity of carcinogen and date it was acquired. Facilities for dispensing should be contiguous to storage area.
Handling
All chemicals should be considered hazardous. Avoid direct physical contact. Use appropriate, approved safety equipment. Untrained individuals should not handle this chemical or its container. Handling should occur in a chemical fume hood.
Protection
Dispensers of liquid detergent should be available. In the laboratory, gloves and protective clothing should always be worn but should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, and disposable plastic aprons might provide additional protection. Protective clothing should be of distinctive color, as a reminder not to be worn outside the laboratory.
Respirators
Use NIOSH/MSHA approved respirator appropriate for exposure of concern.
Small spills/leaks
Evacuate area and ventilate. Wear protective equipment. If required, use an inert absrobent. Sweep up and place in an appropriate container for disposal. Wash contaminated surfaces.
Stability
Change on exposure to light, due to photooxidation.
Incompatibilities
Strong oxidizing agents.

Fire.
Flash Point,°C
96
Fire fighting
Wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use agent most appropriate to extinguish fire.

Health.
Carcinogin
I-2B, CP65
Exposure effects
CNS effects include headache, dizziness, altered mental status, confusion (lethargy progressing coma), seizures, syncope; occur secondary to CNS hypoxia, usually with levels > 20%.
   Ingestion
Nausea and vomiting may occur.
   Inhalation
Dyspnea and tachypnea may occur.
   Skin
Central cyanosis unresponsive to oxygen therapy is classic.

First aid
 
   Ingestion
Emesis: ipecac-induced vomiting is not recommended because of the potential for cns depression and seizures. Activated charcoal: administer charcoal as a slurry (240 ml water/30 g charcoal). Usual dose: 25 to 100 g in adults/adolescents. Consider after ingestion of a potentially life-threatening amount of poison if it can be performed soon after ingestion (generally within 1 hour). Oxygen - administer oxygen to all cyanotic or symptomatic patients. Methemoglobinemia: administer 1 to 2 mg/kg of 1% methylene blue slowly iv in symptomatic patients. Additional doses may be required. Shock and cardiac arrest - treat routinely. Adjunctive therapy - exchange transfusions and hyperbaric oxygen may be useful in severe cases.
   Inhalation
If symptoms develop, move individual away from exposure and into fresh air. If symptoms persist, seek medical attention. If breathing is difficult, administer oxygen. Keep person warm and quiet; seek immediate medical attention.
   Skin
Some methemoglobinemia producing chemicals are readily absorbed through the skin to produce adverse systemic effects. Aniline and related compounds may be rapidly absorbed by all routes. Skin contact with contaminated clothing or shoes may result in adverse systemic effects. Skin should be thoroughly washed with soap and water. Contaminated clothing and shoes should be discarded. Seek medical attention. Administer 100 percent humidified supplemental oxygen with assisted ventilation as required. Treat for methemoglobinemia and sequelae. Signs and symptoms of methemoglobinemia may be delayed. Methemoglobinemia: administer 1 to 2 mg/kg of 1% methylene blue slowly iv in symptomatic patients. Additional doses may be required.
   Eyes
If symptoms develop, immediately move individual away from exposure and into fresh air. Flush eyes gently with water for at least 15 minutes while holding eyelids apart; seek immediate medical attention.

Transport.