Description
4-Chloro-o-phenylene-diamine is a browncrystalline powder or leaflets from water; Freezing/Meltingpoint =67-70℃; also reported at 76℃
Chemical Properties
4-Chloro-o-phenylenediamine is a brown crystalline powder or leaflets from water; freezing/melting point 67-73°C; also reported in lit. @ 76°C. Slightly soluble in water. soluble in benzene, very soluble in ethanol, ether.
Uses
4-Chloro-o-phenylenediamine can be used as an oxidation base for dye preparation, as a chemical intermediate to produce 5-chlorobenzotriazole, as a curing agent for epoxy resins, as a reagent in gas chromatography, and to synthesize experimental pharmaceuticals. It has been used as a chemical intermediate in dye production and was patented as a hair-dye component, but there is no evidence that it is currently used in the United States for these purposes (IARC 1982, HSDB 2009).
Definition
ChEBI: 4-Chloro-ortho-phenylenediamine is a member of monochlorobenzenes. Undergoes cyclizations and cyclocondensations to form benzimidazoles.
Production Methods
Commercial production of 4-chloro-o-PDA in the United
States was first reported in 1941. About 0.45–4.5 thousand kg
was produced by a U.S. company in 1977. It was also
produced by one company in the Federal Republic of
Germany. This compound has been patented as a hair dye
component, fur dyes, inks, and hair coloring formulations,
and is believed to be used to produce 5-chlorobenzotriazole,
an isomer of which is a photographic chemical.
The primary routes of potential human exposure to 4-
chloro-o-PDA are inhalation and dermal contact during its
production. Consumer exposure may occur from use of hair
dyes or products made from 5-chlorobenzotriazole.
General Description
4-chloro-o-phenylenediamine appears as brown crystalline solid or powder. (NTP, 1992)
Air & Water Reactions
4-Chloro-1,2-diaminobenzene may be sensitive to prolonged exposure to air and light. Insoluble in water.
Reactivity Profile
4-Chloro-1,2-diaminobenzene is incompatible with strong oxidizers. 4-Chloro-1,2-diaminobenzene reacts with alpha-ketoacids to form quinoxalones.
Fire Hazard
Flash point data for 4-Chloro-1,2-diaminobenzene are not available. 4-Chloro-1,2-diaminobenzene is probably combustible.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic and
neoplastigenic data. Human mutation data
reported. When heated to decomposition it
emits toxic fumes of Cland NOx. See also
AROMATIC AMINES.
Potential Exposure
This organochlorine material has been
patented as a hair dye component. It is believed to be used
in production of photographic chemicals. In varying
degrees, organochlorines are absorbed from the gut and
also by the lung and across the skin.
First aid
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least20 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit
Carcinogenicity
4-Chloro-o-phenylenediamine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity fromstudies in experimental animals.
storage
Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. A regulated, marked area should be establishedwhere this chemical is handled, used, or stored in compliance with OSHA Standard 1910.1045. Store in tightlyclosed containers in a cool, well-ventilated place or arefrigerator.
Shipping
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. UN3143 Dyes, solid, toxic, n.o.s. or Dye
intermediates, solid, toxic, n.o.s., Hazard Class: 6.1;
Labels: 6.1-Poisonous materials, Technical Name Required.
Purification Methods
Recrystallise the diamine from pet. ether. [Beilstein 13 IV 68.]
Incompatibilities
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Light sensitive. It reacts
with alpha-ketoacids to form quinoxalones or
benzopyrazines.
Waste Disposal
Disposal of unused product
must be undertaken by qualified personnel who are knowledgeable in all applicable regulations and follow all pertinent safety precautions including the use of appropriate
protective equipment. For proper handling and disposal,
always comply with federal, state, and local regulations.
References
[1] Journal of Organic Chemistry, 2013, vol. 78, # 9, p. 4530 - 4542
[2] Synlett, 2014, vol. 25, # 10, p. 1403 - 1408
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 22, p. 4367 - 4379
[4] Journal of Organic Chemistry, 1995, vol. 60, # 18, p. 5838 - 5842
[5] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 2, p. 187 - 190
