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p-Phenylenediamine(CAS No. 106-50-3)

p-Phenylenediamine C6H8N2 (cas 106-50-3) Molecular Structure

106-50-3 Structure

Identification and Related Records

【Name】
p-Phenylenediamine
【CAS Registry number】
106-50-3
【Synonyms】
1,4-Diaminobenzene
p-Phenylenediamine 97+ %
1,4-Phenylenediamine
para Phenylene diamine
P-Phene Diamine
3,4-Dichloraniline
1,4-benzenediamie
PDA
【EINECS(EC#)】
203-404-7
【Molecular Formula】
C6H8N2 (Products with the same molecular formula)
【Molecular Weight】
108.14
【Inchi】
InChI=1/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2
【InChIKey】
CBCKQZAAMUWICA-UHFFFAOYSA-N
【Canonical SMILES】
C1=CC(=CC=C1N)N
【MOL File】
106-50-3.mol

Chemical and Physical Properties

【Appearance】
white to light purple solid
【Density】
1.15 g/cm3
【Melting Point】
138-143℃
【Boiling Point】
267℃
【Vapour】
0.00817mmHg at 25°C
【Refractive Index】
1.66
【Flash Point】
156℃
【Water】
47 g/L (25℃)
【Solubilities】
47 g/L (25 °C)
【Color/Form】
WHITE TO SLIGHTLY RED CRYSTALS
WHITE PLATES FROM BENZENE, ETHER
【Stability】
Stable, but oxidizes when exposed to air. Incompatible with oxidizing agents. Store under inert atmosphere.
【HS Code】
29215119
【Storage temp】
2-8°C
【Spectral properties】
MAX ABSORPTION (CYCLOHEXANE): 246 NM (LOG E= 3.93), 315 NM (LOG E= 3.30); SADTLER REFERENCE NUMBER: 4111 (IR, PRISM); 1187 (UV)
IR: 8322 (Sadtler Research Laboratories IR Grating Collection)
UV: 6-80 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
MASS: 45 (Aldermaston, Eight Peak Index of Mass Spectra, UK)
【Computed Properties】
Molecular Weight:108.14112 [g/mol]
Molecular Formula:C6H8N2
XLogP3:-0.3
H-Bond Donor:2
H-Bond Acceptor:2
Rotatable Bond Count:0
Exact Mass:108.068748
MonoIsotopic Mass:108.068748
Topological Polar Surface Area:52
Heavy Atom Count:8
Formal Charge:0
Complexity:54.9
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Donor Count:2
Feature 3D Cation Count:2
Feature 3D Ring Count:1
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
T:Toxic
【Risk Statements】
R23/24/25;R36;R43;R50/53
【Safety Statements 】
S28;S36/37;S45;S60;S61
【HazardClass】
6.1
【Safety】

When tested by the United States Environmental Protection Agency, the EPA reported that in rats and mice chronically exposed to PPD in their diet, it simply depressed body weights, but there were no other clinical signs of toxicity, as were observed in several studies.?From?1992 to 2005 years, thirty-one published articles had been investigating a causal association between PPD and cancer . Associations between personal hair dye use and non-Hodgkin's lymphoma, multiple myeloma, acute leukemia, and bladder cancer ?were observed in at least one well-designed study with detailed exposure assessment, but were not consistently observed across studies.?
Hazard Codes:?ToxicT,DangerousN,VeryT+,HarmfulXn
Risk Statements: 23/24/25-36-43-50/53-63-36/37/38-45-40?
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.?
R36:Irritating to eyes.?
R43:May cause sensitization by skin contact.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R63:Possible risk of harm to the unborn child.?
R36/37/38:Irritating to eyes, respiratory system and skin.?
R45:May cause cancer.?
R40:Limited evidence of a carcinogenic effect.
Safety Statements: 28-36/37-45-60-61-28A-24/25-23-53?
S28:After contact with skin, wash immediately with plenty of soap-suds.?
S36/37:Wear suitable protective clothing and gloves.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S60:This material and its container must be disposed of as hazardous waste.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.?
S24/25:Avoid contact with skin and eyes.?
S23:Do not breathe vapour.?
S53:Avoid exposure - obtain special instructions before use.
RIDADR: UN 1673 6.1/PG 3
WGK Germany: 3
RTECS: SS8050000
F: 8-10-23
HazardClass: 6.1
PackingGroup: III
HS Code: 29215119

【PackingGroup 】
III
【Skin, Eye, and Respiratory Irritations】
... Is a skin and respiratory system sensitizer ...
Eye irritation.
【Transport】
UN 1673
【Fire Fighting Procedures】
WATER, CARBON DIOXIDE, DRY CHEM ... .
【Fire Potential】
COMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME.
【Formulations/Preparations】
ONE TECHNICAL GRADE OF PARA-PHENYLENEDIAMINE AVAILABLE IN THE USA HAS THE FOLLOWING SPECIFICATIONS: PURITY, 99.2% MINIMUM; MOISTURE CONTENT, 0.1% MAXIMUM; ORTHO-PHENYLENEDIAMINE (1,2-DIAMINOBENZENE) CONTENT, 0.1% MAXIMUM; AND IRON CONTENT, 50 MG/KG MAXIMUM.
【DOT Emergency Guidelines】
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Phenylenediamines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Phenylenediamines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Phenylenediamines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Phenylenediamines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Evacuation: ... Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /Phenylenediamines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire: Small fires: Dry chemical, CO2 or water spray. Large fires: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. /Phenylenediamines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. /Phenylenediamines/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Phenylenediamines/
【Reactivities and Incompatibilities】
Contact with strong oxidizers may cause fires and explosions.
Strong oxidizers.
【Other Preventative Measures】
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
The worker should immediately wash the skin when it becomes contaminated.
The worker should wash daily at the end of each work shift.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
【Protective Equipment and Clothing】
Employees should be provided with and required to use impervious clothing, gloves, face shields (eight-inch minimum), and other protective clothing necessary to prevent skin contact ... .
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Recommendations for respirator selection. Max concn for use: 2.5 mg/cu m. Respirator Class(es): Any supplied-air respirator operated in a continuous flow mode. Eye protection needed.
Recommendations for respirator selection. Max concn for use: 5 mg/cu m. Respirator Class(es): Any self-contained breathing apparatus with a full facepiece. Any supplied-air respirator with a full facepiece.
Recommendations for respirator selection. Max concn for use: 25 mg/cu m. Respirator Class(es): Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode.
Recommendations for respirator selection. Condition: Emergency or planned entry into unknown concn or IDLH conditions: Respirator Class(es): Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode. Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained breathing apparatus operated in pressure-demand or other positive-pressure mode.
Recommendations for respirator selection. Condition: Escape from suddenly occurring respiratory hazards: Respirator Class(es): Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted canister providing protection against the compound of concern and having a high-efficiency particulate filter. Any appropriate escape-type, self-contained breathing apparatus.
【Specification】

?p-Phenylenediamine , its cas register number is 106-50-3. It also can be called 1,4-Benzenediamine ; 1,4-Phenylenediamine ; 4-Phenylenediamine ; CI 76060 ; p-Phenylenediamine ; 1,4-Diaminobenzene ; 4-Aminoaniline ; 6PPD ; AI3-00710 ; BASF ursol D ; Benzofur D ; C.I. 76060 ; C.I. Developer 13 ; C.I. Oxidation Base 10 ; CCRIS 509 ; Fenylenodwuamina ; Fouramine D ; Paraphenylenediamine ; Pelagol D ; p-Aminoaniline ; p-Benzenediamine ; p-Diaminobenzene ; p-Fenylendiamin ; p-Phenyldiamine ; p-Phenylenediamine ; 1,4-Benzenediamine ; Phenylenediamine, para- ; p-Phenylenediamine .It is a white to light purple solid.

【Octanol/Water Partition Coefficient】
log Kow= -0.25
【Disposal Methods】
The following wastewater treatment technologies have been investigated for p-phenylenediamine: biological treatment.
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

REDUCTION OF 1-AMINO-4-NITROBENZENE WITH IRON AND HYDROCHLORIC ACID.
Prepn: A. Rinne, T. Zincke, Ber. 7, 869 (1874); Ger. pat. 202,170 (1907 to BASF), C. A. 3, 382 (1909); A.J. Quick, J. Am. Chem. Soc. 42, 1033 (1920); J.F. Norris, E.O. Cummings, Ind. & Eng. Chem. 17, 305 (1925). See also: Beilstein XIII, 61 (1930).
U.S. Imports

(1978) 1.50X10+6 G (PRINCPL CUSTMS DISTS)
(1982) 9.99X10+4 G (PRINCPL CUSTMS DISTS)
U.S. Production

(1978) PROBABLY GREATER THAN 4.54X10+6 G
(1982) PROBABLY GREATER THAN 4.54X10+6 G
【Usage】

Dyeing furs, also in photochemical measurements, accelerating vulcanization, manufacture azo dyes.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS.
【Therapeutic Uses】
A hair dye component, paraphenylenediamine, as a contact allergen for treatment of inflammatory diseases.
【Biomedical Effects and Toxicity】
PARAPHENYLENEDIAMINE HYDROCHLORIDE WAS APPLIED TO THE SKIN OF DOGS IN GELS AND FLUIDS, AS THEY ARE USED IN HAIR DYEING; ABSORPTION WAS DETERMINED BY COMPARING BLOOD CONCENTRATIONS WITH THAT OBTAINED AFTER IV INJECTION OF THE DIAMINE OVER A COMPARABLE PERIOD OF TIME. IT WAS CALCULATED THAT 16 MG WERE ABSORBED WHEN 50 ML OF A LAURYL SULFATE-BASED GEL CONTAINING 1.5 G PARAPHENYLENEDIAMINE WAS APPLIED FOR 3 HOURS AND FREE ACCESS TO AIR WAS ALLOWED (THE MAXIMAL BLOOD CONCENTRATION WAS 0.15 UG/ML). THIS AMOUNT ROSE TO 110 MG IF THE TREATED AREA WAS IMMEDIATELY COVERED WITH ALUMINUM FOIL (THE MAXIMAL BLOOD CONCENTRATION WAS 0.5 UG/ML). /P-PHENYLENEDIAMINE HYDROCHLORIDE/
THE DISTRIBUTION KINETICS OF THE (3)H-LABELED P-PHENYLENEDIAMINE HYDROCHLORIDE WAS STUDIED WHEN ADMINISTERED IV AND WHEN APPLIED PERCUTANEOUSLY IN MICE AND RABBITS. IN RABBITS, IV ADMINISTRATION LED TO A BIPHASIC BLOOD CLEARANCE WITH T/2 VALUES OF 24 MINUTES AND 43.5 HOURS AND QUICK PERCUTANEOUS ABSORPTION. THE TISSUE DISTRIBUTION PATTERN INVESTIGATED AFTER IV AND PERCUTANEOUS ADMINISTRATION IN 16 DIFFERENT TISSUES AND ALSO IN BLOOD DID NOT DEMONSTRATE ANY TARGET ORGAN FOR SELECTIVE LOCALIZATION OF THE DYE. NO GREATER THAN 0.06% OF THE IV ADMINISTERED RADIOACTIVITY WAS MEASURED PER 10 G OF ANY TISSUE AT THE 12TH DAY. /P-PHENYENEDIAMINE HYDROCHLORIDE/ [REHANI MM ET AL; INDIAN J MED RES 74 (JULY): 129-34 (1981)] PubMed Abstract
After the /dog abdominal/ skin was washed, m-phenylenediamine concentration in the blood was observed to decline more rapidly than was the case with p-phenylenediamine and 2,5-diaminotoluene.
A homologous series of hair dyes was selected for percutaneous absorption studies with excised human skin. The permeability constants obtained for the dyes were compared with octanol/water and skin membrane/water partition coefficients. The compounds examined were: p-phenylenediamine, o-phenylenediamine, 2-nitro-p-phenylenediamine, 2-amino-4-nitrophenol, 4-chloro-m-phenylenediamine, and 4-amino-2-nitrophenol. Skin absorption of the dyes was observed when they were applied in an aqueous solution. With one exception, the octanol/water partition coefficients were in the same rank order as the permeability constants. The determination of the partitioning of the hair dyes between water and either stratum corneum or epidermis was more complex. Preliminary stratum corneum/water partition studies resulted in values that were in the reverse order of skin permeation. When binding of the compounds to components of the membrane was saturated, the partition values more closely duplicated the rank order of permeability of the dyes. Prediction of percutaneous absorption of substances based on their partition coefficients may be confounded if these compounds are capable of binding to skin. [Bronaugh RL, Congdon ER; J Invest Dermatol 83 (2): 124-27 (1984)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 16(SRC), determined from a measured log Kow of -0.30(2), and a recommended regression-derived equation(3), indicates that 1,4-benzenediamine is expected to have high mobility in soil(SRC); however it may form covalent bonds to humic material which would limit movement through soil(4). Volatilization of 1,4-benzenediamine is not expected from moist soil surfaces(SRC) given an estimated Henry's Law constant of 6.7X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Volatilization of 1,4-benzenediamine from dry soil surfaces is not expected(SRC) based on an extrapolated vapor pressure of 0.005 mm Hg(SRC) at 25 deg C(6). Biodegradation is expected to occur slowly in soils based on standard biodegradability tests conducted with activated sludge(7-11).
AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 16(SRC), determined from a measured log Kow of -0.30(2), and a recommended regression-derived equation(3), indicates that 1,4-benzenediamine is not expected to adsorb to suspended solids and sediment in water(SRC). 1,4-benzenediamine is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 6.7X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Degradation of 1,4-benzenediamine by photochemically produced peroxy radicals will be an important environmental fate process in surface waters(5,SRC). The half-life of this reaction is estimated as 1 day for a solution concentration of 1X10-9 M of peroxy radicals and an estimated rate constant of 1X10+4 L/mol-s(5). According to a classification scheme(6), an estimated BCF value of 0.3(3,SRC), from a measured log Kow of -0.3(2,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Biodegradation in aquatic environments is not expected to be an important environmental fate process(SRC). A 0% theoretical oxygen demand was observed for 1,4-benzenediamine in a Warburg apparatus during a 5 day incubation period(7). A measured pKb value of 6.2 indicates that the protonated form of 1,4-benzenediamine will exist at environmentally significant pH and this may affect the environmental fate of this compound in aquatic environments(8).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,4-benzenediamine, which has an extrapolated vapor pressure of 0.005 mm Hg at 25 deg C(2,SRC), is expected to exist primarily as a vapor in the ambient atmosphere. Vapor-phase 1,4-benzenediamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 2 hours(3,SRC).

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