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Name |
p-Phenylenediamine |
EINECS | 203-404-7 |
CAS No. | 106-50-3 | Density | 1.15 g/cm3 |
PSA | 52.04000 | LogP | 2.01340 |
Solubility | 47 g/L (25 °C) in water | Melting Point |
139 °C |
Formula | C6H8N2 | Boiling Point | 267.4 °C at 760 mmHg |
Molecular Weight | 108.143 | Flash Point | 135.9 °C |
Transport Information | UN 1673 6.1/PG 3 | Appearance | white to light purple solid |
Safety | 28-36/37-45-60-61-28A-24/25-23-53 | Risk Codes | 23/24/25-36-43-50/53-63-36/37/38-45-40 |
Molecular Structure | Hazard Symbols | T,N,T+,Xn | |
Synonyms |
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; |
Article Data | 551 |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In water at 50℃; for 0.0833333h; Green chemistry; | 100% |
With hydrogen In tetrahydrofuran at 20℃; under 760.051 Torr; for 3h; chemoselective reaction; | 100% |
With sodium hypophosphite monohydrate; 5%-palladium/activated carbon; hypophosphorous acid In 2-methyltetrahydrofuran; water for 3h; Sonication; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
Stage #1: 4-nitrophenyl azide With hydrazine hydrate at 135℃; for 3h; Stage #2: With potassium hydroxide at 135℃; for 24h; | 100% |
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 5h; | 94% |
With hydrogenchloride; tin |
Conditions | Yield |
---|---|
With palladium diacetate; carbon monoxide; triphenylphosphine In water; acetic acid at 56℃; under 532 Torr; for 11h; | 100% |
With triethylsilane; palladium dichloride In ethanol at 20℃; for 1h; Inert atmosphere; | 100% |
With 10% palladium on activated charcoal; hydrogen for 2h; | 100% |
Conditions | Yield |
---|---|
With graphitic carbon nitride; hydrazine hydrate In water at 70℃; for 24h; Irradiation; Sealed tube; Green chemistry; chemoselective reaction; | 100% |
Conditions | Yield |
---|---|
Stage #1: nitrobenzene With Oxalamide; tetramethyl ammoniumhydroxide; ammonia In dimethyl sulfoxide at 100℃; under 18751.9 Torr; for 7h; Autoclave; Stage #2: With 5%-palladium/activated carbon; hydrogen In methanol at 55℃; under 9000.9 Torr; for 4h; Reagent/catalyst; Autoclave; | 99.1% |
Multi-step reaction with 2 steps 1: urea, monosodium salt; urea / dimethyl sulfoxide / 2 h / 90 °C 2: 5%-palladium/activated carbon; hydrogen / ethanol / 80 °C / 15001.5 - 22502.3 Torr View Scheme |
Conditions | Yield |
---|---|
With ammonium bromide; ethylenediamine at 70℃; for 5h; Microwave irradiation; Inert atmosphere; neat (no solvent); | 99% |
With ammonium iodide; hydrazine at 50℃; for 12h; | 99% |
With ammonium iodide; hydrazine hydrate at 50℃; for 12h; Inert atmosphere; Sealed tube; | 99% |
4-azidoaniline
1,4-phenylenediamine
Conditions | Yield |
---|---|
With iron(III) oxide; hydrazine hydrate In water at 120℃; for 2h; Concentration; Temperature; Time; Inert atmosphere; | 99% |
With zinc In methanol at 20℃; for 5h; | 95% |
With hydrazine hydrate In ethanol at 20℃; chemoselective reaction; | 90% |
Conditions | Yield |
---|---|
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h; | 99% |
With ammonia; C16H16N2O2*0.8Ni*0.2Cu at 85℃; under 1500.15 Torr; for 8.5h; Autoclave; Inert atmosphere; | 92% |
Multi-step reaction with 2 steps 1: copper(ll) sulfate pentahydrate; sodium L-ascorbate; potassium carbonate; ammonium hydroxide / dimethyl sulfoxide; glycerol / 8 h / 100 °C 2: copper(ll) sulfate pentahydrate; sodium L-ascorbate; potassium carbonate; ammonium hydroxide / dimethyl sulfoxide; glycerol / 8 h / 100 °C View Scheme |
Conditions | Yield |
---|---|
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h; | 99% |
With ammonia at 20℃; Reagent/catalyst; Temperature; | 97% |
With [10%-Pd/Al2O3]; ammonia at 250℃; Catalytic behavior; Temperature; Reagent/catalyst; Inert atmosphere; |
Conditions | Yield |
---|---|
With hydrogen In ethanol at 109.84℃; under 18751.9 Torr; for 7.5h; Autoclave; Green chemistry; chemoselective reaction; | 99% |
Molecular structure of p-Phenylenediamine (CAS NO.106-50-3) is:
Product Name: p-Phenylenediamine
CAS Registry Number: 106-50-3
IUPAC Name: Benzene-1,4-diamine
Molecular Weight: 108.14112 [g/mol]
Molecular Formula: C6H8N2
XLogP3: -0.3
H-Bond Donor: 2
H-Bond Acceptor: 2
EINECS: 203-404-7
Melting Point: 139 °C
Storage temp.: 2-8°C
Water Solubility: 47 g/L (25 ºC)
Stability: Stable, but oxidizes when exposed to air. Incompatible with oxidizing agents. Store under inert atmosphere.
Surface Tension: 57.5 dyne/cm
Density: 1.15 g/cm3
Flash Point: 135.9 °C
Enthalpy of Vaporization: 50.54 kJ/mol
Boiling Point: 267.4 °C at 760 mmHg
Vapour Pressure: 0.00817 mmHg at 25°C
Other Registry Number: 56481-76-6
Related Registry Number: 16245-77-5 (monosulfate); 540-24-9 (mono-hydrochloride); 624-18-0 (di-hydrochloride); 62654-17-5 (monooxalate)
Product Categories: Variousamine; Intermediates of Dyes and Pigments; 1,4-Benzenediamine; Fluorenes, etc. (reagent for high-performance polymer research); Functional Materials; Reagent for High-Performance Polymer Research; Chemistry
p-Phenylenediamine (CAS NO.106-50-3) is added to real henna to create so called "Black Henna".In many cases, it can cause allergic reaction, and cause scarring in some people. PPD should never be applied directly to the skin in its pure form or mixed with anything else. This product is used in almost every hair dye on the market, whatever brand. Also it is a precursor to aramid plastics and fibers such as Kevlar. It is mainly used as a component of engineering polymers and composites. Its use is controversial because of its high toxicity.It may cause allergic reactions, which makes it a controversial chemical to be included in hair dyes.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
bird - wild | LD50 | oral | 100mg/kg (100mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
cat | LDLo | oral | 100mg/kg (100mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Journal of Industrial Hygiene. Vol. 4, Pg. 386, 1923. |
dog | LDLo | intravenous | 17mg/kg (17mg/kg) | Journal of Industrial Hygiene. Vol. 4, Pg. 386, 1923. | |
dog | LDLo | subcutaneous | 100mg/kg (100mg/kg) | BEHAVIORAL: COMA GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS GASTROINTESTINAL: NAUSEA OR VOMITING | U.S. Public Health Service, Public Health Bulletin. Vol. 271, Pg. 40, 1941. |
guinea pig | LD50 | oral | 145mg/kg (145mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(7), Pg. 62, 1988. | |
guinea pig | LD50 | unreported | 145mg/kg (145mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(8), Pg. 46, 1987. | |
man | TDLo | oral | 71mg/kg (71mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Human Toxicology. Vol. 8, Pg. 345, 1989. |
mouse | LD50 | intraperitoneal | 50mg/kg (50mg/kg) | National Technical Information Service. Vol. AD277-689, | |
mouse | LD50 | unreported | 331mg/kg (331mg/kg) | BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 50(6), Pg. 78, 1985. |
mouse | LDLo | oral | 100mg/kg (100mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 23(5), Pg. 14, 1958. | |
mouse | LDLo | subcutaneous | 140mg/kg (140mg/kg) | Journal of the Society of Cosmetic Chemists. Vol. 12, Pg. 500, 1961. | |
quail | LD50 | oral | 100mg/kg (100mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
rabbit | LDLo | intraperitoneal | 150mg/kg (150mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Journal of Infectious Diseases. Vol. 42, Pg. 473, 1928. |
rabbit | LDLo | intravenous | 300mg/kg (300mg/kg) | LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Archives of Internal Medicine. Vol. 36, Pg. 724, 1925. |
rabbit | LDLo | oral | 250mg/kg (250mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Journal of Industrial Hygiene. Vol. 4, Pg. 386, 1923. |
rabbit | LDLo | skin | 5gm/kg (5000mg/kg) | Journal of Toxicology and Environmental Health. Vol. 2, Pg. 657, 1977. | |
rabbit | LDLo | subcutaneous | 200mg/kg (200mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Journal of Industrial Hygiene. Vol. 4, Pg. 386, 1923. |
rat | LC50 | inhalation | 920mg/m3/4H (920mg/m3) | BEHAVIORAL: GENERAL ANESTHETIC KIDNEY, URETER, AND BLADDER: HEMATURIA GASTROINTESTINAL: NAUSEA OR VOMITING | National Technical Information Service. Vol. OTS0530403, |
rat | LD50 | intraperitoneal | 37mg/kg (37mg/kg) | Journal of Toxicology and Environmental Health. Vol. 2, Pg. 657, 1977. | |
rat | LD50 | oral | 80mg/kg (80mg/kg) | Journal of Toxicology and Environmental Health. Vol. 2, Pg. 657, 1977. | |
rat | LD50 | unreported | 133mg/kg (133mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(8), Pg. 46, 1987. | |
rat | LDLo | intravenous | 50mg/kg (50mg/kg) | Bulletin de la Societe Royale des Sciences de Liege. Vol. 41, Pg. 302, 1972. | |
rat | LDLo | subcutaneous | 170mg/kg (170mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Journal of Industrial Hygiene. Vol. 4, Pg. 386, 1923. |
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: T,N,T+,Xn
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
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.