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106-50-3

Basic Information
CAS No.: 106-50-3
Name: p-Phenylenediamine
Article Data: 551
Cas Database
Molecular Structure:
Molecular Structure of 106-50-3 (p-Phenylenediamine)
Formula: C6H8N2
Molecular Weight: 108.143
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;
EINECS: 203-404-7
Density: 1.15 g/cm3
Melting Point: 139 °C
Boiling Point: 267.4 °C at 760 mmHg
Flash Point: 135.9 °C
Solubility: 47 g/L (25 °C) in water
Appearance: white to light purple solid
Hazard Symbols: ToxicT,DangerousN,VeryT+,HarmfulXn
Risk Codes: 23/24/25-36-43-50/53-63-36/37/38-45-40
Safety: 28-36/37-45-60-61-28A-24/25-23-53
Transport Information: UN 1673 6.1/PG 3
PSA: 52.04000
LogP: 2.01340
Synthetic route
100-25-4

para-dinitrobenzene

106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
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%
1516-60-5

4-nitrophenyl azide

106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
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
100-01-6

4-nitro-aniline

106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
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%
1984-23-2

p-nitrophenyl isocyanide

106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With graphitic carbon nitride; hydrazine hydrate In water at 70℃; for 24h; Irradiation; Sealed tube; Green chemistry; chemoselective reaction;100%
98-95-3

nitrobenzene

106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
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
122-80-5

N-acetyl-p-phenylenediamine

106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
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%
14860-64-1

4-azidoaniline

106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
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%
106-37-6

1.4-dibromobenzene

106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
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
624-38-4

para-diiodobenzene

106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
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;
100-25-4

para-dinitrobenzene

12percent nickel/Al-SBA-15 fiber

12percent nickel/Al-SBA-15 fiber

106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With hydrogen In ethanol at 109.84℃; under 18751.9 Torr; for 7.5h; Autoclave; Green chemistry; chemoselective reaction;99%
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Chemistry

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

Uses

 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.

Toxicity Data With Reference

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.

Safety Profile

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

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.