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o-Phenylenediamine

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Name

o-Phenylenediamine

EINECS 202-430-6
CAS No. 95-54-5 Density 1.15 g/cm3
PSA 52.04000 LogP 2.01340
Solubility water: <0.1 g/100 mL at 20 °C Melting Point 99-102 °C
Formula C6H8N2 Boiling Point 257 °C at 760 mmHg
Molecular Weight 108.143 Flash Point 124.9 °C
Transport Information UN 1673 6.1/PG 3 Appearance brown yellow, red brown or brown crystals
Safety 28-36/37-45-60-61-1/2 Risk Codes 20/21-25-36-40-43-50/53-68
Molecular Structure Molecular Structure of 95-54-5 (o-Phenylenediamine) Hazard Symbols ToxicT,DangerousN
Synonyms

o-Phenylenediamine(8CI);1,2-Diaminobenzene;1,2-Phenylenediamine;2-Aminoaniline;C.I. 76010;C.I. Oxidation Base 16;IK 3;IK 3 (amine);NSC 5354;Orthamine;o-Aminoaniline;o-Aminophenylamine;o-Benzenediamine;

Article Data 373

o-Phenylenediamine Synthetic route

88-74-4

2-nitro-aniline

95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
With hydrazine hydrate at 90℃; for 1.16667h; chemoselective reaction;100%
With hydrazine hydrate In ethanol; water at 80℃; for 3h; chemoselective reaction;100%
With sodium tetrahydroborate In water for 0.116667h; Kinetics; Catalytic behavior; Reagent/catalyst;100%
34801-09-7

N-(2-aminophenyl)acetamide

95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reagent/catalyst; Cooling with ice;99.98%
528-29-0

1,2-Dinitrobenzene

95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; ammonium formate; silica gel In methanol for 1.5h; Milling;99%
With sodium tetrahydroborate In water at 90℃;99%
With hydrazine hydrate In ethanol at 20℃; for 4h; chemoselective reaction;98%
583-53-9

1,2-dibromobenzene

95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h;99%
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 130℃; for 18h; Reagent/catalyst; Time; Sealed tube; Inert atmosphere;92%
With ammonium hydroxide In water at 20℃; for 12h; Green chemistry;92%
With ammonia; water; copper(II) sulfate at 180 - 190℃;
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 120℃; for 16h; Sealed tube;100 %Spectr.
1005-07-8

o-azidoaniline

95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
With ammonium chloride; zinc In ethanol; water at 20℃;98%
1635-61-6

5-chloro-2-nitroaniline

95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrazine hydrate In methanol at 120℃; for 0.25h; Microwave irradiation;97%
With palladium on activated charcoal; hydrogen In ethanol; ethyl acetate at 20℃; under 760.051 Torr; for 5h;
5228-61-5

5-bromo-2-nitroaniline

95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrazine hydrate In methanol at 120℃; for 0.25h; Microwave irradiation;96%
480-96-6

benzofurazan oxide

95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
With Saccharomyces cerevisiae BY In methanol at 20℃; for 6h; pH=7.0; aq. buffer; Enzymatic reaction;95%
With ammonium sulfate; sodium tetrahydroborate In ethanol for 0.583333h; Ambient temperature;86%
With ammonium sulfate; magnesium In methanol Ambient temperature;80%
273-13-2, 22706-22-5

benzo[1,2,5]thiadiazole

95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
With sodium tetrahydroborate; cobalt(II) chloride In ethanol for 3h; Heating;95%
With methanol; samarium diiodide In tetrahydrofuran at 20℃; for 0.25h;88%
583-55-1

1-Bromo-2-iodobenzene

95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 120℃; for 16h; Sealed tube; chemoselective reaction;95%
Multi-step reaction with 2 steps
1: copper(l) iodide; tetra(n-butyl)ammonium hydroxide; ammonia / water / 48 h / 45 °C / Inert atmosphere; Sealed tube
2: copper(l) iodide; tetra(n-butyl)ammonium hydroxide; ammonia / water / 48 h / 80 °C / Inert atmosphere; Sealed tube
View Scheme

o-Phenylenediamine Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

o-Phenylenediamine Standards and Recommendations

ACGIH TLV: TWA 0.1 mg/m3; Animal Carcinogen
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans
DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD

o-Phenylenediamine Specification

 o-Phenylenediamine, with the CAS NO.95-54-5, has the synonyms of 1,2-Benzenediamine; 1,2-Diaminobenzene; C.I. 76010; C.I. Oxidation base 16; Orthamine. o-Phenylenediamine is an organic compound with the formula C6H4(NH2)2. It condenses with ketones and aldehydes to give rise to a variety of useful products. Condensation of substituted o-phenylenediamine with various diketones is used in the preparation of a variety of pharmaceuticals.

 Physical properties about o-Phenylenediamine are: (1)ACD/LogP: 0.052; (2)ACD/LogD (pH 5.5): 0.02; (3)ACD/LogD (pH 7.4): 0.05; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 23.31; (7)ACD/KOC (pH 7.4): 25.41; (8)#H bond acceptors: 2 ; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.66; (12)Molar Refractivity: 34.725 cm3; (13)Molar Volume: 93.994 cm3; (14)Polarizability: 13.766 10-24cm3; (15)Surface Tension: 57.5979995727539 dyne/cm; (16)Density: 1.15 g/cm3; (17)Flash Point: 124.929 °C; (18)Enthalpy of Vaporization: 49.454 kJ/mol; (19)Boiling Point: 256.999 °C at 760 mmHg; (20)Vapour Pressure: 0.0149999996647239 mmHg at 25°C

Preparation of o-Phenylenediamine: Most commonly 2-nitrochlorobenzene is treated with ammonia, and the resulting 2-aminonitrobenzene is then hydrogenated:
ClC6H4NO2 + 2 NH3 → H2NC6H4NO2 + NH4Cl
H2NC6H4NO2 + 3 H2 → H2NC6H4NH2 + 2 H2O

When you are using this chemical, please be cautious about it as the following:
1. After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer);
2. Wear suitable protective clothing and gloves;
3. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
4. This material and/or its container must be disposed of as hazardous waste;
5. Avoid release to the environment. Refer to special instructions safety data sheet;
6. Keep locked up and out of the reach of children;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C6H8N2/c7-5-3-1-2-4-6(5)8/h1-4H,7-8H2;
(2)InChIKey=GEYOCULIXLDCMW-UHFFFAOYSA-N;
(3)Smilesc1(c(cccc1)N)N;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 133mg/kg (133mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
cat LDLo oral 250mg/kg (250mg/kg)   "Documentation of the Threshold Limit Values and Biological Exposure Indices," 5th ed., Cincinnati, OH, American Conference of Governmental Industrial Hygienists, Inc., 1986Vol. 6, Pg. 1214, 1991.
guinea pig LD50 oral 360mg/kg (360mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(7), Pg. 62, 1988.
guinea pig LD50 unreported 360mg/kg (360mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(1), Pg. 73, 1986.
mouse LC50 inhalation > 91mg/m3/4H (91mg/m3)   "Documentation of the Threshold Limit Values and Biological Exposure Indices," 5th ed., Cincinnati, OH, American Conference of Governmental Industrial Hygienists, Inc., 1986Vol. 6, Pg. 1214, 1991.
mouse LD50 intraperitoneal 245mg/kg (245mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 oral 366mg/kg (366mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(7), Pg. 62, 1988.
mouse LD50 subcutaneous 450mg/kg (450mg/kg)   Kyushu Journal of Medical Science. Vol. 13, Pg. 175, 1962.
mouse LD50 unreported 336mg/kg (336mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 50(6), Pg. 78, 1985.
rabbit LDLo skin 1500mg/kg (1500mg/kg) KIDNEY, URETER, AND BLADDER: HEMATURIA

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. OTS0571626,
rat LC50 inhalation 1873mg/m3 (1873mg/m3) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(1), Pg. 73, 1986.
rat LD50 intraperitoneal 516mg/kg (516mg/kg)   Journal of Toxicology and Environmental Health. Vol. 2, Pg. 657, 1977.
rat LD50 oral 510mg/kg (510mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(9), Pg. 50, 1988.
rat LD50 skin > 5gm/kg (5000mg/kg)   "Documentation of the Threshold Limit Values and Biological Exposure Indices," 5th ed., Cincinnati, OH, American Conference of Governmental Industrial Hygienists, Inc., 1986Vol. 6, Pg. 1214, 1991.
rat LD50 unreported 660mg/kg (660mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(1), Pg. 73, 1986.

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