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o-Phenylenediamine

o-Phenylenediamine structure

o-Phenylenediamine 

structure
  • CAS No:

    95-54-5

  • Formula:

    C6H8N2

  • Chemical Name:

    o-Phenylenediamine

  • Synonyms:

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

  • Categories:

    Organic Chemistry  >  Amides

Description

O-phenylenediamine has active chemical properties, being able to have condensation reaction with acid, aldehydes, ketones and other compounds, generating heterocyclic compounds; it can also have oxidation, condensation, substitution and diazotization reaction.

Figure 2 is o-phenylenediamine oxidation.

Figure 3 is o-phenylenediamine condensation reaction. It appears as colorless monoclinic crystal with air and sunlight in the darker. It is slightly soluble in cold water


o-Phenylenediamine is an organic compound with the formula C6H4(NH2)2. This aromatic diamine is an important precursor to many heterocyclic compounds. It is isomeric with m-phenylenediamine and p-phenylenediamine, and is commonly referred to as OPD.


1,2-phenylenediamine appears as colorless monoclinic crystals if pure; technical grade brownish-yellow crystals or a sandy brown solid. Used in manufacture of dyes, photography, organic synthesis.|DryPowder; Liquid|BROWN-TO-YELLOW CRYSTALS. TURNS DARK ON EXPOSURE TO LIGHT.|Colorless monoclinic crystals if pure; technical grade brownish-yellow crystals or a sandy brown solid.


1,2-phenylenediamine appears as colorless monoclinic crystals if pure; technical grade brownish-yellow crystals or a sandy brown solid. Used in manufacture of dyes, photography, organic synthesis.|1,2-phenylenediamine is a phenylenediamine in which the two amino groups are ortho to each other. It has a role as a hydrogen donor. It derives from a hydride of a benzene.

o-Phenylenediamine Basic Attributes

108.14100

108.14

202-430-6

8B713N8Q0F

1441

5354

1673

DTXSID3025881

Brownish-yellow leaflets from water; plates from chloroform|Tan crystals or leaflets from water|White crystalline solid when pure

29215119

Characteristics

52.04000

2.01340

1,2-phenylenediamine appears as colorless monoclinic crystals if pure; technical grade brownish-yellow crystals or a sandy brown solid. Used in manufacture of dyes, photography, organic synthesis.

1.27

103-104 °C

256-258 °C

110ºC

1.66

H2O: 1 tablet/10 mL, clear, colorless

2-8ºC

0.01 mm Hg ( 25 °C)

3.7 (vs air)

LD50 in rats (mg/kg): 1070 orally; 516 i.p., C. Burnett et al., J. Toxicol. Environ. Health 2, 657 (1977)

Lower flammable limit: 1.5%

vol% in air: 1.5

Henry's Law constant = 7.20X10-9 atm-cu m/mol at 25 °C (est)

pKa1 = less than 2; pKa2 = 4.47 at 25 °C

129.1 Ų [M+H]+

Hydroxyl radical reaction rate constant = 1.76X10-10 cu cm/molec-sec at 25 °C (est)

Soluble in water [Hawley]. Melting point 219 F. Flash point 277 F. Toxic by skin absorption, inhalation or ingestion. Even as a solid will spot downwind area brown/purple (Roger Patrick, DuPont Engineer).

Amines, Aromatic

1,2-PHENYLENEDIAMINE a weak aromatic amine base neutralizes acids in exothermic reactions to form salts. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Darkens on exposure to air (Roger Patrick, DuPont Engineer).

Lower flammable limit: 1.5%

Dust explosion possible if in powder or granular form, mixed with air.

Safety Information

III

6.1

UN 1673

3

R20/21; R36; R40; R43; R50/53; R68

S1/2-S28-S36/37-S45-S60-S61

SS7875000

T; N

Separated from food and feedstuffs. Well closed.

Stable. Incompatible with strong oxidizing agents.

Missing Phrase - N15.00950417-P261-P280-P305 + P351 + P338

H301-H312 + H332-H317-H319-H341-H351-H410

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.|Recommendable method: Incineration. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

TSCA CHIPs present a preliminary assessment of 1,2-Benzenediamine's potential for injury to human health & the environment (available at EPA's TSCA Assistance Office: (202) 554-1404.

UN 1673

P261; P280; P305 + P351 + P338

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P322, P330, P333+P313, P337+P313, P363, P391, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 437 companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P272, P280, P281, P301+P312, P302+P352, P305+P351+P338, P307+P311, P308+P313, P309+P311, P314, P321, P330, P333+P313, P337+P313, P363, P405, and P501|P201, P202, P260, P261, P264, P270, P271, P272, P280, P281, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P309+P311, P310, P314, P320, P321, P330, P332+P313, P333+P313, P337+P313, P363, P403+P233, P405, and P501|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P309+P311, P312, P314, P321, P330, P333+P313, P337+P313, P363, P391, P403+P233, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: 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. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. 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. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, protect it from light, and store it at refrigerated temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Closed system, ventilation, explosion-proof electrical equipment and lighting.|Use local exhaust or breathing protection.|Protective gloves. Protective clothing.|Wear safety goggles or eye protection in combination with breathing protection.

Finely dispersed particles form explosive mixtures in air.|Explosive limits , vol% in air: 1.5-?

Use water spray, powder.

Spillage Disposal. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do not let this chemical enter the environment. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance.

Do not eat, drink, or smoke during work. Wash hands before eating.

/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/|For more DOT Emergency Guidelines (Complete) data for O-PHENYLENEDIAMINE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Separated from food and feedstuffs. Well closed.

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.

The substance is irritating to the eyes. The substance is mildly irritating to the skin and respiratory tract. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.

Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the blood. This may result in anaemia. This substance is possibly carcinogenic to humans.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

STRICT HYGIENE!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection.

| 3 - Materials that, under emergency conditions, can cause serious or permanent injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Toxicity

LD50 Rat oral 660-1284 mg/kg, females more sensitive than males.|LD50 Mouse oral 331-450 mg/kg|LD50 Guinea pig oral 360 mg/kg|LD50 Rat ip 516 mg/kg|For more Non-Human Toxicity Values (Complete) data for O-PHENYLENEDIAMINE (13 total), please visit the HSDB record page.

/AQUATIC SPECIES/ The static acute toxicities and degradative rates of the unsubstituted phenylenediamines (pdas) varied significantly among the ortho, para and meta isomers. With fathead minnows, the nominal 96 hr LC50s were 0.06, 44 and 1,600 mg/L for p-pda, o-pda and m-pda, respectively. In daphnid tests, the nominal 48 hr EC50s were 0.28, 0.87 and 5.9 mg/L for p-pda, o-pda and m-pda, respectively. The nominal 96 hr EC50s in algae were 0.28, 0.16, and 2.4 mg/L for p-pda, o-pda and m-pda, respectively. With oxygenation, the times to reach 1/2 initial concentrations were 4 to 9 hr for p-pda, 650 to 1,100 hr for o-pda and 3,200 to 8,100 hr for m-pda. Results suggest that acute toxicities of pdas are related to their chemical reactivities (degradative rates) and that pdas may degrade rapidly under environmental conditions.|/OTHER TERRESTRIAL SPECIES/ ...The toxicity of 10 benzamines was tested by the well diffusion assay technique against 18 common bacterial species including the nitrogen-fixing bacterium Azotobacter vinelandii. ... o-Phenylenediamine was inhibitory to Escherichia coli, Klebsiella pnemoniae, Salmonella enteritidis, and Shigella sonnei. ... Because many of these organisms are common soil and aquatic bacteria, the accumulation of these benzamine compounds in the environment may have an adverse impact on soil biochemical activities.|/PLANTS/ Three isomers of the promutagen phenylenediamine at mM concentrations were plant-activated and induced mutation in stamen hairs of Tradescantia clone 4430. The rank order of the mutagenicity of the isomers was: o-phenylenediamine > m-phenylenediamine > p-phenylenediamine with corresponding mutagenic potencies of 5.60, 1.43, and 0.46 mutant stamen hair cells/mumole, respectively. Diethyldithiocarbamate (DEDTC) and ammonium meta-vanadate (vanadate) repressed the mutagenic activity of o-phenylenediamine (o-PDA) in intact plants. Based on inhibition kinetics and reaction rates, the mechanism of DEDTC antimutagenicity was attributed to the inhibition of peroxidases that are required in the plant activation of o-PDA to mutagenic product(s). Spectrophotometric measurements of equimolar concentrations of o-PDA and vanadate demonstrated that the antimutagenic property of vanadate was mainly due to its reactivity with o-PDA.

o-Phenylenediamine occurs as degradation product of thiophanate methyl & benomyl (benzimidazole fungicides).|o-Phenylenediamine's production and use as a chemical intermediate in the manufacture of dyes, photographic developing agent, organic synthesis, and as a laboratory reagent(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a structure estimation method(2), indicates that o-phenylenediamine is expected to have very high mobility in soil(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC). Volatilization of o-phenylenediamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.2X10-9 atm-cu m/mole(SRC), based upon its vapor pressure, 2.06X10-3 mm Hg(5), and water solubility, 4.04X10+4 mg/L(6). o-Phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). A 100% of total decomposition required greater than 64 days using a soil inoculum(7), suggesting that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a structure estimation method(2), indicates that o-phenylenediamine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization of the neutral species from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.2X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 1.06X10-3 mm Hg(4), and water solubility, 4.04X10+4 mg/L(5). The pKa values of <2 and 4.47(6) indicate o-phenylenediamine will exist partially in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(7), an estimated BCF of 3(SRC),from its log Kow of 0.15(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). o-Phenylenediamine exhibited 33% removal after 5 days incubation using acclimated activated sludge inoculum(10), suggesting that biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), o-phenylenediamine, which has a vapor pressure of 2.06X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase o-phenylenediamine 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 0.7 hours(SRC), calculated from its rate constant of 1.8X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). o-Phenylenediamine absorbs light at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of o-phenylenediamine with photochemically-produced hydroxyl radicals has been estimated as 1.8X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 0.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). o-Phenylenediamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). As a class, aromatic amines react relatively rapidly in sunlit natural water via reaction with photochemically-produced hydroxyl radicals and peroxy radicals(3); typical half-lives for peroxy radical and hydroxyl radical reactions are on the order of 19 and 30 sunlight hours, respectively(3). o-Phenylenediamine absorbs light at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for o-phenylenediamine(SRC), using a log Kow of 0.15(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of o-phenylenediamine can be estimated to be 34(SRC). According to a classification scheme(2), this estimated Koc value suggests that o-phenylenediamine is expected to have very high mobility in soil. However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC).

The Henry's Law constant for o-phenylenediamine is estimated as 7.2X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 2.06X10-3 mm Hg(1), and water solubility, 4.04X10+4 mg/L(2). This Henry's Law constant indicates that the neutral species of o-phenylenediamine is expected to be essentially nonvolatile from water an dmoist soil surfaces(3). o-Phenylenediamine may exist partially in the ionized form at pH values of 5 to 9 based on pKa values of less than 2 and 4.47 at 25 °C(4). o-Phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of o-phenylenediamine is 1000 or greater; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 3,076 workers (1,372 of these were female) were potentially exposed to o-phenylenediamine in the US(1). Occupational exposure to o-phenylenediamine may occur through inhalation and dermal contact with this compound at workplaces where o-phenylenediamine is produced or used. Use data indicate that the general population may be exposed to o-phenylenediamine via dermal contact with consumer products containing o-phenylenediamine(SRC).

Drug Information

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.

O-phenylenediamine yields o-acetamidoaniline in yeast; yields o-quinone probably in tea. /From table/

SYMPTOMS: Symptoms of exposure to this chemical may include skin and eye irritation, headache, drowsiness, mental confusion and liver damage. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. It is highly toxic by inhalation and skin absorption. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic bases/Amines and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/

/SIGNS AND SYMPTOMS/ Produces severe local reactions and systemic effects from percutaneous absorption and from ingestion. Local actions include severe dermatitis and urticaria; in the eye, chemosis, lacrimation, exophthalmos, ophthalmia, and even permanent blindness. Systemic actions include asthma, gastritis (regardless of portal of entry), rise in blood pressure, transudation into serous cavities, vertigo, tremors, convulsions and coma. ... The ortho isomer (diolene) is less toxic than the para (orsin). Neither is believed to be capable of inducing significant methemoglobinemia.|/GENOTOXICITY/ Chromosomal aberration tests that were performed ... in peripheral human lymphocytes were ... positive with metabolic activation.

1,2-diaminobenzene

The substance can be absorbed into the body by inhalation and by ingestion.

Blue lips, fingernails and skin. Confusion. Convulsions. Dizziness. Headache. Nausea. Unconsciousness.


Redness.


Redness. Pain.

o-Phenylenediamine Use and Manufacturing

Methods of Manufacturing

The principal route to o-phenylenediamine is by the reduction of 2-nitroaniline, which is produced by the amination of 2-chloronitrobenzene with ammonia. Hydrogenation can be achieved with a variety of reducing agents, such as iron powder, hydrazine, or hydrogen sulfide, but commercially it is performed catalytically in the liquid phase over a palladium catalyst.|AMMONOLYSIS FOLLOWED BY REDUCTION OF O-CHLORONITROBENZENE; REDUCTION OF O-NITROANILINE WITH SODIUM SULFIDE IN AN AUTOCLAVE|Made by reducing o-nitroaniline with Zn and NaOH.|Reduction of ortho-dinitrobenzene or nitroaniline with iron and hydrochloric acid. Method of purification: crystallization.

Uses

1. Am amino substituted benzene used in the manufacture of dyes. Potential use in sensitive immunosensor for cancer biomarker.
2. An amino substituted benzene used in the manufacture of dyes. Potential use in sensitive immunosensor for cancer biomarker.
3. It is actively involved in the preparation of pharmaceuticals by reacting substituted o-phenylenediamine with various diketones.


Intermediates


Personal care products

Production

1,000,000 - 10,000,000 lb|(1972) PROBABLY GREATER THAN 1.36X10+6 GRAMS|(1975) PROBABLY GREATER THAN 1.36X10+6 GRAMS|1,2-Benzenediamine is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#4279]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,2-Benzenediamine. Aggregated National Production Volume: 1 to < 10 million pounds.

Grades: Technical; 99.0% minimum purity.

All other basic organic chemical manufacturing|1,2-Benzenediamine: ACTIVE

Method: OSHA 87; Procedure: high performance liquid chromatography using ultraviolet detector; Analyte: o-phenylenediamine; Matrix: air; Detection Limit: 2.1 ug/cu m.|Identification and estimation of hair dye components by high-performance liquid phase chromatography.|Method No. 87; m-, o- and p-Phenylenediamine, HPLC, quantitation limit 2.1 ug/cu-m (based on a 100-L air volume).

Computed Properties

Molecular Weight:108.14
XLogP3:0.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:108.068748264
Monoisotopic Mass:108.068748264
Topological Polar Surface Area:52
Heavy Atom Count:8
Complexity:62.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Downstream Products

Price Analysis

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  • Data: 2026-08-16
  • Price: 10980.00Yuan/ton
  • Change: 0

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