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Home > Encyclopedia > 3,4-Diaminotoluene

3,4-Diaminotoluene

3,4-Diaminotoluene structure

3,4-Diaminotoluene 

structure
  • CAS No:

    496-72-0

  • Formula:

    C7H10N2

  • Chemical Name:

    3,4-Diaminotoluene

  • Synonyms:

    1,2-Benzenediamine,4-methyl-;Toluene-3,4-diamine;4-Methyl-1,2-benzenediamine;3,4-Diaminotoluene;4-Methyl-1,2-diaminobenzene;4-Methyl-o-phenylenediamine;3,4-Diamino-1-methylbenzene;3,4-Tolylenediamine;4-Methyl-1,2-phenylenediamine;1,2-Diamino-4-methylbenzene;4-Methyl-2-aminoaniline;2-Amino-5-methylaniline;2-Amino-4-methylaniline;NSC 1495;5-Methylbenzene-1,2-diamine;2-Amino-4-methylphenylamine

  • Categories:

    Cosmetic Ingredient  >  Hair Dyeing

Description

Off-white small blocks


3,4-diaminotoluene appears as a colorless to brownish purple crystalline solid. Toxic by ingestion and inhalation and an irritant to skin and eyes. Soluble in water, alcohol and ether. Decomposes to emit toxic oxides of nitrogen when heated to high temperature. Used in making dyes.|OtherSolid


3,4-diaminotoluene appears as a colorless to brownish purple crystalline solid. Toxic by ingestion and inhalation and an irritant to skin and eyes. Soluble in water, alcohol and ether. Decomposes to emit toxic oxides of nitrogen when heated to high temperature. Used in making dyes.

3,4-Diaminotoluene Basic Attributes

122.17

122.17

507965

207-826-2

OE7HJ54P5C

1495

2810

DTXSID9024930

LEAFLETS FROM PETROLEUM ETHER

29215119

Characteristics

52

0.51

Brown to grayish-brown Crystalline Chunks or Flakes

1.1±0.1 g/cm3

80-90 °C

265 °C

155-156°C/18mm

1.636

H2O: 16 g/L (20 ºC);VERY SOL IN WATER

Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ) that bears appropriate label. An inventory should be kept, showing quantity of carcinogen & date it was acquired Facilities for dispensing should be contiguous to storage area.

6.29e-04 mmHg

Insoluble in water.

Amines, Aromatic

3,4-DIAMINOTOLUENE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Safety Information

III

6.1(b)

UN 2811

2

20/21/22-36/37/38-52/53-40-36-22

26-37/39-61-36/37/39

XS9820000

Xn

Stable. Incompatible with strong oxidizing agents.

P261-P280-P305 + P351 + P338

H302 + H312 + H332-H315-H319-H335

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous sodium hypochlorite can also be used as an oxidizing agent. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": Carcinogens that are alkylating, arylating or acylating agents per se can be destroyed by reaction with appropriate nucleophiles, such as water, hydroxyl ions, ammonia, thiols & thiosulfate. The reactivity of various alkylating agents varies greatly ... & is also influenced by sol of agent in the reaction medium. To facilitate the complete reaction, it is suggested that the agents be dissolved in ethanol or similar solvents. ... No method should be applied ... until it has been thoroughly tested for its effectiveness & safety on material to be inactivated. For example, in case of destruction of alkylating agents, it is possible to detect residual compounds by reaction with 4(4-nitrobenzyl)-pyridine. /Chemical Carcinogens/

REVIEW: UNITED STATES EPA; PHENYLENEDIAMINES; RESPONSE TO INTERAGENCY TESTING COMMITTEE; FED REGIST 47 (5): 973 (1982). EVIDENCE IS GIVEN SUPPORTING TESTING OF THE CLASS OF COMPOUNDS PHENYLENEDIAMINES FOR THEIR TOXIC EFFECTS ON HUMAN HEALTH AND THE ENVIRONMENT. THE RESULTS OF TOXICITY TESTING OF 22 COMPOUNDS ARE TABULATED AS ARE THE EFFECTS FOR WHICH TESTING IS BEING CONSIDERED FOR 13 COMPOUNDS, AND THE USES OR POTENTIAL USES OF 47 PHENYLENEDIAMINES. /PHENYLENEDIAMINES/

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

|Danger|H301 (77.74%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 265 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P272, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P333+P313, P363, 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: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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 store this material in a refrigerator. (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)|Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Toluenediamine/|PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources. /2,4-Toluenediamine/

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

If material not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. /Toluenediamine/|Personnel protection: Avoid breathing vapors. Keep upwind. Do not handle broken packages unless wearing appropriate personal protective equipment. /Toluenediamine/|PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/|For more Preventive Measures (Complete) data for 3,4-DIAMINOTOLUENE (12 total), please visit the HSDB record page.

/GUIDE 151: SUBSTANCES - TOXIC (NON-COMBUSTIBLE)/ Health: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. 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. /2,4-Toluenediamine; 2,4-Toluylenediamine; 2,4-Toluylenediamine, solid; 2,4-Toluylenediamine, solution/|/GUIDE 151: SUBSTANCES - TOXIC (NON-COMBUSTIBLE)/ Fire or Explosion: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways. /2,4-Toluenediamine; 2,4-Toluylenediamine; 2,4-Toluylenediamine, solid; 2,4-Toluylenediamine, solution/|/GUIDE 151: SUBSTANCES - TOXIC (NON-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 lease 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /2,4-Toluenediamine; 2,4-Toluylenediamine; 2,4-Toluylenediamine, solid; 2,4-Toluylenediamine, solution/|/GUIDE 151: SUBSTANCES - TOXIC (NON-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. /2,4-Toluenediamine; 2,4-Toluylenediamine; 2,4-Toluylenediamine, solid; 2,4-Toluylenediamine, solution/|For more DOT Emergency Guidelines (Complete) data for 3,4-DIAMINOTOLUENE (8 total), please visit the HSDB record page.

A POTENT SKIN SENSITIZER. /PHENYLENEDIAMINE/

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Toxicity

3,4-TOLUENEDIAMINE WAS TESTED FOR ITS ABILITY TO ENHANCE THE TRANSFORMATION OF PRIMARY HAMSTER EMBRYO CELLS BY SIMIAN ADENOVIRUS 7 WHEN ADMINISTERED PRIOR TO OR AFTER VIRUS INOCULATION AND FOR THEIR ABILITY TO TRANSFORM SECONDARY HAMSTER EMBRYO CELLS. 3,4-TOLUENEDIAMINE WAS ACTIVE WHEN ADDED PRIOR TO SIMIAN ADENOVIRUS 7 AND ALSO WHEN GIVEN AFTER THE VIRUS.

LDLo Rat sc 500 mg/kg|LDLo Rabbit sc 1800 mg/kg

Drug Information

The substituted-benzenediamines appear to be least active when the amino groups are para to one another, whereas activity increases when the para position is occupied by a nonamino substituent. Activity also tends to increase as the two amino groups become ortho to the substituted group. The degree of activity may be explained by the capacity of N-acetyltransferase to interact with particular amino groups of the substituted-benzenediamines, leading to their detoxification.

SYMPTOMS: Symptoms of exposure to this compound may include skin and eye irritation. ACUTE/CHRONIC HAZARDS: This compound may cause irritation of the skin and eyes. (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. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, the exposure level and the route of exposure. (NTP, 1992)

... Toluenediamine used as a dye on the eyelashes is reported in one instance to have caused keratoconjunctivitis and blepharitis with opacities of the cornea which gradually cleared in the course of several weeks. /Toluenediamine/|A POTENT SKIN SENSITIZER. ... PRODUCES SEVERAL LOCAL REACTIONS & SYSTEMIC EFFECTS FROM PERCUTANEOUS ABSORPTION & FROM INGESTION. LOCAL ACTIONS INCL SEVERE DERMATITIS & URTICARIA. IN THE EYE, CHEMOSIS, LACRIMATION, EXOPHTHALMOS, OPHTHALMIA & EVEN PERMANENT BLINDNESS. SYSTEMIC ACTIONS INCLUDE ASTHMA, GASTRITIS (REGARDLESS OF PORTAL OF ENTRY), RISE IN BLOOD PRESSURE, TRANSUDATION INTO SEROUS CAVITIES, VERTIGO, TREMORS, CONVULSIONS, & COMA. /PHENYLENEDIAMINE/|... There have been variable reports of decreased sperm count or normal sperm count with toluene diamine ... . /Toluenediamine/

1-methyl-3,4-phenylenediamine

3,4-Diaminotoluene Use and Manufacturing

Methods of Manufacturing

From 4-methyl-2-nitroaniline by reduction.

Uses

5-Methylbenzotriazole intermediate.


Corrosion inhibitors and anti-scaling agents

Production

(1977) AT LEAST 1.86X10+8 GRAMS|(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

65:35 MIXT OF 3,4- & 2,3-DIAMINOTOLUENES & 2,4-DIAMINOTOLUENE

All other basic organic chemical manufacturing|1,2-Benzenediamine, 4-methyl-: ACTIVE

The use of high performance liquid chromatography (HPLC) for the determination of carcinogenic phenylenediamines was studied. Detection limits using UV and electrochemical detectors showed that electrochemical detectors were superior in most cases. Chromatographic conditions and sample preparation procedures were described for many phenylenediamines of environmental significance. /Phenylenediamines/|EPA Method 8250. Packed Column Gas Chromatography/Mass Spectrometry Technique for the determination of semivolatile organic compounds in extracts prepared from all types of solid waste matrices, soil, and groundwater. This method is applicable to quantify most neutral, acidic, and basic organic compounds that are soluble in methylene chloride and capable of being eluted with derivatization as sharp peaks from a gas chromatographic packed column. Under the prescribed conditions, 3,4-toluenediamine has no given detection limit. Precision and method accuracy were found to be directly related to the concentration of the analyte and essentially independent of the sample matrix.

Cosmetics -> Hair dyeing

Computed Properties

Molecular Weight:122.17
XLogP3:0.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:122.084398327
Monoisotopic Mass:122.084398327
Topological Polar Surface Area:52
Heavy Atom Count:9
Complexity:92.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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