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1,3-Benzenediamine, 2-methyl-, hydrochloride (1:2)

HCID 27324
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Basic information

CAS
15481-70-6
Standard SMILES
Cc1c(N)cccc1N.Cl.Cl
InChIKey
LXIJUYQULXUMDO-UHFFFAOYSA-N
Molecular formula
C7H10N2.2ClH
Average molar mass
195.09 g/mol
Monoisotopic mass
194.0377538

Overview

2,6-toluenediamine dihydrochloride appears as white microcrystalline solid or light brown solid. Starts to darken in color (decompose) at approximately 437 °F; continues to darken until the melting point (525 °F) at which temperature it is a very dark brown liquid. (NTP, 1992)

Names & identifiers

Preferred name
1,3-Benzenediamine, 2-methyl-, hydrochloride (1:2)
IUPAC
2-methylbenzene-1,3-diamine;dihydrochloride
English name
2-methylbenzene-1,3-diamine dihydrochloride
Molecular formula
C7H12Cl2N2
Molecular weight
195.08958

Names & synonyms

15481-70-62,6-Toluenediamine dihydrochloride2,6-Diaminotoluene dihydrochlorideNCI-C50317TOLUENE-2,6-DIAMINE, DIHYDROCHLORIDE2NR4TK287EDTXSID40204041,3-BENZENEDIAMINE, 2-METHYL-, HYDROCHLORIDE (1:2)RefChem:906848DTXCID60404239-505-82-Methylbenzene-1,3-diamine dihydrochloride
Show more names
2,6-DIAMINOTOLUENE2HCL2,6-TOLUENEDIAMINEDIHYDROCHLORIDE2,6-Diaminotoluene dihydrochloride.DIHYDROGEN 2,6-DIAMINOTOLUENE DICHLORIDE
2,6-Diaminotoluene.2HCl2-methylbenzene-1,3-diamine;dihydrochloride1,3-Benzenediamine, 2-methyl-, dihydrochlorideCCRIS 594HSDB 6194EINECS 239-505-8UNII-2NR4TK287ESCHEMBL8643455

Database identifiers

CAS
15481-70-6
PubChem CID
27324
DTXSID

Properties

Computed structural properties

Topological polar surface area
52 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
11
Formal charge
0
Complexity
82.9

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amines, Aromatic
Color/FormWhite microcrystalline material
Solubility · 2 items

greater than or equal to 100 mg/mL at 70 °F (NTP, 1992)

Solubility in water greater than or equal to 100 mg/mL at 21 °C

DecompositionWhen heated to decomposition it emits very toxic fumes of Nitrogen oxides and Hydrogen chloride.
Melting Point · 2 items

525 °F (Decomposes) (NTP, 1992)

274 °C

Physical Description · 2 items

2,6-toluenediamine dihydrochloride appears as white microcrystalline solid or light brown solid. Starts to darken in color (decompose) at approximately 437 °F; continues to darken until the melting point (525 °F) at which temperature it is a very dark brown liquid. (NTP, 1992)

White or light brown solid; [CAMEO]

Other Experimental PropertiesWhen heated to decomposition it emits very toxic fumes of NOx and HCl

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 3 items

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P272, P280, P301+P317, P302+P352, P317, P318, P321, P330, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory InformationChemical: 1,3-Benzenediamine, 2-methyl-, dihydrochloride
Other Safety InformationIMAP assessments - Salts of 2,6-toluenediamine: Human health tier II assessment
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: When heated to decomposition this chemical emits very toxic fumes of NOx and hydrogen chloride. (NTP, 1992)
Hazards SummaryNo evidence of carcinogenicity in rats or mice; Emergency treatment: Methemoglobinemia; [HSDB] Causes changes in thyroid weight (goiter) and bone marrow in high-dose feeding studies of rats; [RTECS] See 2,6-Diaminotoluene.
Reactive GroupSalts, Acidic
Special ReportsDHEW/NCI; Bioassay of 2,6-Toluenediamine Dihydrochloride for Possible Carcinogenicity (1980) Technical Rpt Series No. 200 DHEW Pub No. (NIH) 80-1756
Reactivity Profile · 1 item

2,6-TOLUENEDIAMINE DIHYDROCHLORIDE behaves as a weak organic acid. Materials in this group are generally soluble in water. The resulting solutions contain moderate concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible.

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

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.

MeSH Pharmacological Classification · 2 items

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.

Uses & manufacturing

UsesUsed mainly in the manufacture of dyes and dye intermediates /Toluenediamines/
Applications · 1 item

General DescriptionWhite microcrystalline solid or light brown solid. Starts to darken in color (decompose) at approximately 437° F; continues to darken until the melting point (525° F) at which temperature 2-methylbenzene-1,3-diamine dihydrochloride is a very dark brown liquid .

Related reactions

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Compound notes

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DTXSID4020404
UNII
2NR4TK287E
EC Number
239-505-8

Physicochemical properties

Toxicology and Carcinogenesis
2 · Bioassay of 2,6-Toluenediamine Dihydrochloride for Possible Carcinogenicity (CASRN 15481-70-6)
FDA UNII
2 NR4TK287E · 2NR4TK287E
EPA Substance Registry System
2 · 2,6-Toluenediamine dihydrochloride (15481-70-6)
Hazardous Substances Data
15481 · 15481-70-6(Hazardous Substances Data)
Air and Water ReactionsWater soluble.
Hazard Classes and CategoriesAcute toxicity (ingestion) - category 4
Shipping Name/ Number DOT/UN/NA/IMONA 1709; Toluenediamine

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

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.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces 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.

Disposal Methods · 1 item

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.

Personal Protective Equipment (PPE) · 1 item

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)

Toxicology

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Ongoing Test Status · 1 item

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of November 6, 2012: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=15481-70-6]

Carcinogen Classification · 6 items

2,6-Toluenediamine dihydrochloride (2,6-diaminotoluene dihydrochloride)

TR-200: Bioassay of 2,6-Toluenediamine Dihydrochloride for Possible Carcinogenicity (CASRN 15481-70-6) (1980 )

02/15/80

No Evidence

No Evidence

No Evidence

Non-Human Toxicity Excerpts · 4 items

/LABORATORY ANIMALS: Acute Exposure/ The acute oral toxicity of toluene-2,6-diamine (2,6-TDA) or its dihydrochloride salt was moderate in rats but (based on a single study) high in mice.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Repeated oral administration of toluene-2,6-diamine dihydrochloride to rats affected various organs including the thyroid gland, bone marrow, heart and liver, while similar studies in mice revealed heart, liver and uterus abnormalities.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ A bioassay of 2,6-toluenediamine dihydrochloride for possible carcinogenicity was conducted by feeding diets containing the test chemical to F344 rats and B6C3F1 mice. Groups of 50 rats of each sex were fed the test chemical at 250 or 500 ppm, for 103 weeks. Groups of 50 mice of each sex fed the test chemical at two doses, 50 or 100 ppm, for 103 weeks. Groups of 50 untreated rats and 50 untreated mice of each sex were used as matched controls. In male rats, islet-cell adenomas of the pancreas and neoplastic nodules or carcinomas of the liver occurred in non-significant dose-related trends.The occurrences of tumor in dosed female rats were not significantly different from those in control rats. Significant results in the negative direction were observed in the incidences of C-cell tumors of the thyroid in male rats and of fibroadenomas of the mammary gland in female rats. In low dose male mice, lymphomas but were not statistically significant, and the occurrence of hepatocellular carcinomas in female mice was dose related but not statistically significant. It was concluded that, under conditions of the bioassay, 2,6- toluenediamine dihydrochloride was not carcinogenicity for male and female F344 rats or for male and female B6C3F1 mice.

/GENOTOXICITY/ In genotoxicity tests in rodents, however, 2,6-TDA or its dihydrochloride induced chromosomal and DNA damage after intraperitoneal injection or oral dosing, while various assays in mammalian cells were similarly positive. Mutagenic activity was evident in Ames bacterial tests.

Antidote and Emergency Treatment · 3 items

/SRP:/ 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/

/SRP:/ 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/

/SRP:/ 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/

National Toxicology Program Studies · 1 item

F344 rats of each sex were fed 2,6-toluenediamine dihydrochloride at 250 or 500 ppm for 103 wk; B6C3F1 mice of each sex were fed at 2 doses, 50 or 100 ppm for 103 wk. 2,6-Toluenediamine dihydrochloride was not carcinogenic for male and female rats or for male and female mice.

Safety data

Hazardous Substances Data
15481-70-6(Hazardous Substances Data)