3-Bromotoluene
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3-Bromotoluene
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CAS No:
591-17-3
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Formula:
C7H7Br
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Chemical Name:
3-Bromotoluene
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Synonyms:
Benzene,1-bromo-3-methyl-;Toluene,m-bromo-;1-Bromo-3-methylbenzene;3-Bromo-1-methylbenzene;m-Bromotoluene;3-Bromotoluene;m-Tolyl bromide;m-Methylbromobenzene;3-Methylbromobenzene;3-Methyl-1-bromobenzene;5-Bromotoluene;3-Methylphenyl bromide;m-Methylphenyl bromide;3-Tolyl bromide;m-Bromomethylbenzene
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CAS No:
Description
colorless to light yellow liqui
M-bromotoluene is a clear colorless liquid. (NTP, 1992)
M-bromotoluene is a clear colorless liquid. (NTP, 1992)
3-Bromotoluene Basic Attributes
171.03
171.03
1903633
209-702-3
9426O61G73
1992
DTXSID3024659
LIQUID
29036990
Characteristics
0
3.41
Clear colorless to light yellow Liquid
1.4099 g/cm3 @ Temp: 20 °C
-39.8 °C
183.7 °C @ Press: 760 Torr
140 °F
1.549
H2O: insoluble
Store below +30°C.
1 mm Hg at 58.6° F (NTP, 1992)
Oral-Mouse LD50: 1436 mg/kg; Abdominal cavity-mouse LD50: 1215 mg/kg
Open flame is flammable; heated to decompose toxic bromide gas
Dielectric constant 5.36
Highly flammable. Insoluble in water.
Aryl Halides
Highly Flammable
M-BROMOTOLUENE is incompatible with strong oxidizing agents. (NTP, 1992)
10,537.1 gcal/gmole
Safety Information
I; II; III
UN 1993 3/PG 3
3
22-36/37/38
26-36-37/39
XS7965400
Xn,Xi
The warehouse is ventilated, low temperature and dry; stored and transported separately from oxidants and food materials
Harmful/Irritant
Stable at room temperature in closed containers under normal storage and handling conditions.
P261-P305 + P351 + P338
H226-H302-H315-H319-H335
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
This chemical is combustible. (NTP, 1992)
|Warning|H226 (83.67%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 49 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. 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 you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed 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 store this chemical under refrigerated temperatures, and keep it away from oxidizing materials. STORE AWAY FROM SOURCES OF IGNITION. (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)
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Irritant
The major hazards encountered in the use and handling of 3-bromotoluene stem from its toxicologic properties. Exposure to 3-bromotoluene may occur through inhalation or dermal contact at sites where the substance is manufactured, used as a solvent, or used as a chemical intermediate. This substance has the potential to cause respiratory irritation and CNS depression. Entry into contaminated areas warrants the wearing of a full-face mask, self-contained breathing apparatus which provides eye protection. This substance is normally stable, even under fire conditions; requiring moderate heating before ignition will occur. Normal procedures may be used to fight a 3-bromotoluene fire; using water to blanket the fire. Before transporting 3-bromotoluene, the regulatory requirements of the DOT must be consulted. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance.
Toxicity
moderately toxic
3-Bromotoluene's production and use as a solvent(1) and chemical intermediate(2) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 434(SRC), derived from a molecular structure estimation method(2), suggests that 3-bromotoluene will have moderate mobility in soil(SRC). Its high Henry's Law constant, 6.71X10-3 atm-cu m/mole(SRC), estimated from its water solubility(3), high vapor pressure, 1.53 mm Hg at 25 °C(5), and moderate adsorptivity to soil suggests that volatilization may be an important fate process from both moist and dry soil surfaces(4,SRC). Experimental data suggests that 3-bromotoluene may be subject to direct photolysis on the soil surface(6). 3-Bromotoluene's potential for biodegradation in soil is unknown(SRC).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 430(SRC) determined from molecular structure(2), indicates that 3-bromotoluene may adsorb to sediment and particulate matter in the water column(SRC). It is expected to readily volatilize from water based on its Henry's Law constant of 6.7X10-3 atm-cu m/mole(SRC), estimated from its water solubility(3) and vapor pressure(7). Estimated half-lives for a model river and model lake are 4.0 hours and 5.2 days, respectively(4,SRC). Using a model which takes adsorption into account(7), the volatilization half-life of 3-bromotoluene in an environmental pond is estimated to be 14.9 days. According to a recommended classification scheme(6), an estimated BCF value of 230(4,SRC), based on its log Kow(5,SRC), suggests that bioconcentration in aquatic organisms will be moderately high(SRC).|ATMOSPHERIC FATE: According to a theory of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-bromotoluene, which has a vapor pressure of 1.53 mm Hg at 25 °C(2) will exist as a vapor in the ambient atmosphere(SRC). Vapor-phase 3-bromotoluene degrades in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction is estimated to be 4.8 days(3,SRC).
The rate constant for the vapor-phase reaction of 3-bromotoluene with photochemically-produced hydroxyl radicals is estimated to be 3.34X10-12 cu m/molecule-sec at 25 °C(1,SRC). Assuming an average atmospheric hydroxyl radical concn of 5X10+5 molecules/cu cm, the half-life for this reaction is estimated to be 4.8 days(1,SRC). 3-Bromotoluene does not contain any functional groups that are susceptible to hydrolysis(2); therefore, hydrolysis is not expected to be significant in natural waters(SRC). Irradiation of 3-bromotoluene (in hexane solution) with artificial UV light above 290 nm resulted in a dehalogenation of 0.36% over a two hour period(3).
A BCF of 230 was estimated for 3-bromotoluene(SRC), using its log Kow of 3.41(1,SRC), and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that 3-bromotoluene has a moderately high potential for bioconcentration in fish and aquatic organisms(SRC).
Using an estimation method based on molecular connectivity indices(1), the Koc for 3-bromotoluene is estimated to be 430(SRC). According to a suggested classification scheme(2), this Koc value suggests that 3-bromotoluene will have medium mobility in soil(SRC).
The Henry's Law constant of 3-bromotoluene calculated from its vapor pressure, 1.53 mm Hg at 25 °C(3), and water solubility, 513 mg/l(1), is 6.7X10-3 atm-cu m/mole(SRC), which indicates that volatilization from environmental waters is probably significant, and may be rapid(2). The volatilization half-life of 3-bromotoluene from a model river (1 meter deep flowing 1 m/sec with a wind speed of 3 m/sec) and model lake (1 meter deep flowing at 0.05 m/sec with a wind speed of 0.5 m/sec) is estimated to be 4.0 hr and 5.2 days, respectively(2,SRC); these estimates do not consider the effect of adsorption to sediment which may be important(SRC). The volatilization half-life of 3-bromotoluene in an environmental pond which considers adsorption is estimated to be 14.9 days(4,SRC).
Occupational exposure may occur through inhalation or dermal contact at sites where 3-bromotoluene is manufactured, used as a solvent, or used as chemical intermediate. (SRC)
Drug Information
SYMPTOMS: Symptoms of exposure to this compound include eye and skin irritation. ACUTE/CHRONIC HAZARDS: This compound is an irritant. It may be harmful by inhalation, ingestion or skin absorption. Decomposition results in toxic fumes. (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)
3-Bromotoluene Use and Manufacturing
It is derived from 3-bromo-4-aminotoluene by diazotization and reduction. The mixture of 95% ethanol, concentrated sulfuric acid and 3-bromo-4-aminotoluene was stirred and cooled to 10°C, and sodium nitrite solution was added to keep the reaction temperature not exceeding 10°C. After the addition, continue to stir for 20 minutes. Add the copper powder washed with ether and heat it carefully. After the reaction starts, stop heating. Nitrogen gas will be released vigorously to generate acetaldehyde. When the reaction is moderate, heat appropriately to complete the reaction. Then steam distillation is carried out until no oily substance is evaporated. Separate the organic phase from the distillate and wash with 10% sodium hydroxide, water, concentrated sulfuric acid, and 5% sodium carbonate solution in sequence. Dry with anhydrous calcium chloride, filter, distill, collect 180-183°C (99.75kPa) distillate to obtain colorless pure product with a yield of over 50%.
Used in organic synthesis, solvent.
Benzene, 1-bromo-3-methyl-: ACTIVE
Analyte: Chlorobenzene; Matrix: air; Procedure: Gas chromatography, flame ionization detector; Desorption: 1 ml CS2, stand 30 min; Range: 0.4-10 mg/ samp; Precision: 0.025; Est LOD: 0.01 mg/samp; Interferences: none /Hydrocarbons, halogenated, Chlorobenzene/
Computed Properties
Molecular Weight:171.03
XLogP3:3.3
Exact Mass:169.97311
Monoisotopic Mass:169.97311
Heavy Atom Count:8
Complexity:70.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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