4-Methylbenzyl bromide
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4-Methylbenzyl bromide
structure -
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CAS No:
104-81-4
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Formula:
C8H9Br
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Chemical Name:
4-Methylbenzyl bromide
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Synonyms:
Benzene,1-(bromomethyl)-4-methyl-;p-Xylene,α-bromo-;1-(Bromomethyl)-4-methylbenzene;α-Bromo-p-xylene;p-Methylbenzyl bromide;p-Xylyl bromide;p-Xylyl α-bromide;α-Bromo-p-xylol;4-Methylbenzyl bromide;p-(Bromomethyl)toluene;4-(Bromomethyl)toluene;NSC 8050;1-(Bromomethy)-4-methylbenzene
- Categories:
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CAS No:
4-Methylbenzyl bromide Basic Attributes
185.06
185.06
507389
203-240-6
V2DIK2AP5I
8050
DTXSID7059305
Needles from alcohol
2903999090
Characteristics
0
3.43 (est)
White to light yellow Crystalline Mass
1.324 g/cm3
38 °C
218-220 °C @ Press: 740 Torr
208 °F
1.560
Practically insoluble in water;soluble in ethanol; very soluble in ethyl ether, chloroform
2-8°C
9.92X10-2 mm Hg at 25 deg C (est)
Henry's Law constant = 7.6X10-4 amt-cu m/mol at 25 °C (est)
Hydrolyzes in water|Hydroxyl radical reaction rate constant = 3.7X10-12 cu cm/molec-sec at 25 °C (est)
Safety Information
II
6.1
UN 3417 6.1/PG 2
3
34-20/21/22
26-36/37/39-45
CY9039300
C
Stable under recommended storage conditions.
P280-P305 + P351 + P338-P310
H314
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.|Contaminated packaging: Dispose of as unused product.|Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Avoid moisture. Materials to avoid: Alcohols, Bases, Amines, Oxidizing agents
|Danger|H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501|Aggregated GHS information provided by 45 companies from 4 notifications to the ECHA C&L Inventory.
Skin and body protection: Complete suit protecting against chemicals.|Eye protection: Face shield and safety glasses Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Personnel protection: ... Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective gloves, boots, and googles. /Xylyl bromide, liquid; Xylyl bromide, solid/
Wear self contained breathing apparatus for fire fighting if necessary.|Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|If material on fire or involved in fire: Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Use water spray to knock-down vapors. /Xylyl bromide, liquid; Xylyl bromide, solid/|Personnel protection: ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Xylyl bromide, liquid; Xylyl bromide, solid/
Do not let product enter drains.|Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Use water spray to knock-down vapors. /Xylyl bromide, liquid; Xylyl bromide, solid/|Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. ... If contact with the material anticipated, wear appropriate chemical protective clothing. /Xylyl bromide, liquid; Xylyl bromide, solid/|Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
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.
Powerful lacrimator.
Toxicity
p-Xylyl bromide's production and presense in a in mixture with the o- and m-isomers in organic synthesis(1) may result in its release to the environment through various waste streams. Its use in mixture with o- and m-isomers as a tear gas will result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 710(SRC), determined from a structure estimation method(2), indicates that p-xylyl bromide is expected to have moderate mobility in soil(SRC). Volatilization of p-xylyl bromide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.6X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). p-Xylyl bromide is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). However, due to a reported hydrolysis half-life of 4.3 minutes at 25 °C for p-xylyl bromide(4) adsorption, volatilization, and biodegradation are not expected to be important environmental fate processes in moist soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 710(SRC), determined from a structure estimation method(2), indicates that p-xylyl bromide is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 7.6X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 6 hrs and 6 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 85(SRC), from an estimated log Kow of 3.43(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). However, due to a reported hydrolysis half-life of 4.3 minutes at 25 °C for p-xylyl bromide(6) adsorption, volatilization, bioconcentration, and biodegradation are not expected to be important environmental fate processes in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), p-xylyl bromide, which has an estimated vapor pressure of 0.10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase p-xylyl bromide 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 4.3 days(SRC), calculated from its rate constant of 3.7X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). p-Xylyl bromide does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of p-xylyl bromide with photochemically-produced hydroxyl radicals has been estimated as 3.7X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4.3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A hydrolysis rate constant of 2.56X10-3/sec was reported, corresponding to a half-life of 4.3 minutes at pH 7 and 25 °C(2). p-Xylyl hydroxide and hydrobromic acid were observed as hydrolysis products(2). p-Xylyl bromide does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 85 was calculated in fish for p-xylyl bromide(SRC), using an estimated log Kow of 3.43(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). However, a hydrolysis half-life of 4.3 minutes at 25 °C(3) will pre-empt bioconcentration(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of p-xylyl bromide can be estimated to be 710(SRC). According to a classification scheme(2), this estimated Koc value suggests that p-xylyl bromide is expected to have moderate mobility in soil. However, a hydrolysis half-life of 4.3 minutes at 25 °C(3) will pre-empt soil adsorption(SRC).
The Henry's Law constant for p-xylyl bromide is estimated as 7.6X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that p-xylyl bromide is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 6 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 6 days(SRC). p-Xylyl bromide's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). However, a hydrolysis half-life of 4.3 minutes at 25 °C(3) will pre-empt volatilization from moist surfaces(SRC). p-Xylyl bromide is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.10 mm Hg(SRC), determined from a fragment constant method(4).
DRINKING WATER: Drinking water samples were obtained from various U.S. cities (Cincinnati, OH; Miami, FL: New Orleans, LA; Ottumwa, IA; Philadelphia, PA and Seattle, WA) and analyzed for organic pollutants. p-Xylyl bromide was detected at trace amounts (concentration not reported) in drinking water from Cincinnati, OH(1).
Occupational exposure to p-xylyl bromide may occur through inhalation and dermal contact with this compound at workplaces where p-xylyl bromide is produced or used. The most likely pathway by which the general public is exposed to p-xylyl bromide is by dermal contact and inhalation due to the release of this substance in tear gas. (SRC)
Drug Information
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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Bromine, methyl bromide, 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 patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Bromine, methyl bromide, 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 ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if 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. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Bromine, methyl bromide, and related compounds/|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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Aromatic hydrocarbons and related compounds/|For more Antidote and Emergency Treatment (Complete) data for P-XYLYL BROMIDE (6 total), please visit the HSDB record page.
/OTHER TOXICITY INFORMATION/ Powerful lacrimator.|/OTHER TOXICITY INFORMATION/ ... Strongly lacrimatory. /Xylyl bromides/
4-Methylbenzyl bromide Use and Manufacturing
From the reaction of p-xylene and bromine. P-xylene was heated to 120°C, and bromine was added to stir the reaction under strong light irradiation. After the reaction, the hydrobromic acid was removed. The reaction product was dried and then distilled under reduced pressure to obtain 4-methylbromobenzyl.
In organic syntheses; in war-gas formulations.
Grade: technical. /Mixture of ortho-, meta-, and para-isomers/
Benzene, 1-(bromomethyl)-4-methyl-: INACTIVE
Gas chromatographic method is presented for qual & quant analysis of mixt of benzyl bromide, xylyl bromide, chloracetophenone & others.
Computed Properties
Molecular Weight:185.06
XLogP3:3
Rotatable Bond Count:1
Exact Mass:183.98876
Monoisotopic Mass:183.98876
Heavy Atom Count:9
Complexity:72.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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