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METHYL TRIBROMIDE

Methyl tribromide is a brominated organic solvent, colorless liquid at room temperature, with a high refractive index, very high density, and sweet odor is similar to that of chloroform.
Methyl tribromide is one of the four haloforms, the others being fluoroform, chloroform, and iodoform.

CAS Number: 75-25-2
EC Number: 200-854-6
IUPAC Name: Tribromomethane
Chemical Formula: CHBr3

Other names: Bromoform, tribromomethane, 75-25-2, Methane, tribromo-, Tribrommethan, Methenyl tribromide, Methyl tribromide, Tribrommethaan, Tribromometan, Bromoforme, Bromoformio, CHBr3, RCRA waste number U225, NCI-C55130, NSC 8019, MFCD00000128, TUT9J99IMU, BROMOFORM (13C), 4471-18-5, DTXSID1021374, CHEBI:38682, NSC-8019, Bromoforme [French], Bromoformio [Italian], Tribrommethaan [Dutch], Tribrommethan [German], Tribromometan [Italian], CCRIS 98, Bromoform [USP], MBR, HSDB 2517, EINECS 200-854-6, UNII-TUT9J99IMU, UN2515, RCRA waste no. U225, BRN 1731048, Tribromomethane; Bromoform; Methenyl tribromide; NSC 8019, bromo form, AI3-28587, Tri bromo methane, BROMOFORM [MI], WLN: EYEE, BROMOFORM [HSDB], BROMOFORM [IARC], Bromoform, technical grade, BROMOFORM [WHO-DD], SCHEMBL18691, 4-01-00-00082 (Beilstein Handbook Reference), BIDD, Bromoform, puriss., 97.0%, CHEMBL345248, DTXCID401374, NSC8019, Bromoform [UN2515] [Poison], AMY21869, BCP10566, Bromoform (stabilized with Ethanol), Bromoform - Stabilized with ethanol, Tox21_200189, Bromoform 100 microg/mL in Methanol, Bromoform, 96%, stab. with ethanol, AKOS009031540, AT27291, Bromoform 5000 microg/mL in Methanol, DB03054, InChI=1/CHBr3/c2-1(3)4/h1, UN 2515, CAS-75-25-2, Bromoform, puriss., >=99.0% (GC), NCGC00091318-01, NCGC00091318-02, NCGC00257743-01, BP-21414, Tribromomethane (stabilized with Ethanol), Tribromomethane 100 microg/mL in Methanol, Bromoform Solution in Methanol, 1000ug/mL, 1ST000954-1000M, B0806, NS00002299, S0653, T0348, EN300-19388, Bromoform, amylene stabilized, analytical standard, Q409799, J-519947, Bromoform, contains 1-3% ethanol as stabilizer, 96%, F0001-1896

Methyl tribromide can be prepared by the haloform reaction using acetone and sodium hypobromite, by the electrolysis of potassium bromide in ethanol, or by treating chloroform with aluminium bromide.
Currently Methyl tribromide main use is as a laboratory reagent.

Methyl tribromide is widely used as a solvent for waxes, oils and greases.
Methyl tribromide is utilized for mineral ore separation in geological tests.

Methyl tribromide is used as an intermediate in chemical synthesis as well as a laboratory reagent.
Methyl tribromide is the ingredient of fire-resistant chemicals and fluid gauges.
Methyl tribromide acts as a sedative and as cough reducing agent.

Methyl tribromide is a brominated organic solvent with the formula CHBr3.
Methyl tribromide has an odor similar to chloroform and Methyl tribromide density is very high (2,89).
Miscible with chloroform, benzene, ethanol, petroleum ether, acetone, diethyl ether and oils.

Methyl tribromide, also known as Tribromomethane or Methyl tribromide, is classified as a member of the Trihalomethanes.
Trihalomethanes are organic compounds in which exactly three of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms.
Trace amounts of 1,2-dibromoethane occur naturally in the ocean, where Methyl tribromide is formed probably by algae and kelp.

Molecular Weight: 252.73
Density: 2.81
Melting Point: 8°C to 9°C
Boiling Point: 148°C to 150°C

Flash Point: None
XLogP3-AA: 2.8
Exact Mass: 251.76079
Monoisotopic Mass: 249.76284

Heavy Atom Countv: 4
Complexity: 8
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Methyl tribromide (CHBr3) is a brominated organic solvent, pale yellow liquid at room temperature, with a high refractive index, very high density, and sweet odor is similar to that of chloroform.
It is a trihalomethane, and is one of the four haloforms, the others being fluoroform, chloroform, and iodoform.
Methyl tribromide can be prepared by the haloform reaction using acetone and sodium hypobromite, by the electrolysis of potassium bromide in ethanol, or by treating chloroform with aluminum bromide.

Most of the Methyl tribromide that enters the environment is formed as disinfection byproducts known as the trihalomethanes when chlorine is added to drinking water or swimming pools to kill bacteria.
In the past, it was used as a solvent, sedative and flame retardant, but now it is mainly used as a laboratory reagent.
Bromine is a halogen element with the symbol Br and atomic number 35.
Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock.

Exposure to Methyl tribromide may occur from the consumption of chlorinated drinking water.
The acute (short- term) effects from inhalation or ingestion of high levels of Methyl tribromide in humans and animals consist of nervous system effects such as the slowing down of brain functions, and injury to the liver and kidney.

Chronic (long-term) animal studies indicate effects on the liver, kidney, and central nervous system (CNS) from oral exposure to Methyl tribromide.
Human data are considered inadequate in providing evidence of cancer by exposure to Methyl tribromide, while animal data indicate that long-term oral exposure can cause liver and intestinal tumors.
Methyl tribromide has been classified as a Group B2, probable human carcinogen.

Methyl tribromide is formally rated as an unfounded non-carcinogenic (IARC 3) potentially toxic compound.
Exposure to Methyl tribromide may occur from the consumption of chlorinated drinking water.

The acute (short-term) effects from inhalation or ingestion of high levels of Methyl tribromide in humans and animals consist of nervous system effects such as the slowing down of brain functions, and injury to the liver and kidney.
Chronic (long-term) animal studies indicate effects on the liver, kidney, and central nervous system (CNS) from oral exposure to Methyl tribromide.

Human data are considered inadequate in providing evidence of cancer by exposure to Methyl tribromide, while animal data indicate that long-term oral exposure can cause liver and intestinal tumors.
Methyl tribromide has been classified as a Group B2, probable human carcinogen.
Most of the Methyl tribromide that enters the environment is formed as disinfection byproducts known as the trihalomethanes when chlorine is added to drinking water or swimming pools to kill bacteria.

In the past, Methyl tribromide was used as a solvent, sedative and flame retardant, but now Methyl tribromide is mainly used as a laboratory reagent.
Bromine is a halogen element with the symbol Br and atomic number 35.

Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock.
Methyl tribromide is a pale yellow liquid at room temperature, with a high refractive index, very high density, and sweet odor is similar to that of chloroform.

Methyl tribromide can be prepared by the haloform reaction using acetone and sodium hypobromite, by the electrolysis of potassium bromide in ethanol, or by treating with aluminum bromide.
Currently Methyl tribromide main use is as a laboratory reagent.

Methyl tribromide is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.
Methyl tribromide is used in formulation or re-packing, at industrial sites and in manufacturing.

Methyl tribromide (CHBr3) is a pale yellowish liquid with a sweet odor similar to chloroform, a halomethane or haloform.
Methyl tribromide refractive index is 1.595 (20 °C, D).

Small amounts are formed naturally by plants in the ocean.
Methyl tribromide is somewhat soluble in water and readily evaporates into the air.
Most of the Methyl tribromide that enters the environment is formed as byproducts when chlorine is added to drinking water to kill bacteria.

Methyl tribromide is one of the trihalomethanes closely related with fluoroform, chloroform and iodoform.
Methyl tribromide is soluble in about 800 parts water and is miscible with alcohol, benzene, chloroform, ether, petroleum ether, acetone, and oils.
Methyl tribromide LD50 is 7.2 mmol/kg in mice, or 1.8g/kg.

Methyl tribromide can be prepared by the haloform reaction using acetone and sodium hypobromite or by the electrolysis of alcoholic solution of potassium or sodium bromide.

A colorless liquid with a chloroform-like odor.
Denser than water (density: 2.9 g / cm3 ) and slightly soluble in water.
Hence sinks in water.

Nonflammable.
Toxic by ingestion, inhalation and skin absorption.
A lachrymator.

Methyl tribromide is used as a solvent and to make pharmaceuticals.
Often stabilized with 1 to 3% ethanol.

Reactivity Profile of Methyl tribromide:
Heating Methyl tribromide to decomposition produces highly toxic fumes of carbon oxybromide (carbonyl bromide) and hydrogen bromide.
Reaction with powdered potassium or sodium hydroxide, Li or Na/K alloys, is violently exothermic.
Explosive reaction with crown ethers in the presence of potassium hydroxide.

Physical Description of Methyl tribromide:
Methyl tribromide appears as a colorless liquid with a chloroform-like odor.
Denser than water (density: 2.9 g / cm3 ) and slightly soluble in water.

Hence sinks in water.
Nonflammable.
Toxic by ingestion, inhalation and skin absorption.

A lachrymator.
Methyl tribromide is used as a solvent and to make pharmaceuticals.
Often stabilized with 1 to 3% ethanol.

Colourless liquid with characteristic odour.
Turns yellow on exposure to light and air.

Colorless to yellow liquid with a chloroform-like odor.

Structure of Methyl tribromide:
The molecule adopts tetrahedral molecular geometry with C3v symmetry.

Physical Properties of Methyl tribromide:
Methyl tribromide is a colorless to pale yellow liquid with a sweetish odor.
The chemical formula for Methyl tribromide is CBr3H and the molecular weight is 252.75 g/mol.

The vapor pressure for Methyl tribromide is 5 mm Hg at 20 °C, and Methyl tribromide has an octanol/water partition coefficient(log Kow) of 2.38.
Methyl tribromide has an odor threshold of 1.3 parts per million (ppm).

Methyl tribromide is slightly soluble in water and is nonflammable.
Methyl tribromide can form in drinking water as a by-product from the reaction of chlorine with dissolved organic matter and bromide ions.

Application of Methyl tribromide:
Methyl tribromide is widely used as a solvent for waxes, oils and greases.
Methyl tribromide is utilized for mineral ore separation in geological tests.

Uses of Methyl tribromide:
As a fluid for mineral ore separation; as a laboratory reagent; in the electronics industry for quality assurance programs; formerly as a sedative and antitussive

Methyl tribromide is a colorless to yellow liquid with a density about three times that of water.
Methyl tribromide has an odor and sweetish taste similar to chloroform and is not combustible.

Methyl tribromide has been used as a degreasing solvent, in chemical synthesis, and in fire extinguishers, and is no longer used as a sedative for children with whooping cough.
Currently, Methyl tribromide is produced only in small amounts for use in laboratories and in geological and electronics testing.

In separating mixtures of minerals.
Methyl tribromide is used as a fluid for mineral ore separation in geological tests, as a laboratory reagent, and in the electronics industry in quality assurance programs.

Methyl tribromide was formerly used as a solvent for waxes, greases, and oils, as an ingredient in fire-resistant chemicals and in fluid gauges.
Methyl tribromide was also used in the early part of this century as a medicine to help children with whooping cough get to sleep.
Currently, Methyl tribromide is only produced in small amounts for use in laboratories and in geological and electronics testing.

Methyl tribromide is used as a fluid for mineral ore separation in geological tests, as a laboratory reagent, and in the electronics industry in quality assurance programs.
Methyl tribromide was formerly used as a solvent for waxes, greases, and oils, as an ingredient in fire-resistant chemicals and in fluid gauges.
Methyl tribromide has also been used as an intermediate in chemical synthesis, as a sedative, and as a cough suppression agent.

Only small quantities of Methyl tribromide are currently produced industrially in the United States.
In the past, Methyl tribromide was used as a solvent, and flame retardant, but now Methyl tribromide is mainly used as a laboratory reagent, for example as an extraction solvent.

Methyl tribromide's high density makes Methyl tribromide useful for separation of minerals by density.
When two samples are mixed with Methyl tribromide and then allowed to settle, the top layer will contain minerals lighter than Methyl tribromide, and the bottom layer will contain heavier minerals.
Slightly less dense minerals can be separated in the same way by mixing the Methyl tribromide with a small amount of a less dense and fully miscible solvent.

Only small quantities of Methyl tribromide are currently produced industrially in the United States.
In the past, Methyl tribromide was used as a solvent, sedative and flame retardant, but now Methyl tribromide is mainly used as a laboratory reagent, for example as an extraction solvent.

Methyl tribromide also has medical uses; injections of Methyl tribromide are sometimes used instead of epinephrine to treat severe asthma cases.

Methyl tribromide's high density makes Methyl tribromide useful for separation of minerals by density.
When two samples are mixed with Methyl tribromide and then allowed to settle, the top layer will contain minerals less dense than Methyl tribromide, and the bottom layer will contain denser minerals.
Slightly less dense minerals can be separated in the same way by mixing the Methyl tribromide with a small amount of a less dense and miscible solvent.

Methyl tribromide is known as an inhibitor of methanogenesis and is a common component of seaweed.
Following research by CSIRO and Methyl tribromide spin-off FutureFeed, several companies are now growing seaweed, in particular from the genus Asparagopsis, to use as a feed additive for livestock to reduce methane emissions from ruminants.

Methyl tribromide is used as a intermediate for pharmaceuticals and other organic compounds; also used as a solvent for waxes and oils.

Methyl tribromide is used for synth of pharmaceuticals; used in shipbuilding, aircraft, and aerospace industries; used in fire extinguishers.

Methyl tribromide is used as a heavy liquid floatation agent in mineral separation, sedimentary petrographical surveys, and purification of materials such as quartz.
Methyl tribromide is used as an industrial solvent in liquid-solvent extractions, in nuclear magnetic resonance studies.
Methyl tribromide is used as a catalyst, initiator, or sensitizer in polymer reactions, and in vulcanization of rubber.

Use Classification of Methyl tribromide:
Hazardous Air Pollutants (HAPs)

Health Hazards - Carcinogens

Therapeutic Uses of Methyl tribromide:
Methyl tribromide was formerly used as an antiseptic and sedative.

Chemical Properties of Methyl tribromide:
Methyl tribromide is a colorless to pale yellow liquid with a high refractive index, very high density, and sweetish odor is similar to that of chloroform.
Methyl tribromide is slightly soluble in water and is nonflammable.
Methyl tribromide can form in drinking water as a by-product from the reaction of chlorine with dissolved organic matter and bromide ions.

Physical properties of Methyl tribromide:
Clear, colorless to yellow liquid with a chloroform-like odor.
Odor threshold concentration in water is 0.3 mg/kg

Methods of Manufacturing of Methyl tribromide:
Prepared from acetone and sodium hypobromite.

By heating acetone or ethanol with bromine and alkali hyroxide and recovery of distillation (similar to acetone process of chloroform).

Analytic Laboratory Methods of Methyl tribromide:
To support studies exploring the relation between exposure to trihalomethanes (THMs) and health effects, we have developed an automated analytical method using headspace solid-phase microextraction coupled with capillary gas chromatography and mass spectrometry.

This method quantitates trace levels of THMs (chloroform, bromodichloromethane, dibromochloromethane, and Methyl tribromide) and methyl tertiary-butyl ether in tap water.
Detection limits of less than 100 ng/L for all analytes and linear ranges of three orders of magnitude are adequate for measuring the THMs in tap water samples tested from across the United States.

Method: NIOSH 1003, Issue 3; Procedure: gas chromatography with flame ionization detection; Analyte: Methyl tribromide; Matrix: air; Detection Limit: 6.0 ug/sample.

Method: ASTM D5790; Procedure: gas chromatography/mass spectrometry; Analyte: Methyl tribromide; Matrix: treated drinking water, wastewater, and ground water; Detection Limit: 0.2 ug/L.

Method: EPA-EAD 601; Procedure: gas chromatography with electrolytic conductivity or microcoulometric detector; Analyte: Methyl tribromide; Matrix: municipal and industrial discharges; Detection Limit: 0.2 ug/L.

Clinical Laboratory Methods of Methyl tribromide:
To support studies exploring the relation between exposure to trihalomethanes (THMs) and adverse health effects, an automated analytical method was developed using capillary gas chromatography (GC) and high-resolution mass spectrometry (MS) with selected ion mass detection and isotope-dilution techniques.
This method quantified trace levels of THMs (including chloroform, bromodichloromethane, dibromochloromethane, and Methyl tribromide) and methyl tert-butyl ether (MTBE) in human blood.

Analyte responses were adequate for measuring background levels after extraction of these volatile organic compounds with either purge-and-trap extraction or headspace solid-phase microextraction (SPME).
The SPME method was chosen because of Methyl tribromide ease of use and higher throughput.

Detection limits for the SPME GC-MS method ranged from 0.3 to 2.4 ng/L, with linear ranges of three orders of magnitude.
This method proved adequate for measuring the THMs and MTBE in most blood samples tested from a diverse U.S. reference population.

Purification Methods of Methyl tribromide:
The storage and stability of Methyl tribromide and chloroform are similar.
Ethanol, added as a stabilizer, is removed by washing with H2O or with saturated CaCl2 solution, and the CHBr3, after drying with CaCl2 or K2CO3, is fractionally distilled.

Prior to distillation, CHBr3 has also been washed with conc H2SO4 until the acid layer is no longer coloured, then dilute NaOH or NaHCO3, and H2O.
A further purification step is fractional crystallisation by partial freezing.

MeSH Pharmacological Classification of Methyl tribromide:

Carcinogens:
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.

Teratogens:
An agent that causes the production of physical defects in the developing embryo.

Environment and Toxicology of Methyl tribromide:
Natural production of Methyl tribromide by phytoplankton and seaweeds in the ocean is thought to be Methyl tribromide predominant source in the environment.

However, locally significant amounts of Methyl tribromide enter the environment formed as disinfection byproducts known as trihalomethanes when chlorine is added to drinking water to kill bacteria.
Methyl tribromide is somewhat soluble in water and readily evaporates into the air.

Methyl tribromide is the main trihalomethane produced in beachfront salt water swimming pools with concentrations as high as 1.2 ppm (parts per million).
Concentrations in freshwater pools are 1000 times lower.
Occupational skin exposure limits are set at 0.5 ppm.

Methyl tribromide may be hazardous to the environment, and special attention should be given to aquatic organisms.
Methyl tribromide volatility and environmental persistence makes Methyl tribromide's release, either as liquid or vapor, strongly inadvisable.

Methyl tribromide can be absorbed into the body by inhalation and through the skin.
Methyl tribromide is irritating to the respiratory tract, the eyes, and the skin, and may cause effects on the central nervous system and liver, resulting in impaired functions.

Methyl tribromide is soluble in about 800 parts water and is miscible with alcohol, benzene, chloroform, ether, petroleum ether, acetone, and oils.
Methyl tribromide LD50 is 7.2 mmol/kg in mice, or 1.8g/kg.

The International Agency for Research on Cancer (IARC) concluded that Methyl tribromide is not classifiable as to human carcinogenicity.
The EPA classified Methyl tribromide as a probable human carcinogen.

Safe Storage of Methyl tribromide:
Separated from strong bases, oxidants, metals and food and feedstuffs.
Keep in the dark.
Ventilation along the floor.

Store only if stabilized.
Store in an area without drain or sewer access.
Provision to contain effluent from fire extinguishing.

Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.

Store at +15°C to +25°C.

Safety Profile of Methyl tribromide:
Suspected carcinogen with experimental neoplastigenic data.
A human poison by ingestion.

Moderately toxic by intraperitoneal and subcutaneous routes.
Human mutation data reported.
A lachrymator.

Methyl tribromide can damage the liver to a serious degree and cause death.
Methyl tribromide has anesthetic properties simdar to those of chloroform, but is not sufficiently volatile for inhalation purposes and is far too toxic for human use.
As a sedative and antitussive Methyl tribromide medicinal application has resulted in numerous poisonings.

Inhalation of small amounts causes irritation, provoking the flow of tears and saliva, and reddening of the face.
Abuse can lead to adhction and serious consequences.
Explosive reaction with crown ethers or potassium hydroxide.

Violent reaction with acetone or bases.
Incompatible with Li or NaK alloys.
When heated to decomposition Methyl tribromide emits hghly toxic fumes of Br-.

First Aid of Methyl tribromide:
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.

IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop.
IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air.
IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop.

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, Methyl tribromide chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure.

Fire Fighting of Methyl tribromide:
SMALL FIRE: Dry chemical, CO2, water spray or regular foam.

LARGE FIRE: Water spray, fog or regular foam.
Move containers from fire area if you can do Methyl tribromide without risk.
Dike fire-control water for later disposal; do not scatter the material.

FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles.
Do not get water inside containers.

Cool containers with flooding quantities of water until well after fire is out.
Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank.

ALWAYS stay away from tanks engulfed in fire.
For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn.

Fire Fighting Procedures of Methyl tribromide:
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped.
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.
Cool all affected containers with flooding quantities of water.

Apply water from as far a distance as possible.
Use foam, dry chemical, or carbon dioxide.
Keep run-off water out of sewers and water sources.