Dibromomethane

log Kow = 1.70

1.88 (estimated)

2.497 at 68 °F (USCG, 1999) - Denser than water; will sink

2.4969 g/cc @ 20 °C

Relative density (water = 1): 2.5

2.497 @ 20°C

1.320 mPa @ 0 °C; 0.980 mPa @ 25 °C

0.39 mm²/s at 25 °C

11.70 g/1000 g water @ 15 °C; 11.93 g/1000 g water @ 30 °C

Miscible with chloroform, alcohol, ether, acetone

> 10% in acetone

> 10% in ether

For more Solubility (Complete) data for DIBROMOMETHANE (6 total), please visit the HSDB record page.

Solubility in water, g/100ml at 15 °C: 1.2 (moderate)

206.6 °F at 760 mmHg (USCG, 1999)

97 °C

97 °C

97 °C @760 [mm Hg]

-62.5 °F (USCG, 1999)

-52.5 °C

-52.7 °C

-52.7 °C

6.05 (Air= 1)

Relative vapor density (air = 1): 6.0

Warning

H332: Harmful if inhaled [Warning Acute toxicity, inhalation]

P261, P271, P273, P304+P340, P317, and P501 (click each P-code to see the statement)

Danger

H301 (22.4%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P270, P271, P273, P301+P316, P304+P340, P317, P321, P330, P405, and P501 (click each P-code to see the statement)

Chemical: Methane, dibromo-

Methane, dibromo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methane, dibromo- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 23-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/24154

Dibromomethane: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Special Hazards of Combustion Products: Dissociation products generated in a fire may be irritating or toxic. (USCG, 1999)

· Some of these materials may burn, but none ignite readily.

Not combustible. Gives off irritating or toxic fumes (or gases) in a fire. Heating will cause rise in pressure with risk of bursting. Risk of fire and explosion. See Chemical Dangers.

INHALATION: Anesthetic effects, nausea and drunkenness. CONTACT WITH SKIN AND EYES: Skin irritation of eyes and nose. (USCG, 1999)

· Toxic by ingestion.

In laboratory studies, animals experienced CNS depression at 2400-2800 ppm and liver and kidney damage after repeated exposures to 1000 ppm. [CHEMINFO] Dichloromethane seldom causes hepatotoxicity unless exposure is very heavy or agent ingested. [Zimmerman, p. 333] If left on clothes, may cause reddening of skin; [CHRIS] May have effects on nervous system and blood, causing impaired functions, carboxyhemoglobinemia, and lowering of consciousness; Chronic exposure may cause liver and kidney effects; [ICSC] An irritant; Harmful by inhalation; A simple asphyxiant; May cause blood disorders, cardiac irregularities, and CNS depression; [Sigma-Aldrich MSDS]

Osterman-Golkar S et al; Chem-Biol Interact 46 (1): 121-30 (1983). Dibromomethanes reactivity towards nucleophilic compounds of different strengths in water solution and with respect to its toxicity and mutagenic effectiveness in bacterial test systems.

U068; As stipulated in 40 CFR 261.33, when methylene bromide, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Excerpt from ERG Guide 160 [Halogenated Solvents]:

In case of fire in the surroundings, use appropriate extinguishing media. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Administration of oxygen may be needed. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

INHALATION: Remove from exposure. Give oxygen if needed.

General First Aid:

... MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS DUE TO CONTACT WITH HEAT, MOISTURE, ACID, OR ACID FUMES, SHOULD BE STORED IN COOL, WELL VENTILATED PLACE, OUT OF DIRECT RAYS OF SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD & SHOULD BE PERIODICALLY INSPECTED & MONITORED.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U068, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

If material not on fire and not involved in fire: Build dikes to contain flow as necessary.

Personnel protection: Avoid breathing vapors. ... Avoid bodily contact with the material.

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627)

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 24(SRC), determined from a structure estimation method(2), indicates that dibromomethane is expected to have very high mobility in soil(SRC). Volatilization of dibromomethane from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 8.22X10-4 atm-cu m/mole(3). The potential for volatilization of dibromomethane from dry soil surfaces may exist based upon a vapor pressure of 44.4 mm Hg (4). Biodegradation potential in soil is unknown(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 24(SRC), determined from an estimation method(2), indicates that dibromomethane is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 8.22X10-4 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 hours and 6 days, respectively(SRC). Biodegradation potential in water is unknown(SRC). According to a classification scheme(5), an estimated BCF of 4(SRC), from its log Kow of 1.70(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. The rate constant for the aqueous-phase reaction of dibromomethane with hydroxyl radicals is 9.9X10+7(8). This corresponds to a half-life of about 22 years at an aqueous concn of 1X10-17 mole/L hydroxyl radicals cm.

ATMOSPHERIC FATE: According to a model of gas partitioning of semivolatile organic compounds in the atmosphere(1), dibromomethane, which has a vapor pressure of 44.4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dibromomethane 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 142 days(SRC), calculated from its rate constant of 1.13X10-13 cu cm/molecule-sec at 25 °C(3). The ozone depleting potential and atmospheric lifetime for dibromomethane have been calculated as 0.17 and 0.41 years, respectively(3). Dibromomethane is very soluble in water (11,900 g/l at 30 °C(4)) and therefore it should be readily scavenged by rain and snow(SRC).

The substance can be absorbed into the body by inhalation, by ingestion and through the skin.

Oral (L626) ; inhalation (L626) ; dermal (L626)

Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (L626, L627, A543)

AIR INTAKE: Remote areas (assume air concn of 2.4-15 parts per trillion (1,2) and inhalation rate of 20 cu meters/day (4)) - 0.3-2.2 ug, Source areas (assume air concn of 900 parts per trillion(3) and inhalation rate of 20 cu meters/day (4)) - 130 ug; WATER INTAKE: insufficient data; FOOD INTAKE: insufficient data(SRC).

Cough. Dizziness. Drowsiness. Headache. Nausea. Weakness. Unconsciousness.

Dry skin. Redness.

Redness.

See Inhalation.

Bromine vapour causes irritation and direct damage to the mucous membranes. Symptoms include lacrimation, rhinorrhoea, eye irritation with mucous secretions from the oropharyngeal and upper airways, coughing, dyspnoea, choking, wheezing, epistaxis, and headache. The bromide ion is a central nervous system depressant producing ataxia, slurred speech, tremor, nausea, vomiting, lethargy, dizziness, visual disturbances, unsteadiness, headaches, impaired memory and concentration, disorientation and hallucinations. This is called bromism. (L626, L627)

In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, dibromomethane was identified in discharges of the following industrial categories (positive occurrences, median concn in ppb): nonferrous metals (8; 2.2), organics and plastics (2; 32.9), inorganic chemicals (2; 1.9), pesticides manufacture (2; 104.6), publicly owned treatment works (9; 0.3)(1). Maximum effluent concn >100 ppb were found in the nonferrous metals industry (286 ppb) and in pesticide manufacturing (151 ppb)(1). In a previous survey of 63 wastewaters from a wide range of chemical manufacturers across the U.S., 1 effluent contained dibromomethane(2). The level of dibromomethane in that sample was >100 ppb.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for dibromomethane can be estimated to be 24(SRC). According to a classification scheme(2), this estimated Koc value suggests that dibromomethane is expected to have very high mobility in soil.

U068; As stipulated in 40 CFR 261.33, when methylene bromide, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Dibromomethane is included on this list.

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 1000 lb or 454 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).

IT IS METABOLIZED TO CARBON MONOXIDE AND BROMIDE.

MASS SPECTRAL STUDIES USING (18)O2 SHOWED THAT (18)O-CO WAS PRODUCED INDICATING THAT OXYGEN WAS INCORPORATED DURING THE REACTION. A PRIMARY DEUTERIUM ISOTOPE EFFECT WAS OBSERVED FOR CONVERSION OF DICHLOROMETHANE TO CARBON MONOXIDE BOTH BY LONG-EVANS RAT HEPATIC MICROSOMAL FRACTIONS & BY STANNOUS PHOSPHATE MODEL SYSTEM. INCUBATION OF DIBROMOMETHANE IN THE MODEL SYSTEM IN THE PRESENCE OF 3,4-DIMETHYLANILINE RESULTED IN FORMATION OF 3,4-FORMOXYLIDIDE, SUPPORTING THE INTERMEDIACY OF A FORMYL HALIDE. A MECHANISM FOR THE METABOLISM OF DIHALOMETHANES TO CARBON MONOXIDE IS PROPOSED.

Halogenated methanes, in particular the brominated homologs, including dibromomethane and tribromomethane were subjected to biochemical decomposition in vitro by the cytochrome p450 rich fraction of the monooxygenase liver system. No significant contribution of GSH addition to the overall rate of metabolism of the halogenated methanes could be observed.

Treatment of Sprague-Dawley rats with sodium phenobarbital (50 mg/kg in 0.9% saline for 4 days) or 3-methylcholanthrene (20 mg/kg in corn oil for 2 days) resulted in increased metabolism of dibromomethane (3 m mol/kg) to carbon monoxide.

Biotransformation of dihalomethanes leads to dehalogenation & end product is carbon monoxide. In the case of dichloromethane the carbon monoxide appears to arise from formyl halide. This intermediate, as an alternative to losing carbon monoxide, can covalently bind to cellular protein or lipid. The involvement of nonmicrosomal enzymes in dihalomethane biotransformation leads to prodn of formaldehyde & halide. A necessary step is the reaction of dihalomethane with glutathione, which results in loss of one halide. The resulting halomethylglutathione is postulated to undergo nonenzymatic hydrolytic dehalogenation leaving hydroxymethylglutathione. The next step would result in the release of the hydroxymethyl group as formaldehyde. Alternatively it has been shown that in the presence of formaldehyde dehydrogenase & NAD /nicotinamide-adenine dinucleotide/ formic acid can be formed. /Dichloromethane/

Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (L626)

Used as a chemical intermediate and a solvent for fats, waxes, and resins; [HSDB] Produced in nature by microalgae commonly found along beaches and coastlines; Used as an intermediate, solvent for chemical manufacture, gauge fluid, and in fire extinguishing fluids; [Reference #1]

Organic synthesis, solvent

SOLVENT FOR FATS, WAXES, & RESINS; HEAVY LIQUID IN SOLID SEPARATIONS; INGREDIENT OF FIRE EXTINGUISHING FLUIDS; GAGE FLUID

Solvent, as a gauge fluid, and in producing pesticides...can be used as dense, readily volatile media for mineral and salt separations.

It may be produced synthetically or naturally by marine algae. Dibromomethane is used as a solvent, gage fluid and in organic synthesis. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock.

2023: 1,000,000 - <5,000,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 G

(1975) PROBABLY GREATER THAN 4.54X10+5 G

Manufactured along with bromochloromethane, from dichloromethane: Lake, Asadorian, US patent 2,553,518 (1951 to Dow).

Prepn: Hartman, Dreger Org Synth Coll Vol 1, 357 (1941)

Reaction of dichloromethane with anhydrous aluminum bromide, treatment with bromine and aluminum, or by reaction with hydrogen bromide in the presence of an aluminum halide catalyst...allowing the reaction to proceed to completion.

Pharmaceutical and Medicine Manufacturing

Methane, dibromo-: ACTIVE

A laboratory preparation involves removing a bromine from bromoform using sodium arsenite.