Basic information
- Standard SMILES
CC(=O)Br- InChIKey
FXXACINHVKSMDR-UHFFFAOYSA-N- Molecular formula
- C2H3BrO
- Average molar mass
- 122.95 g/mol
- Monoisotopic mass
- 121.93672682
Overview
Acetyl bromide appears as a colorless fuming liquid with a pungent odor. Vapors irritate eyes and mucous membranes. Corrosive to metals and tissue. Density 13.9 lb / gal.
Names & identifiers
- Preferred name
- Acetyl bromide
- IUPAC
- acetyl bromide
- English name
- ACETYL BROMIDE-2-13C
- Molecular formula
- C2H3BrO
- Molecular weight
- 123.96
Names & synonyms
Show more names
Database identifiers
- CAS
506-96-7、74787-38-5- PubChem CID
- 10482
- DTXSID
DTXSID5060140- UNII
- O18V5XYO0G
- EC Number
- 208-061-7、693-093-8
- Nikkaji
- J2.611E
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 4
- Formal charge
- 0
- Complexity
- 33
Experimental & physicochemical properties
Chemical Classes
Toxic Gases & Vapors -> Acid Halides
Corrosives
Odor
Sharp unpleasant odor
Pungent odor
Density
1.66 at 60.8 °F (USCG, 1999) - Denser than water; will sink
Density: 1.52 at 9 °C
Saturated liquid density: 103.599 lb/cu ft at 70 °F
Vapor specific gravity: 4.24; Saturated vapor density: 0.04488 lb/cu ft at 70 °F
Relative density (water = 1): 1.5
1.66 @ 20°C
Color/Form
Fuming liquid
Colorless fuming liquid
Solubility
Violently decomposed by water or alcohol
Miscible with ether, chloroform, benzene
Soluble in ether, chloroform, benzene
Miscible with ether, benzene, chloroform; soluble in acetone
Solubility in water: reaction
Corrosivity
Corrosive
Corrosive to metals and tissue
Flash Point
110 °C (230 °F) - closed cup
75 °C
Boiling Point
169 °F at 760 mmHg (USCG, 1999)
74 °C
76 °C
76.7 °C @760 [mm Hg]
Decomposition
Hazardous decomposition products formed under fire conditions - Carbon oxides, hydrogen bromide gas.
When heated to decomposition it emits highly corrosive and toxic fumes of carbonyl bromide and bromine.
Violently decomposed by water, or by alcohol.
Melting Point
-141.7 °F (USCG, 1999)
-95.5 °C
-96 °C
-96.5 °C
Physicochemical properties
- Melting point
- 96 °C · −96 °C(lit.)
- Boiling point
- 75 · 75-77 °C(lit.)
- Density
- 1.677 g/mL · 1.677 g/mL at 25 °C
- refractive index
- 20 · n20/D 1.45(lit.)
- Flash point
- 230 °F · >230 °F
- InChI
- 1S/C2H3BrO/c1-2(3)4/h1H3/i1+1
- InChIKey
- FXXACINHVKSMDR-OUBTZVSYSA-N
- SMILES
- [13CH3]C(Br)=O
- UNSPSC Code
- 12352202 · 12352202
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314
- Precautionary statements
- 280 · P280-P305+P351+P338-P310
- Hazard Codes
- C
- Risk Statements
- 14 · 14-34-36/37
- Safety Statements
- 26 · 26-27-28-36/37/39-45
- RIDADR
- 1716 · UN 1716
- WGK Germany
- 3 · 3
- HazardClass
- 8 · 8
- PackingGroup
- II
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 1 Met · Eye Dam. 1Met. Corr. 1Skin Corr. 1B
Safety & regulation
GHS classification
GHS Classification
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 51 reports by companies from 8 notifications to the ECHA C&L Inventory.
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
Hazard information
Regulatory Information
Chemical: Acetyl bromide
Status: Active Update: 06-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/16238
Acetyl bromide: 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.)
Fire Hazards
Special Hazards of Combustion Products: Toxic and irritating hydrogen bromide fumes may form in fires.
· Combustible material: may burn but does not ignite readily.
Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Health Hazards
Inhalation produces primary irritation of the respiratory tract; symptoms of lung damage may be delayed. Contact with liquid produces primary irritation of eyes and severe skin damage; delayed blistering is not uncommon. INGESTION: Sore throat, abdominal pain, and vomiting. (USCG, 1999)
· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.
TSCA Requirements
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. Acetyl bromide is included on this list. Effective date: 6/1/87; Sunset date: 12/19/95.
Safety & protection
Fire Fighting
Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Use foam, powder, carbon dioxide, dry sand. NO water. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water.
First Aid Measures
Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .
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 .
Accidental Release Measures
· 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.
First Aid
INHALATION: remove victim from exposure; if breathing has stopped, give artificial respiration; if breathing is difficult, give oxygen; watch for delayed lung damage.
General First Aid:
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).
TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].
Fire Fighting Procedures
Suitable extinguishing media: Dry powder.
Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.
To fight fire, use dry chemical, /carbon dioxide/.
Reacts violently with water-based extinguishers, such as foam. Do not use water or foam extinguishers. Use dry chemical or carbon dioxide extinguishers. ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. ... The only respirators recommended for firefighting are self-contained breathing apparatuses that have full face-pieces and are operated in a pressure-demand or other positive-pressure mode.
If material on fire or involved in fire: Use dry chemical or carbon dioxide. Do not use water on material itself. If large quantities of combustibles are involved, use water in flooding quantities as spray and fog. Use water spray to knock-down vapors. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.
Storage Conditions
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. Never allow product to get in contact with water during storage. Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials.
Store separately in a corrosion-resistant location. ... Store in a secure poison location. Prior to working with this chemical you should be trained on its proper handling and storage. Store in tightly closed containers in a cool, well-ventilated area away from moisture and sunlight. Where possible, automatically pump liquid from drums or other storage containers to process containers. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers of this chemical. Sources of ignition, such as smoking and open flames, are prohibited where this chemical is used, handled, or stored in a manner that could create a potential fire or explosion hazard.
Protect from water.
Cleanup Methods
ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Do not flush with water. Keep in suitable, closed containers for disposal.
Prevent liquid from reaching water if possible. This material creates large amounts of toxic hydrogen bromide (HBr) vapor when spilled in water, and is considered by the North American Emergency Response Guide to be dangerous from 0.5 to 10 km (0.3-6.0 miles downwind). Enter area from upwind side. Evacuate area and issue warning of danger, including possible explosion. Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Absorb liquids using dry lime or soda ash. Do not use water or wet method. Ventilate area of spill or leak after cleanup is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. ... Initial isolation and protective action distances: Distances shown are likely to be affected during the first 30 min after materials are spilled and could increase with time. If more than one tank car, cargo tank, portable tank, or large cylinder involved in the incident is leaking, the protective action distance may need to be increased. You may need to seek emergency information from CHEMTREC ... or seek professional environmental engineering assistance from the US EPA Environmental Response Team ... . Small spills (From a small package or a small leak from a large package), when spilled in water: First: Isolate in all directions (100 feet/30 meters). Then: Protect persons downwind - Day 0.1 mi/0.2 km, Night 0.2 mi/0.3 km). Large spills (From a large package or from many small packages): First: Isolate in all directions (200 feet/60 meters). Then: Protect persons downwind - Day 0.4 mi/0.6 km, Night 1.1 mi/1.8 km.
Environmental considerations - Water spill: If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Adjust pH to neutral (pH=7). Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
Environmental considerations - Air spill: Apply water spray or mist to knock down vapors. Vapor knockdown water is corrosive or toxic and should be diked for containment.
Environmental considerations - Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash or cement powder.
Disposal Methods
SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
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; Contaminated packaging: Dispose of as unused product.
Toxicology
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that acetyl bromide is expected to have very high mobility in soil(SRC). In view of its violent decomposition in the presence of water(3) and the high reactivity of structurally-similar compounds with active hydrogen groups which occur in soil(4), it is unlikely that acetyl bromide would persist for long in moist soils(SRC). Acetyl bromide is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 122 mm Hg at 25 °C(5). Biodegradation data in soil were not available(SRC, 2018).
AQUATIC FATE: Acetyl bromide decomposes violently in the presence of water(1) and, therefore, will not persist in the aquatic environment(SRC). Adsorption to sediment, volatilization, bioconcentration in aquatic species or biodegradation are not expected because of the very short lifetime of this compound in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acetyl bromide, which has a vapor pressure of 122 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase acetyl bromide may be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5 years(SRC), calculated from its rate constant of 9.1X10-15 cu cm/molecule-sec at 25 deg(SRC) determined using a structure estimation method(3). Acetyl bromide contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
Toxicity Summary
IDENTIFICATION AND USE: Acetyl bromide is a colorless fuming liquid. It is used in organic synthesis and dye manufacture. HUMAN STUDIES: It could cause severe ocular damage if splashed in eye. However, in one instance of corneal burn, recovery is reported to have been complete in 48 hr. ANIMAL STUDIES: There are no data available.
Signs and Symptoms
Abdominal pain. Sore throat. Cough. Burning sensation. Shortness of breath. Laboured breathing. Symptoms may be delayed.
Pain. Redness. Blisters. Skin burns.
Pain. Redness. Severe deep burns. Loss of vision.
Burning sensation. Abdominal pain. Shock or collapse.
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of acetyl bromide can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that acetyl bromide is expected to have very high mobility in soil(SRC). However, acetyl bromide will decompose violently in the presence of water(3). High reactivity of structurally-similar compounds such as acetyl chloride towards molecules with active hydrogen groups such as natural products containing amine, phenol, and alcohol functional groups that occur in soil has been reported(4). Therefore, it is unlikely that acetyl bromide would persist for long in moist soils(SRC).
Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ Strong irritant to eyes and skin.
/SIGNS AND SYMPTOMS/ ... Could cause severe ocular damage if splashed in eye. However, in one instance of corneal burn, recovery is reported to have been complete in 48 hr.
Volatilization from Water/Soil
Acetyl bromide will decompose violently in water(1) forming gaseous hydrogen bromide(2), preempting volatilization from water or soil surfaces as an environmental fate process(SRC). For the same reason, volatilization from moist soil surfaces is very unlikely(SRC). The potential for volatilization of acetyl bromide from dry soil surfaces may exist(SRC) based upon a vapor pressure of 122 mm Hg(3).
Regulatory information
TSCA Requirements
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. Acetyl bromide is included on this list. Effective date: 6/1/87; Sunset date: 12/19/95.
CERCLA Reportable Quantities
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 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
Clean Water Act Requirements
Acetyl bromide is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.
DHS Chemicals of Interest (COI)
Acetyl bromide
A Commercial Grade
A Placarded Amount
Chemical or material that can be mixed with readily available materials.
Safety data
- wgk
- 3
- ridadr
- UN 1716
- risk_code
- 14-34-36/37
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- C
- safety_code
- 26-27-28-36/37/39-45
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- II
- Hazard statements
- H314
- Hazard Classifications
- Eye Dam. 1Met. Corr. 1Skin Corr. 1B
- Precautionary statements
- P280-P305+P351+P338-P310
Chemistry & industry
Uses & manufacturing
Uses
Used in organic synthesis; [HSDB]
Toxic Gas from Spilling Chemical in Water [Category: Other]
Organic synthesis, dye manufacture.
Methods of Manufacturing
Prepared from phosphorus tribromide and glacial acetic acid or acetic anhydride ... .
Interaction of acetic acid and phosphorus pentabromide.
Suppliers50 total
Related reactions
Linked notes
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