Basic information
- Standard SMILES
O=C(CBr)c1ccccc1- InChIKey
LIGACIXOYTUXAW-UHFFFAOYSA-N- Molecular formula
- C8H7BrO
- Average molar mass
- 199.04 g/mol
- Monoisotopic mass
- 197.96802694
Overview
Phenacyl bromide appears as a crystalline solid or a liquid with a sharp odor. Toxic by inhalation, ingestion and skin absorption. A severe eye irritant (a lachrymator). Used to make other chemicals.
Names & identifiers
- Preferred name
- Phenacyl bromide
- IUPAC
- 2-bromo-1-phenylethanone
- English name
- 2-Bromoacetophenone
- Molecular formula
- C8H7BrO
- Molecular weight
- 199.04
Names & synonyms
Show more names
Database identifiers
- CAS
70-11-1- PubChem CID
- 6259
- DTXSID
DTXSID2049426- ChEMBL
CHEMBL102953- ChEBI
CHEBI:51846- UNII
- 754Y0U325I
- EC Number
- 200-724-9
- Nikkaji
- J4.874G
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 116
Experimental & physicochemical properties
Physical Description
Phenacyl bromide appears as a crystalline solid or a liquid with a sharp odor. Toxic by inhalation, ingestion and skin absorption. A severe eye irritant (a lachrymator). Used to make other chemicals.
Solid; [Merck Index] Beige crystalline solid; [Aldrich MSDS]
Physicochemical properties
- Melting point
- 48 · 48-51 °C (lit.)
- Boiling point
- 135 °C/18 · 135 °C/18 mmHg (lit.)
- Density
- 1.476 · 1.476
- refractive index
- 1.57 · 1.5700 (estimate)
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- form
- Crystals or Powder
- color
- White to dark green-brown
- Water Solubility
- PRACTICALLY INSOLUBLE
- Merck
- 14 · 14,1402
- BRN
- 606474 · 606474
- Stability
- Stable. Incompatible with strong bases, strong oxidizing agents. Combustible.
- InChI
- 1S/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2
- InChIKey
- LIGACIXOYTUXAW-UHFFFAOYSA-N
- SMILES
- BrCC(=O)c1ccccc1
- CAS DataBase Reference
- 70 · 70-11-1(CAS DataBase Reference)
- FDA UNII
- 754 Y0U325I · 754Y0U325I
- NIST Chemistry Reference
- 2 · Ethanone, 2-bromo-1-phenyl-(70-11-1)
- EPA Substance Registry System
- 2 · Ethanone, 2-bromo-1-phenyl- (70-11-1)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 5 · GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301+H311+H331-H314
- Precautionary statements
- 501 · P501-P260-P270-P271-P264-P280-P361+P364-P303+P361+P353-P301+P330+P331-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P405
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- C
- Risk Statements
- 34 · 34-20/21/22
- Safety Statements
- 26 · 26-36/37/39-45
- RIDADR
- 2645 · UN 2645
- WGK Germany
- 3 · 3
- F
- 8 · 8-19
- Hazard Note
- Corrosive
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- II
- HS Code
- 29143990 · 29143990
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 1 B · Skin Corr. 1B
- Limited Quantities
- 0.5 Kg · 0.5 Kg (solid)
- Excepted Quantities
- Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H301 (20.6%): Toxic if swallowed [Danger Acute toxicity, oral]
P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 63 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Ethanone, 2-bromo-1-phenyl-
2-Bromoacetophenone: Does not have an individual approval but may be used under an appropriate group standard
Fire Hazards
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
· Combustible material: may burn but does not ignite readily.
Health Hazards
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.
Hazards Summary
A lachrymator; A severe skin, eye, and mucous membrane irritant; [Merck Index] Slowly reacts with moisture producing hydrogen bromide; A lachrymator; Toxic by ingestion, inhalation, and skin absorption; [CAMEO] Causes burns and lachrymation; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Aldrich MSDS] See alpha-Chloroacetophenone.
DOT Hazard Classification
Phenacyl bromide
UN2645
Div 6.1 Poisonous materials (49 eCFR § 173.132)
PG II: the degree of danger presented by the material is medium
Safety & protection
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
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
General First Aid:
Isolation and Evacuation
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Immediate precautionary measure
Toxicology
Treatment
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.
Toxicity Summary
Organobromide compounds such as phenacyl bromide are strong alkylating agents. Consequently they can readily modify free thiols (cysteines) and methionine residues of the surfaces of proteins leading to the disruption of enzyme, transporter or membrane functions. One of the most probable protein targets is the TRPA1 ion channel that is expressed in sensory nerves (trigeminal nerve) of the eyes, nose, mouth and lungs. Human liver aldehyde dehydrogenase isozymes E1 and E2 are both completely and irreversibly inactivated by phenacyl bromide. This kind targeted modification may lead to liver toxicity.
Signs and Symptoms
Phenacyl bromide is a strong lachrymator. Eye exposure produces irritation, characterized by a burning sensation, redness, tearing, inflammation, and possible corneal injury. Causes skin irritation and possible burns. May cause gastrointestinal irritation with nausea, vomiting and diarrhea. Causes respiratory tract irritation.
Safety data
- F
- 8-19
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 2645
- hs_code
- 29143990
- risk_code
- 34-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS06
- hazard_code
- C
- hazard_note
- Corrosive
- safety_code
- 26-36/37/39-45
- hazard_class
- 6.1
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- Hazard statements
- H301+H311+H331-H314
- Limited Quantities
- 0.5 Kg (solid)
- Excepted Quantities
- Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
- Hazard Classifications
- Skin Corr. 1B
- Precautionary statements
- P501-P260-P270-P271-P264-P280-P361+P364-P303+P361+P353-P301+P330+P331-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P405
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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)
Uses & manufacturing
Uses
Used to make other chemicals; [CAMEO]
Phenacyl bromide is an industrial and laboratory chemical.
Applications
Uses2-Bromoacetophenone is a brominated acteophenone derivative. 2-Bromoacetophenone has been shown to completely and irreversibly inactivate human liver aldehyde dehydrogenase (EC 1.2.1.3) isoenzymes E1 and E2. 2-Bromoacetophenone and its derivatives display some inhibitory activity on neutral protein tyrosine.inhibitors
UsesIt is used in preparation of crystalline esters from acids. 2-Bromoacetophenone is a complete and irreversible inactivator of human liver aldehyde dehydrogenase isoenzymes E1 and E2.
General DescriptionA crystalline solid or a liquid with a sharp odor. Toxic by inhalation, ingestion and skin absorption. A severe eye irritant (a lachrymator). Used to make other chemicals.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: An alpha-bromoketone that is acetophenone substituted by a bromo group at position 2.
Related reactions
Linked notes
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