HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenacyl bromide
2-BROMO-1-PHENYLETHANONE · α-Bromoacetophenone · A-BROMOACETOPHENONE · 1-Phenyl-2-broMoethanone · 2-Bromoacetophenone ,99% · NSC 9807 · Stauffer 4644 · AKOS BBS-00004003
Identifiers & Physical Properties
| CAS No. | 70-11-1 |
|---|---|
| Molecular formula | C8H7BrO |
| Average molar mass | 199.04 g/mol |
| Monoisotopic mass | 197.96802694 g/mol |
| SMILES | O=C(CBr)c1ccccc1 |
| InChIKey | LIGACIXOYTUXAW-UHFFFAOYSA-N |
| PubChem CID | 6259 |
| ChEMBL | CHEMBL102953 |
| ChEBI | CHEBI:51846 |
| EC No. | 200-724-9 |
| DTXSID | DTXSID2049426 |
Chemical & Physical Properties
| XLogP | 2.5 |
|---|---|
| Topological polar surface area | 17.1 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 2 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 116 |
| Chemical classes | Other Classes -> Aromatic Ketones, Halogenated |
| SpringerMaterials Properties | Chemical shift |
| LogP (partition coefficient) | 2.19 |
| Vapor pressure | 0.01 [mmHg] |
| 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.[Merck Index] Beige crystalline solid[Aldrich MSDS] |
| Melting point | 48-51 °C (lit.) |
| Boiling point | 135 °C/18 mmHg (lit.) |
| Density | 1.476 |
| Refractive index | 1.5700 (estimate) |
| Flash point | >230 °F |
| Storage conditions | 2-8°C |
| Solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)PRACTICALLY INSOLUBLE |
| Physical state | Crystals or Powder |
| Color | White to dark green-brown |
| Merck | 14,1402 |
| BRN | 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 | 70-11-1(CAS DataBase Reference) |
| FDA UNII | 754Y0U325I |
| NIST Chemistry Reference | Ethanone, 2-bromo-1-phenyl-(70-11-1) |
| EPA Substance Registry System | Ethanone, 2-bromo-1-phenyl- (70-11-1) |
| UNSPSC Code | 12352200 |
| NACRES | NA.24 |
| GHS pictogram | GHS05,GHS06 |
| Signal word | Danger |
| GHS hazard statements | H301+H311+H331-H314 |
| GHS 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 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Hazard symbols | C |
| Risk statements (R) | 34-20/21/22 |
| Safety statements (S) | 26-36/37/39-45 |
| UN transport number | UN 2645 |
| Water hazard class (WGK) | 3 |
| F | 8-19 |
| Hazard Note | Corrosive |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1Skin Corr. 1B |
| Packing group | II |
| Customs code | 29143990 |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Limited quantities | 0.5 Kg (solid) |
| Excepted quantities | Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | DangerH301 (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. |
|---|---|
| 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 |
| DOT label | Poison |
| 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 CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death. |
| Hazards summary | A lachrymatorA severe skin, eye, and mucous membrane irritant[Merck Index] Slowly reacts with moisture producing hydrogen bromideToxic by ingestion, inhalation, and skin absorption[CAMEO] Causes burns and lachrymationInhalation may cause corrosive injuries to upper respiratory tract and lungs[Aldrich MSDS] See alpha-Chloroacetophenone. |
| DOT ID and guide | 2645 153 |
| Reactive group | Halogenated Organic Compounds |
| Reactivity Profile | PHENACYL BROMIDE reacts slowly with metals causing mild corrosion. |
| DOT Hazard Classification | Phenacyl bromideUN2645Div 6.1 Poisonous materials (49 eCFR § 173.132)PG II: the degree of danger presented by the material is medium |
| Air and Water Reactions | Reacts slowly with moisture in air to form hydrogen bromide. |
| Hazard Classes and Categories | Acute Tox. 3 (20.6%) |
| Fire fighting | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| 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: |
| Exposure control and personal protection | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Nonfire spill response | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:Immediate precautionary measure |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Emergency Response Planning Guidelines | Small Fire |
| 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. |
| Health effects | A strong lachrymator. Inhalation, ingestion or skin contact with material may cause severe injury or death. Potentially hepatotoxic. It is not carcinogenic or mutagenic. |
| Adverse effects | Dermatotoxin - Skin burns. |
| Exposure routes | Oral (L626)inhalation (L626)dermal (L626) |
| 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. |
| Carcinogen Classification | No indication of carcinogenicity (not listed by IARC). (L135) |
| F | 8-19 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| UN transport number | UN 2645 |
| Customs code | 29143990 |
| Risk statements (R) | 34-20/21/22 |
| Signal word | Danger |
| GHS pictogram | GHS05,GHS06 |
| Hazard symbols | C |
| hazard_note | Corrosive |
| Safety statements (S) | 26-36/37/39-45 |
| Hazard class | 6.1Skin Corr. 1B |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Packing group | II |
| GHS 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) |
| GHS 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 |
Applications & Uses
Uses
2-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
Uses
It 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 Description
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.