| Record Information |
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| Version | 2.0 |
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| Creation Date | 2009-06-22 16:08:37 UTC |
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| Update Date | 2014-12-24 20:24:39 UTC |
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| Accession Number | T3D1801 |
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| Identification |
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| Common Name | Phenacyl bromide |
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| Class | Small Molecule |
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| Description | Phenacyl bromide is an organobromide compound. It is a powerful lachrymator as well as a useful precursor to other organic compounds. In particular, henacyl bromide can be used for the identification of organic acids via their conversion to crystalline phenacyl esters. Phenacyl bromide can also be used for the determination of global DNA methylation by reversed phase HPLC with spectrofluorimetric detection. It has also been used as a protein modification or labeling agent for the selective modification of cysteine residues in a number of enzymes for biochemical studies. It is a white solid that reacts slowly with metals causing mild corrosion. It is combustible and may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air. |
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| Compound Type | - Aromatic Hydrocarbon
- Bromide Compound
- Ester
- Industrial/Workplace Toxin
- Ketone
- Lachrymator
- Organic Compound
- Organobromide
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Synonym | | .alpha.-bromoacetophenone | | .omega.-bromacetophenone | | .omega.-bromoacetophenone | | 2-Bromo-1-phenylethanone | | 2-Bromoacetophenone | | a-bromoacetophenone | | Acetophenone, 2-bromo- (8CI) | | Alpha-bromoacetophenone | | Benzoylmethyl bromide | | Bromoacetophenone | | Bromomethyl phenyl ketone | | Halomethyl Phenyl Ketone deriv. 23 | | Omega-bromacetophenone | | Omega-bromoacetophenone | | Stauffer 4644 |
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| Chemical Formula | C8H7BrO |
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| Average Molecular Mass | 199.045 g/mol |
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| Monoisotopic Mass | 197.968 g/mol |
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| CAS Registry Number | 70-11-1 |
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| IUPAC Name | 2-bromo-1-phenylethan-1-one |
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| Traditional Name | phenacyl bromide |
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| SMILES | BrCC(=O)C1=CC=CC=C1 |
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| InChI Identifier | InChI=1S/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2 |
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| InChI Key | InChIKey=LIGACIXOYTUXAW-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbonyl compounds |
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| Direct Parent | Alkyl-phenylketones |
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| Alternative Parents | |
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| Substituents | - Alkyl-phenylketone
- Aryl alkyl ketone
- Benzoyl
- Benzenoid
- Monocyclic benzene moiety
- Alpha-haloketone
- Organic oxide
- Hydrocarbon derivative
- Organobromide
- Organohalogen compound
- Alkyl halide
- Alkyl bromide
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White crystals, greenish on exposure to light. Easily volatile with steam and soluble in organic solvents. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 50.5°C | | Boiling Point | 250°C | | Solubility | Not Available | | LogP | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0900000000-f43aaeb3a157fc58f563 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0900000000-fa7f1b7274ff37b5b9db | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-9500000000-e2c4b851750422b24ef3 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-bf88d5a7dcf96607b954 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-1900000000-17e09742ff49997a69dc | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9200000000-3b50b5874cd98eb50a75 | 2016-08-03 | View Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-0a4i-9600000000-3437d0f76ecee59a2305 | 2014-09-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | Not Available | 2014-09-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | Not Available | 2014-09-23 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Oral (9) ; inhalation (9) ; dermal (9) |
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| Mechanism of Toxicity | 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. |
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| Metabolism | 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. (9) |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity (not listed by IARC). (10) |
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| Uses/Sources | Phenacyl bromide is an industrial and laboratory chemical. |
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| Minimum Risk Level | Not Available |
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| 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. |
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| 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. |
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| 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. |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| PubChem Compound ID | 6259 |
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| ChEMBL ID | CHEMBL102953 |
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| ChemSpider ID | 6023 |
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| KEGG ID | Not Available |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 51846 |
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| BioCyc ID | CPD-4361 |
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| CTD ID | C013190 |
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| Stitch ID | Phenacyl bromide |
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| PDB ID | Not Available |
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| ACToR ID | Not Available |
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| Wikipedia Link | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | T3D1801.pdf |
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| General References | - Glover GI, Mariano PS, Petersen JR: Reinvestigation of the phenacyl bromide modification of alpha-chymotrypsin. Biochemistry. 1976 Aug 24;15(17):3754-60. [8093 ]
- Arabaci G, Yi T, Fu H, Porter ME, Beebe KD, Pei D: alpha-bromoacetophenone derivatives as neutral protein tyrosine phosphatase inhibitors: structure-Activity relationship. Bioorg Med Chem Lett. 2002 Nov 4;12(21):3047-50. [12372498 ]
- Yanez Barrientos E, Wrobel K, Lopez Torres A, Gutierrez Corona F, Wrobel K: Application of reversed-phase high-performance liquid chromatography with fluorimetric detection for simultaneous assessment of global DNA and total RNA methylation in Lepidium sativum: effect of plant exposure to Cd(II) and Se(IV). Anal Bioanal Chem. 2013 Mar;405(7):2397-404. doi: 10.1007/s00216-013-6703-x. Epub 2013 Jan 16. [23322354 ]
- MacKerell AD Jr, MacWright RS, Pietruszko R: Bromoacetophenone as an affinity reagent for human liver aldehyde dehydrogenase. Biochemistry. 1986 Sep 9;25(18):5182-9. [3768340 ]
- Chatterjee T, Edelstein I, Marcus F, Eby J, Reardon I, Heinrikson RL: Identification of the highly reactive sulfhydryl group of pig kidney fructose 1,6-bisphosphatase at cysteine 128. J Biol Chem. 1984 Mar 25;259(6):3834-7. [6323443 ]
- Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
- Marrs, Timothy T., Robert L. Maynard, and Frederick Sidell, eds. (2007). Chemical Warfare Agents: Toxicology and Treatment. 2nd edition. John Wiley & Sons. [ISBN: 978-0-470-01359-5]
- Wikipedia. Phenacyl bromide. Last Updated 19 April 2009. [Link]
- International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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