Phenacyl bromide

HCID 6259CAS 70-11-1

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

2-BromoacetophenonePhenacyl bromide70-11-12-Bromo-1-phenylethanoneBromoacetophenone2-Bromo-1-Phenylethan-1-OneBromomethyl phenyl ketoneEthanone, 2-bromo-1-phenyl-omega-BromoacetophenoneALPHA-BROMOACETOPHENONEAcetophenone, 2-bromo-Stauffer 4644
Show more names
α-BromoacetophenoneA-BROMOACETOPHENONE1-Phenyl-2-broMoethanone2-Bromoacetophenone ,99%NSC 9807AKOS BBS-00004003Bromoacetylbenzene-Bromoacetophenone
phenacylbromideBenzoylmethyl bromideomega-BromacetophenoneDTXSID2049426UN2645STAUFFER-4644phenyl bromomethyl ketoneNSC-9807

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

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Aromatic Ketones, Halogenated
SpringerMaterials PropertiesChemical shift
LogP2.19
Vapor Pressure0.01 [mmHg]
Physical Description · 2 items

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

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 2 items

Chemical: Ethanone, 2-bromo-1-phenyl-

2-Bromoacetophenone: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelPoison
Fire Hazards · 2 items

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

Health Hazards · 2 items

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 · 1 item

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 ID and Guide2645 153

Safety & protection

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Accidental Release Measures · 2 items

· 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 · 2 items

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 ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Isolation and Evacuation · 2 items

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

Toxicology

Treatment · 1 item

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 EffectsA strong lachrymator. Inhalation, ingestion or skin contact with material may cause severe injury or death. Potentially hepatotoxic. It is not carcinogenic or mutagenic.
Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesOral (L626) ; inhalation (L626) ; dermal (L626)
Toxicity Summary · 1 item

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 · 1 item

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

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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 · 2 items

Used to make other chemicals; [CAMEO]

Phenacyl bromide is an industrial and laboratory chemical.

General Manufacturing InformationEthanone, 2-bromo-1-phenyl-: ACTIVE
Applications · 3 items

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]

Additional notes

DefinitionChEBI: An alpha-bromoketone that is acetophenone substituted by a bromo group at position 2.

Related reactions

1,060 records

Linked notes

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