フェナシルブロミド

Phenacyl bromide

HCID 6259CAS 70-11-1

基本情報

標準SMILES
O=C(CBr)c1ccccc1
InChIKey
LIGACIXOYTUXAW-UHFFFAOYSA-N
分子式
C8H7BrO
平均分子量
199.04 g/mol
単同位体質量
197.96802694

概要

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.

名称と識別子

優先名称
Phenacyl bromide
IUPAC
2-bromo-1-phenylethanone
現地名
フェナシルブロミド
英語名
2-Bromoacetophenone
分子式
C8H7BrO
分子量
199.04

名称と別名

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
名称をさらに表示
フェナシルブロミド臭化フェナシルブロモアセチルベンゼンα-ブロモアセトフェノン1-フェニル-2-ブロモエタン-1-オン(ブロモアセチル)ベンゼン2-ブロモアセトフェノンフェニルカルボニルメチルブロミドω-ブロモアセトフェノンフェニル(ブロモメチル)ケトン2-ブロモ-1-フェニルエタノン1-(ブロモアセチル)ベンゼン1-フェニル-2-ブロモエタノン2-プロモアセトンフェノンフェナシル ブロミドΑ‐ブロモアセトフェノンα-BromoacetophenoneA-BROMOACETOPHENONE1-Phenyl-2-broMoethanone2-Bromoacetophenone ,99%NSC 9807AKOS BBS-00004003Bromoacetylbenzene-Bromoacetophenone
phenacylbromideBenzoylmethyl bromideomega-BromacetophenoneDTXSID2049426UN2645STAUFFER-4644phenyl bromomethyl ketoneNSC-9807

データベース識別子

CAS
70-11-1
PubChem CID
6259
DTXSID
DTXSID2049426
ChEMBL
CHEMBL102953
ChEBI
CHEBI:51846
UNII
754Y0U325I
EC Number
200-724-9
Nikkaji
J4.874G

物性

構造計算による物性

XLogP
2.5
極性表面積
17.1 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
2
重原子数
10

実験および物理化学的性質

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

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]

物理化学的性質

融点
48 · 48-51 °C (lit.)
沸点
135 °C/18 · 135 °C/18 mmHg (lit.)
比重(密度)
1.476 · 1.476
屈折率
1.57 · 1.5700 (estimate)
闪点
230 °F · >230 °F
貯蔵温度
2 · 2-8°C

化学的性質

化学的特性Off white-grey green crystaline powder

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Regulatory Information · 2 件

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 件

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

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

Health Hazards · 2 件

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 件

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

安全と保護具

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

· 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 件

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 件

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

Immediate precautionary measure

毒性情報

Treatment · 1 件

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 件

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 件

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.

安全データ

F
8-19
wgk
3
tsca
TSCA listed
ridadr
UN 2645
hs_code
29143990
risk_code
34-20/21/22

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

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)

用途と製造

Uses · 2 件

Used to make other chemicals; [CAMEO]

Phenacyl bromide is an industrial and laboratory chemical.

General Manufacturing InformationEthanone, 2-bromo-1-phenyl-: ACTIVE
応用分野 · 3 件

用途有機合成原料。

使用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

一般的な説明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.

調製方法

純化方法Crystallise the bromide from EtOH, MeOH or pet ether (b 80-100o). [Tanner J Org Chem 52 2142 1987, Beilstein 7 IV 649.]

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補足説明

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

関連反応

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