2-bromo-1-phenylethan-1-one

• ChemBase编号: 76533
• 分子式: C8H7BrO
• 平均质量: 199.04458
• 单一同位素质量: 197.96802684
• SMILES: O=C(c1ccccc1)CBr
• Canonical SMILES: BrCC(=O)c1ccccc1
• InChI: InChI=1S/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2
• InChIKey: LIGACIXOYTUXAW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-bromo-1-phenylethan-1-one
• IUPAC传统名: phenacyl bromide
• 别名: ω-溴苯乙酮; 苯甲酰甲基溴; 2-溴苯乙酮; 1-Bromo-2-phenylethan-2-one; 1-Phenyl-2-bromoethanone; 2-Bromo-1-phenylethanone; Benzoylmethyl Bromide; Bromoacetophenone; NSC 9807; Phenyl Bromomethyl Ketone; Stauffer 4644; β-Bromoacetophenone; ω-Bromacetophenone; 2-Bromoacetophenone; ω-Bromoacetophenone; Phenacyl bromide; 2-Bromoacetophenone; 2-bromo-1-phenylethanone; 2-Bromoacetophenone; 2-Bromo-1-phenylethan-1-one; Phenacyl bromide 98%; α-Bromoacetophenone; Bromomethyl phenyl ketone; Phenacyl bromide; 2-bromo-1-phenylethan-1-one

登记号

• CAS号: 70-11-1
• EC号: 200-724-9
• MDL号: MFCD00000195
• Beilstein号: 606474
• 默克索引号: 141402
• PubChem SID: 24847241; 24887194; 162041437; 24887195
• PubChem CID: 6259
• CHEBI ID: 51846
• CHEMBL: 102953
• Chemspider ID: 6023
• 维基百科标题: Phenacyl_bromide

理论计算性质

• Acid pKa: 15.502873
• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 2.2537324
• LogD (pH = 7.4): 2.2537324
• Log P: 2.2537324
• 摩尔折射率: 44.1975 cm^3
• 极化性: 16.77298 Å^3
• 极化表面积: 17.07 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: Colorless solid; Off-White Solid
• 熔点: 47-50 °C; 48 - 51°C; 48-51 °C(lit.); 48-51°C; 48-51°C; 49-50 °C; 49-51°C; 50 °C
• 沸点: 135 °C/18 mmHg(lit.); 136 °C / 18mmHg; 140°C/11mm
• 闪点: >110°C(230°F); 113 °C; 235.4 °F
• 密度: 1.650
• 疏水性(logP): 1.834

安全信息

• 保存条件: Refrigerator, Under Inert Atmosphere
• 保存注意事项: Toxic/Irritant/Corrosive/Lachrymatory/Light Sensitive/Air Sensitive/Store under Argon/Keep Cold
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); 有毒(Toxic) (T)
• 联合国危险货物编号: 2645; UN2645
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 23-34; 34
• 安全公开号: 26-36/37/39-45
• TSCA收录: 是
• GHS危险品标识: GHS05; GHS06
• GHS警示词: Danger
• 主要危害: Toxic(T)
• GHS危险声明: H314; H331-H314-H318
• GHS警示性声明: P280-P305 + P351 + P338-P310; P280-P305+P351+P338-P309-P310
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2645 6.1/PG 2
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... PTPN6(5777)

产品相关信息

• 纯度: ≥97.0% (GC); ≥99.0%; ≥99.0% (GC); 95%; 98%
• 级别: for GC derivatization; purum
• 线性分子式: C6H5COCH2Br

详细说明

Sigma Aldrich - 115835

Frequently Asked Questions
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包装
5, 100, 500 g in glass bottle

Sigma Aldrich - 77450

Frequently Asked Questions
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Application
与酸反应生成酯晶体

Toronto Research Chemicals - B679065

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

参考文献

• MacKerell, A.D. et al.: Biochemistry, 25, 5182 (1986)
• Arabaci, G. et al.: Biiorg. Med. Chem. Lett., 12, 3047 (1986)
• Reagent for carboxyl protection as phenacyl esters, stable to acid hydrolysis but readily cleaved by nucleophiles or by reduction. See Appendix 6. Protection can be effected in the presence of triethylamine: J. Chem. Soc. (C), 1191 (1966), or, better, KF in DMF: Tetrahedron Lett., 599 (1977). Phase-transfer conditions have also been reported: Synth. Commun., 26, 1747 (1996). Cleavage has been described using a variety of reagents, including Zn-AcOH: Tetrahedron Lett., 343 (1970), catalytic hydrogenolysis, treatment with PhS^-, PhSeH, or NaHTe: Synth. Commun., 18, 116 (1988); TBAF: J. Org. Chem., 56, 5465 (1991); or photolysis: J. Org. Chem., 62, 6245 (1997).
• Has also been used to block the imidazole ring in histidine residues during peptide synthesis, and is stable to TFA, TfOH and HBr-AcOH: J. Chem. Soc., Chem. Commun., 472 (1978); J. Chem. Soc., Perkin 1, 2261 (1979).
• For formation of the Sn enolate using SnCl₂, see: Synth. Commun., 23, 271 (1993). 1,4-Diketones may be synthesized from ɑ-bromoketones and Sn enolates: J. Chem. Soc., Perkin 1, 3205 (1990).