2-溴-1-(4-氟苯基)-1-乙酮肟 | 334709-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-溴-1-(4-氟苯基)-1-乙酮肟
• 英文名称: 2-bromo-1-(p-fluorophenyl)ethanone oxime
• 英文别名: 2-bromo-1-(4-fluorophenyl)ethanone oxime；α-bromo-p-fluoroacetophenone oxime；N-[2-bromo-1-(4-fluorophenyl)ethylidene]hydroxylamine
• CAS: 334709-76-1
• 化学式: C₈H₇BrFNO
• 分子量: 232.052
• InChiKey: UGORWQMWPIUIGG-UHFFFAOYSA-N

物化性质

• 熔点：
  84 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090

SDS

Name:	2-Bromo-1-(4-fluorophenyl)-1-ethanone oxime 97% Material Safety Data Sheet
Synonym:
CAS:	334709-76-1

Section 1 - Chemical Product MSDS Name:2-Bromo-1-(4-fluorophenyl)-1-ethanone oxime 97% Material Safety Data Sheet
Synonym:

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
334709-76-1	2-Bromo-1-(4-fluorophenyl)-1-ethanone	97%	unlisted

Hazard Symbols: C
Risk Phrases: 34

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

---

Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:
Treat symptomatically and supportively.

---

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

---

Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 334709-76-1: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: off-white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 84 - 90 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H7BrFNO
Molecular Weight: 232.05

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide, hydrogen fluoride gas, hydrogen bromide.
Hazardous Polymerization: Has not been reported.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 334709-76-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Bromo-1-(4-fluorophenyl)-1-ethanone oxime - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: CORROSIVE SOLID, N.O.S.*
Hazard Class: 8
UN Number: 1759
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing group: III

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 334709-76-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 334709-76-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 334709-76-1 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-溴-1-(4-氟苯基)-1-乙酮肟 在 copper(II) bis(trifluoromethanesulfonate) 、 N,N-二异丙基乙胺 作用下， 以 氯仿 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 dimethyl 3-(4-fluorophenyl)isoxazole-4,5-dicarboxylate
  参考文献：
  名称：

  α-亚硝基苯乙烯作为 (3+1) 环化反应的三原子单元：容易获得 2,3-二氢二氮杂氮氧化物及其多样化的合成转化

  摘要：

  开发了由 α-溴肟和N-甲苯磺酰氧基氨基甲酸酯原位生成的 α-亚硝基苯乙烯的前所未有的 (3+1) 环化，这使得能够合成一系列结构独特且迄今为止尚未开发的 2,3-二氢二氮杂氮氧化物中到高产。该产品具有高度应变的四元环结构，包含两个氮原子。产品的合成适用性也通过许多重要的转化为不同的含氮化合物来证明。

  DOI：

  10.1021/acs.orglett.2c00024
• 作为产物：
  描述：

  2-溴-4'-氟苯乙酮 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 为溶剂， 生成 2-溴-1-(4-氟苯基)-1-乙酮肟
  参考文献：
  名称：

  α-亚硝基苯乙烯作为 (3+1) 环化反应的三原子单元：容易获得 2,3-二氢二氮杂氮氧化物及其多样化的合成转化

  摘要：

  开发了由 α-溴肟和N-甲苯磺酰氧基氨基甲酸酯原位生成的 α-亚硝基苯乙烯的前所未有的 (3+1) 环化，这使得能够合成一系列结构独特且迄今为止尚未开发的 2,3-二氢二氮杂氮氧化物中到高产。该产品具有高度应变的四元环结构，包含两个氮原子。产品的合成适用性也通过许多重要的转化为不同的含氮化合物来证明。

  DOI：

  10.1021/acs.orglett.2c00024

文献信息

• Hetero-Diels-Alder and Ring-Opening Reactions of Furans Applied to the Synthesis of Functionalized Heterocycles
  作者：Américo J. S. Alves、Susana M. M. Lopes、Marta S. C. Henriques、José A. Paixão、Teresa M. V. D. Pinho e Melo

  DOI：10.1002/ejoc.201700453

  日期：2017.7.25

  converted efficiently into 6H-1,2-oxazines through a furan ring-opening reaction upon thermolysis in the presence of a catalytic amount of p-toluenesulfonic acid. The tetrahydrofuro[3,2-c]pyridazines derived from furan and dimethylfuran underwent acid-catalysed addition reactions, leading to 6-substituted hexahydrofuro[3,2-c]pyridazines, when in the presence of alcohols or water.

  呋喃已被用作合成一系列杂环化合物的支架，第一步是探索其对亚硝基和偶氮烯烃的亲二烯键行为。这些环加合物，4a，7a-二氢-4 H-呋喃[2,3- e ] [1,2]恶嗪和1,4,4a，7a-四氢呋喃[3,2- c ]的酸催化重排对哒嗪进行了研究。使用1当量 在TFA中，衍生自呋喃和2-甲基呋喃的双环杂环通过六元环的开环伴随呋喃环的芳构化而转化为带有掺入肟和基的侧链的呋喃。使用TFA作为溶剂导致经由螺环中间体的重排，随后呋喃开环以提供官能化的异恶唑或吡唑。此外，在催化量的p存在下，通过热分解的呋喃开环反应，将呋喃芳构化被排除的2,5-二甲基呋喃衍生的呋喃恶嗪有效地转化为6 H -1,2-恶嗪。-甲苯磺酸。四氢呋喃[3,2- c衍生自呋喃和二甲基呋喃的]哒嗪经过酸催化的加成反应，当在醇或水存在下，生成6-取代的六氢呋喃[3,2- c ]哒嗪。
• Biological Evaluation of Dipyrromethanes in Cancer Cell Lines: Antiproliferative and Pro-apoptotic Properties
  作者：Radek Jorda、Susana M. M. Lopes、Eva Řezníčková、Vladimír Kryštof、Teresa M. V. D. Pinho e Melo

  DOI：10.1002/cmdc.201700152

  日期：2017.5.9

  Functionalized dipyrromethanes were synthesized by hetero-Diels-Alder reactions of nitroso- and azoalkenes and screened for their in vitro activity as anticancer agents. The studied dipyrromethanes were tested against leukemia and lymphoma cell lines, and showed GI50 values in the mid-micromolar range. The pro-apoptotic activities of two candidates, (E)-1-(2'-ethoxycarbonylhydrazono-1'-benzyl-1H-tetrazol-5-yl)-5

  通过亚硝基-和偶氮-烯烃的杂-Diels-Alder反应合成功能化的二吡咯甲烷，并筛选它们作为抗癌剂的体外活性。对所研究的二吡咯甲烷进行了针对白血病和淋巴瘤细胞系的测试，结果显示GI50值处于中微摩尔范围。（E）-1-（2'-乙氧基羰基肼基-1'-苄基-1H-四唑-5-基）-5,5'-二乙基二吡咯甲烷和（E）-1-（2描述了'-对硝基苯基-2'-羟基亚氨基乙基）-5-苯基二吡咯甲烷及其对细胞周期的影响。发现后一种化合物以剂量依赖的方式减少S期细胞群，并不可逆地阻断G2 / M期的细胞。
• 2,3-二氢-1,2-二氮环丁烯氮氧化物及其制备方法
  申请人：成都大学

  公开号：CN113735773B

  公开（公告）日：2023-05-19

  本发明公开了一类2,3‑二氢‑1,2‑二氮环丁烯氮氧化物及其制备方法，属于有机合成领域，所述制备方法为向α‑卤代苯乙酮肟、氨基甲酸酯及碱的混合物中加入有机溶剂，反应在一定温度下搅拌2‑24小时，反应完成后，分离纯化即得；本发明通过分步的[3+1]环加成反应，实现了2,3‑二氢‑1,2‑二氮环丁烯氮氧化物的合成，该类化合物作为为典型的1,3‑偶极子可用于1,3‑偶极环加成反应构建其他一系列杂环化合物；本发明的制备方法具有反应条件温和、转化效率高、操作简便及底物适应范围广等优点。
• Potential of Vitamin B6 Dioxime Analogues to Act as Cholinesterase Ligands
  作者：Dajana Gašo Sokač、Antonio Zandona、Sunčica Roca、Dražen Vikić-Topić、Gabriela Lihtar、Nikola Maraković、Valentina Bušić、Zrinka Kovarik、Maja Katalinić

  DOI：10.3390/ijms232113388

  日期：——

  Seven pyridoxal dioxime quaternary salts (1–7) were synthesized with the aim of studying their interactions with human acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The synthesis was achieved by the quaternization of pyridoxal monooxime with substituted 2-bromoacetophenone oximes (phenacyl bromide oximes). All compounds, prepared in good yields (43–76%) and characterized by 1D and 2D NMR spectroscopy, were evaluated as reversible inhibitors of cholinesterase and/or reactivators of enzymes inhibited by toxic organophosphorus compounds. Their potency was compared with that of their monooxime analogues and medically approved oxime HI-6. The obtained pyridoxal dioximes were relatively weak inhibitors for both enzymes (Ki = 100–400 µM). The second oxime group in the structure did not improve the binding compared to the monooxime analogues. The same was observed for reactivation of VX-, tabun-, and paraoxon-inhibited AChE and BChE, where no significant efficiency burst was noted. In silico analysis and molecular docking studies connected the kinetic data to the structural features of the tested compound, showing that the low binding affinity and reactivation efficacy may be a consequence of a bulk structure hindering important reactive groups. The tested dioximes were non-toxic to human neuroblastoma cells (SH-SY5Y) and human embryonal kidney cells (HEK293).

  合成了七种吡哆醛二肟季铵盐（1-7），旨在研究它们与人类乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）的相互作用。合成是通过将吡哆醛单肟与取代的2-溴乙酰苯肟（苯乙酰溴肟）季铵化而实现的。所有化合物均以良好的收率（43-76％）制备，并通过1D和2D NMR光谱表征，被评估为乙酰胆碱酯酶的可逆抑制剂和/或被有毒有机磷化合物抑制的酶的再活化剂。它们的效力与其单肟类似物和经医学批准的肟类HI-6进行了比较。所得的吡哆醛二肟对两种酶都是相对较弱的抑制剂（Ki = 100-400 µM）。结构中的第二个肟基与单肟类似物相比并没有改善结合。在重新激活被VX、塔本和对硫磷酸酯抑制的AChE和BChE方面也是如此，没有观察到显着的效率爆发。通过计算机模拟和分子对接研究，将动力学数据与测试化合物的结构特征联系起来，表明低结合亲和力和再活化效力可能是由于臃肿的结构阻碍了重要的反应基团。测试的二肟对人神经母细胞瘤细胞（SH-SY5Y）和人胚胎肾细胞（HEK293）无毒。
• 10.1016/j.tetlet.2024.155183
  作者：Li, Xia、Li, Wen-Sheng、Fu, Xiao、Wan, Wen-Juan、Wang, Li-Xin

  DOI：10.1016/j.tetlet.2024.155183

  日期：——

  isatin –cyclic azomethine 1,3-dipole and nitrosoalkenes in situ generated from α-haloketone oximes has been disclosed. This new protocol is tolerable for a series of substrates and a novel series of seven-membered spiro oxindoles containing oxygen and nitrogen atoms were obtained in moderate to good yields (up to 83 %) under mild conditions.

  已经公开了靛红-环状偶氮甲碱1,3-偶极子和由α-卤代酮肟原位生成的亚硝基烯烃之间的新的[4 + 3]成环。这种新方案适用于一系列底物，并且在温和条件下以中等至良好的收率（高达 83%）获得了一系列含有氧和氮原子的新型七元螺吲哚。