2-丙酮氧基-3,4-二氟硝基苯 | 82419-32-7

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟硝基苯系列
• 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-丙酮氧基-3,4-二氟硝基苯
• 中文别名: 2-丙酮基氧基-3,4-二氟硝基苯；醚酮
• 英文名称: 3,4-difluoro-2-(2-oxopropyloxy)nitrobenzene
• 英文别名: 1-(2,3-difluoro-6-nitrophenoxy)propan-2-one；1-(2,3-difluoro-6-nitrophenoxy)acetone；2-acetonyloxy-3,4-difluoronitrobenzene；2-propanonoxy-3,4-difluoronitrobenzene
• CAS: 82419-32-7
• 化学式: C₉H₇F₂NO₄
• mdl: MFCD00792468
• 分子量: 231.156
• InChiKey: ZJVPAAJHCJMGGL-UHFFFAOYSA-N

物化性质

• 熔点：
  40-45 °C
• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  29155000
• 储存条件：
  存储于阴凉干燥处。

SDS

Name:	1-(2 3-Difluoro-6-Nitrophenoxy)-2-Propanone Material Safety Data Sheet
Synonym:	None Known
CAS:	82419-32-7

Section 1 - Chemical Product MSDS Name:1-(2 3-Difluoro-6-Nitrophenoxy)-2-Propanone Material Safety Data Sheet
Synonym:None Known

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
82419-32-7	1-(2,3-Difluoro-6-Nitrophenoxy)-2-Prop	ca. 100	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

---

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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

---

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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

---

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# 82419-32-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Not available.
Specific Gravity/Density:
Molecular Formula: C9H7F2NO4
Molecular Weight: 231.15

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 82419-32-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(2,3-Difluoro-6-Nitrophenoxy)-2-Propanone - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 82419-32-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 82419-32-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 82419-32-7 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用

2-丙酮氧基-3,4-二氟硝基苯是一种芳烃类衍生物，可用作医药中间体，主要用于合成氧氟沙星的中间体。

反应信息

• 作为反应物：
  描述：

  2-丙酮氧基-3,4-二氟硝基苯 在 盐酸 、 氢气 、 镍 作用下， 以 乙醇 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 17.0h， 生成 氧氟沙星
  参考文献：
  名称：

  Synthesis and antibacterial activities of substituted 7-oxo-2,3-dihydro-7H-pyrido(1,2,3-de)(1,4)benzoxazine-6-carboxylic acids.

  摘要：

  作为寻找新的合成抗菌剂以对抗全身感染的一部分，合成了多种7-氧代-2,3-二氢-7H-吡啶并[1,2,3-de][1,4]苯并噁嗪-6-羧酸类似物。在合成的新化合物中，9-氟-3-甲基-10-(4-甲基-1-哌嗪基)-7-氧代-2,3-二氢-7H-吡啶并[1,2,3-de][1,4]苯并噁嗪-6-羧酸（DL-8280）显示出对革兰氏阳性和阴性病原体，包括铜绿假单胞菌的强效抗菌活性，并且其代谢情况在单独的实验中显示为有利。

  DOI：

  10.1248/cpb.32.4907
• 作为产物：
  描述：

  2,3,4-三氟硝基苯 在 氢氧化钾 、 potassium carbonate 、 potassium iodide 作用下， 以 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 6.0h， 生成 2-丙酮氧基-3,4-二氟硝基苯
  参考文献：
  名称：

  Synthesis and antibacterial activities of substituted 7-oxo-2,3-dihydro-7H-pyrido(1,2,3-de)(1,4)benzoxazine-6-carboxylic acids.

  摘要：

  作为寻找新的合成抗菌剂以对抗全身感染的一部分，合成了多种7-氧代-2,3-二氢-7H-吡啶并[1,2,3-de][1,4]苯并噁嗪-6-羧酸类似物。在合成的新化合物中，9-氟-3-甲基-10-(4-甲基-1-哌嗪基)-7-氧代-2,3-二氢-7H-吡啶并[1,2,3-de][1,4]苯并噁嗪-6-羧酸（DL-8280）显示出对革兰氏阳性和阴性病原体，包括铜绿假单胞菌的强效抗菌活性，并且其代谢情况在单独的实验中显示为有利。

  DOI：

  10.1248/cpb.32.4907

文献信息

• Palladium Supported on Carbon Nanoglobules as a Promising Catalyst for Selective Hydrogenation of Nitroarenes
  作者：R. M. Mironenko、O. B. Belskaya、L. N. Stepanova、T. I. Gulyaeva、M. V. Trenikhin、V. A. Likholobov

  DOI：10.1007/s10562-019-02974-6

  日期：2020.3

  1 wt% palladium supported on carbon nanoglobules (CNGs) were shown to be highly active in the liquid-phase hydrogenation of various nitroarenes and provided nearly 100% selectivity to aromatic amines at complete conversion under mild conditions (323 K, 0.5 MPa, 1 h). The catalytic activity (in terms of turnover frequency and substrate conversion) and selectivity depend on the kind of CNGs support, catalyst

  负载在碳纳米球 (CNG) 上的 1 wt% 钯催化剂在各种硝基芳烃的液相加氢反应中表现出高活性，并且在温和条件 (323 K, 0.5 MPa, 1 小时）。催化活性（在转化频率和底物转化率方面）和选择性取决于 CNG 载体的种类、催化剂制备方法和反应条件（溶剂性质）。Pd/CNGs 催化剂可以重复使用，同时保持相同的催化性能。Pd/CNGs 催化剂的优异性能可能是由于载体的球状形态以及没有微孔和明显的表面缺陷。图形摘要
• Benzoxazine derivatives
  申请人：Daiichi Seiyaku Co., Ltd.

  公开号：US04382892A1

  公开（公告）日：1983-05-10

  Pyrido[1,2,3-de][1,4]benzoxazine derivatives are described having the formula (I) ##STR1## wherein X is a halogen atom, R is a hydrogen atom or an alkyl group of 1 to 6 carbon atoms and Z represents mono-substituted, di-substituted or cyclic-substituted amino group which may contain a hetero atom and may have a substituent such as hydroxyl, alkyl having 1 to 6 carbon atoms, amino, hydroxyalkyl having 1 to 6 carbon atoms or mono- or di-alkylamino having 1 to 6 carbon atoms in each alkyl moiety and the pharmaceutically acceptable salt thereof, having antibacterial activity.

  Pyrido[1,2,3-de][1,4]benzoxazine衍生物的化学式为(I) ##STR1## 其中X是卤素原子，R是氢原子或1至6个碳原子的烷基基团，Z代表单取代、双取代或环取代的氨基团，可能含有杂原子，并且可能具有取代基，如羟基、1至6个碳原子的烷基、氨基、1至6个碳原子的羟基烷基或每个烷基部分中具有1至6个碳原子的单取代或双取代烷基氨基，以及其药学上可接受的盐，具有抗菌活性。
• Enantioselective Biocatalytic Reduction of 2<i>H</i>-1,4-Benzoxazines Using Imine Reductases
  作者：Nadine Zumbrägel、Paul Machui、Jannis Nonnhoff、Harald Gröger

  DOI：10.1021/acs.joc.8b02867

  日期：2019.2.1

  A biocatalytic reduction of 2H-1,4-benzoxazines using imine reductases is reported. This process enables a smooth and enantioselective synthesis of the resulting cyclic amines under mild conditions in aqueous media by means of a catalytic amount of the cofactor NADPH as hydride source as well as glucose as the reducing agent used in stoichiometric amounts for in situ cofactor recycling. Several substrates

  据报道，使用亚胺还原酶可生物催化还原2 H -1,4-苯并恶嗪。通过催化量的辅因子NADPH作为氢化物源以及葡萄糖作为化学计量的还原剂用于原位辅因子再循环，该方法能够在温和条件下在水性介质中平稳且对映选择性地合成所得环胺。研究了几种底物，并获得了具有高达99％ee的3,4-二氢-2 H -1,4-苯并恶嗪。此外，已经证明，以亚胺还原酶为催化剂的这种还原过程的效率在实验室负载较高的实验室条件下，以10 g L –1的底物负荷运行时，可用于一种2 H -1,4-苯并恶嗪。 在量身定制的全细胞催化剂存在下。
• 一种新氧氟沙星中间体的合成方法
  申请人：千辉药业（安徽）有限责任公司

  公开号：CN106632444A

  公开（公告）日：2017-05-10

  本发明涉及药物合成领域，具体涉及一种结构如式(Ⅱ)所示的新氧氟沙星中间体的合成方法，所述合成方法为：先将2,3,4‑三氟硝基苯于氢氧化钾反应生成2,3‑二氟‑6‑硝基苯酚；再将2,3‑二氟‑6‑硝基苯酚与氯丙酮在一定条件下合成2‑丙酮氧基‑3,4‑二氟硝基苯，然后在2‑丙酮氧基‑3,4‑二氟硝基苯中加入乙醇和雷尼镍，并通入氢气，反应得到式(Ⅰ)化合物，式(Ⅰ)化合物与乙氧基甲叉丙二酸二乙酯反应，并通过进一步反应得到式(Ⅱ)化合物，本发明制备得到的结构如(Ⅱ)所示的新氧氟沙星中间体质量好，产率高，杂质少，合成方法适于推广应用。
• Chemoenzymatic Asymmetric Synthesis of 1,4-Benzoxazine Derivatives: Application in the Synthesis of a Levofloxacin Precursor
  作者：María López-Iglesias、Eduardo Busto、Vicente Gotor、Vicente Gotor-Fernández

  DOI：10.1021/acs.joc.5b00056

  日期：2015.4.17

  A versatile and general route has been developed for the asymmetric synthesis of a wide family of 3-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazines bearing different pattern substitutions in the aromatic ring. Whereas hydrolases were not suitable for resolution of these racemic cyclic nitrogenated amines, alternative chemoenzymatic strategies were designed through independent pathways leading to both amine

  已经开发了一种通用且通用的路线，用于在芳香环中带有不同图案取代的3-甲基-3,4-二氢-2 H-苯并[ b ] [1,4]恶嗪家族的不对称合成。尽管水解酶不适合拆分这些外消旋环状的硝化胺，但通过导致两种胺对映体的独立途径设计了替代的化学酶策略。一方面，生物降解1-（2-硝基苯氧基）丙烷-2-酮可使用红球菌（ADH-A）的醇脱氢酶以高收率回收对映纯（S）-醇，而evo-1.1。 200 ADH导致对方（R）-对映异构体也具有完全的选择性和定量转化率。或者，这些外消旋醇的脂肪酶催化的乙酰化作用，以及乙酸酯类似物的互补水解，使得可以得到具有高立体鉴别性的相应的光学富集的产物。特别吸引人的是六步生产化学酶策略的设计，以生产（S）-（-）-7,8-二氟-3-甲基-3,4-二氢-2 H-苯并-[ b ] [1 ，4]恶嗪，它是抗菌药物左氧氟沙星的关键前体。