4-溴-2-三氟甲氧基乙酰苯胺 | 175278-18-9

• 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: 4-溴-2-三氟甲氧基乙酰苯胺
• 英文名称: N-(4-bromo-2-(trifluoromethoxy)phenyl)acetamide
• 英文别名: N-(4-bromo-2-trifluoromethoxy-phenyl)-acetamide；N-[4-bromo-2-(trifluoromethoxy)phenyl]acetamide
• CAS: 175278-18-9
• 化学式: C₉H₇BrF₃NO₂
• mdl: MFCD00203979
• 分子量: 298.059
• InChiKey: SHHWWZMWTUTJPY-UHFFFAOYSA-N

物化性质

• 熔点：
  135 °C
• 沸点：
  302.4±42.0 °C(Predicted)
• 密度：
  1.664±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 储存条件：
  保存方法：密封于阴凉、通风的干燥处。

SDS

Name:	N1-[4-bromo-2-(trifluoromethoxy)phenyl]acetamide 97% Material Safety Data Sheet
Synonym:	2-Acetamido-5-bromo(trifluoromethoxy)benzen
CAS:	175278-18-9

Section 1 - Chemical Product MSDS Name:N1-[4-bromo-2-(trifluoromethoxy)phenyl]acetamide 97% Material Safety Data Sheet
Synonym:2-Acetamido-5-bromo(trifluoromethoxy)benzen

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
175278-18-9	N1-[4-Bromo-2-(trifluoromethoxy)phenyl	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 22 36/37/38

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

---

Section 4 - FIRST AID MEASURES
Eyes: 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.
Ingestion:
Get medical aid. 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.
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 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.

---

Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
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# 175278-18-9: 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: white crystalline solid
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 135 - 137 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: C9H7BrF3NO2
Molecular Weight: 298

---

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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 175278-18-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N1-[4-Bromo-2-(trifluoromethoxy)phenyl]acetamide - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
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# 175278-18-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 175278-18-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 175278-18-9 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

• 作为产物：
  描述：

  N-羟基-4-碘苯胺 在 sodium hydride 、 碳酸氢钠 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 4-溴-2-三氟甲氧基乙酰苯胺
  参考文献：
  名称：

  芳烃的三氟甲氧基化：通过OCF3迁移合成邻三氟甲氧基化的苯胺衍生物

  摘要：

  介绍了由N-芳基-N-羟胺衍生物的O-三氟甲基化的两步序列和分子内OCF 3 迁移形成的芳基三氟甲氧基化。该协议允许轻松访问各种合成有用的邻-OCF 3苯胺衍生物。此外，它还使用了稳定的试剂，操作简单，具有较高的官能团耐受性，并且可以进行克级和一锅合成。所述N个的异裂的反应机理 OCF 3键，然后将所得nitrenium离子的重组和trifluoromethoxide拟为OCF 3 -migration反应。

  DOI：

  10.1002/anie.201409375

文献信息

• Mechanistic studies on intramolecular C–H trifluoromethoxylation of (hetero)arenes via OCF₃-migration
  作者：Katarzyna N. Lee、Zhen Lei、Cristian A. Morales-Rivera、Peng Liu、Ming-Yu Ngai

  DOI：10.1039/c6ob00132g

  日期：——

  operationally simple approach to access a wide range of unprecedented and valuable OCF3-containing building blocks. Herein we describe our investigations to elucidate its reaction mechanism. Experimental data indicate that the O-trifluoromethylation of N-(hetero)aryl-N-hydroxylamine derivatives is a radical process, whereas the OCF3-migration step proceeds via a heterolytic cleavage of the N–OCF3 bond followed

  我们小组最近报道的一锅两步分子内芳基和杂芳基C–H三氟甲氧基化提供了一种通用的、可扩展的且操作简单的方法来获得各种前所未有的、有价值的含OCF 3 结构单元。在这里，我们描述了我们的研究，以阐明其反应机制。实验数据表明，N- (杂)芳基-N-羟胺衍生物的O-三氟甲基化是一个自由基过程，而OCF 3 -迁移步骤是通过N-OCF 3键的杂解断裂然后快速重组来进行的。短寿命离子对。计算研究进一步支持了所提出的 OCF 3迁移过程的离子对反应途径。我们希望当前的研究将为使用多功能N- (杂)芳基-N-羟胺合成子开发新的转化提供有用的见解。
• [EN] TRIFLUOROMETHOXYLATION OF ARENES VIA INTRAMOLECULAR TRIFLUOROMETHOXY GROUP MIGRATION<br/>[FR] TRIFLUOROMÉTHOXYLATION D'ARÈNES VIA UNE MIGRATION INTRAMOLÉCULAIRE DU GROUPE TRIFLUOROMÉTHOXY
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2016057931A1

  公开（公告）日：2016-04-14

  The present invention provides a process of producing a trifluoromethoxylated aryl or trifluoromethoxylated heteroaryl having the structure: (I), wherein A is an aryl or heteroaryl, each with or without subsutitution; and R1 is -H, -(alkyl), -(alkenyl), -(alkynyl), -(aryl), -(heteroaryl), - (alkylaryl), - (alkylheteroaryl), -NH-(alkyl), -N(alkyl)2, -NH-(alkenyl), -NH-(alkynyl) -NH-(aryl), -NH-(heteroaryl), -O-(alkyl), -O-(alkenyl), -O-(alkynyl), -O-(aryl), -O-(heteroaryl), -S-(alkyl), -S- (alkenyl), -S-(alkynyl), -S-(aryl), or -S-(heteroaryl), comprising: (a) reacting a compound having the structure: (II), with a trifluoromethylating agent in the presence of a base in a first suitable solvent under conditions to produce a compound having the structure: (III); and (b) maintaining the compound produced in step (a) in a second suitable solvent under conditions sufficient to produce the trifluoromethoxylated aryl or trifluormethoxylated heteroaryl having the structure: (I).

  本发明提供了一种生产具有结构式(I)的三氟甲氧基取代的芳基或三氟甲氧基取代的杂芳基的方法，其中A是芳基或杂芳基，每个芳基或杂芳基可以有或无取代基；R1是-H，-(烷基)，-(烯基)，-(炔基)，-(芳基)，-(杂芳基)，-(烷基芳基)，-(烷基杂芳基)，-NH-(烷基)，-N(烷基)2，-NH-(烯基)，-NH-(炔基)-NH-(芳基)，-NH-(杂芳基)，-O-(烷基)，-O-(烯基)，-O-(炔基)，-O-(芳基)，-O-(杂芳基)，-S-(烷基)，-S-(烯基)，-S-(炔基)，-S-(芳基)或-S-(杂芳基)，包括：(a)使具有结构式(II)的化合物与三氟甲基化剂在第一适宜溶剂中的碱的存在下反应，在适宜条件下生成具有结构式(III)的化合物；以及(b)将步骤(a)中产生的化合物维持在第二适宜溶剂中，在足以生成具有结构式(I)的三氟甲氧基取代的芳基或三氟甲氧基取代的杂芳基的条件下保持。
• Substituted 2-dialkylaminoalkylbiphenyl derivatives
  申请人：——

  公开号：US20020198251A1

  公开（公告）日：2002-12-26

  Substituted 2-dialkylaminoalkylbiphenyl derivatives, processes for their preparation, pharmaceutical compositions comprising these compounds and methods using these compounds for the preparation of medicaments and for the treatment of diseases.

  取代的2-二烷基氨基烷基联苯衍生物，其制备方法，包含这些化合物的药物组合物，以及使用这些化合物制备药物和治疗疾病的方法。
• Selective C–O bond formation via a photocatalytic radical coupling strategy: access to perfluoroalkoxylated (OR_F) arenes and heteroarenes
  作者：Johnny W. Lee、Dominique N. Spiegowski、Ming-Yu Ngai

  DOI：10.1039/c7sc01684k

  日期：——

  Development of an efficient process that employs commercially available and cost effective reagents for the synthesis of perfluoroalkoxylated aromatic compounds (Ar–ORF) remains a daunting challenge in organic synthesis. Herein, we report the first catalytic protocol using readily available perfluoroalkyl iodides (RFI) and N-(hetero)aryl-N-hydroxylamides to access a wide range of perfluoroalkoxylated

  利用有机合成的全氟烷氧基化芳族化合物（Ar-OR F）的有效方法的开发仍然是一项艰巨的挑战，该方法采用可商购的且具有成本效益的试剂来合成全氟烷氧基化的芳族化合物。在本文中，我们报道了第一个催化方案，该方案使用易于获得的全氟烷基碘化物（R F I）和N-（杂）芳基-N-羟基叠氮化物来访问各种全氟烷氧基化的（杂）芳烃。温和的反应条件可在较宽的底物范围内形成选择性的O-R F键，并能耐受多种官能团。机理研究表明，持久性N-羟基自由基的形成和重组与瞬态R F自由基在光催化反应条件下生成N–OR F化合物，这些化合物会重新排列以提供所需的产物。
• SUBSTITUTED PYRAZOLO-QUINAZOLINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS KINASE INHIBITORS
  申请人：Caruso Michele

  公开号：US20100216808A1

  公开（公告）日：2010-08-26

  Pyrazolo-quinazoline derivatives of formula (I) as defined in the specification, and pharmaceutically acceptable salts thereof, process for their preparation and pharmaceutical compositions comprising them are disclosed; the compounds of the invention may be useful, in therapy, in the treatment of diseases associated with a disregulated protein kinase activity, like cancer.

  本发明揭示了式（I）中所定义的吡唑并喹唑啉衍生物及其药学上可接受的盐，以及它们的制备方法和包含它们的制药组合物；本发明中的化合物在治疗与蛋白激酶活性失调相关的疾病，如癌症中可能有用。