3-乙酰氨基三氟甲苯 | 351-36-0

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟甲苯系列
• 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: 3-乙酰氨基三氟甲苯
• 中文别名: 3-(三氟甲氧基)乙酰胺
• 英文名称: N-acetyl-3-trifluoromethylbenzenamine
• 英文别名: N-(3-(trifluoromethyl)phenyl)acetamide；N-[3-(trifluoromethyl)phenyl]acetamide
• CAS: 351-36-0
• 化学式: C₉H₈F₃NO
• mdl: MFCD00000383
• 分子量: 203.164
• InChiKey: HNIPNANLYHXYDE-UHFFFAOYSA-N

物化性质

• 熔点：
  103-106 °C(lit.)
• 沸点：
  185-187.5 °C
• 密度：
  1.2812 (estimate)
• 保留指数：
  1400

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温环境下。

SDS

Name:	3-Acetamidobenzotrifluoride Material Safety Data Sheet
Synonym:	,,-Trifluoro-m-acetotoluidide; 3-Trifluoromethylacetanilid
CAS:	351-36-0

Section 1 - Chemical Product MSDS Name:3-Acetamidobenzotrifluoride Material Safety Data Sheet
Synonym:,,-Trifluoro-m-acetotoluidide; 3-Trifluoromethylacetanilid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
351-36-0	3-Acetamidobenzotrifluoride	>98	206-512-2

Hazard Symbols: XN
Risk Phrases: 22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
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:

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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:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep containers tightly closed.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 351-36-0: United States OSHA: 2.5 mg/m3 TWA (as F) (listed under Fluorides 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 103.00 - 106.00 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: CH3CONHC6H4CF3
Molecular Weight: 203.16

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents; strong bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 351-36-0: AN3740000 LD50/LC50:
CAS# 351-36-0: Oral, mouse: LD50 = 550 mg/kg.
Carcinogenicity:
3-Acetamidobenzotrifluoride - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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

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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.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
Safety Phrases:
WGK (Water Danger/Protection)
CAS# 351-36-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 351-36-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 351-36-0 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-乙酰氨基三氟甲苯 在 乙醇 、 硫酸 、 硝酸 、 钯 作用下， 生成 邻溴三氟甲苯
  参考文献：
  名称：

  Jones, Journal of the American Chemical Society, 1947, vol. 69, p. 2352

  摘要：

  DOI：
• 作为产物：
  描述：

  间三氟甲基苯乙酮 在 甲烷磺酸 、 叠氮化四丁基铵 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.08h， 以77%的产率得到3-乙酰氨基三氟甲苯
  参考文献：
  名称：

  连续流微反应器中DME溶液中酮的Schmidt反应

  摘要：

  施密特反应是在强酸存在下用氢偶氮酸处理，可将酮直接转化为酰胺，已广泛应用于有机合成中。在这种交流中，酮的Schmidt反应在连续流动的微反应器中的DME溶液中进行，得到酰胺产物。微反应器的封闭式小体积功能使该反应安全，快速且具有成本效益。

  DOI：

  10.1021/op500269j

文献信息

• Evaluation of dipole moment and electrophilicity on the nature of click-type coupling reaction between thioamide and sulfonyl azide
  作者：Muhammad Aswad、Junya Chiba、Takenori Tomohiro、Yasumaru Hatanaka

  DOI：10.1016/j.tetlet.2016.02.028

  日期：2016.3

  computational investigation on sulfonyl amidine formation from thioamides and sulfonyl azides is described. The data support a non-concerted two-step pathway for the coupling reaction and also indicate that dipole moment of thioamide and electrophilicity of sulfonyl azide would be significant factors for the reaction efficiency. A simple reactivity prediction of the coupling reaction was demonstrated by preliminary

  描述了由硫代酰胺和磺酰基叠氮化物形成磺酰基am的实验和计算研究的合作。数据支持偶合反应的非证实性两步途径，并且还表明硫酰胺的偶极矩和磺酰叠氮化物的亲电性将是影响反应效率的重要因素。通过对这些因素的初步计算机评估，证明了偶联反应的简单反应性预测，由此我们成功地从库存中的几种硫代酰胺和磺酰叠氮化物中成功选出了一对具有高反应性的良好反应物。
• NAPHTHALENE-BASED INHIBITORS OF ANTI-APOPTOTIC PROTEINS
  申请人：Pellechia Maurizio

  公开号：US20100267781A1

  公开（公告）日：2010-10-21

  Methods of using apogossypol and its derivatives for treating inflammation is disclosed. Also, there is described a group of compounds having structure A, or a pharmaceutically acceptable salt, hydrate, N-oxide, or solvate thereof are provided: wherein each R is independently H, C(O)X, C(O)NHX, NH(CO)X, SO 2 NHX, or NHSO 2 X, wherein X is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, heterocycle, or substituted heterocycle. Compounds of group A may be used for treating various diseases or disorders, such as cancer.

  使用阿波戈朴和其衍生物治疗炎症的方法被披露。此外，还描述了一组具有结构A的化合物，或其药学上可接受的盐、水合物、N-氧化物或溶剂化合物： 其中每个R独立地是H、C(O)X、C(O)NHX、NH(CO)X、SO2NHX或NHSO2X，其中X是氢、烷基、取代烷基、芳基、取代芳基、烷基芳基、取代烷基芳基、杂环或取代杂环。A组化合物可用于治疗各种疾病或疾病，如癌症。
• Conversion of Aromatic Amino into Trifluoromethyl Groups through a Sandmeyer­-Type Transformation
  作者：Jianbo Wang、Xi Wang、Yan Xu、Yujing Zhou、Yan Zhang

  DOI：10.1055/s-0033-1338659

  日期：——

  strategy for aromatic trifluoromethylation by converting amino into trifluoromethyl groups via a Sandmeyer-type reaction is reported. The transformation involves diazotization of the aromatic amines with tert-butyl nitrite and hydrochloric acid to form aryldiazonium chlorides, followed by trifluoromethylation with trifluoromethylsilver at low temperature. Various readily available aromatic amines are

  摘要 报道了通过Sandmeyer型反应将氨基转化为三氟甲基的芳香族三氟甲基化的新策略。该转化包括用亚硝酸叔丁酯和盐酸将芳族胺重氮化以形成芳基重氮氯化物，然后在低温下用三氟甲基银进行三氟甲基化。各种容易获得的芳族胺在温和条件下均能平稳转化。 报道了通过Sandmeyer型反应将氨基转化为三氟甲基的芳香族三氟甲基化的新策略。该转化包括用亚硝酸叔丁酯和盐酸将芳族胺重氮化以形成芳基重氮氯化物，然后在低温下用三氟甲基银进行三氟甲基化。各种容易获得的芳族胺在温和条件下均能平稳转化。
• Synthesis of Acetamides from Aryl Amines and Acetonitrile by Diazotization under Metal-Free Conditions
  作者：Yao-Fu Zeng、Yi-Na Li、Na-Na Zhang、Huan Kang、Pan Duan、Fang Xiao、Yu Guo、Xianghao Wen

  DOI：10.1055/s-0039-1690237

  日期：2019.12

  An efficient and metal-free coupling reaction has been developed that affords acetamides from the corresponding aryl amines and acetonitrile. This method tolerates a wide range of functional groups and is selective toward aryl amines. Preliminary mechanistic studies were conducted.

  已开发出一种有效且无金属的偶联反应，可从相应的芳胺和乙腈中生成乙酰胺。该方法可耐受范围广泛的官能团，并且对芳基胺具有选择性。进行了初步的机理研究。
• Selective C–F Functionalization of Unactivated Trifluoromethylarenes
  作者：David B. Vogt、Ciaran P. Seath、Hengbin Wang、Nathan T. Jui

  DOI：10.1021/jacs.9b06004

  日期：2019.8.21

  Fluorinated organic molecules are pervasive within the pharmaceutical and agrochemical industries due to the range of structural and physicochemical properties that fluorine imparts. To date, the most abundant methods for the synthesis of the aryl CF2-functionality have relied on the deoxyfluorination of ketones and aldehydes using expensive and poorly atom economical reagents. Here, we report a general

  由于氟赋予的结构和物理化学性质的范围，氟化有机分子在制药和农业化学工业中普遍存在。迄今为止，合成芳基 CF2 官能团的最丰富的方法依赖于使用昂贵且原子经济性差的试剂对酮和醛进行脱氧氟化。在这里，我们报告了通过激活相应的三氟甲基芳烃前体合成芳基-CF2R 和芳基-CF2H 化合物的一般方法。这种策略是通过吸能电子转移事件实现的，该事件提供了对位于催化剂还原电位之外的芳烃自由基阴离子的访问。

表征谱图