4-(三氟甲基)苯甲酰胺 | 1891-90-3

• 物质功能分类: 化学试剂 - 有机试剂 - 酰亚胺
• 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-(三氟甲基)苯甲酰胺
• 中文别名: 对三氟甲基苯甲酰胺；4-三氟甲基苯甲酰胺
• 英文名称: p-trifluoromethylbenzamide
• 英文别名: 4-trifluoromethylbenzamide；p-Trifluormethylbenzamid；4-(Trifluoromethyl)benzamide
• CAS: 1891-90-3
• 化学式: C₈H₆F₃NO
• mdl: MFCD00007998
• 分子量: 189.137
• InChiKey: WEJHBEDHLLBJFW-UHFFFAOYSA-N

物化性质

• 熔点：
  184-186 °C(lit.)
• 沸点：
  254.2±40.0 °C(Predicted)
• 密度：
  1.3305 (estimate)
• 稳定性/保质期：

  如果按照规格使用和储存，则不会分解，未有已知危险反应，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2924299090
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将贮藏器密封保存，在阴凉、干燥处存放，并确保工作环境有良好的通风或排气设施。

SDS

Name:	4-(Trifluoromethyl)benzamide 99% Material Safety Data Sheet
Synonym:
CAS:	1891-90-3

Section 1 - Chemical Product MSDS Name:4-(Trifluoromethyl)benzamide 99% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1891-90-3	4-(Trifluoromethyl)benzamide	99	217-571-9

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation.
Chronic:
No information found.

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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. 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.
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.

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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:
Use extinguishing media most appropriate for the surrounding fire.
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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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.

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

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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# 1891-90-3: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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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: 184 - 186 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: C8H6F3NO
Molecular Weight: 189.14

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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:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1891-90-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(Trifluoromethyl)benzamide - Not listed by ACGIH, IARC, or NTP.

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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: 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# 1891-90-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1891-90-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1891-90-3 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

制备方法与用途

化学性质：白色粉末状的固体。

反应信息

• 作为反应物：
  描述：

  4-(三氟甲基)苯甲酰胺 在 劳森试剂 作用下， 生成 4-(三氟甲基)硫代苯甲酰胺
  参考文献：
  名称：

  在无溶剂条件下，通过硫醇化和氧化二聚作用，从伯酰胺一锅两步合成 1,2,4-噻二唑：一种更环保的方法

  摘要：

  首次证明了在无溶剂的情况下，用劳森试剂（LR）和叔丁基过氧化氢（TBHP）从伯酰胺高效实用的一锅两步合成1,2,4-噻二唑。这种突破性且环保的方法利用了现成的原材料，并消除了反应过程中传统溶剂的使用。广泛的底物范围、在温和和无金属条件下出色的官能团耐受性、快速转化和出色的产率是该方法的基本特征。所有化合物均无需柱色谱法纯化。

  DOI：

  10.1039/d4ra03993a
• 作为产物：
  描述：

  对三氟甲基苯腈 在 fac-[(CO)₃Mn(ⁱPr₂P(CH₂)₂PⁱPr₂)(triflato)] 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以88%的产率得到4-(三氟甲基)苯甲酰胺
  参考文献：
  名称：

  含有i Pr 2 P（CH 2）2 P i Pr 2配体的 Mn（i）有机金属，用于芳族腈的催化水合作用†

  摘要：

  报道了由锰分子化合物催化的芳族腈均匀水合的第一个例子。合成了Mn（I）有机金属fac -[（CO）3 Mn（dippe）（Z）] 1- n X 1- n（n = 0，1; Z = Br，OTf，PhCN; X = OTf）表征，并研究了它们的反应性。将种类fac -[（CO）3 Mn（dippe）（OTf）]（2）用作基准苯甲腈（2 mol％2，THF / H 2）选择性水合的催化剂前体O 1：2 v / v，18 h，100°C）产生苯甲酰胺，分离产率为90％。将一系列（杂）芳族腈水合以合成相应的酰胺，产率非常好（88-94％）。同位素标记研究认为质子转移是决定速率的步骤。

  DOI：

  10.1039/c8cy00416a

文献信息

• [EN] 1-AKAN-2-OL SUBSTITUTED PIPERAZINE AND PIPERIDINE COMPOUNDS<br/>[FR] COMPOSES PIPERAZINE ET PIPERAZINE 1-AKAN-2-OL SUBSTITUES
  申请人：CV THERAPEUTICS INC

  公开号：WO2005061470A1

  公开（公告）日：2005-07-07

  Disclosed are novel substituted heterocyclic derivatives having the structure of Formula (I): The compounds are useful for the treatment of various disease states, in particular cardiovascular diseases such as atrial and ventricular arrhythmias, intermittent claudication, Prinzmetal's (variant) angina, stable and unstable angina, exercise induced angina, congestive heart disease, diabetes, and myocardial infarction.

  揭示了具有以下结构的新型取代杂环衍生物（I）的化合物：这些化合物对于治疗各种疾病状态有用，特别是心血管疾病，如心房和心室心律失常，间歇性跛行，普林兹梅塔（变异）心绞痛，稳定和不稳定心绞痛，运动诱发性心绞痛，充血性心脏病，糖尿病和心肌梗死。
• A novel oxidative procedure for the synthesis of benzamides from styrenes and amines under metal-free conditions
  作者：Muhammad Sharif、Jin-Long Gong、Peter Langer、Matthias Beller、Xiao-Feng Wu

  DOI：10.1039/c4cc01054j

  日期：——

  An interesting procedure for the oxidative synthesis of amides from styrenes and amines has been developed. Various primary amides were formed in moderate yields (25–81%). Secondary amides can be produced in moderate yields as well (41–68%). Notably, no transition metal catalyst was needed for this transformation. This is the first example of oxidative transformation of styrenes to benzamides.

  开发了一种从苯乙烯和胺进行氧化合成酰胺的有趣方法。在适度的产率（25-81%）下形成各种伯酰胺。仲酰胺也能以适度的产率（41-68%）生成。值得注意的是，这种转化不需要过渡金属催化剂。这是苯乙烯氧化转化为苯甲酰胺的首例。
• A general and practical oxidation of alcohols to primary amides under metal-free conditions
  作者：Xiao-Feng Wu、Muhammad Sharif、Jian-Bo Feng、Helfried Neumann、Anahit Pews-Davtyan、Peter Langer、Matthias Beller

  DOI：10.1039/c3gc40668g

  日期：——

  A general procedure for oxidation of both benzyl alcohols and alkyl alcohols to primary amides under catalyst free conditions has been developed. 34 examples of primary amides were produced from their corresponding alcohols in moderate to excellent yields. This is a practical procedure for primary amides synthesis; water and tert-butanol are the only by-products. A commercial drug, Piracetam, was prepared

  一般程序 氧化作用 两者 苄醇 和 烷基醇 到 伯酰胺 在下面 催化剂自由条件得到了发展。34个例子伯酰胺 是从它们对应的 酒类产量中等至优异。这是一个实际的程序伯酰胺 合成; 水 和 叔丁醇是唯一的副产品。商业广告药品， 拉西坦一步制备了，收率为73％。
• Design, synthesis and fungicidal activity of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide
  作者：Peng Lei、Yan Xu、Juan Du、Xin-Ling Yang、Hui-Zhu Yuan、Gao-Fei Xu、Yun Ling

  DOI：10.1016/j.bmcl.2016.03.085

  日期：2016.5

  excellent fungicidal activities, and the position of the substituents played an important role in fungicidal activities. Especially, compound 5n, exhibited better fungicidal activities than the commercial fungicide flutolanil against two tested fungi Valsa mali and Sclerotinia sclerotiorum, with EC50 values of 3.44 and 2.63 mg/L, respectively. And it also displayed good in vivo fungicidal activity against

  为了寻找具有高生物活性的新的铅化合物，采用连接活性亚结构法设计了一系列N-取代的苯甲酰基-1,2,3,4-四氢喹啉基-1-羧酰胺。由取代的苯甲酸按四个步骤合成目标化合物，并通过1 H NMR，IR光谱和元素分析确定其结构。体外生物测定结果表明，某些目标化合物表现出优异的杀真菌活性，且取代基的位置在杀真菌活性中起重要作用。特别是，化合物5n对两种测试真菌Valsa mali和Sclerotionia sclerotiorum的杀真菌活性比市售杀真菌剂氟苯尼更好。，其EC 50值分别为3.44和2.63 mg / L。而且它还显示出良好的针对核盘菌的体内杀真菌活性，其EC 50值为29.52 mg / L。
• Suzuki–Miyaura Cross-Coupling of <i>N</i>-Acylpyrroles and Pyrazoles: Planar, Electronically Activated Amides in Catalytic N–C Cleavage
  作者：Guangrong Meng、Roman Szostak、Michal Szostak

  DOI：10.1021/acs.orglett.7b01575

  日期：2017.7.7

  The formation of C–C bonds from amides by catalytic activation of the amide bond has been thus far possible by steric distortion. Herein, we report the first example of a general Pd-catalyzed Suzuki–Miyaura cross-coupling of planar amides enabled by the combination of (i) electronic-activation of the amide nitrogen in N-acylpyrroles and pyrazoles and (ii) the use of a versatile Pd-NHC catalysis platform

  迄今为止，由于空间扭曲，通过酰胺键的催化活化作用由酰胺形成C–C键是可能的。本文中，我们报道了一般的Pd催化的Suzuki-Miyaura平面酰胺交叉偶联的第一个例子，该偶联可通过以下方式组合实现：（i）电子活化N-酰基吡咯和吡唑中的酰胺氮，以及（ii）使用多功能的Pd-NHC催化平台。讨论了形成酰基金属的起源和选择性，包​​括扭曲的作用。

表征谱图