N-甲基苯甲酰胺 | 613-93-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酰胺
• 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: N-甲基苯甲酰胺
• 中文别名: N-甲基苯甲醯胺；N甲基苯甲酰胺
• 英文名称: N-methylbenzamide
• 英文别名: N-Methylbenzamid；acetanilide
• CAS: 613-93-4
• 化学式: C₈H₉NO
• mdl: MFCD00011642
• 分子量: 135.166
• InChiKey: NCCHARWOCKOHIH-UHFFFAOYSA-N

物化性质

• 熔点：
  76-78 °C (lit.)
• 沸点：
  167 °C/11 mmHg (lit.)
• 密度：
  1.1031 (rough estimate)
• 溶解度：
  乙醇：可溶50mg/mL，澄清，黄绿色
• 物理描述：
  N-methylbenzamide is an off-white crystalline solid. (NTP, 1992)
• 保留指数：
  1404
• 稳定性/保质期：
  性质与稳定性： 在常温常压下，该物质不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xn
• 安全说明：
  S24/25
• 危险类别码：
  R20/21/22
• WGK Germany：
  1
• 海关编码：
  29242990
• 危险品运输编号：
  NONH for all modes of transport
• RTECS号：
  CV5570000
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  贮存： 将密封的药瓶放入密封的主容器中，并存放在阴凉、干燥处。

SDS

Name:	N-Methylbenzamide 99+% Material Safety Data Sheet
Synonym:	N-Methylbenzenecarboxamide
CAS:	613-93-4

Section 1 - Chemical Product MSDS Name:N-Methylbenzamide 99+% Material Safety Data Sheet
Synonym:N-Methylbenzenecarboxamide

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
613-93-4	N-Methylbenzamide	99+%	210-362-3

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
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. May be harmful if swallowed.
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: 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.
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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam. Use agent most appropriate to extinguish fire.

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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:
Wash thoroughly after handling. Use with adequate ventilation.
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.
Storage:
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# 613-93-4: 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: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 167 deg C @ 11.00mmHg
Freezing/Melting Point: 76 - 78 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: C8H9NO
Molecular Weight: 135.17

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 613-93-4: CV5570000 LD50/LC50:
CAS# 613-93-4: Oral, mouse: LD50 = 840 mg/kg.
Carcinogenicity:
N-Methylbenzamide - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 613-93-4: 1
Canada
CAS# 613-93-4 is listed on Canada's NDSL List.
CAS# 613-93-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 613-93-4 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

N-甲基苯甲酯甲酯胺是一种浅黄色或白色的固体，熔点为74°C，是重要的农药中间体。

生物活性

N-Methylbenzamide 是一种有效的磷酸二酯酶 10A (PDE10A) 抑制剂，并且具有抗癌活性。

靶点

| PDE10A |

体内研究

N-Methylbenzamide（化合物21；给药剂量为100-800 mg/kg，腹腔注射，持续17天）在供体雌性BDF小鼠（体重18-23 g）的肿瘤模型中表现出活性。

反应信息

• 作为反应物：
  描述：

  N-甲基苯甲酰胺 在 4-二甲氨基吡啶 、 1-[2-[methoxy-[2-(methylaminomethyl)phenyl]boranyl]phenyl]-N-methylmethanamine 作用下， 以 四氢呋喃 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 苯甲酸甲酯
  参考文献：
  名称：

  氨基有机硼配合物的双重分子识别：β-二羰基衍生物的选择性醇解

  摘要：

  双重职责：氨基有机硼酸盐（AOB）络合物识别醇和β-二羰基单元，从而促进后者的化学和位点选择性醇解（请参阅方案）。该复合物激活了两个反应伙伴。此策略可在接近中性pH的条件下在加成/消除反应中裂解CC，CN和CO键，并为官能团转化提供了一种新方法。

  DOI：

  10.1002/anie.201200304
• 作为产物：
  描述：

  马尿酸 以 丙酮 为溶剂， 反应 1.0h， 以97%的产率得到N-甲基苯甲酰胺
  参考文献：
  名称：

  Sato, Yasuhiko; Nakai, Hideo; Mizoguchi, Tomishige, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 4, p. 1263 - 1270

  摘要：

  DOI：
• 作为试剂：
  描述：

  1,2-二碘苯 、 4-甲苯硫酚 在 N-甲基苯甲酰胺 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 mineral oil 为溶剂， 以93 %的产率得到2-iodophenyl 4-tolyl sulfide
  参考文献：
  名称：

  芳基硫醇或硫脲与邻二碘芳烃/NaH反应生成邻碘芳基硫醚

  摘要：

  在此，我们报道了一种通过芳基机理形成 C(芳基)-S 键来合成硫醚的方法。室温下，邻二碘芳烃和 NaH 在 THF 中可以生成活性芳炔，然后导致多种芳基硫醇和硫脲的芳基化。与过渡金属催化的交叉偶联反应不同，我们的方案中没有形成双取代的副产物。邻碘芳基硫醚产品是可以转化为药学上感兴趣的分子的中间体。

  DOI：

  10.1002/adsc.202301426

文献信息

• Dealkoxylation of <i>N</i>-alkoxyamides without an external reductant driven by Pd/Al cooperative catalysis
  作者：Hirotsugu Suzuki、Takahiro Shiomi、Kenji Yoneoka、Takanori Matsuda

  DOI：10.1039/d0ob01815e

  日期：——

  Lewis acid-assisted palladium-catalysed dealkoxylation of N-alkoxyamides has been realised in the absence of an external reductant.

  Lewis酸辅助钯催化的N-烷氧基酰胺脱烷氧化反应在无外部还原剂的情况下实现。
• Homogeneous Catalytic Hydrogenation of Amides to Amines
  作者：Jacorien Coetzee、Deborah L. Dodds、Jürgen Klankermayer、Sandra Brosinski、Walter Leitner、Alexandra M. Z. Slawin、David J. Cole-Hamilton

  DOI：10.1002/chem.201204270

  日期：2013.8.12

  Hydrogenation of amides in the presence of [Ru(acac)3] (acacH=2,4‐pentanedione), triphos [1,1,1‐tris‐ (diphenylphosphinomethyl)ethane] and methanesulfonic acid (MSA) produces secondary and tertiary amines with selectivities as high as 93 % provided that there is at least one aromatic ring on N. The system is also active for the synthesis of primary amines. In an attempt to probe the role of MSA and

  在[Ru（acac）3 ]（acacH = 2,4-戊二酮），三[[1,1,1-三（二苯基膦甲基）乙烷]]和甲磺酸（MSA）的存在下进行酰胺加氢生成仲胺和叔胺如果在N上至少有一个芳环，则其选择性高达93％。该系统对伯胺的合成也具有活性。为了探索MSA的作用和反应机理，已经从[Ru（acac）3 ]，三醇和MSA或[RuX（OAc）（triphos）]的反应中制备了一系列甲磺酸钠络合物。 （X = H或OAc）或[RuH 2（CO）（triphos ）]与MSA。晶体学表征复合物包括：[茹（OAC-κ 1 O）2（H 2O）（triphos）]，[Ru（OAc‐κ 2 O，O'）（CH 3 SO 3 ‐κ 1 O）（triphos ）]，[Ru（CH 3 SO 3‐ κ 1 O）2（H 2 O）（三膦）]和[孺2（μ-CH 3 SO 3）3（三磷酸）2 ] [CH 3 SO 3 ]，而其他复合物，例如[茹（OAC-κ
• Combining Transition Metal Catalysis with Radical Chemistry: Dramatic Acceleration of Palladium-Catalyzed CH Arylation with Diaryliodonium Salts
  作者：Sharon R. Neufeldt、Melanie S. Sanford

  DOI：10.1002/adsc.201200738

  日期：2012.12.14

  This paper describes a photoredox palladium/iridium-catalyzed C-H arylation with diaryliodonium reagents. Details of the reaction optimization, substrate scope, and mechanism are presented along with a comparison to a related method in which aryldiazonium salts are used in place of diaryliodonium reagents. The unprecedentedly mild reaction conditions (25 masculineC in methanol), the requirement for

  本文描述了光氧化还原钯/铱催化 CH 与二芳基碘试剂的芳基化反应。详细介绍了反应优化、底物范围和机理，并与使用芳基重氮盐代替二芳基碘试剂的相关方法进行了比较。前所未有的温和反应条件（甲醇中 25 摄氏度）、对光和光催化剂的要求、自由基清除剂的抑制作用以及观察到的化学选择性趋势都与二芳基碘试剂的自由基热反应一致，该反应被认为是通过一种“离子”2e - 途径，需要更高的反应温度（100 ℃）。
• Iridium(III)-Catalyzed Direct Arylation of C–H Bonds with Diaryliodonium Salts
  作者：Pan Gao、Wei Guo、Jingjing Xue、Yue Zhao、Yu Yuan、Yuanzhi Xia、Zhuangzhi Shi

  DOI：10.1021/jacs.5b06758

  日期：2015.9.30

  arylation of complex compounds. Mechanistic studies by density functional theory calculations suggested that the sp(3) C-H activation was realized by a triflate-involved concerted metalation-deprotonation process, and the following oxidation of Ir(III) to Ir(V) is the most favorable when a bistriflimide is contained in the diaryliodonium salt. Calculations indicated that both steps are enabled by initial anion

  通过开发一种新的 Ir(III) 催化的 CC 交叉偶联，已经建立了一种将酮肟、含氮杂环、各种芳烃和烯烃中的 sp(2) 和 sp(3) CH 键直接芳基化的通用方法。该芳基化的关键取决于适当的催化剂选择和使用二芳基碘鎓Triflate Salts作为偶联伴侣。这种转化具有良好的官能团兼容性，可以作为复杂化合物后期 CH 芳基化的有力合成工具。通过密度泛函理论计算的机理研究表明 sp(3) CH 活化是通过三氟甲磺酸酯参与的协同金属化-去质子化过程实现的，当双氟甲磺酰亚胺包含在二芳基碘鎓盐中。
• A polymer-supported thionating reagent
  作者：Steven V. Ley、Andrew G. Leach、R. Ian Storer

  DOI：10.1039/b008814p

  日期：——

  A new polymer-supported reagent for the conversion of carbonyls to thiocarbonyls has been developed and its use demonstrated on a range of amides. Secondary or tertiary amides are converted cleanly and efficiently through to the corresponding thioamides and primary amides are converted to the corresponding nitriles. The reactions can be facilitated by conventional heating. However, if microwave heating

  一个新的 聚合物己开发的用于羰基转化为硫代羰基的试剂，其用途已在一系列 酰胺类。中学或叔酰胺 干净高效地转化为相应的硫代酰胺 伯酰胺 转换为相应的 腈。常规加热可促进反应。但是，如果使用微波加热，则存在离子液体，可以提高反应速度。

表征谱图