4-氟-N,N-二甲基苯甲酰胺 | 24167-56-4

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 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-氟-N,N-二甲基苯甲酰胺
• 中文别名: N,N-二甲基-4-氟苯甲酰胺,97；N,N-二甲基-4-氟苯甲酰胺,97%
• 英文名称: N,N-dimethyl-4-fluorobenzamide
• 英文别名: 4-fluoro-N,N-dimethylbenzamide；4-Fluor-N,N-dimethylbenzamid；p-Fluor-N,N-dimethylbenzamid；N,N-Dimethyl-p-fluorbenzamid；N,n-dimethyl-p-fluoro-benzamide
• CAS: 24167-56-4
• 化学式: C₉H₁₀FNO
• mdl: MFCD01214152
• 分子量: 167.183
• InChiKey: NUOGEPIJFRZXIN-UHFFFAOYSA-N

物化性质

• 熔点：
  64 °C
• 沸点：
  269.4±23.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 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：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放于室温、干燥密封的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
N,N-Dimethyl 4-fluorobenzamide
Product Name:
Synonyms: 4-Fluoro-N,N-dimethylbenzamide

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
N,N-Dimethyl 4-fluorobenzamide
Ingredient name:
CAS number: 24167-56-4

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels.

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H10FNO
Molecular weight: 167.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen fluoride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  4-氟-N-甲基苯甲酰胺	4-fluoro-N-methylbenzamide	701-49-5	C8H8FNO	153.156
  对氟苯甲酰胺	p-fluorobenzamide	824-75-9	C7H6FNO	139.129
  N,N-二甲基-4-溴苯甲酰胺	4-bromo-N,N-dimethylbenzamide	18469-37-9	C9H10BrNO	228.088
  4-羟基-N,N-二甲基苯甲酰胺	4-hydroxy-N,N-dimethyl-benzamide	20876-99-7	C9H11NO2	165.192

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  4-氟-N-甲基苯甲酰胺	4-fluoro-N-methylbenzamide	701-49-5	C8H8FNO	153.156
  [(4-氟苯基)甲基]二甲胺	4-fluoro-N,N-dimethylbenzylamine	702-11-4	C9H12FN	153.199

反应信息

• 作为反应物：
  描述：

  4-氟-N,N-二甲基苯甲酰胺 在 bis(cyclopentadienyl)dihydrozirconium 、 频那醇硼烷 、 盐酸 作用下， 以 乙醚 、 水 为溶剂， 反应 2.0h， 以83%的产率得到[(4-氟苯基)甲基]二甲胺
  参考文献：
  名称：

  氢化锆催化的酰胺位点选择性硼氢化反应合成胺：机理、范围和应用

  摘要：

  开发用于选择性合成胺的温和高效的催化方法是一个长期的研究目标。在这方面，催化脱氧酰胺还原已被证明是有前途但具有挑战性的，因为这种方法需要选择性的 C-O 键裂解。在此，我们报告了伯、仲和叔酰胺在室温下由地球丰富的金属催化剂 Zr-H 催化的选择性硼氢化反应，以获取不同的胺。各种易于还原的官能团，如酯、炔烃和烯烃，都具有良好的耐受性。此外，该方法还扩展到生物和药物衍生胺的合成。详细的机理研究揭示了一个反应途径，通过一个不寻常的 C-N 键断裂-重整过程形成醛和酰胺复合物，然后是 C-O 键断裂。

  DOI：

  10.1016/s1872-2067(21)63853-6
• 作为产物：
  描述：

  N,N-二甲基-4-溴苯甲酰胺 在 potassium fluoride 、 C₉₄H₁₃₄O₄P₂Pd₂ 、 silver fluoride 作用下， 以 环己烷 为溶剂， 反应 14.0h， 以94%的产率得到4-氟-N,N-二甲基苯甲酰胺
  参考文献：
  名称：

  Pd-Catalyzed Nucleophilic Fluorination of Aryl Bromides

  摘要：

  On the basis of mechanism-driven reaction design, a Pd-catalyzed nucleophilic fluorination of aryl bromides and iodides has been developed. The method exhibits a broad substrate scope, especially with respect to nitrogen-containing heteroaryl bromides, and proceeds with minimal formation of the corresponding reduction products. A facilitated ligand modification process was shown to be critical to the success of the reaction.

  DOI：

  10.1021/ja5009739

文献信息

• Reduction of <i>N</i> ,<i>N</i> -Dimethylcarboxamides to Aldehydes by Sodium Hydride-Iodide Composite
  作者：Guo Hao Chan、Derek Yiren Ong、Zhihao Yen、Shunsuke Chiba

  DOI：10.1002/hlca.201800049

  日期：2018.5

  established using sodium hydride (NaH) in the presence of sodium iodide (NaI) under mild reaction conditions. The present protocol with the NaH‐NaI composite allows for reduction of not only aromatic and heteroaromatic but also aliphatic N,N‐dimethylamides with wide substituent compatibility. Retention of α‐chirality in the reduction of α‐enantioriched amides was accomplished. Use of sodium deuteride (NaD)

  在温和的反应条件下，在碘化钠（NaI）存在下，使用氢化钠（NaH）建立了一种新的简洁的协议，用于将N，N-二甲基酰胺选择性还原为醛。具有NaH-NaI复合材料的本协议不仅可以还原具有广泛取代基相容性的芳族和杂芳族化合物，而且还可以还原脂肪族N，N-二甲基酰胺。在减少α-对映体酰胺的过程中，保留了α-手性。氘化钠（NaD）的使用为制备氘掺入率高的氘代醛提供了一种新的经济实惠的替代方法。NaH-NaI复合材料具有独特的化学选择性，可减少N，N-二甲基酰胺比酮。
• 一种酰胺化合物还原制备胺类化合物的方法
  申请人：中国科学院兰州化学物理研究所

  公开号：CN112299938A

  公开（公告）日：2021-02-02

  本发明涉及一种酰胺化合物还原制备胺类化合物的方法，该方法是指在保护气氛中，将酰胺类化合物或环状酰胺、锆金属催化剂、频哪醇硼烷混合，于室温条件下进行酰胺还原反应，12~48h后通过氯化氢的乙醚溶液后处理，即得胺的盐酸盐化合物。本发明操作简单、成本低且具有良好的官能团耐受性和广泛的底物范围。
• Easy Access to Amides through Aldehydic C–H Bond Functionalization Catalyzed by Heterogeneous Co-Based Catalysts
  作者：Cuihua Bai、Xianfang Yao、Yingwei Li

  DOI：10.1021/cs501822r

  日期：2015.2.6

  synthesis strategy for amides by oxidative amidation of aldehydes is developed using a heterogeneous Co-based catalyst. The Co composite was prepared by simple pyrolysis of a Co-containing MOF, to obtain well-dispersed Co nanoparticles enclosed by carbonized organic ligands. The catalysts were characterized by powder X-ray diffraction (PXRD), N2 physical adsorption, atomic absorption spectroscopy (AAS)

  使用非均相钴基催化剂，开发了一种通过醛的氧化酰胺化酰胺合成酰胺的新策略。通过简单地热解含Co的MOF来制备Co复合物，以获得被碳化的有机配体包围的分散良好的Co纳米颗粒。催化剂通过粉末X射线衍射（PXRD），N 2进行表征物理吸附，原子吸收光谱（AAS），透射电子显微镜（TEM），扫描电子显微镜（SEM）和X射线光电子能谱（XPS）。嵌入N掺杂碳中的小Co纳米颗粒高度分散，平均尺寸约为。7纳米。与商业来源相比，[电子邮件保护的]材料在醛的氧化酰胺化中显示出显着增强的催化活性。可以容易地以高至优异的产率获得一系列酰胺。发现该反应在温和的条件下通过自由基进行，酰胺产物中的羰基来自醛。而且，
• One‐step Conversion of Amides and Esters to Acid Chlorides with PCl ₃
  作者：Fangshao Li、Xiaofang Wu、Fengzhe Guo、Zi‐Long Tang、Jing Xiao

  DOI：10.1002/ejoc.202100630

  日期：2021.8.13

  and efficient iodine-promoted chlorination of amides and esters with phosphorus trichloride is described. For the first time, various inactivated amides including secondary and tertiary amides were directly converted to the corresponding acid chlorides in one-step. The substrate scope of methyl esters including aromatic and aliphatic esters was also explored under this system. This method is simple

  描述了酰胺和酯与三氯化磷的一般和有效的碘促进氯化。包括仲酰胺和叔酰胺在内的各种失活酰胺首次一步直接转化为相应的酰氯。在该体系下还探索了包括芳香族和脂肪族酯在内的甲酯的底物范围。该方法简单、可扩展、适用范围广，为这些酰氯的制备提供了一种途径。
• Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides
  作者：Derek Yiren Ong、Zhihao Yen、Asami Yoshii、Julia Revillo Imbernon、Ryo Takita、Shunsuke Chiba

  DOI：10.1002/anie.201900233

  日期：2019.4

  New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH‐ZnI2 system delivers alcohols and NaH‐ZnCl2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc

  使用氢化钠（NaH）和卤化锌（ZnX 2）的组合，建立了将羧酰胺控制还原为醇或胺的新方案。在ZnX 2上使用不同的卤化物决定了选择性，其中NaH-ZnI 2系统提供醇，而NaH-ZnCl 2系统提供胺。通过实验和理论方法进行的广泛机理研究表明，聚合氢化锌（ZnH 2）∞负责醇的形成，而二聚氯化锌氢化物（H-Zn-Cl）2是生产胺的关键物质。