N-乙苯甲醯胺 | 614-17-5

• 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-乙苯甲醯胺
• 中文别名: N-乙基苯甲酰胺
• 英文名称: N-ethylbenzamide
• CAS: 614-17-5
• 化学式: C₉H₁₁NO
• mdl: MFCD00026702
• 分子量: 149.192
• InChiKey: SDIDYFBTIZOPLA-UHFFFAOYSA-N

物化性质

• 熔点：
  70.5°C
• 沸点：
  317℃
• 密度：
  1.019
• 闪点：
  184℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090
• 储存条件：
  室温、密封、干燥

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : N-ETHYLBENZAMIDE
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 614-17-5
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C9H11NO
Molecular Weight : 149,19 g/mol
CAS-No. : 614-17-5
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
N-ETHYLBENZAMIDE
Acute Tox. 4; H302 -
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 1,381
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: CV4920000
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-乙苯甲醯胺 在 tetrabutylammonium tetrafluoroborate 、 水 作用下， 以 乙腈 为溶剂， 以41 %的产率得到N-乙酰基-苯甲酰胺
  参考文献：
  名称：

  使用 H2O 将 N-烷基酰胺可持续电催化氧化为无环酰亚胺

  摘要：

  由于酰亚胺在生物分子、无机化合物和有机化合物中的广泛应用，其合成在各种科学学科和工业应用中具有重要意义。传统的酰亚胺合成方法通常依赖于使用有毒或昂贵的氧化剂，限制了其可持续性和实用性。在此，我们提出了一种绿色环保的方法，以H 2 O为绿色氧源，利用电催化氧化从N-烷基酰胺合成酰亚胺。这种可持续且原子效率高的方法优于传统方法，无需使用有毒或昂贵的氧化剂，同时在温和的反应条件下实现高产率。该方案具有广泛的底物兼容性，能够将多种N-烷基（甲基、乙基和环丙基）酰胺转化为酰亚胺。所得酰亚胺产物可以作为合成生物学相关的 1,2,4-三唑化合物的有价值的构建模块。此外，该方法的实用性通过克级反应得到证明，证实了其效率和工业应用潜力。我们的工作提出了一种可持续且多功能的酰亚胺合成策略，符合绿色化学原则和可持续制造实践。

  DOI：

  10.1039/d3gc04010k
• 作为产物：
  描述：

  N-乙基苄胺 在 叔丁基过氧化氢 、 碘 作用下， 以 水 、 乙腈 为溶剂， 反应 18.0h， 以63%的产率得到N-乙苯甲醯胺
  参考文献：
  名称：

  温和条件下I 2催化苄胺和苄基氰化物的氧化酰胺化

  摘要：

  我们报告了一种新颖有效的方法，用于在温和的反应条件下，通过苄基碳原子的C–H键裂解，使用催化量的I 2和TBHP作为绿色氧化剂，将苄基碳原子（胺和氰化物）氧化为相应的苯甲酰胺。根据文献调查，这是第一个关于在无金属条件下在一个罐中进行苄胺的氧化酰胺化和苄基氰化物脱氰的报道。

  DOI：

  10.1021/acs.joc.7b02211

文献信息

• Fungicides for the control of take-all disease of plants
  申请人：Monsanto Company

  公开号：US05498630A1

  公开（公告）日：1996-03-12

  A method of controlling Take-All disease of plants by applying a fungicide of the formula ##STR1## wherein Z1 and Z2 are C and are part of an aromatic ring which is benzothiophene; and A is selected from --C(X)-amine wherein the amine is an unsubstituted, monosubstituted or disubstituted amino radical, --C(O)--SR.sub.3, --NH--C(X)R.sub.4, and --C(.dbd.NR.sub.3)--XR.sub.7 ; B is --W.sub.m --Q(R.sub.2).sub.3 or selected from O-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R.sub.4 ; Q is C, Si, Ge, or Sn; W is --C(R.sub.3).sub.p H.sub.(2-p) --; or when Q is C, W is selected from --C(R.sub.3).sub.p H(.sub.2-p), --N(R.sub.3).sub.m H(.sub.1-m)--, --S(O)p--, and --O--; X is 0 or S; n is 0, 1, 2, or 3; m is 0 or 1; p is 0, 1, or 2; each R and R.sub.2 is independently defined herein; R.sub.3 is C.sub.1 -C.sub.4 alkyl; R.sub.4 is C.sub.1 -C.sub.4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; and R.sub.7 is C.sub.1 -C.sub.4 alkyl, haloalkyl, or phenyl, optionally substituted with halo, nitro, or R.sub.4 ; or an agronomic salt thereof.

  一种通过施用公式##STR1##的杀菌剂来控制植物全蚀病的方法，其中Z1和Z2为C，并且是苯并噻吩的芳香环的一部分；A从--C(X)-胺中选择，其中胺是未取代的、单取代的或双取代的氨基基团，--C(O)--SR.sub.3，--NH--C(X)R.sub.4和--C(.dbd.NR.sub.3)--XR.sub.7；B为--W.sub.m --Q(R.sub.2).sub.3或从O-甲苯基、1-萘基、2-萘基和9-菲基中选择，每个都可以选择性地用卤素或R.sub.4取代；Q为C、Si、Ge或Sn；W为--C(R.sub.3).sub.p H.sub.(2-p)--；或当Q为C时，W从--C(R.sub.3).sub.p H(.sub.2-p)，--N(R.sub.3).sub.m H(.sub.1-m)--，--S(O)p--和--O--中选择；X为0或S；n为0、1、2或3；m为0或1；p为0、1或2；每个R和R.sub.2在此独立定义；R.sub.3为C.sub.1 -C.sub.4烷基；R.sub.4为C.sub.1 -C.sub.4烷基、卤代烷基、烷氧基、烷硫基、烷基氨基或二烷基氨基；R.sub.7为C.sub.1 -C.sub.4烷基、卤代烷基或苯基，可以选择性地用卤素、硝基或R.sub.4取代；或其农艺学盐。
• Deoxygenative hydroboration of primary, secondary, and tertiary amides: Catalyst‐free synthesis of various substituted amines
  作者：Jaeeun Yi、Hyun Tae Kim、Ashok Kumar Jaladi、Duk Keun An

  DOI：10.1002/bkcs.12438

  日期：2022.1

  less reactive functional groups under catalyst-free conditions is an interesting aspect and requires a typical protocol. Herein, we report the synthesis of various primary, secondary, and tertiary amines through hydroboration of amides using pinacolborane under catalyst-free and solvent-free conditions. The deoxygenative hydroboration of primary and secondary amides proceeded with excellent conversions

  在无催化剂条件下相对较少反应性官能团的转化是一个有趣的方面，需要一个典型的协议。在此，我们报告了在无催化剂和无溶剂条件下，使用频哪醇硼烷对酰胺进行硼氢化合成各种伯胺、仲胺和叔胺。伯酰胺和仲酰胺的脱氧硼氢化反应以优异的转化率进行。在无催化剂条件下，反应性相对较低的叔酰胺也以中等收率转化为相应的N，N-二胺，尽管作为次要产物获得了醇。
• Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application
  作者：Bo Han、Jiong Zhang、Haijun Jiao、Lipeng Wu

  DOI：10.1016/s1872-2067(21)63853-6

  日期：2021.11

  diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.

  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。
• NaOTs-promoted transition metal-free C–N bond cleavage to form C–X (X = N, O, S) bonds
  作者：Yuqi Zhang、Xiaojing Ye、Sicheng Liu、Wei Chen、Irfan Majeed、Tingting Liu、Yulin Zhu、Zhuo Zeng

  DOI：10.1039/d1ob01409a

  日期：——

  Multifunctional transformation of amide C–N bond cleavage is reported. The protocol applies to benzamide, thioamide, alcohols, and mercaptan under similar reaction conditions catalyzed by NaOTs. It is noteworthy that NaOTs can not only be recycled and reused for up to three cycles without significant loss in catalytic activity, but also catalyze gram-grade reactions. This study provides a novel solution

  报道了酰胺C-N键断裂的多功能转化。该协议适用于在 NaOT 催化的类似反应条件下的苯甲酰胺、硫代酰胺、醇和硫醇。值得注意的是，NaOTs 不仅可以回收和重复使用多达三个循环而不会显着降低催化活性，而且还可以催化克级反应。本研究为多种酰胺的转化提供了一种条件温和、程序简单的新型解决方案。
• The Selective<i>N</i>-Monoalkylation of Amides with Alkyl Halides in the Presence of Alumina and KOH
  作者：Kazuaki Sukata

  DOI：10.1246/bcsj.58.838

  日期：1985.3

  The effects of alumina impregnated with KOH (KOH/Al2O3) and a mixture of alumina and powdered KOH (KOH+Al2O3) have been examined using the alkylation of benzamide under various conditions. In each case, alkylation occurs exclusively in the pores of the alumina, the extent depending upon the alumina-pore size. For both yield and selectivity for N-monoalkylation, KOH+Al2O3 is superior to KOH/Al2O3. Dioxane is the best of the solvents employed. It is proposed that, in dioxane, an enolate-like species, (Remark: Graphics omitted.), exists as stable ion-pair aggregates, which are the true reactants in the pore. This method, using KOH/Al2O3 or KOH+Al2O3, has been applied to N-alkylation of the other amides, giving the N-monoalkylated products in substantial yields with extremely high selectivities. 2-Phenylacetamide is regioselectively N-monoalkylated in high yields. This regioselectivity is explained in terms of steric hindrance.

  使用KOH浸渍的氧化铝（KOH/Al2O3）和氧化铝与粉末状KOH的混合物（KOH+Al2O3），在不同条件下研究了苯甲酰胺的烷基化反应。在每种情况下，烷基化反应仅在氧化铝的孔隙中发生，其程度取决于氧化铝的孔径大小。对于N-单烷基化的产率和选择性，KOH+Al2O3优于KOH/Al2O3。二氧六环是所使用溶剂中最好的。研究表明，在二氧六环中，类似于烯醇盐的物种（注：图形省略）以稳定的离子对聚集形式存在，这些是孔隙中的真正反应物。这种方法使用KOH/Al2O3或KOH+Al2O3，已应用于其他酰胺的N-烷基化，以极高的选择性获得了大量的N-单烷基化产物。2-苯基乙酰胺以高产率选择性地进行N-单烷基化。这种区域选择性可通过空间位阻来解释。

表征谱图