N-(2-氯乙基)苯甲酰胺 | 26385-07-9

• 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-(2-氯乙基)苯甲酰胺
• 中文别名: N-(4-氯乙基)乙酰胺；N-(2-氯乙基)乙酰胺
• 英文名称: N-(2-chloro-ethyl)-benzamide
• 英文别名: N-(2-Chlor-ethyl)benzamid；2-(benzoylamino)-1-chloroethane；N-Benzoyl-β-chlor-ethylamin；2-benzoylaminoethyl chloride；N-(2-Chloroethyl)benzamide
• CAS: 26385-07-9
• 化学式: C₉H₁₀ClNO
• 分子量: 183.637
• InChiKey: FYQJUYCGPLFWQR-UHFFFAOYSA-N

物化性质

• 熔点：
  103-106 °C(lit.)
• 沸点：
  366.4±25.0 °C(Predicted)
• 密度：
  1.1611 (rough estimate)
• 稳定性/保质期：
  如果遵照规格使用和储存，则不会分解。避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2924299090
• 储存条件：
  将贮藏器密封后，放入一个紧密的容器中，并将其存放在阴凉、干燥的地方。

SDS

Name:	N-(2-Chloroethyl)benzamide 99% Material Safety Data Sheet
Synonym:	None known
CAS:	26385-07-9

Section 1 - Chemical Product MSDS Name:N-(2-Chloroethyl)benzamide 99% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
26385-07-9	N-(2-Chloroethyl)benzamide	99	247-641-4

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.
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.
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:
Use agent most appropriate to extinguish 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:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. 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# 26385-07-9: 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: Powder
Color: beige
Odor: none reported
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 applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H10ClNO
Molecular Weight: 183.64

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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, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 26385-07-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N-(2-Chloroethyl)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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 26385-07-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 26385-07-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 26385-07-9 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：

  N-(2-氯乙基)苯甲酰胺 在 正丁基锂 、 水 、 naphthalen-1-yl-lithium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 N-苯甲酰基-beta-丙氨酸
  参考文献：
  名称：

  N-锂乙基-N-（2-锂乙基）- 和 N-锂-N-（3-锂丙基）-苯甲酰胺：2-锂乙基-和 3-锂丙基胺当量的直接制备和合成应用

  摘要：

  2-氯乙基和 3-氯丙基苯甲酰胺与 N-丁基锂和萘化锂在 -78°C 至 -50°C 的温度范围内连续反应，产生 N-锂基-N-（2-锂乙基）- 和 N-锂基-N-（3-锂基-丙基）苯甲酰胺 [（8）， （9）]，通过用不同的亲电试剂（H2O、D2O、Me2S2、CO2、Pr1CHO、PhCHO、Me2CO、Ph2CO 和 O2）处理得到预期的官能化苯甲酰胺 [（10）， 化合物 （10） 和 （11） 的酸性和碱性水解根据底物的结构和反应条件得出不同的结果。

  DOI：

  10.1016/s0040-4020(01)80078-8
• 作为产物：
  描述：

  1-苯甲酰基氮丙啶 在 盐酸 作用下， 生成 N-(2-氯乙基)苯甲酰胺
  参考文献：
  名称：

  388.硫化氢的添加到2-苯基Δ 2 -恶唑啉和benzoylethyleneimine：稠合的噻唑烷环butyroazlactone系统的尝试合成

  摘要：

  DOI：

  10.1039/jr9480001919

文献信息

• One-pot triflic anhydride-mediated synthesis of 1,2-disubstituted 2-imidazolines from N-(2-haloethyl)amides and amines
  作者：Alyssa A. Ellsworth、Christina L. Magyar、Grace E. Hubbell、Chelsea C. Theisen、Daniel Holmes、R. Adam Mosey

  DOI：10.1016/j.tet.2016.08.040

  日期：2016.10

  A one-pot synthesis of 1,2-disubstituted 2-imidazolines from N-(2-haloethyl)amides has been developed. The reaction affords high yields of diverse 1,2-disubstituted 2-imidazolines from triflic anhydride-mediated dehydration of amides followed by installation of a primary amine.

  已经开发了由N-（2-卤代乙基）酰胺一锅合成1，2-二取代的2-咪唑啉。该反应从三氟甲磺酸酐介导的酰胺脱水，然后安装伯胺的方法中，可得到高产率的各种1,2-二取代的2-咪唑啉。
• Pyrimidinedione derivatives and antiarrhythmic agents containing same
  申请人：Mitsui Toatsu Chemicals, Incorporated

  公开号：US05332739A1

  公开（公告）日：1994-07-26

  Pyrimidinedione derivatives of the formula: ##STR1## wherein R.sup.1 and R.sup.2 is so linked with each other as to make an alkylene chain and thus form a heterocyclic structure, A, R.sup.3, R.sup.4, X.sup.1, X.sup.2 and X.sup.3 are substituents, respectively, and n is 2 or 3 have a basic backbone in which a phenyl group part and a pyrimidinedione part are linked by a structure comprising an alkyl chain and a heterocyclic ring having two nitrogen atoms. These compounds are useful for a medical treatment of cardiac arrhythmias.

  Pyrimidinedione衍生物的化学式为：##STR1## 其中R.sup.1和R.sup.2通过一个烷基链相连，从而形成一个杂环结构，A，R.sup.3，R.sup.4，X.sup.1，X.sup.2和X.sup.3分别是取代基，n为2或3，具有一个基本骨架，其中苯基部分和嘧啶二酮部分通过一个包含一个烷基链和一个含有两个氮原子的杂环环的结构相连。这些化合物对于治疗心律失常很有用。
• Formamides as Lewis Base Catalysts in S_NReactions-Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers
  作者：Peter H. Huy、Sebastian Motsch、Sarah M. Kappler

  DOI：10.1002/anie.201604921

  日期：2016.8.16

  and waste‐balance (E‐factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one‐pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac‐Clopidogrel and S‐Fendiline.

  简单的甲酰胺催化剂可促进以苯甲酰氯为唯一试剂将醇类有效转化为烷基氯。这些亲核取代是通过亚胺基活化的醇作为中间体进行的。这种新颖的方法甚至可以在无溶剂条件下进行，其特点是具有出色的官能团耐受性，可扩展性（> 100 g）和废物平衡（电子因子低至2）。手性底物的转化具有优异的立体化学转化水平（99％→≥95％ee）。在实际的一锅法中，初步形成的氯化物可以进一步转化为胺，叠氮化物，醚，硫化物和腈。该方法的价值在药物rac ‐ Clopidogrel和S‐芬迪林。
• [EN] METHOD OF CONVERTING ALCOHOL TO HALIDE<br/>[FR] PROCÉDÉ DE CONVERSION D'UN ALCOOL EN HALOGÉNURE
  申请人：UNIV SAARLAND

  公开号：WO2016202894A1

  公开（公告）日：2016-12-22

  The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

  本发明涉及一种将醇转化为相应卤化物的方法。该方法包括在N-取代甲酰胺的存在下，将醇与可选择取代的芳香羧酸卤化物反应，以通过卤原子取代醇的羟基。本发明还涉及一种将醇转化为相应取代产物的方法。第二种方法包括：(a)执行将醇转化为相应卤化物的本发明方法；以及(b)将相应卤化物与亲核试剂反应，将卤化物转化为亲核取代产物。
• Catalytic Phosphorus(V)-Mediated Nucleophilic Substitution Reactions: Development of a Catalytic Appel Reaction
  作者：Ross M. Denton、Jie An、Beatrice Adeniran、Alexander J. Blake、William Lewis、Andrew M. Poulton

  DOI：10.1021/jo201085r

  日期：2011.8.19

  from stoichiometric waste products into catalysts and a new concept for catalytic phosphorus-based activation and nucleophilic substitution of alcohols has been validated. The present study has focused on a full exploration of the scope and limitations of phosphine oxide catalyzed chlorination reactions as well as the development of the analogous bromination reactions. Further mechanistic studies, including

  已经开发了催化磷（V）介导的醇的氯化和溴化反应。新反应构成了经典Appel卤化反应的催化形式。在这些新反应中，草酰氯用作消耗化学计量试剂，以产生卤化catalytic盐，这些卤化salts盐由催化氧化膦。因此，氧化膦已经从化学计量的废物转化为催化剂，并且已经验证了基于催化磷的醇的活化和亲核取代的新概念。本研究集中于对氧化膦催化的氯化反应的范围和局限性的全面探索，以及类似溴化反应的发展。进一步的机理研究，包括对催化循环中间体的密度泛函理论计算，与以卤代和烷氧基phosph盐为中间体的催化循环是一致的。

表征谱图