N-[4-(2-氯乙酰基)苯基]甲磺酰胺 | 64488-52-4

• 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 - 有机氧化合物
• 中文名称: N-[4-(2-氯乙酰基)苯基]甲磺酰胺
• 中文别名: 4-氯乙酰基甲磺酰苯胺；N-(4-(2-氯乙酰基)苯基)甲磺酰胺
• 英文名称: N-[4-(chloroacetyl)phenyl]methanesulfonamide
• 英文别名: N-[4-(2-chloro-1-oxoethyl)phenyl]methanesulfonamide；N-[4-(2-chloroacetyl)phenyl]methanesulfonamide
• CAS: 64488-52-4
• 化学式: C₉H₁₀ClNO₃S
• mdl: MFCD00144999
• 分子量: 247.702
• InChiKey: DRQKKEYKSSAVTO-UHFFFAOYSA-N

物化性质

• 熔点：
  197.5-199.0 °C
• 沸点：
  410.4±51.0 °C(Predicted)
• 密度：
  1.433±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2935009090

SDS

Name:	n-(4-Chloroacetylphenyl)methanesulfonamide 98% (uv-vis) Material Safety Data Sheet
Synonym:
CAS:	64488-52-4

Section 1 - Chemical Product MSDS Name:n-(4-Chloroacetylphenyl)methanesulfonamide 98% (uv-vis) Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
64488-52-4	Methanesulfonamide, n-4-(chloroacetyl)		unlisted

Hazard Symbols: Not available.
Risk Phrases:

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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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 lids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes.
Remove contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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 agent most appropriate to extinguish fire.
Autoignition Temperature: Not available.
Flash Point: Not available.
NFPA Rating: Not published.
Explosion Limits, Lower: Not available.
Upper: Not available.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Keep container closed when not in use.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Personal Protective Equipment Eyes: Wear chemical goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements must be followed whenever workplace conditions warrant a respirator's use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Not available.
Appearance: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Vapor Density: Not available.
Evaporation Rate: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 0 deg C
Decomposition Temperature: Not available.
Solubility: Not available.
Specific Gravity/Density: Not available.
Molecular Formula: C9H10ClNO3S
Molecular Weight: 247.70

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 64488-52-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methanesulfonamide, n-4-(chloroacetyl)phenyl- - Not listed by ACGIH, IARC, NIOSH, NTP, or OSHA.
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION
For further information, contact Fisher Scientific.

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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

CDG/CPL
IMO
Not regulated as a hazardous material.
IATA
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.
Canadian TDG
No information available.

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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# 64488-52-4:
Canada
CAS# 64488-52-4 is listed on Canada's DSL/NDSL List.
WHMIS: Not available.
CAS# 64488-52-4 is not listed on Canada's Ingredient Disclosure List.
Exposure Limits
US FEDERAL
TSCA
CAS# 64488-52-4 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N-[4-(2-氯乙酰基)苯基]甲磺酰胺 在 palladium on activated charcoal 氢气 作用下， 以 水 、 乙腈 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 22.0h， 生成 N-[4-[2-(2,3-dimethylimidazol-3-ium-1-yl)-1-hydroxyethyl]phenyl]methanesulfonamide;chloride
  参考文献：
  名称：

  Synthesis and antiarrhythmic activity of novel 3-alkyl-1-[.omega.-[4-[(alkylsulfonyl)amino]phenyl]-.omega.-hydroxyalkyl]-1H-imidazolium salts and related compounds

  摘要：

  Novel 3-alkyl-1-[omega-[4-[(alkylsulfonyl)amino]phenyl]-omega-hydroxyalkyl]-1H -imidazolium salts were synthesized and investigated for their class III electrophysiological activity on isolated canine cardiac Purkinje fibers and ventricular muscle tissue. Structure-activity relationships are discussed for a series of 25 compounds. Compound 3, 1-[2-hydroxy-2-[4-[(methylsulfonyl)amino]phenyl]ethyl]-3-methyl-1H- imidazolium chloride, prolonged the functional refractory period in anesthetized dogs when given intraduodenally and was also effective in preventing reentrant ventricular tachycardia induced by programmed electrical stimulation when administered intravenously in anesthetized dogs 24 h after an acute myocardial infarction. Both enantiomers of 3 were synthesized. No enantioselectivity was found in the electrophysiological effects of 3.

  DOI：

  10.1021/jm00387a020
• 作为产物：
  描述：

  N-苯基甲磺酰胺 、 氯乙酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以75%的产率得到N-[4-(2-氯乙酰基)苯基]甲磺酰胺
  参考文献：
  名称：

  Chemoenzymatic synthesis of (S) and (R)-propranolol and sotalol employing one-pot lipase resolution protocol

  摘要：

  Synthesis of both enantiomers of biologically active propranolol and sotalol has been achieved in high optical purity by one-pot reduction of 3 and 7 followed by in situ lipase resolution of the respective chlorohydrins. Pseudomonas cepacia lipase immobilized on ceramic particles (PS-C) provided the chlorohydrin and acetate, which on nucleophilic substitution with isopropyl amine afforded the target amino alcohols in high enantio selectivity under mild reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.084

文献信息

• Synthesis and Antimicrobial Activities of (4,5,6,7-Tetrahydro-1H-indazol- 2(3H)-yl)thiazole Derivatives
  作者：Krzysztof Laczkowski、Konrad Misiura、Anna Biernasiuk、Anna Malm

  DOI：10.2174/1570180811666140516233913

  日期：2014.8.8

  Synthesis, characterization and investigation of antimicrobial activities of ten novel tetrahydroindazolylthiazoles is presented. Their structures were determined using 1H and 13C NMR, FAB(+)-MS and HRMS analyses. Among the derivatives, compound 3f shows strong antibacterial activity against S. aureus ATCC 43300, S. aureus ATCC 25923, and S. epidermidis ATCC 12228 with MIC 7.81 µg/ml, and good activity against S. aureus ATCC 6538 with MIC 31.25 µg/ml. Compounds 3a-e and 3j show good antifungal activity with MIC values ranging from 31.25 µg/ml to 250 µg/ml.

  本文介绍了十种新型四氢吲达佐里噻唑的合成、表征及其抗菌活性研究。通过1H和13C NMR、FAB(+)-MS和HRMS分析确定了它们的结构。在衍生物中，化合物3f对S. aureus ATCC 43300、S. aureus ATCC 25923和S. epidermidis ATCC 12228表现出强烈的抗菌活性，MIC值为7.81 µg/ml，对S. aureus ATCC 6538也显示出良好的活性，MIC值为31.25 µg/ml。化合物3a-e和3j表现出良好的抗真菌活性，MIC值范围从31.25 µg/ml到250 µg/ml。
• Synthesis, Antimicrobial Activities and Molecular Docking Studies of Novel 6-Hydroxybenzofuran-3(2H)-one Based 2,4-Disubstituted 1,3- Thiazoles
  作者：Krzysztof La..czkowski、Konrad Misiura、Anna Biernasiuk、Anna Malm、Agata Siwek、Tomasz Plech

  DOI：10.2174/15701808113109990010

  日期：2013.9.1

  Synthesis, characterization and investigation of antibacterial and antifungal activities of thirteen novel 6- hydroxybenzofuran-3(2H)-one based 2,4-disubstituted 1,3-thiazoles are presented. Their structures were determined using NMR, FAB MS and HRMS analyses. The results of microbiological screening reveal that three derivatives containing fluorine, bromine and hydrogen substituents at the phenyl

  介绍了十三种新型的6-羟基苯并呋喃-3（2H）-一为基础的2,4-二取代的1,3-噻唑的合成，表征和抗菌活性。使用NMR，FAB MS和HRMS分析确定其结构。微生物筛选的结果表明，在苯环上含有氟，溴和氢取代基的三种衍生物是活性最高的抗菌化合物。所有化合物在微生物酶活性位点上的分子对接研究表明可能存在靶标Nmyristoyltransferase（NMT）。
• Synthesis, In Vitro Biological Screening and Molecular Docking Studies of Novel Camphor-Based Thiazoles
  作者：Krzysztof Laczkowski、Konrad Misiura、Anna Biernasiuk、Anna Malm、Agata Siwek、Tomasz Plech、Emilia Ciok-Pater、Krzysztof Skowron、Eugenia Gospodarek

  DOI：10.2174/15734064113096660054

  日期：2014.8.4

  Synthesis, characterization and investigation of antibacterial and antifungal activities of twelve camphor based 2,4-disubstituted 1,3-thiazoles is presented. Their structures were determined using NMR, IR, FAB MS and HRMS analyses. Among the derivatives, 3i and 5 were found to exhibit antifungal and antibacterial activities comparable to that of fluconazole and ciprofloxacin against yeast belonging to Candida spp., MIC 0.12-0.98 μg/ml and Gram-positive bacteria including both pathogenic S. aureus and opportunistic S. epidermidis, MIC 0.98-7.81 μg/ml, B. subtilis and B. cereus, MIC 3.91-31.25 μg/ml, and M. luteus, MIC 0.98 μg/ml species, respectively. Molecular docking studies of all compounds into the active sites of microbial enzymes indicated a possible targets SAP and NMT, thiazoles 3a-j, 4, 5 showed more favourable affinity than the native ligand.

  本文介绍了十二种樟脑基2,4-二取代1,3-噻唑的合成、表征及其抗菌和抗真菌活性研究。它们的结构通过NMR、IR、FAB MS和HRMS分析确定。在这些衍生物中，3i和5表现出与氟康唑和环丙沙星相当的抗真菌和抗菌活性，对属于念珠菌属的酵母菌（MIC 0.12-0.98 μg/ml）、包括致病性金黄色葡萄球菌和机会性表皮葡萄球菌在内的革兰氏阳性细菌（MIC 0.98-7.81 μg/ml）、枯草芽孢杆菌和蜡样芽孢杆菌（MIC 3.91-31.25 μg/ml）以及藤黄微球菌（MIC 0.98 μg/ml）具有活性。所有化合物的分子对接研究显示，它们与微生物酶的活性位点结合，可能的目标是SAP和NMT，噻唑3a-j、4、5显示出比原生配体更有利的亲和性。
• Practical Synthesis of Optically Active Styrene Oxides via Reductive Transformation of 2-Chloroacetophenones with Chiral Rhodium Catalysts
  作者：Takayuki Hamada、Takayoshi Torii、Kunisuke Izawa、Ryoji Noyori、Takao Ikariya

  DOI：10.1021/ol020213o

  日期：2002.11.1

  [reaction: see text] A practical method for the synthesis of optically active styrene oxides has been developed via formation of optically active 2-chloro-1-phenylethanols generated by reductive transformation of ring-substituted 2-chloroacetophenones. The optically active alcohols with up to 98% ee are obtainable from the asymmetric reduction of acetophenones with an S/C = 1000-5000 with a formic

  [反应：见正文]通过形成由环取代的2-氯苯乙酮的还原转化而生成的光学活性的2-氯-1-苯基乙醇，已经开发了一种合成光学活性的苯乙烯氧化物的实用方法。ee高达98％的旋光性醇可通过将S / C = 1000-5000的苯乙酮与含有明确定义的手性Rh络合物CpRhCl [（R，R）- tsdpen]。
• A practical synthesis of optically active aromatic epoxides via asymmetric transfer hydrogenation of α-chlorinated ketones with chiral rhodium–diamine catalyst
  作者：Takayuki Hamada、Takayoshi Torii、Kunisuke Izawa、Takao Ikariya

  DOI：10.1016/j.tet.2004.06.076

  日期：2004.8

  A practical method for the synthesis of optically active aromatic epoxides has been developed via the formation of optically active α-chlorinated alcohols and intramolecular etherification. Optically active alcohols with up to 99% ee can be obtained from the asymmetric reduction of aromatic ketones with a substrate/catalyst ratio of 1000–5000 using a formic acid/triethylamine mixture containing a well-defined

  通过形成光学活性的α-氯化醇和分子内醚化，已经开发了一种合成光学活性的芳族环氧化物的实用方法。使用含有明确定义的手性Rh络合物Cp * RhCl [（[R， [R）-Tsdpen]。由于二胺基Cp * Rh（III）氢化物配合物的配位饱和特性，用手性Rh催化剂不对称还原α-氯化芳族酮的特征是快速且羰基选择性转化。还原的结果受酮底物的结构以及氢源（如甲酸或2-丙醇）的影响很大。无需特殊纯化即可在该反应中使用市售的试剂和溶剂。一锅法或两锅法的这种环氧化物合成方法是实用的，对于从α-氯代酮大规模生产旋光性苯乙烯氧化物特别有用。