(4-氯苯磺酰)丙酮 | 5000-48-6

• 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-氯苯磺酰)丙酮
• 中文别名: 4-氯苯基磺酰基丙酮
• 英文名称: 1-[(4-chlorophenyl)sulfonyl]-2-propanone
• 英文别名: 1-((4-chlorophenyl)sulfonyl)-propan-2-one；(4-Chlorphenylsulfonyl)aceton；(4-chloro-benzenesulfonyl)-acetone；(4-Chlor-benzolsulfonyl)-aceton；(4-Chlor-phenylsulfon)-aceton；1-(4-chloro-benzenesulfonyl)-propan-2-one；(4-Chlor-phenyl)-acetonyl-sulfon；4-chlorophenylsulfonylacetone；1-(4-chlorophenyl)sulfonylpropan-2-one
• CAS: 5000-48-6
• 化学式: C₉H₉ClO₃S
• mdl: MFCD00018663
• 分子量: 232.688
• InChiKey: BRDBHPZILGTBFY-UHFFFAOYSA-N

物化性质

• 熔点：
  89-91 °C
• 沸点：
  396.2±42.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 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：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22,R36/37/38
• 海关编码：
  2914700090
• 安全说明：
  S26,S37/39
• 储存条件：
  请将药品存放在避光、阴凉干燥处，并密封保存。

SDS

Name:	4-Chlorophenylsulfonylacetone Material Safety Data Sheet
Synonym:
CAS:	5000-48-6

Section 1 - Chemical Product MSDS Name:4-Chlorophenylsulfonylacetone Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5000-48-6	4-Chlorophenylsulfonylacetone		unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical 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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 5000-48-6: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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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: Not available.
Freezing/Melting Point: 89 - 91 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: Insoluble.
Specific Gravity/Density:
Molecular Formula: C9H9ClO3S
Molecular Weight: 232.69

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5000-48-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Chlorophenylsulfonylacetone - 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.
WGK (Water Danger/Protection)
CAS# 5000-48-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5000-48-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5000-48-6 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：

  (4-氯苯磺酰)丙酮 在 溴 、 溶剂黄146 作用下， 生成 1-(4-chloro-benzenesulfonyl)-3-(toluene-4-sulfonyl)-acetone
  参考文献：
  名称：

  Troeger; v. Seelen, Journal fur praktische Chemie (Leipzig 1954), 1922, vol. <2> 105, p. 214

  摘要：

  DOI：
• 作为产物：
  描述：

  (4-氯苯基硫)丙-2-酮 在 potassium permanganate 、 溶剂黄146 作用下， 生成 (4-氯苯磺酰)丙酮
  参考文献：
  名称：

  Ohta; Sudoh, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1949, vol. 69, p. 43,45

  摘要：

  DOI：

文献信息

• (Arylsulfonyl)acetones and -acetonitriles: New Activated Methylenic Building Blocks for Synthesis of 1,2,3-Triazoles
  作者：Nazariy Pokhodylo、Vasyl Matiychuk、Mykola Obushak

  DOI：10.1055/s-0029-1216850

  日期：2009.7

  for 1,2,3-triazole synthesis in the Dimroth cyclization. It was shown, that sulfone reagents undergo base-catalyzed cyclization under mild conditions (at room temperature) to give 1,2,3-triazoles in moderate to excellent yields. This fact has confirmed the high nucleophilicity of sulfonylmethylenic compounds and allows new synthetic applications. azides - triazoles - sulfones - Dimroth reaction

  在Dimroth环化反应中，β-酮砜和β-腈砜被用作合成1,2,3-三唑的基础。结果表明，砜试剂在温和的条件下（在室温下）进行碱催化的环化反应，以中等至极好的收率得到1,2,3-三唑。这一事实证实了磺酰基亚甲基化合物的高度亲核性，并允许新的合成应用。 叠氮化物-三唑-砜-Dimroth反应
• Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones
  作者：Mikhail Krasavin、Dmitry Dar’in、Grigory Kantin、Olga Bakulina

  DOI：10.1055/s-0040-1707525

  日期：2020.8

  approach to the preparation of α-diazo-β-ketosulfones from sulfonyl chlorides is described. It involves the conversion of the sulfonyl chloride to sodium sulfinate, alkylation of the latter with α-haloketones followed by diazo transfer using the ‘sulfonyl-azide-free’ (‘SAFE’) protocol in aqueous medium. The simple and expedient method relies on readily available starting materials and provides facile

  描述了一种从磺酰氯制备α-重氮-β-酮砜的方便的一锅法。它包括将磺酰氯转化为亚磺酸钠，将后者用α-卤代烷烷基化，然后在水性介质中使用“无磺酰叠氮化物”（'SAFE'）方案进行重氮转移。简单方便的方法依赖于容易获得的起始原料，并且可以轻松获得用于有机合成的各种有价值的重氮试剂。
• Selective Formation of Products of Interrupted Feist-Benary Reaction under the Conditions of Hantzsch Pyrrole Synthesis
  作者：V. S. Matiichuk、D. A. Frolov、N. T. Pokhodylo、V. V. Pavlyuk、M. D. Obushak

  DOI：10.1134/s1070428018050238

  日期：2018.5

  Reaction of 3-aryl-2-chloropropanal with 1-arylsulfonylpropan-2-ones in aqueous ammonia and alcohol under the conditions of Hantzsch pyrrole synthesis led to the selective formation of the products of interrupted Feist-Benary reaction, 2-(R-benzyl)-4-arylsulfonyl-5-methyl-2,3-dihydrofuran-3-ols.

  在Hantzsch吡咯合成条件下，3-芳基-2-氯丙醛与1-芳基磺酰基丙-2-酮在氨水和醇中的反应导致选择性Feist-Benary反应2-（R-苄基）中断的产物选择性形成）-4-芳基磺酰基-5-甲基-2,3-二氢呋喃-3-醇。
• An Unexpected Domino Reaction of β-Keto Sulfones with Acetylene Ketones Promoted by Base: Facile Synthesis of 3(2<i>H</i> )-Furanones and Sulfonylbenzenes
  作者：Wei Tong、Qian-Yu Li、Yan-Li Xu、Heng-Shan Wang、Yan-Yan Chen、Ying-Ming Pan

  DOI：10.1002/adsc.201700830

  日期：2017.11.23

  An unexpected domino reaction of β‐keto sulfones with acetylene ketones has been developed. The domino reaction of β‐keto sulfones with diynones proceeded smoothly in the presence of 30 mol% K2CO3 without other additives, and afforded the novel 3(2H)‐furanone derivatives. On replacing the diynones with terminal alkyne ketones, the reaction regioselectivity was changed and sulfonylbenzenes were obtained

  β-酮砜与乙炔酮发生了意想不到的多米诺反应。在没有其他添加剂的情况下，在30 mol％K 2 CO 3的存在下，β-酮砜与二炔酮的多米诺反应顺利进行，得到了新颖的3（2 H）-呋喃酮衍生物。用末端炔烃酮取代二炔酮后，反应区域选择性改变，并通过苯环化获得磺酰苯，收率很高。
• Copper-Catalyzed Oxidative Reaction of β-Keto Sulfones with Alcohols via C−S Bond Cleavage: Reaction Development and Mechanism Study
  作者：Bingnan Du、Wenmin Wang、Yang Wang、Zhenghang Qi、Jiaqi Tian、Jie Zhou、Xiaochen Wang、Jianlin Han、Jing Ma、Yi Pan

  DOI：10.1002/asia.201701694

  日期：2018.2.16

  A Cu‐catalyzed cascade oxidative radical process of β‐keto sulfones with alcohols has been achieved by using oxygen as an oxidant. In this reaction, β‐keto sulfones were converted into sulfinate esters under the oxidative conditions via cleavage of C−S bond. Experimental and computational studies demonstrate that a new pathway is involved in this reaction, which proceeds through the formation of the

  通过使用氧气作为氧化剂，实现了β-酮砜与醇的Cu催化级联氧化自由基过程。在该反应中，β-酮砜在氧化条件下通过裂解C-S键转化为亚磺酸酯。实验和计算研究表明，该反应涉及新途径，该过程通过关键的四配位Cu II中间体的形成，O-O键均溶引起的CS键断裂和Cu催化的酯化反应形成最终途径。产品。该反应为磺化酯提供了新的策略，丰富了CS键断裂和转化的研究内容。

表征谱图