4-乙酰基苯磺酰氯 | 1788-10-9

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酰卤化物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-乙酰基苯磺酰氯
• 中文别名: 4-乙酰苯磺酰氯；4-乙酰基苯磺酰基氯；对乙酰基苯磺酰氯
• 英文名称: 4-Acetylbenzenesulfonyl chloride
• 英文别名: 4-acetylbenzene-1-sulfonyl chloride
• CAS: 1788-10-9
• 化学式: C₈H₇ClO₃S
• mdl: MFCD00800269
• 分子量: 218.661
• InChiKey: FXVDNCRTKXMSEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  84-87 °C
• 沸点：
  338.6±25.0 °C(Predicted)
• 密度：
  1.3949 (estimate)
• 溶解度：
  可溶于氯仿（少量）、DMSO（少量）、甲醇（少量）
• 稳定性/保质期：

  常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• TSCA：
  No
• 危险等级：
  8
• 危险等级：
  CORROSIVE
• 危险品标志：
  C
• 安全说明：
  S25,S26,S36/37/39,S45
• 危险类别码：
  R34
• WGK Germany：
  3
• 海关编码：
  29147000
• 危险品运输编号：
  UN 3261 8/PG 3
• 危险类别：
  CORROSIVE
• 包装等级：
  III
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H314
• 储存条件：
  密封贮藏，应存放在阴凉干燥处，并远离氧化剂和火源。

SDS

Name:	4-Acetylbenzenesulfonyl Chloride Material Safety Data Sheet
Synonym:	None Known
CAS:	1788-10-9

Section 1 - Chemical Product MSDS Name:4-Acetylbenzenesulfonyl Chloride Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1788-10-9	4-Acetylbenzenesulfonyl Chloride	ca. 100	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Moisture sensitive.Corrosive.
Potential Health Effects
Eye:
Causes eye burns. May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin burns. May cause skin rash (in milder cases), and cold and clammy skin with cyanosis or pale color.
Ingestion:
May cause severe and permanent damage to the digestive tract. Causes gastrointestinal tract burns. May cause perforation of the digestive tract. May cause systemic effects.
Inhalation:
Causes chemical burns to the respiratory tract. Inhalation may be fatal as a result of spasm, inflammation, edema of the larynx and bronchi, chemical pneumonitis and pulmonary edema. Aspiration may lead to pulmonary edema. May cause systemic effects. May cause burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Get medical aid immediately. Do NOT allow victim to rub eyes or keep eyes closed. Extensive irrigation with water is required (at least 30 minutes).
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Destroy contaminated shoes.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
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. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Water hydrolyzes material liberating acidic gas which in contact with metal surfaces can generate flammable and/or explosive hydrogen gas. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide. DO NOT USE WATER! Do NOT get water inside containers.

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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. Do not get water inside containers.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing.
Keep container tightly closed. Do not ingest or inhale. Do not allow contact with water. Use only in a chemical fume hood. Discard contaminated shoes. Keep from contact with moist air and steam.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Corrosives area. Store protected from moisture.

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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# 1788-10-9: 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:
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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 81-85 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:
Specific Gravity/Density:
Molecular Formula: C8H7ClO3S
Molecular Weight: 218.5602

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, moisture, excess heat, strong oxidants, exposure to moist air or water.
Incompatibilities with Other Materials:
Moisture, oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, oxides of sulfur, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1788-10-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Acetylbenzenesulfonyl Chloride - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: Pseudomonas putida:

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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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 25 Avoid contact with eyes.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
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# 1788-10-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1788-10-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1788-10-9 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：

  4-乙酰基苯磺酰氯 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 生成 4-acetylbenzenesulfonyl azide
  参考文献：
  名称：

  室温下铱催化的芳基亚硝基与磺酰叠氮化物的直接C–H磺酰胺化

  摘要：

  已开发出Ir（III）催化的芳基硝酮的直接C–H磺酰胺化反应，以中等至优异的收率，优异的区域选择性和宽泛的官能团耐受性，合成了各种磺酰胺化的硝酮。在没有外部氧化剂，酸或碱的情况下，这种转变可以在室温下以低催化剂负载平稳地进行。分子氮作为唯一的副产物释放，因此提供了对环境无害的磺酰胺化过程。该方案可以通过一步转化从产物中高效合成取代的苯并异恶唑啉。

  DOI：

  10.1021/acs.joc.5b01377
• 作为产物：
  描述：

  4-氨基苯乙酮 在 CuCl₂*H₂O 盐酸 、 sodium nitrite 、 二氧化硫 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.0h， 以55%的产率得到4-乙酰基苯磺酰氯
  参考文献：
  名称：

  Simple and Efficient Synthesis of 3,4-Dihydro-2-pyridones via Novel Solid-Supported Aza-Annulation

  摘要：

  A diverse array of 3,4-dihydro-2-pyridones 13 were produced utilizing the unique properties of solid-supported reactions to both drive the reactions to completion and isolate the desired products. The pyridones were: synthesized in high purity by a simple sequence of navel steps commencing from an acetophenone-functionalized resin. The para-substituted acetophenone 9 could be anchored to the resin through either a sulfonamide or a carboxamide linkage. The sulfonamide resin 9a, which gave the best results, was treated with several aryl aldehydes and ethoxide to give a variety of chalcones 10a-k, in excellent yield (82-99%) upon TFA cleavage. Addition of either methyl or allyl malonate and DBU to 10a-k afforded smoothly the Michael adducts 11a-j (70-99%) which were subsequently cyclized in one step employing acetic acid as a catalyst and several diverse amines to give pure 3,4-dihydro-2-pyridones 13a-p in moderate to excellent yields (30-98%).

  DOI：

  10.1021/jo005609x
• 作为试剂：
  描述：

  resin-bound 2-Amino-4,7-dihydro-5H-thieno[2,3-c]pyridine-3,6-dicarboxylic acid 6-tert-butyl ester 在 烟酰氯 、 丙酰氯 、 N,N-二异丙基乙胺 、 异丁酰氯 、 4-正丁氧基苯甲酰氯 、 7-甲氧基苯并呋喃-2-甲酸 、 4-氟苯磺酰氯 、 4-乙酰基苯磺酰氯 、 1-萘磺酰氯 、 5-氯-2-甲氧基苯磺酰氯 、 对乙酰氨基苯甲酸 、 1-羟基苯并三唑 、 5-氯-1,3-二甲基-1H-吡唑-4-磺酰氯 、 N,N'-二异丙基碳二亚胺 、 2,4-二氟苯甲酸 作用下， 以 二氯甲烷 、 三氟乙酸 、 四氢呋喃 、 N,N-di-isopropylcarbodiimide 为溶剂， 反应 96.5h， 生成 6-(4-Fluoro-benzenesulfonyl)-2-isobutyrylamino-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid 、 6-(4-Acetylamino-benzoyl)-2-isobutyrylamino-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid
  参考文献：
  名称：

  Bicyclic thiophene derivatives and combinatorial libraries thereof

  摘要：

  本发明涉及以下式子的新型双环硫吡啶衍生物化合物：1其中R1至R2、X和n具有本文所提供的含义。本发明还涉及包含两个或更多这样的化合物的组合式库，以及制备双环硫吡啶衍生物化合物的方法。

  公开号：

  US20030232994A1

文献信息

• Triblock Peptide and Peptide Thioester Synthesis With Reactivity-Differentiated Sulfonamides and Peptidyl Thioacids
  作者：David Crich、Indrajeet Sharma

  DOI：10.1002/anie.200903050

  日期：2009.9.28

  One after the other: Triblock peptide synthesis was achieved at ambient temperature by sequential reaction of sulfonamide‐protected peptidyl thioacids first with highly reactive 2,4‐dinitrobenzenesulfonamides and second with more moderately reactive sulfonamides to produce the oligopeptides in good yields. The method is compatible with C‐terminal thioesters and thus presents a new approach for native

  一个接一个：三嵌段肽的合成是在环境温度下通过磺酰胺保护的肽基硫酸首先与高反应性的 2,4-二硝基苯磺酰胺，然后与反应性中等的磺酰胺顺序反应来实现的，从而以良好的收率生产寡肽。该方法与 C 端硫酯兼容，因此为天然化学连接策略提供了一种新方法。
• KMnO4-mediated oxidative C N bond cleavage of tertiary amines: Synthesis of amides and sulfonamides
  作者：Zhang Zhang、Yong-Hong Liu、Xi Zhang、Xi-Cun Wang

  DOI：10.1016/j.tet.2019.03.047

  日期：2019.5

  KMnO4-mediated oxidative CN bond cleavage of tertiary amines producing secondary amine was introduced, which was trapped by electrophiles (acyl chloride and sulfonyl chloride) to form amides and sulfonamides. The reaction could take place at mild condition, tolerating a wide range of function groups and affording products in moderate to excellent yields.

  引入了KMnO 4介导的叔胺氧化C N键裂解生成仲胺的方法，该方法被亲电子试剂（酰氯和磺酰氯）捕获，形成酰胺和磺酰胺。反应可以在温和的条件下进行，可以耐受各种官能团，并提供中等至极好的收率的产物。
• The palladium-catalyzed desulfitative cyanation of arenesulfonyl chlorides and sodium sulfinates
  作者：Jianbin Chen、Yang Sun、Bin Liu、Dongfang Liu、Jiang Cheng

  DOI：10.1039/c1cc16134b

  日期：——

  A palladium-catalyzed desulfitative cyanation of arenesulfonyl chlorides and sodium sulfinates has been developed, providing aryl nitriles in moderate to excellent yields. It represents a facile procedure to access aryl nitriles.

  已经开发了芳烃磺酰氯和亚磺酸钠的钯催化的脱硫氰化，以中等至优异的产率提供了芳基腈。它代表了获取芳基腈的简便程序。
• Discovery, Biological Evaluation, and Structure–Activity and −Selectivity Relationships of 6′-Substituted (<i>E</i>)-2-(Benzofuran-3(2<i>H</i>)-ylidene)-<i>N</i>-methylacetamides, a Novel Class of Potent and Selective Monoamine Oxidase Inhibitors
  作者：Leonardo Pisani、Maria Barletta、Ramon Soto-Otero、Orazio Nicolotti、Estefania Mendez-Alvarez、Marco Catto、Antonellina Introcaso、Angela Stefanachi、Saverio Cellamare、Cosimo Altomare、Angelo Carotti

  DOI：10.1021/jm4000769

  日期：2013.3.28

  The use of selective inhibitors of monoamine oxidase A (MAO-A) and B (MAO-B) holds a therapeutic relevance in the treatment of depressive disorders and Parkinson’s disease (PD), respectively. Here, the discovery of a new class of compounds acting as monoamine oxidase inhibitors (MAO-Is) and bearing a 6′-substituted (E)-2-(benzofuran-3(2H)-ylidene)-N-alkylacetamide skeleton is reported. 6′-Sulfonyloxy

  使用单胺氧化酶A（MAO-A）和B（MAO-B）的选择性抑制剂分别在抑郁症和帕金森氏病（PD）的治疗中具有治疗意义。在这里，发现了一类新的充当单胺氧化酶抑制剂（MAO-Is）并带有6'-取代的（E）-2-（苯并呋喃-3（2 H）-亚烷基）-N-烷基乙酰胺骨架的化合物报告。6'-磺酰氧基衍生物表现出对MAO-A的出色亲和力（7.0 nM
• SULFONAMIDE DERIVATIVE AND MEDICINAL USE THEREOF
  申请人：AJINOMOTO CO., LTD.

  公开号：US20150051395A1

  公开（公告）日：2015-02-19

  Provided are sulfonamide derivatives of a specific chemical structure in which a sulfonamide group having, as a substituent, a phenyl group or a heterocyclic group having a hetero atom(s) as a constituent element(s) is present at its terminal, and pharmaceutically acceptable salts thereof. These compounds are novel compounds having excellent α4 integrin-inhibitory action.

  提供的是具有特定化学结构的磺酰胺衍生物，在其末端有一个带有苯基或含杂原子的杂环基团作为取代基的磺酰胺基团，以及药用可接受的盐。这些化合物是具有卓越的α4整合素抑制作用的全新化合物。