对甲砜基苯甲醛 | 5398-77-6

• 物质功能分类: 有机原料 - 醛类化合物
• 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: 对甲砜基苯甲醛
• 中文别名: 4-甲基磺酰基苯甲醛；对甲磺酰基苯甲醛
• 英文名称: para-methanesulfonylbenzaldehyde
• 英文别名: 4-Methylsulfonylbenzaldehyde；p-methylsulfonylbenzaldehyde；4-methanesulfonylbenzaldehyde；4-(Methylsulfonyl)benzaldehyde
• CAS: 5398-77-6
• 化学式: C₈H₈O₃S
• mdl: MFCD00216485
• 分子量: 184.216
• InChiKey: PSVPUHBSBYJSMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  155-161 °C
• 沸点：
  288.16°C (rough estimate)
• 密度：
  1.3761 (rough estimate)
• 溶解度：
  可溶于氯仿、甲醇
• 稳定性/保质期：

  在常温常压下保持稳定，应避免与不相容的材料接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 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

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R36
• 海关编码：
  2913000090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  密封储存，宜存放在阴凉、干燥的库房中。

SDS

Name:	4-Methylsulphonyl Benzaldehyde 95+% Material Safety Data Sheet
Synonym:	None Known
CAS:	5398-77-6

Section 1 - Chemical Product MSDS Name:4-Methylsulphonyl Benzaldehyde 95+% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5398-77-6	4-Methylsulphonyl Benzaldehyde	95+%	unlisted

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. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire.

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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:
Keep container closed when not in use. 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 process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 5398-77-6: 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: Powder
Color: beige to slight yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 156.00 - 159.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H8O3S
Molecular Weight: 184.22

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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:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, sulfur oxides (SOx), including sulfur oxide and sulfur dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5398-77-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Methylsulphonyl Benzaldehyde - 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
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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 5398-77-6: 1
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5398-77-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5398-77-6 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

制备方法与用途

概述

对甲砜基苯甲醛是合成甲砜霉素的重要原料。甲砜霉素属于第二代广谱抗菌药物，与氯霉素具有相似的抗菌作用和机制。它能抑制需氧革兰氏阴性菌及阳性菌、厌氧菌、链球菌属和双球菌属等，并对革兰氏阴性菌有更强的抑制效果。然而，甲砜霉素在血液中很少与蛋白质结合，在尿液和胆汁中的浓度高于氯霉素，且为长效药物，因此其体内抗菌作用比氯霉素更强大。此外，一些对氯霉素耐药的细菌对甲砜霉素更加敏感。

研究还证明，甲砜霉素能增强机体免疫能力。虽然氯霉素在临床上被广泛应用，但它对人和动物的骨髓细胞及肝细胞具有毒性作用，可能会导致剂量相关的骨髓抑制或不可逆的再生障碍性贫血、严重胃肠道反应、二重感染、周围神经炎以及“灰婴综合症”等。另外，它还可能引起肉鸡和小白鼠的免疫抑制反应和遗传毒性，并被认为是一种致畸剂。

副作用

多年临床应用表明，甲砜霉素也具有多种毒副作用，主要分为非血液系统毒性和血液系统毒性两大类。前者包括胃肠道反应（如腹痛、恶心、呕吐）、口腔黏膜发甜、厌食、头痛以及多神经炎；后者则表现为较高的血清铁增加率和白细胞、红细胞数量轻度下降，严重时可导致骨髓抑制。此外，该药物还可能引发周围神经炎。

近年来抗生素的滥用导致了严重的耐药性问题，因此研究开发低毒、高效的新型抗菌药物具有重要的现实意义。

化学性质

对甲砜基苯甲醛为结晶体（乙醇水溶液），熔点为158-159℃。

用途

甲砜基苯甲醛用作合成甲砜霉素的中间体，同时也用作医药中间体。

反应信息

• 作为反应物：
  描述：

  对甲砜基苯甲醛 在 叔丁基过氧化氢 作用下， 以 水 为溶剂， 反应 24.0h， 生成 4-甲砜基苯甲酸
  参考文献：
  名称：

  通过串联邻萘醌催化和 TBHP 促进的氧化序列将伯胺一锅直接氧化成羧酸

  摘要：

  胺到羧酸的串联氧化序列是通过o -NQ 催化的胺有氧氧化成亚胺，然后是自由基引发的 TBHP 促进的亚胺中间体氧化。从机制上讲，通过 TBAI 的帮助促进了o- NQ 催化剂体系的选择性亚胺形成，这在随后 TBHP 促进的亚胺衍生物氧化以将亚胺分解为醛和胺中也很关键。反过来，释放的胺重新进入o - NQ 催化循环以产生亚胺中间体。

  DOI：

  10.1002/chem.202103450
• 作为产物：
  描述：

  4-甲基茴香硫醚 在 air 作用下， 以61%的产率得到对甲砜基苯甲醛
  参考文献：
  名称：

  一种对甲砜基苯甲醛的制备方法

  摘要：

  本发明公开一种对甲砜基苯甲醛的制备方法。本发明的对甲砜基苯甲醛的制备方法是：首先如式所示在惰性气体保护下，在溶剂中化合物2与甲硫醇钠在催化剂作用下反应，再将得到的产物与水混合，在催化剂作用下进行氧化反应，产物经水中析晶过滤，得到目标产物对甲砜基苯甲醛。本发明的方法步骤简短，原材料价格低廉；利用固定床反应器的高效热质传递特性，使本发明显著区别于现有釜式合成工艺；本发明的催化剂高催化活性使对甲硫基甲苯转化完全，催化剂可重复回收套用，生产过程绿色环保，可减少三废排放，更适合于工业化生产。

  公开号：

  CN110003064B
• 作为试剂：
  描述：

  threo-3-[4-(methylsulfonyl)phenyl]serinamide hydrochloride 在 对甲砜基苯甲醛 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以5%的产率得到
  参考文献：
  名称：

  Synthesis of 4-Sulfur-Substituted (2S,3R)-3-Phenylserines by Enzymatic Resolution. Enantiopure Precursors for Thiamphenicol and Florfenicol

  摘要：

  Enantiomerically pure 4-methylthio- and 4-methylsulfonyl-substituted (2S,3R)-3-phenylserines are prepared by enzymatic resolution of the corresponding racemic three almides using the amidase from Ochrobactrum anthropi NCIMB 40321. The unwanted (2R,3S) enantiomers of the amides are separated from the enantiopure amino acids and easily racemized after Schiff base formation with the corresponding 4-(methylthio)- and 4-(methylsulfonyl)benzaldehyde. The racemization can be combined with the preparation of the racemic amides by aldol reaction under crystallization conditions to yield only the threo isomers. Enantiopure (2S, 3R)-3-[4-(methylthio)phenyl]serine and (2S,3R)-3-[4-(methylsulfonyl)phenyl are thus obtained in 78% and 62% overall yields starting from the corresponding substituted benzaldehydes, (2S,3R)-3-[4-(methylsulfonyl)phenyl]serine is reduced to (1R,2R)-2-amino-1-[4-(methylthio)phenyl]propane-1,3-diol with NaBH4/H2SO4 and can be used for the synthesis of thiamphenicol and florfenicol.

  DOI：

  10.1021/op970045t

文献信息

• Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2‐Substituted‐Alkynyl‐1‐Sulfonyl Fluoride (SASF) Hubs
  作者：Christopher J. Smedley、Gencheng Li、Andrew S. Barrow、Timothy L. Gialelis、Marie‐Claire Giel、Alessandra Ottonello、Yunfei Cheng、Seiya Kitamura、Dennis W. Wolan、K. Barry Sharpless、John E. Moses

  DOI：10.1002/anie.202003219

  日期：2020.7.20

  Diversity Oriented Clicking (DOC) is a unified click‐approach for the modular synthesis of lead‐like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease” , by combining classic C−C π‐bond click chemistry with recent developments in connective SuFEx‐technologies. We showcase 2‐Substituted‐Alkynyl‐1‐Sulfonyl Fluorides

  面向多样性的点击 (DOC) 是一种统一的点击方法，用于通过应用广泛的点击转换家族来模块化合成类先导结构。DOC 从实现“轻松实现多样性”的概念演变而来，将经典的 C−C π 键点击化学与连接性 SuFEx 技术的最新发展相结合。我们展示了 2-取代的- A炔基-1-磺酰基F氟化物（SASFs）作为一类新的连接枢纽，与多种点击环加成过程相结合。通过具有一系列偶极子和环状二烯的 SASF 的选择性 DOC，我们以最少的合成步骤报告了 173 种独特功能分子的多样化点击库。SuFExable 库包含 10 个离散的杂环核心结构，这些核心结构源自 1,3- 和 1,5- 偶极子；而与环状二烯的反应会产生几种三维双环 Diels-Alder 加合物。通过对 96 孔板中的磺酰氟侧基进行 SuFEx 点击衍生化，可以通过后期修饰将文库增加到 278 种离散化合物——证明了 DOC 方法在快速合成不同功能结构方面的多功能性。
• 2-Substituted and 4-substituted aryl nitrone compounds
  申请人：Kelly G. Michael

  公开号：US20050182060A1

  公开（公告）日：2005-08-18

  The present invention provides aryl nitrones, compositions comprising the same and methods of their use for the treatment or prevention of oxidative, ischemic, ischemia/reperfusion-related and chemokine mediated conditions.

  本发明提供芳基亚硝基酮，包括其在内的组合物以及它们用于治疗或预防氧化性、缺血性、缺血/再灌注相关和趋化因子介导的疾病的方法。
• Synthesis and Biological Activity of Novel (E)-N’-(Substituted)-3,4,5-Trimethoxybenzohydrazide Analogs
  作者：Namala Rambabu、Bhavani Ram、Pramod Kumar Dubey、Bhavani Vasudha、Bhavani Balram

  DOI：10.13005/ojc/330126

  日期：2017.2.28

  Aspergillus niger and Candida albicans (Fungal strains). The results revealed that most of the hydrazone derivatives exhibited significant antibacterial activity. Furthermore, the synthesized hydrazone derivatives were found to exhibit significant antidiabetic activity when compared to insulin.

  通过3，4，5-三甲氧基苯并酰肼3与各种芳族和杂芳族醛a1的缩合描述了酰肼-hydr类似物4a-4l。利用各种光谱技术，即（1 H NMR，13 C NMR，IR和MS）来确定合成的化合物的结构。对这些化合物进行了针对金黄色葡萄球菌，酿脓链球菌，大肠杆菌，铜绿假单胞菌，黑曲霉和白色念珠菌（真菌菌株）的抗菌，抗真菌筛选。结果表明，大多数derivatives衍生物表现出显着的抗菌活性。此外，发现与胰岛素相比，合成的derivatives衍生物显示出显着的抗糖尿病活性。
• Palladium‐Catalyzed Reductive Carbonylation of (Hetero) Aryl Halides and Triflates Using Cobalt Carbonyl as CO Source
  作者：Bhushanarao Dogga、C. S. Ananda Kumar、Jayan T. Joseph

  DOI：10.1002/ejoc.202001328

  日期：2021.1.15

  A generalized protocol for the reductive carbonylation of (hetero) aryl halides and triflates under CO gas‐free conditions using Pd/Co2(CO)8 and triethylsilane has been developed. The mild reaction conditions, enhanced safety, and wide substrate scope highlight its importance in routine organic synthesis.

  已经开发了一种通用协议，用于在无CO气体条件下使用Pd / Co 2（CO）8和三乙基硅烷对（杂）芳基卤化物和三氟甲磺酸进行还原羰基化。温和的反应条件，增强的安全性和广泛的底物范围突出了其在常规有机合成中的重要性。
• Oxidative alkoxycarbonylation of terminal alkenes with carbazates
  作者：Yu-Han Su、Zhao Wu、Shi-Kai Tian

  DOI：10.1039/c3cc42994f

  日期：——

  A range of terminal alkenes smoothly underwent palladium-catalyzed oxidative alkoxycarbonylation with carbazates under an oxygen atmosphere to afford structurally diverse α,β-unsaturated esters in moderate to good yields with excellent regioselectivity and E selectivity.

  一系列末端烯烃在氧气氛围下顺利经历钯催化的氧化烷氧羰基化反应，与卡巴肼反应，以中等至良好的产率得到结构多样的α,β-不饱和酯，具有优异的区域选择性和E选择性。