2,3,5,6-四甲基苯磺酰氯 | 60706-63-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酰卤
• 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: 2,3,5,6-四甲基苯磺酰氯
• 中文别名: 2,3,5,6-四甲苯磺酰氯
• 英文名称: 2,3,5,6-tetramethylbenzenesulfonyl chloride
• 英文别名: 2,3,5,6-tetramethyl-benzene-1-sulfonyl chloride
• CAS: 60706-63-0
• 化学式: C₁₀H₁₃ClO₂S
• mdl: MFCD00014723
• 分子量: 232.731
• InChiKey: ZCXRROBIIMQMHR-UHFFFAOYSA-N

物化性质

• 熔点：
  97-101 °C
• 沸点：
  343.8±42.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  避免接触氧化物、碱、活性金属和水分。

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• 海关编码：
  2904909090
• 包装等级：
  II
• 危险类别：
  8
• 危险品运输编号：
  3261
• 危险性防范说明：
  P260,P280,P303+P361+P353,P301+P330+P331,P304+P340+P310,P305+P351+P338+P310
• 危险性描述：
  H314

SDS

Name:	2 3 5 6-Tetramethylbenzenesulfonyl chloride Material Safety Data Sheet
Synonym:
CAS:	60706-63-0

Section 1 - Chemical Product MSDS Name:2 3 5 6-Tetramethylbenzenesulfonyl chloride Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
60706-63-0	2,3,5,6-Tetramethylbenzenesulfonyl chl		unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
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 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.
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:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

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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# 60706-63-0: 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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 98 - 99 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: C10H13ClO2S
Molecular Weight: 232.6028

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases.
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# 60706-63-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,3,5,6-Tetramethylbenzenesulfonyl chloride - 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: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3261
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
RID/ADR
No information available.

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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 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
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# 60706-63-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 60706-63-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 60706-63-0 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：

  2,3,5,6-四甲基苯磺酰氯 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 2,3,5,6-四甲基苯硫醇
  参考文献：
  名称：

  聚合中的双型改性剂。一、各种二硫化物在苯乙烯本体聚合中的行为

  摘要：

  具有双型结构的改性剂作为将反应性基团赋予聚合物链末端的最高可能分数的手段而受到关注。比较了各种二硫化物和其他双类化合物（一些带有反应性基团）作为低转化率本体苯乙烯聚合中的改性剂的有效性，并研究了它们的裂解机制。伯硫醇的烷基二硫化物的转移常数太低，即使在硫 - 硫键附近的碳上被取代，对这项工作也不感兴趣。芳基二硫化物证明具有更高的转移常数，并且在每个环上用适当的基团取代提供了增加转移常数和引入所需基团的方法。已经非常确定地表明，芳基二硫化物裂解从而将一半的分子赋予聚合物的每一端。这通过分析包含各种类型端基（羧基、氨基、萘基和苯并噻唑基）的宽分子量范围的苯乙烯聚合物的端基浓度并在可能的情况下与用含有相似基团的硫醇改性的聚合物进行比较来证明。聚合在 25、50 和 75°C 下进行。使用某些双型化合物以及正硫醇和叔硫醇表明，如果转移常数高，活化能非常小，并且仅在转移常数低时才开始达到显着水平。这

  DOI：

  10.1002/pol.1955.120178407
• 作为产物：
  描述：

  1,2,4,5-四甲苯 在 氯磺酸 、 sodium chloride 作用下， 以 四氯化碳 、 正己烷 、 氯仿 为溶剂， 以85%的产率得到2,3,5,6-四甲基苯磺酰氯
  参考文献：
  名称：

  受阻磺酰基化合物溶剂化过程中过渡态的溶剂网络

  摘要：

  在甲醇中，无阻碍的苯磺酰氯（X‐ArSO 2 Cl，X = H‐； 4-Br‐； 4-Me‐）的醇解速率相似。在乙醇中也观察到相同的行为，而在异丙醇中的反应顺序为4 Me-

  DOI：

  10.1002/poc.3588
• 作为试剂：
  描述：

  Phosphoric acid (2R,3R,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(4-methoxy-benzyloxy)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester; compound with triethyl-amine 、 2',3'-二-O-苯甲酰基尿苷 在 N-甲基咪唑 、 2,3,5,6-四甲基苯磺酰氯 作用下， 以 吡啶 为溶剂， 反应 0.33h， 以88%的产率得到
  参考文献：
  名称：

  Losse, Guenter; Stang, Norbert, Liebigs Annalen der Chemie, 1989, p. 19 - 24

  摘要：

  DOI：

文献信息

• Ligand-Free, Quinoline N-Assisted Copper-Catalyzed Nitrene Transfer Reaction To Synthesize 8-Quinolylsulfimides
  作者：Xinsheng Xiao、Sanping Huang、Shanshan Tang、Guokai Jia、Guangchuan Ou、Yangyan Li

  DOI：10.1021/acs.joc.9b00281

  日期：2019.6.21

  An efficient copper-catalyzed, quinolyl N-directed nitrene transfer reaction to 8-quinolylsulfides was described. A variety of 8-quinolylsulfimides with different functional groups were synthesized in moderate to high yields. The obtained 8-quinolylsulfimides were proved to be promising novel type of bidentate ligands in Pd(II)-catalyzed allylic alkylation.

  描述了一种有效的铜催化的，喹啉基N定向的腈转移反应生成8-喹啉基硫化物的方法。以中等至高收率合成了具有不同官能团的多种8-喹啉基亚磺酰亚胺。事实证明，在Pd（II）催化的烯丙基烷基化反应中，所获得的8-喹啉硫磺酰亚胺是有前途的新型二齿配体。
• [EN] SULFONAMIDE SUBSTITUTED XANTHINE DERIVATIVES FOR USE AS PEPCK INHIBITORS<br/>[FR] DERIVES DE XANTHINE SUBSTITUES PAR DES SULFONAMIDES ET UTILES COMME INHIBITEURS DE PEPCK
  申请人：HOFFMANN LA ROCHE

  公开号：WO2004074288A1

  公开（公告）日：2004-09-02

  The present invention is concerned with sulfonamide substituted xanthine derivatives of formula (I) or a pharmaceutically acceptable salts or prodrugs thereof, wherein R1, R2 and R3 are as defined in the specification. Compounds of formula (I) and pharmaceutically acceptable salts or prodrugs thereof show activity as modulators of gluconeogenesis.

  本发明涉及式(I)的磺酰胺取代的黄嘌呤衍生物或其药用可接受的盐或前药，其中R1、R2和R3如说明书中所定义。式(I)的化合物及其药用可接受的盐或前药作为糖异生调节剂显示出活性。
• Synthesis of Ruthenium(II) Complexes Containing Tridentate Triamine (′N ͡N ͡N′) and Bidentate Diamine Ligands (N ͡N′): as Catalysts for Transfer Hydrogenation of Ketones
  作者：Salih Günnaz、Namık Özdemir、Serkan Dayan、Osman Dayan、Bekir Çetinkaya

  DOI：10.1021/om200470p

  日期：2011.8.8

  upon replacement of p-cymene by meridional ′N ͡N ͡N′. The complexes 1–10 were screened for transfer hydrogenation (TH) of aryl ketones with 2-propanol. The highest catalytic activity was obtained with the complexes containing tridentate ′N ͡N ͡N′ and 7, which contain nonsulfonated 2-(aminomethyl)pyridine. However, for complexes 6a–c, containing p-cymene (a facial tridentate ligand), a slower reaction

  一系列中性和阳离子的Ru（II）络合物（1 - 10），轴承吡啶系三齿（'N N N'），吡啶系双齿（N N'），并混合'N N N'+ N N通过从[RuCl 2（DMSO）4 ]和[RuCl 2（p- cymene）] 2前体开始合成''配体。通过单晶X射线衍射确定混合配体络合物9和10的固态结构。两种配合物都不同寻常，因为在无碱条件下，N͡N'配体在空气中自发氧化，在取代p后得到亚胺-胺二齿配体子午线'N͡N′N'。配合物1 - 10筛选芳基酮的转移氢化（TH）与2-丙醇。含有三齿'N͡N͡N'和7的配合物获得了最高的催化活性，所述配合物含有未磺化的2-（氨基甲基）吡啶。但是，对于含有p - Cymene（面部三齿配体）的复合物6 a-c，观察到较慢的反应速率。
• Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds
  作者：Jakob S. Pallesen、Dilip Narayanan、Kim T. Tran、Sara M. Ø. Solbak、Giuseppe Marseglia、Louis M. E. Sørensen、Lars J. Høj、Federico Munafò、Rosa M. C. Carmona、Anthony D. Garcia、Haritha L. Desu、Roberta Brambilla、Tommy N. Johansen、Grzegorz M. Popowicz、Michael Sattler、Michael Gajhede、Anders Bach

  DOI：10.1021/acs.jmedchem.0c02094

  日期：2021.4.22

  Keap1–Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220–380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic

  靶向核因子类红细胞2相关因子2（Nrf2）和与Kelch样ECH相关蛋白1（Keap1）之间的蛋白相互作用是控制涉及氧化应激疾病的潜在治疗策略。在这里，在基于片段的解构重建（FBDR）研究中，将六类已知的小分子Keap1-Nrf2 PPI抑制剂分解为77个片段，并在四个正交试验中进行了测试。这给出了17个片段命中，其中X射线晶体学显示其中6个在Keap1 Kelch结合袋中结合。相对于亲本片段，两个命中片段以220-380倍的亲和力（K i = 16μM）被合并到化合物8中。系统优化产生了一些与K i有关的新颖类似物值0.04–0.5μM，通过X射线晶体学测定的结合模式，以及增强的微粒体稳定性。这证明了FBDR如何可用于发现新的片段片段，阐明重要的配体-蛋白质相互作用以及鉴定Keap1-Nrf2 PPI的新有效抑制剂。
• Propanolysis of arenesulfonyl chlorides: Nucleophilic substitution at sulfonyl sulfur
  作者：Mykyta Iazykov、Moisés Canle、J. Arturo Santaballa、Ludmila Rublova

  DOI：10.1002/poc.3753

  日期：2018.2

  shell, increasing the energy of the reaction (ca. 1 kJ·mol−1). The obtained results suggest the same kinetic mechanism of solvolysis of arenesulfonyl chlorides for propan‐1‐ol and propan‐2‐ol, as in MeOH and EtOH, where bimolecular nucleophilic substitution (SN2) takes place with nucleophilic solvent assistance of one alcohol molecule and the participation of the solvent network involving solvent molecules

  我们研究了在303-323 K时丙-1-醇和丙-2-醇对芳烃磺酰氯的溶剂分解机理。动力学曲线适合一阶动力学。反应性随供电子取代基的增加而增加。芳烃磺酰氯的邻烷基取代衍生物显示出增加的反应性，但这种“正向”邻效应的起源仍不清楚。可能，邻位甲基限制了绕C键的旋转，从而促进了亲核试剂的攻击。就亲核性空间效应而言，未发现丙-1-醇和丙-2-醇的相关反应性变化。所有底物的等动力学关系的存在表明该系列的单一机制。两种醇中所有底物的溶剂分解反应均显示等速温度（T iso）接近工作温度范围，这表明该过程受到次级反应性因素的影响，该因素可能是TS中的空间性质。溶剂化在该反应中起重要作用，调节反应性。在一些情况下，存在吨-Bu代替我在对位位置导致第一溶剂化壳的变化，从而增加了反应能量（约1 kJ·mol -1）。所得结果表明，芳烃磺酰氯对丙-1-醇和丙-2-醇的溶剂化动力学机制与在MeOH和EtOH中相同，其中双分子亲核取代（S

表征谱图