4-(氰基甲基)苯基 4-甲基苯-1-硫酸盐 | 175135-39-4

• 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-(氰基甲基)苯基 4-甲基苯-1-硫酸盐
• 中文别名: 4-(氰基甲基)苯基4-甲基苯-1-硫酸盐
• 英文名称: 4-(cyanomethyl)phenyl 4-methylbenzenesulfonate
• 英文别名: 4-(Cyanomethyl)phenyl 4-methylbenzene-1-sulfonate；[4-(cyanomethyl)phenyl] 4-methylbenzenesulfonate
• CAS: 175135-39-4
• 化学式: C₁₅H₁₃NO₃S
• mdl: MFCD00067750
• 分子量: 287.339
• InChiKey: HYACJSQRJBCQDO-UHFFFAOYSA-N

物化性质

• 沸点：
  476.2±45.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  75.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090

SDS

Name:	4-(Cyanomethyl)phenyl 4-methylbenzene-1-sulfonate 97% Material Safety Data Sheet
Synonym:	4-Tosyloxyphenylacetonitril
CAS:	175135-39-4

Section 1 - Chemical Product MSDS Name:4-(Cyanomethyl)phenyl 4-methylbenzene-1-sulfonate 97% Material Safety Data Sheet
Synonym:4-Tosyloxyphenylacetonitril

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
175135-39-4	4-(Cyanomethyl)phenyl 4-methylbenzene-	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. May cause respiratory tract irritation.
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. 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.
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# 175135-39-4: 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: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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: C15H13NO3S
Molecular Weight: 287

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 175135-39-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(Cyanomethyl)phenyl 4-methylbenzene-1-sulfonate - 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: NITRILES, SOLID, TOXIC, N.O.S.*
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
IMO
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
RID/ADR
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 175135-39-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 175135-39-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 175135-39-4 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-(氰基甲基)苯基 4-甲基苯-1-硫酸盐 、 C₁₁H₁₁F₃O₆S 在 Ni(TMHD)₂ 、 新铜试剂 、 palladium diacetate 、 双(二环己基膦)甲烷 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以64%的产率得到methyl (R)-2-((4'-(cyanomethyl)-[1,1'-biphenyl]-4-yl)oxy)propanoate
  参考文献：
  名称：

  两种苯酚衍生物之间的镍/钯双重催化的交叉还原偶联反应。

  摘要：

  可以容易地衍生自苯酚的底物之间的交叉偶联由于苯酚的含量高而极具吸引力。在这里，我们报道了芳基甲苯磺酸盐和芳基三氟甲磺酸酯之间双重的镍/钯催化的还原交叉偶联。可以从一个容易获得的苯酚中仅一步之遥就获得两种底物。该反应具有宽泛的官能团耐受性和底物范围（> 60个实例）。此外，它显示出对空间效应的低敏感性，这是通过合成2,2'-二取代的联芳基和完全取代的芳基产物证明的。天然产品和药品中苯酚的广泛存在使简单的后期功能化成为可能，例如ezetimibe和酪氨酸。

  DOI：

  10.1021/acs.orglett.0c02165
• 作为产物：
  描述：

  4-chlorophenyl p-toluenesulfonate 、 sodium cyanoacetate 在 2-双环己基膦-2',6'-二甲氧基联苯 、 bis(η3-allyl-μ-chloropalladium(II)) 作用下， 以 均三甲苯 为溶剂， 反应 5.17h， 以88%的产率得到4-(氰基甲基)苯基 4-甲基苯-1-硫酸盐
  参考文献：
  名称：

  钯乙酸盐与芳基卤化物和三氟甲磺酸酯的钯催化脱羧偶联合成α-芳基腈

  摘要：

  值得其盐：描述了氰基乙酸盐及其与芳基氯化物，溴化物和三氟甲磺酸酯的钯催化的脱羧偶联反应（参见方案）。该反应对于制备各种α-芳基腈具有潜在的实用性，并具有良好的官能团耐受性。S-Phos = 2-（（2,6-二甲氧基联苯）二环己基膦），Xant-Phos = 4,5-双（二苯基膦基）-9,9-二甲基x吨。

  DOI：

  10.1002/anie.201006763

文献信息

• Accelerated SuFEx Click Chemistry For Modular Synthesis**
  作者：Christopher J. Smedley、Joshua A. Homer、Timothy L. Gialelis、Andrew S. Barrow、Rebecca A. Koelln、John E. Moses

  DOI：10.1002/anie.202112375

  日期：2022.1.21

  We report accelerated SuFEx click chemistry utilizing a synergistic BTMG-HMDS catalytic system. The power and versatility of the reaction are showcased by the SuFEx synthesis of >100 unique molecules from diverse SuFExable hubs. Accelerated SuFEx is a next generation click reaction that improves upon existing protocols and expands the scope of accessible products.

  我们报告了利用协同 BTMG-HMDS 催化系统加速的 SuFEx 点击化学。来自不同 SuFExable 中心的超过 100 种独特分子的 SuFEx 合成展示了反应的力量和多功能性。Accelerated SuFEx 是下一代点击反应，它改进了现有协议并扩大了可访问产品的范围。
• [EN] A PROCESS FOR THE PALLADIUM-CATALYZED COUPLING OF TERMINAL ALKYNES WITH ARYL TOSYLATES<br/>[FR] PROCÉDÉ POUR LE COUPLAGE CATALYSÉ PAR LE PALLADIUM D'ALCYNES TERMINALES AVEC DES TOSYLATES D'ARYLE
  申请人：SANOFI AVENTIS

  公开号：WO2009003589A1

  公开（公告）日：2009-01-08

  The present invention relates to a process for the regioselective synthesis of compounds of the formula (I), wherein R1; R2; R3; R4; R5; J and W have the meanings indicated in the claims. The present invention provides an efficient and general palladium-catalyzed coupling process for aryl tosylates with terminal alkynes to a wide variety of substituted, multifunctional aryl-1-alkynes of the formula (I) useful for the production of intermediates in the preparation for pharmaceuticals, diagnostic agents, liquid crystals, polymers, herbicides, fungicidals, nematicidals, parasiticides, insecticides, acaricides and arthropodicides.

  本发明涉及一种用于选择性合成公式(I)化合物的过程，其中R1；R2；R3；R4；R5；J和W具有声明中指示的含义。本发明提供了一种高效和通用的钯催化偶联过程，可将芳基磺酸酯与末端炔烃偶联，形成一系列取代的、多功能的芳基-1-炔烃，其化学式为(I)，用于制备制药品、诊断试剂、液晶、聚合物、除草剂、杀菌剂、线虫杀灭剂、寄生虫杀灭剂、杀虫剂、螨虫剂和节肢动物杀灭剂的中间体。
• Process for the palladium-catalyzed coupling of terminal alkynes with aryl tosylates
  申请人：RKYEK Omar

  公开号：US20100261910A1

  公开（公告）日：2010-10-14

  The present invention relates to a process for the regioselective synthesis of compounds of the formula (I), wherein R1; R2; R3; R4; R5; J and W have the meanings indicated in the claims. The present invention provides an efficient and general palladium-catalyzed coupling process for aryl tosylates with terminal alkynes to a wide variety of substituted, multifunctional aryl-1-alkynes of the formula I.

  本发明涉及一种合成式(I)化合物的区域选择性合成方法，其中R1、R2、R3、R4、R5、J和W的含义如权利要求所示。本发明提供了一种高效、通用的钯催化偶联方法，用于将芳基磺酸酯与末端炔烃耦合成式I的多取代多功能芳基-1-炔烃。
• An Efficient Catalyst for Pd-Catalyzed Carbonylation of Aryl Arenesulfonates
  作者：Chaoxian Cai、Nelo R. Rivera、Jaume Balsells、Rick R. Sidler、J. Christopher McWilliams、C. Scott Shultz、Yongkui Sun

  DOI：10.1021/ol062208g

  日期：2006.10.1

  Aryl carboxylic esters were synthesized by Pd-catalyzed carbonylation of aryl p-fluorobenzenesulfonates or -tosylates. A unique Josiphos ligand was discovered through high-throughput catalyst screening, which was the key for the successful carbonylation of various substrates. This catalyst is effective and works well for both electron-rich and electron-poor aryl arenesulfonates. Isolated yields of up to 90% were obtained for aryl p-fluorobenzenesulfonates and -tosylates.
• A PROCESS FOR THE PALLADIUM-CATALYZED COUPLING OF TERMINAL ALKYNES WITH ARYL TOSYLATES
  申请人：Sanofi-Aventis

  公开号：EP2176203A1

  公开（公告）日：2010-04-21