2-(3,4-dichlorophenyl)-2-((trimethylsilyl)oxy)acetonitrile | 95392-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3,4-dichlorophenyl)-2-((trimethylsilyl)oxy)acetonitrile
• 英文别名: (3,4-Dichlorophenyl)-trimethylsilanyloxy-acetonitrile；2-(3,4-dichlorophenyl)-2-trimethylsilyloxyacetonitrile
• CAS: 95392-03-3
• 化学式: C₁₁H₁₃Cl₂NOSi
• 分子量: 274.222
• InChiKey: XIWMJWQCARVYKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2931900090

SDS

Name:	(3 4-Dichloro-phenyl)-trimethylsilanyloxy-acetonitrile Material Safety Data Sheet
Synonym:	None Known
CAS:	95392-03-3

Section 1 - Chemical Product MSDS Name:(3 4-Dichloro-phenyl)-trimethylsilanyloxy-acetonitrile Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
95392-03-3	(3,4-Dichloro-phenyl)-trimethylsilanyl	100	unlisted

Hazard Symbols: XN N
Risk Phrases: 20/21/22 36/37/38 52/53

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin. Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. Harmful if absorbed through the skin. May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration.
Ingestion:
Harmful if swallowed. May cause gastrointestinal irritation with nausea, vomiting and diarrhea. Metabolism may release cyanide, which may result in headache, dizziness, weakness, collapse, unconsciousness and possible death.
Inhalation:
Causes respiratory tract irritation. May be metabolized to cyanide which in turns act by inhibiting cytochrome oxidase impairing cellular respiration. Harmful if inhaled.
Chronic:
Exposure to small amounts of cyanide compounds over long periods of time is reported to cause loss of appetite, headache, weakness, nausea, dizziness, and symptoms of irritation of the upper respiratory tract and eyes.

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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.
Skin:
Get medical aid. Immediately 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:
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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
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 adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 95392-03-3: Personal Protective Equipment Eyes: Wear chemical splash goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Oil
Color: orange-red
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: C11H13Cl2NOSi
Molecular Weight: 274.22

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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, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases, strong acids, strong reducing agents.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 95392-03-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(3,4-Dichloro-phenyl)-trimethylsilanyloxy-acetonitrile - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Products which are considered hazardous for supply are classified as Special Waste and the disposal of such chemicals is covered by regulations which may vary according to location. Contact a specialist disposal company or the local waste regulator for advice. Empty containers must be decontaminated before returning for recycling.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN N
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
R 52/53 Harmful to aquatic organisms, may cause
long-term adverse effects in the aquatic environment.
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# 95392-03-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 95392-03-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 95392-03-3 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-(3,4-dichlorophenyl)-2-((trimethylsilyl)oxy)acetonitrile 在 乙酸酐 、 scandium tris(trifluoromethanesulfonate) 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 48.33h， 生成 1-(3,4-dichlorophenyl)-1-hydroxyacetonitrile
  参考文献：
  名称：

  碳酸亚丙酯中钒催化不对称氰醇合成的动力学和机理。

  摘要：

  碳酸丙烯酯可用作绿色溶剂，用于在 VO(salen)NCS 的催化下由醛和三甲基氰基氰化物不对称合成氰醇三甲基甲硅烷基醚，尽管在该溶剂中的反应比在二氯甲烷中进行的相应反应慢。已经进行了一项机理研究，比较了 VO(salen)NCS 在碳酸亚丙酯和二氯甲烷中的催化活性。在两种溶剂中的反应都遵循整体二级动力学，反应速率取决于醛和三甲基氰化甲硅烷的浓度。确定了关于 VO(salen)NCS 的顺序，发现从二氯甲烷中的 1.2 减少到碳酸丙烯酯中的 1.0，表明在碳酸丙烯酯中，VO(salen)NCS 仅作为单核物质存在，而在二氯甲烷中存在双核物质，它们先前已被证明是造成大部分催化活性的原因。来自 (5)(1)V NMR 光谱的证据表明，碳酸丙烯酯与 VO(salen)NCS 配位，阻断了自由配位位点，从而抑制了其路易斯酸度并解释了催化活性的降低。这一解释得到了哈米特分析研究的进一步支持，该研究表明路易斯碱催化对碳酸亚丙酯中

  DOI：

  10.3762/bjoc.6.119
• 作为产物：
  描述：

  3,4-二氯苯甲醛 以94 %的产率得到2-(3,4-dichlorophenyl)-2-((trimethylsilyl)oxy)acetonitrile
  参考文献：
  名称：

  AZAINDOLE DERIVATIVES AND THEIR USE AS ERK KINASE INHIBITORS

  摘要：

  本发明涉及式(I)的化合物：或其药用盐，尤其用作ERK蛋白激酶的抑制剂，尤其是在ERK2活性方面的抑制剂。

  公开号：

  EP4212531A1

文献信息

• Organo-catalyzed Michael addition of 2-fluoro-2-arylacetonitriles
  作者：De-Yin Chen、Shuai Song、Ling-Yan Chen、Xinfeng Ren、Ya Li

  DOI：10.1016/j.tetlet.2021.152919

  日期：2021.3

  An efficient synthesis of a variety of 2-arylacetonitriles containing a fluorinated stereogenic center through organo-catalyzed Michael addition reaction of 2-fluoro-2-arylacetonitriles has been developed. This protocol uses a cheap organocatalyst (DBU) and has a broad substrate scope: α, β-unsaturated ketones, esters, nitriles and sulfones were all successfully reacted. Importantly, water proved to

  通过2-氟-2-芳基乙腈的有机催化迈克尔加成反应，已开发出一种有效的合成各种含氟立构中心的2-芳基乙腈的方法。该方案使用廉价的有机催化剂（DBU），并具有广泛的底物范围：α，β-不饱和酮，酯，腈和砜均已成功反应。重要的是，事实证明水是该反应的良好溶剂。
• Benzenesulfonamide subtituted imidazolyl compounds for the treatment of
  申请人：——

  公开号：US05620999A1

  公开（公告）日：1997-04-15

  A class of imidazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II ##STR1## wherein R.sup.1 is selected from lower alkyl, lower haloalkyl, lower hydroxyalkyl, lower aralkenyl, lower aryloxyalkyl, lower arylthioalkyl and heteroaryl; wherein R.sup.3 is selected from lower alkyl and amino; and wherein R.sup.4 is one or more radicals selected from hydrido, halo, lower alkyl and lower alkoxy; or where R.sup.4 together with the phenyl radical forms naphthyl or benzodioxolyl; provided R.sup.1 is not lower alkyl when R.sup.3 is methyl and when R.sup.4 is hydrido, methyl, methoxy or chloro; or a pharmaceutically-acceptable salt thereof.

  描述了一类咪唑基化合物，用于治疗炎症和与炎症相关的疾病。特别感兴趣的化合物由式II定义，其中R.sup.1从较低的烷基、较低的卤代烷基、较低的羟基烷基、较低的芳基烯基、较低的芳氧基烷基、较低的芳硫基烷基和杂芳基中选择；其中R.sup.3从较低的烷基和氨基中选择；其中R.sup.4是从氢化物、卤素、较低的烷基和较低的烷氧基中选择的一个或多个基团；或者R.sup.4与苯基一起形成萘基或苯二氧杂基；在R.sup.3为甲基且R.sup.4为氢化物、甲基、甲氧基或氯时，提供R.sup.1不是较低烷基；或其药用盐。
• Enzymatic preparation of optically active cyanohydrin acetates
  作者：Andreas van Almsick、Joachim Buddrus、Petra Hönicke-Schmidt、Kurt Laumen、Manfred P. Schneider

  DOI：10.1039/c39890001391

  日期：——

  A series of cyanohydrin acetates (1)–(47) of widely varying structures, potential chiral building blocks for numerous synthetic applications, has been prepared in good chemical and often high optical yields by enzymatic hydrolysis of their racemic acetates in the presence of an ester hydrolase from Pseudomonas sp.

  通过在酯存在下进行酶促外消旋乙酸酯的酶水解，可以制备出具有良好化学性质且通常具有高光学收率的一系列结构广泛变化的氰氨醇乙酸酯（1）–（47），可用于许多合成应用假单胞菌（Pseudomonas sp）的水解酶。
• Discovery of the First in Vivo Active Inhibitors of the Soluble Epoxide Hydrolase Phosphatase Domain
  作者：Jan S. Kramer、Stefano Woltersdorf、Thomas Duflot、Kerstin Hiesinger、Felix F. Lillich、Felix Knöll、Sandra K. Wittmann、Franca-M. Klingler、Steffen Brunst、Apirat Chaikuad、Christophe Morisseau、Bruce D. Hammock、Carola Buccellati、Angelo Sala、G. Enrico Rovati、Matthieu Leuillier、Sylvain Fraineau、Julie Rondeaux、Victor Hernandez-Olmos、Jan Heering、Daniel Merk、Denys Pogoryelov、Dieter Steinhilber、Stefan Knapp、Jeremy Bellien、Ewgenij Proschak

  DOI：10.1021/acs.jmedchem.9b00445

  日期：2019.9.26

  pharmacological target soluble epoxide hydrolase (sEH) is a bifunctional enzyme exhibiting two different catalytic activities that are located in two distinct domains. Although the physiological role of the C-terminal hydrolase domain is well-investigated, little is known about its phosphatase activity, located in the N-terminal phosphatase domain of sEH (sEH-P). Herein we report the discovery and optimization

  新兴的药理学目标可溶性环氧化物水解酶（sEH）是一种双功能酶，在两个不同的域中表现出两种不同的催化活性。尽管对C末端水解酶结构域的生理作用进行了充分研究，但关于其磷酸酶活性的信息却鲜为人知，它位于sEH（sEH-P）的N末端磷酸酶结构域中。本文中，我们报道了在体内可应用的人和大鼠sEH-P的第一种抑制剂的发现和优化。与抑制剂复合的sEH磷酸酶结构域的X射线结构分析提供了小分子sEH-P抑制的分子基础的见解，并有助于合理化结构-活性关系。4-（4-（3,4-二氯苯基）-5-苯基恶唑-2-基）丁酸（22b，
• Kinetics and mechanism of the racemic addition of trimethylsilyl cyanide to aldehydes catalysed by Lewis bases
  作者：Michael North、Marta Omedes-Pujol、Carl Young

  DOI：10.1039/c2ob25188d

  日期：——

  all of the tetrabutylammonium salts and trimethylsilyl cyanide. The reactions are accelerated by the presence of water in the reaction mixture, an effect which is due to a change in the reaction mechanism from Lewis to Brønsted base catalysis. Tetrabutylammonium thiocyanate is shown to be an excellent catalyst for the synthesis of cyanohydrin trimethylsilyl ethers on a preparative scale.

  四个刘易斯基地的机制， 三乙胺， 四丁基硫氰酸铵， 四丁基叠氮化铵 和 四丁基氰化铵，催化添加 三甲基甲硅烷基氰化物通过动力学和光谱方法相结合的方法研究醛的残留量。反应可以表现出对应于三种不同反应机理的一级或二级动力学。对于所有四丁基铵盐和四丁基铵盐之间的反应，获得了形成高价硅物质的光谱证据。三甲基甲硅烷基氰化物。存在以下物质会加速反应水 在反应混合物中，这种作用是由于反应机理从路易斯转变为布朗斯台德碱催化而引起的。 四丁基硫氰酸铵 已显示出在制备规模上，H2O3是合成氰醇三甲基甲硅烷基醚的极佳催化剂。