(4-甲氧基苄基)三苯基氯化膦 | 3462-97-3

• 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-甲氧基苄基)三苯基氯化膦
• 中文别名: (对甲氧基苄基)三苯基磷氯化物
• 英文名称: (4-methoxybenzyl)triphenylphosphonium bromide
• 英文别名: (4-methoxybenzyl)triphenylphosphonium chloride；chloro-(4-methoxybenzyl)triphenyl-λ5-phosphane；(4-methoxyphenyl)methyl-triphenylphosphanium;chloride
• CAS: 3462-97-3
• 化学式: C₂₆H₂₄OP*Cl
• 分子量: 418.903
• InChiKey: YQXBNCFNXOFWLR-UHFFFAOYSA-M

物化性质

• 熔点：
  236-238°C
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S26,S36
• 储存条件：
  常温、避光、通风干燥处，密封保存。

SDS

Name:	(4-Methoxybenzyl)triphenylphosphonium bromide Material Safety Data Sheet
Synonym:
CAS:	3462-97-3

Section 1 - Chemical Product MSDS Name:(4-Methoxybenzyl)triphenylphosphonium bromide Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3462-97-3	(4-Methoxybenzyl)triphenylphosphonium		unlisted

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

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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.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes 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:
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:
Do NOT use water directly on fire. Use foam, dry chemical, or carbon dioxide.

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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. 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:
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# 3462-97-3: 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: 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: C26H24BrOP
Molecular Weight: 463.35

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Moisture sensitive.
Conditions to Avoid:
Incompatible materials, excess heat, exposure to moist air or water.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of phosphorus, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3462-97-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(4-Methoxybenzyl)triphenylphosphonium bromide - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
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.
WGK (Water Danger/Protection)
CAS# 3462-97-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3462-97-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3462-97-3 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：

  (4-甲氧基苄基)三苯基氯化膦 在 sodium hydroxide 、 正丁基锂 、 四丁基氟化铵 、 sodium methylate 、 苄基三乙基溴化铵 、 乙硫醇钠 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.25h， 生成 虎杖甙
  参考文献：
  名称：

  Synthesis of biologically active polyphenolic glycosides (combretastatin and resveratrol series)

  摘要：

  (E)−3−(葡萄糖-β−D−果糖氧基)−4',5-二羟基联苯（resveratrol 3−β−D− glucoside， 梦他tributes A−1）， (2)− 2',3'-二羟基−3,4,4',5-四甲氧基−联苯（combretastatin A−1）， (Z)−3'-羟基−3,4,4',5-四甲氧基−联苯 (combretastatin A−4)， (Z)−2'-羟基−3,4,4',5-四甲氧基−联苯 (combretastatin iso−A−4)， α,β−双氢−2',3'-二羟基−3,4,4',5-四甲氧基−联苯（combretastatin B−1）及其相应的葡萄糖化物和相关物质通过 Wittig 反应和转移膜催化合成了。目前所合成的大部分化合物已经进行了生物活性测试（细胞抑制，细胞毒性，拟使之 arrest，神经毒性和抗血小板聚集作用）。 (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00087-6
• 作为产物：
  描述：

  4-甲氧基苄基三苯基膦溴化盐 在 正丁基锂 作用下， 以 正己烷 、 苯 为溶剂， 反应 2.0h， 生成 (4-甲氧基苄基)三苯基氯化膦
  参考文献：
  名称：

  有机磷化合物的亲核反应性。第4部分。磷酸根阴离子与'Kenton keten缩醛的烷基化

  摘要：

  报告了of和吡啶酮酮缩醛的制备，并描述了它们与各种磷酸根阴离子的反应。新型吡啶酮酮缩醛是用于非质子，水性和水性乳液介质中各种酸阴离子烷基化的有用试剂。

  DOI：

  10.1039/p19810003059

文献信息

• Stereopure Functionalized Benzosultams via Ruthenium(II)-Catalyzed Dynamic Kinetic Resolution–Asymmetric Transfer Hydrogenation
  作者：Marko Jeran、Andrej Emanuel Cotman、Michel Stephan、Barbara Mohar

  DOI：10.1021/acs.orglett.7b00670

  日期：2017.4.21

  resolution–asymmetric transfer hydrogenation (DKR–ATH) of α-(N-sulfonylimino) and α-(N-sulfonylamino) aryl ketones to 4-hydroxy-benzo-δ- and 3-(α-hydroxy-arylmethyl)-benzo-γ-sultams is presented. By employing enantiopure ansa-Ru[PipSO2DPEN(CH2)4Ph] cat. II with S/C = 10 000 in a HCO2H/Et3N binary mix, up to >99.9% ee and dr >99:1 are obtained with 100% conversion under mild conditions. Application to access the stereopure

  高度非对映和对映选择性的Ru（II）催化的动态动力学拆分-α-（N-磺酰氨基）和α-（N-磺酰氨基）芳基酮的不对称转移氢化（DKR-ATH）生成4-羟基-苯并-δ -和3-（α-羟基-芳基甲基）-苯并-γ-sultams被提出。通过采用对映体纯的柄-Ru [PipSO 2 DPEN（CH 2）4 PH]猫。在HCO 2 H / Et 3 N二元混合物中S / C = 10000的II，在温和条件下以100％的转化率可获得高达> 99.9％ee和dr> 99：1的dr。申请访问立体纯“结构简化的TsDPEN” N，N-配体s yn-3-（α氨基苄基） -苯并-γ-磺内酰胺（“ SYN -ULTAM”）及其结构异构体的反式-4-氨基-3-苯基-苯并-δ-磺内酰胺（反式- 4）是证明。
• Efficient synthesis of functionalized olefins by Wittig reaction using Amberlite resin as a mild base
  作者：Tushar R. Valkute、Eswar K. Aratikatla、Asish K. Bhattacharya

  DOI：10.1080/00397911.2016.1276191

  日期：2017.3.19

  convenient procedure for the synthesis of olefins by the reaction of stabilized, semistabilized, and nonstabilized phosphorous ylides with various aldehydes or ketone using Amberlite resin as a mild base is described. Our developed method offers facile and racemization-free synthesis of α,β-unsaturated amino esters and chiral allylic amine. The developed methodology offers mild reaction conditions, high efficiency

  摘要描述了使用 Amberlite 树脂作为弱碱，通过稳定、半稳定和不稳定的磷叶立德与各种醛或酮反应合成烯烃的简便方法。我们开发的方法提供了 α,β-不饱和氨基酯和手性烯丙胺的简便且无外消旋的合成。所开发的方法提供温和的反应条件、高效率和最终产品的容易分离，是已知程序的实用替代方案。图形概要
• Cycloalkyl amino-hydantoin compounds and use thereof for beta-secretase modulation
  申请人：Malamas Sotirios Michael

  公开号：US20070027199A1

  公开（公告）日：2007-02-01

  The present invention provides a 2-amino-5-cycloalkyl-hydantoin compound of formula I The present invention also provides methods and compositions for the inhibition of β-secretase (BACE) and the treatment of β-amyloid deposits and neurofibrillary tangles.

  本发明提供了一种公式I的2-氨基-5-环烷基乙内酰脲化合物。 本发明还提供了一种用于抑制β-分泌酶（BACE）以及治疗β-淀粉样蛋白沉积和神经纤维缠结的方法和组合物。
• Aqueous Wittig Reactions of Aldehydes with In Situ Formed Semistabilized Phosphorus Ylides
  作者：Jinlong Wu、Dan Li、Da Zhang

  DOI：10.1080/00397910500213054

  日期：2005.10

  Abstract The Wittig reactions of three semistabilized phosphorus ylides generated in situ from the corresponding phosphonium salts with aldehydes in water without any organic cosolvent were investigated. Most of the olefination reactions completed within between 5 min and 4.5 h in refluxing water containing 1.5 equiv of LiOH and 1.4 M LiCl to afford the products in 65–100% yields. The E∶Z selectivity

  摘要 在没有任何有机助溶剂的情况下，研究了由相应的鏻盐与醛在水中原位生成的三种半稳定磷叶立德的 Wittig 反应。大多数烯烃化反应在含有 1.5 当量 LiOH 和 1.4 M LiCl 的回流水中在 5 分钟到 4.5 小时内完成，以 65-100% 的产率得到产物。E∶Z 选择性不仅取决于与叶立德苯环相连的取代基，还取决于与芳醛结合的取代基。LiCl 促进含水维蒂希反应并抑制叶立德或相应鏻盐的分解。
• Rhodium(I)-Catalyzed Carboacylation/Aromatization Cascade Initiated by Regioselective C−C Activation of Benzocyclobutenones
  作者：Tianwen Sun、Yuna Zhang、Bo Qiu、Yafei Wang、Yuting Qin、Guangbin Dong、Tao Xu

  DOI：10.1002/anie.201713179

  日期：2018.3.5

  Described here is the first example of a rhodium‐catalyzed carboacylation/aromatization cascade of a C=O bond by C−C activation. In this transformation, a reactive rhodaindanone complex is regioselectively generated and adds across a C=O bond with subsequent elimination, thus providing a unique strategy to access a multisubstituted benzofuran scaffold. A diverse range of benzofuran analogues were obtained

  这里描述的是第一个通过CC活化的C = O键的铑催化的碳酰化/芳香化级联反应的第一个例子。在这种转化中，反应性的若丹丹酮络合物是区域选择性生成的，并通过一个C = O键加成并随后被消除，从而提供了一种独特的策略来接近多取代的苯并呋喃支架。以高收率获得了多种苯并呋喃类似物。机理研究表明，三环内酯是可行的中间体。将该方法应用于C13-deOH-乙烯基呋喃呋喃和C13-deOH-二氢吲哚酮G的全合成。