二(1-萘基)氯化膦 | 36042-99-6

• 物质功能分类: 有机原料 - 有机膦化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 二(1-萘基)氯化膦
• 中文别名: 氯代二(1-萘基)膦
• 英文名称: chlorodi(1-naphthyl)phosphine
• 英文别名: chloro(dinaphthalen-1-yl)phosphane
• CAS: 36042-99-6
• 化学式: C₂₀H₁₄ClP
• 分子量: 320.758
• InChiKey: ZHRMSAAMUUNWKE-UHFFFAOYSA-N

物化性质

• 熔点：
  154-157°C
• 沸点：
  227-229°C/0.6mm
• 闪点：
  227-229°C/0.6mm
• 稳定性/保质期：
  常规情况下不会分解，没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险等级：
  8
• 危险品运输编号：
  UN3261
• 海关编码：
  2903999090
• 包装等级：
  II
• 危险类别：
  8
• 储存条件：
  密封保存，置于阴凉、干燥、通风处。

SDS

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Section 1: Product Identification
Chemical Name: Bis(1-naphthyl)chlorophosphine, min. 97%
CAS Registry Number: 36042-99-6
Formula: C20H14ClP
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: Chlorodi(1-naphthyl)phosphine

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 36042-99-6 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract.
Primary Routes of Exposure: Ingestion, inhalation
Eye Contact: Causes slight to mild irritation of the eyes.
Skin Contact: Causes slight to mild irritation of the skin.
Inhalation: Irritating to the nose, mucous membranes and respiratory tract.
Ingestion: Harmful if swallowed.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information on long-term chronic effects.
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: no data
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: carbon dioxide, dry powder or foam
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit irritating fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Spill and Leak Procedures: Small spills can be mixed with vermiculite or sodium carbonate and swept up.

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SECTION 7: Handling and Storage
Store in a tightly sealed container under an inert atmosphere of nitrogen or argon. Keep in a cool, dry, well
Handling and Storage:
ventilated place.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: Handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: white to pale-yellow xtl.
Molecular Weight: 320.75
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: none
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: moisture sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: contact with moisture
Incompatibility: water, oxidizing agents and halogens
Decomposition Products: carbon monoxide, carbon dioxide, phosphorus oxides, hydrogen chloride and organic fumes

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: no data
Mutagenic Effects: no data
Tetratogenic Effects: no data

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SECTION 12: Ecological Information
Ecological Information: No information available

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SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory
SARA (Title 313): Title compound not listed
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  二(1-萘基)氯化膦 在 1,2-二溴乙烷 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 三甲基氯硅烷 、 N,N-二甲基甲酰胺 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 15.25h， 生成 (R)-2-tert-Butoxycarbonylamino-3-(di-naphthalen-1-yl-phosphinothioyl)-propionic acid methyl ester
  参考文献：
  名称：

  β-转角衍生的钯膦配合物的高度不对称诱导。

  摘要：

  [反应：见正文]据报道，人们正在努力开发双膦配体体系，用于钯催化环乙酸烯丙酯的加成反应。使用含膦氨基酸和天然氨基酸的平行方法开发了选择性配体系统。在连接到聚合物载体以及溶液中的同时检查配体体系。据报道，具有困难的底物3-乙酰氧基环戊烯的ee高达95％ee。

  DOI：

  10.1021/ol035097j
• 作为产物：
  描述：

  1-溴代萘 在 叔丁基锂 作用下， 以 环己烷 、 正戊烷 、 乙醚 为溶剂， 反应 16.0h， 生成 二(1-萘基)氯化膦
  参考文献：
  名称：

  高效可重复使用的由二芳基膦基聚苯乙烯负载的钯催化剂用于CC键形成交叉偶联反应

  摘要：

  描述了可重复使用的由二芳基膦基聚苯乙烯负载的钯催化剂3a – j的短而通用的合成方法。双（Ô甲苯基）膦基催化剂3B是用于铃木和的Sonogashira交叉偶联特别有效的，而双（米间-甲苯基）膦基催化剂3C是对Heck反应中最活跃的催化剂。偶联是在无水反应条件下进行的，仅需少量负载的钯即可（对于铃木宫浦来说，为0.5 mequivs；对于Sonogashira，为1.0 mequiv。对于Heck反应而言，为0.5 mequivs就足够了）。催化剂3a–j 通过过滤回收的废料可以重复使用四次以上，而不会降低效率。

  DOI：

  10.1002/adsc.200600503

文献信息

• [EN] NICOTINE-BASED COMPOUNDS USEFUL FOR ASYMMETRIC SYNTHESIS<br/>[FR] COMPOSÉS À BASE DE NICOTINE UTILES POUR UNE SYNTHÈSE ASYMÉTRIQUE
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2010040059A1

  公开（公告）日：2010-04-08

  Chiral amino alcohol and amino phosphine compounds are provided herein, which compounds are useful for asymmetric synthesis.

  这里提供了手性氨醇和氨基膦化合物，这些化合物对于不对称合成是有用的。
• [EN] OLIGOMERISATION OF ETHYLENE TO MIXTURES OF 1-HEXENE AND 1-OCTENE<br/>[FR] OLIGOMÉRISATION DE L'ÉTHYLÈNE EN MÉLANGES DE 1-HEXÈNE ET 1-OCTÈNE
  申请人：SASOL TECH PTY LTD

  公开号：WO2014181247A1

  公开（公告）日：2014-11-13

  A process for the otigomerisation of ethylene to predominantly 1-hexene or 1-octene or mixtures of 1-hexene and 1-octene includes contacting ethylene with a catalyst under ethylene oligomerisation conditions. The catalyst comprises a source of chromium, a diphosphine ligating compound, and optionally an activator. The diphosphine ligating compound includes at least one optionally substituted fused cyclic structure including at least two rings, the optionally substituted fused cyclic structure including a 5- to 7- membered aromatic first ring bonded to a phosphorus atom, the aromatic first ring being fused to a 4- to 8-membered heterocyclic second ring, the heterocyclic second ring including a heteroatom which is separated by two ring atoms along the shortest connecting path from the phosphorous atom that is bonded to the first aromatic ring.

  将乙烯催化寡聚化为主要的1-己烯或1-辛烯或1-己烯和1-辛烯混合物的过程包括在乙烯寡聚化条件下将乙烯与催化剂接触。催化剂包括铬源、二膦配体化合物，以及可选的活化剂。二膦配体化合物包括至少一个可选取代的融合环结构，其中包括至少两个环，可选取代的融合环结构包括一个与磷原子键合的5-至7-成员芳香第一环，该芳香第一环与一个4-至8-成员杂环第二环融合，该杂环第二环包括一个杂原子，该杂原子与磷原子沿着与第一芳香环键合的最短连接路径相隔两个环原子。
• Silver-Catalyzed Regioselective Phosphorylation of <i>para</i>-Quinone Methides with P(III)-Nucleophiles
  作者：Shipan Xu、Jun Xie、Yu Liu、Weifeng Xu、Ke-Wen Tang、Biquan Xiong、Wai-Yeung Wong

  DOI：10.1021/acs.joc.1c01703

  日期：2021.11.5

  Moreover, a series of corresponding enantiomers can be obtained by employing dialkyl arylphosphonite (ArP(OR)2) as substrates. The control experiments and 31P NMR tracking experiments were also performed to gain insights for the plausible reaction mechanism. This protocol may have significant implications for the formation of C(sp3)–P bonds in Michaelis–Arbuzov-type reactions.

  P(III)-亲核试剂 (P(OR) 3 , ArP(OR) 2 , Ar 2 P-OR)银催化对醌甲基化物 ( p -QMs )区域选择性磷酸化的简单有效方法通过 Michaelis-Arbuzov 型反应建立。在温和条件下，广泛的 P(III)-亲核试剂和对-醌甲基化物具有良好的耐受性，从而得到预期的二芳基甲基取代的有机磷化合物，具有良好的产率。此外，以二烷基芳基亚膦酸酯(ArP(OR) 2 )为底物，可以得到一系列相应的对映异构体。对照实验和31还进行了 P NMR 跟踪实验以深入了解可能的反应机制。该协议可能对Michaelis-Arbuzov 型反应中 C( sp 3 )-P 键的形成具有重要意义。
• [2,3]-Sigmatropic Rearrangements of 2-Phosphineborane 2-Propen-1-ols: Rapid Access to Enantioenriched Diphosphine Monoxide Derivatives
  作者：Carl A. Busacca、Bo Qu、Elisa Farber、Nizar Haddad、Nicole Grět、Anjan K. Saha、Magnus C. Eriksson、Jiang-Ping Wu、Keith R. Fandrick、Steve Han、Nelu Grinberg、Shengli Ma、Heewon Lee、Zhibin Li、Michael Spinelli、Austin Gold、Zhuzhu Wang、Guijun Wang、Peter Wipf、Chris H. Senanayake

  DOI：10.1021/ol400310h

  日期：2013.3.1

  secondary propargylic alcohols generates phosphine-containing allylic alcohols that undergo facile [2,3]-sigmatropic rearrangements with chlorophosphines, furnishing highly enantioenriched, crystalline diphosphine monoxides. The configuration at the newly formed stereocenter is opposite to that expected based on prior studies, and an ab initio computational evaluation of the possible transition states was

  仲炔丙醇的氢磷化可生成含膦的烯丙醇，并与氯膦进行容易的[2,3]-σ重排，提供高度对映体富集的结晶一氧化二膦。新形成的立体中心的构型与以前的研究预期相反，并且对可能的过渡态进行了从头算计算评估，以帮助解释反应的立体化学过程。
• Copper-Catalyzed Asymmetric Conjugate Addition with Chiral SimplePhos Ligands
  作者：Laëtitia Palais、Alexandre Alexakis

  DOI：10.1002/chem.200901577

  日期：2009.10.12

  they can be highly functionalised. Herein we report the copper‐catalysed asymmetric conjugate addition of diethyl zinc and trialkylaluminium reagents with SimplePhos ligands, which gives high enantioselectivity with cyclic enones, acyclic enones and nitro‐olefins, with up to 98.6 % ee. Of particular interest is the reaction of trialkylaluminium reagents with a wide range of 3‐substituted enones, thus

  SimplePhos配体基于磷原子上的手性胺部分和柔性二芳基，代表一类新型的单齿手性配体。它们可以通过两种不同的途径轻松制备，并且可以高度功能化。在本文中，我们报告了具有SimplePhos配体的铜催化的二乙基锌和三烷基铝试剂的铜催化不对称共轭加成反应，它与环烯酮，无环烯酮和硝基烯烃的对映选择性很高，ee高达98.6％  。特别令人感兴趣的是三烷基铝试剂与各种3-取代的烯酮的反应，从而可以形成立体异构的季碳中心。