丁基三苯基氯化膦 | 13371-17-0

• 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 - 苯和取代衍生物
• 中文名称: 丁基三苯基氯化膦
• 中文别名: (1-丁基)三苯基氯化磷
• 英文名称: butyltriphenylphosphonium chloride
• 英文别名: n-butyltriphenylphosphonium chloride；butyl(triphenyl)phosphanium;chloride
• CAS: 13371-17-0
• 化学式: C₂₂H₂₄P*Cl
• 分子量: 354.859
• InChiKey: MFIUDWFSVDFDDY-UHFFFAOYSA-M

物化性质

• 熔点：
  226-230 °C(lit.)
• 闪点：
  >270°C
• 溶解度：
  溶于甲醇
• 稳定性/保质期：

  在常温常压下稳定，应避免接触水分和潮湿氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1
• 危险品标志：
  Xn
• 安全说明：
  S26,S36,S37/39
• 危险类别码：
  R22,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  常温密闭，阴凉通风干燥。

SDS

Name:	Butyltriphenyl Phosphonium Chloride 98% Material Safety Data Sheet
Synonym:	None Known
CAS:	13371-17-0

Section 1 - Chemical Product MSDS Name:Butyltriphenyl Phosphonium Chloride 98% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13371-17-0	Butyltriphenyl Phosphonium Chloride	98%	236-443-3

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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. 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. 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. Do NOT use mouth-to-mouth resuscitation.
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 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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. 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 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# 13371-17-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Crystalline powder
Color: white - off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 223-227 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: > 265 deg C
Solubility in water: Soluble.
Specific Gravity/Density:
Molecular Formula: C22H24ClP
Molecular Weight: 354.86

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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, light, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents, bases.
Hazardous Decomposition Products:
Hydrogen chloride, phosphine, carbon monoxide, oxides of phosphorus, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13371-17-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Butyltriphenyl Phosphonium 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: Organophosphorus compound, solid, toxic, N.O.S.*
Hazard Class: 6.1
UN Number: 3278
Packing Group: III
IMO
Shipping Name: Organophosphorus compound, toxic, N.O.S.
Hazard Class: 6.1
UN Number: 3278
Packing Group: III
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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 13371-17-0: No information available.
Canada
CAS# 13371-17-0 is listed on Canada's NDSL List.
CAS# 13371-17-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13371-17-0 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用

丁基三苯基氯化膦是一种含一烷基三苯基取代基的季鏻盐。由于磷原子上有三个未成对电子、一对孤对电子以及5个空3d轨道，使Ph₃P⁺具备吸电性，并且季鏻盐阳离子与F⁻有很好的结合能力，有利于氟化反应的顺利进行。因其催化效果好、选择性高、热稳定性高、毒性小且可循环使用，近年来相转移催化剂中的季鏻盐得到了广泛应用。

制备

将7.86g（0.03mol）三苯基膦与20ml乙腈加入装有冷凝管的100ml三口烧瓶中，在氮气保护下恒压滴加8mL（0.06mol）溴丁烷，回流搅拌反应10h。反应完毕后，得到均一黄色油状液体，置于冰箱冷却，待析出白色固体后过滤出白色固体，用乙腈和乙酸乙酯混合溶液重结晶，再减压抽滤，在60℃的真空干燥箱中烘干，最终得到9.22g（0.026mol）丁基三苯基氯化膦，摩尔收率为86.7％。

反应信息

• 作为反应物：
  描述：

  丁基三苯基氯化膦 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 butylidenetriphenylphosphorane
  参考文献：
  名称：

  Endrich, K.; Alburquerque, P.; Korswagen, R. P., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1988, vol. 43, # 10, p. 1293 - 1306

  摘要：

  DOI：
• 作为产物：
  描述：

  三苯基氧化膦 在 草酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.92h， 生成 丁基三苯基氯化膦
  参考文献：
  名称：

  长期寻求从氧化膦合成季phospho盐的方法：逆反应法†

  摘要：

  季phospho盐（QPS）是一类重要的有机磷化合物，以前只能通过涉及亲核性磷的途径获得。我们报告了利用膦氧化物作为亲电子伴侣和格氏试剂作为亲核试剂实现QPS的相反方法的实现。通过衍生的卤化salts盐的关键中间体来实现该过程。该路线不受动力学慢和许多母体膦的有限供应的困扰，并且以优异的产率制备了多种QPS。

  DOI：

  10.1039/c8cc02173b
• 作为试剂：
  描述：

  3 - 氯丙基二甲基乙氧基硅烷 在 N1,N4-二(萘-1-基)苯-1,4-二胺 、 potassium carbonate 、 丁基三苯基氯化膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成
  参考文献：
  名称：

  多功能硅烷偶联剂、其制备及在阻燃天然橡胶中的应用

  摘要：

  本发明公开了一种多功能硅烷偶联剂、其制备及在阻燃天然橡胶中的应用，硅烷偶联剂分子结构中同时含有环状硅氮基官能团和(甲基)丙烯酰氧烃基官能团，所述(甲基)丙烯酰氧烃基官能团包括丙烯酰氧烃基和/或甲基丙烯酰氧烃基，所述环状硅氮基官能团包括环状双烷氧基硅氮基、环状烷基烷氧基硅氮基或环状双烷基硅氮基中的一种或两种以上。本发明的多功能硅烷偶联剂中含环状硅氮基和(甲基)丙烯酰氧烃基官能团，可以同时对无机阻燃剂水合金属氧化物和橡胶进行改性，胶料不需高温热炼且偶联效率高，充分实现无机阻燃剂阻燃橡胶的效果，在保持阻燃性能的同时有效提高胶料的拉伸强度和定伸应力，显著降低压缩永久变形，并显著改善生热性能和蠕变性能。

  公开号：

  CN111116627B

文献信息

• Direct Wittig Olefination of Alcohols
  作者：Qiang-Qiang Li、Zaher Shah、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/acs.joc.7b02720

  日期：2018.1.5

  A base-promoted transition metal-free approach to substituted alkenes using alcohols under aerobic conditions using air as the inexpensive and clean oxidant is described. Aldehydes are relatively difficult to handle compared to corresponding alcohols due to their volatility and penchant to polymerize and autoxidize. Wittig ylides are easily oxidized to aldehydes and consequently form homo-olefination

  描述了在有氧条件下使用醇作为廉价且清洁的氧化剂，使用醇在碱性条件下使用无醇过渡醇取代烯烃的方法。与相应的醇相比，由于醛的挥发性和聚合和自氧化倾向，因此醛相对较难处理。维蒂希酸根易于氧化成醛，因此形成均烯烃化产物。首次通过同时原位生成乙叉和乙叉的策略，无需预先制备醛或乙叉醇就将醇直接转移到烯烃中。因此，实现了二醇的二/单可控烯烃化。这种合成实用的方法已用于克级合成的药物，如DMU-212和白藜芦醇。
• Borrowing Hydrogen: Indirect “Wittig” Olefination for the Formation of C–C Bonds from Alcohols
  作者：Phillip J. Black、Michael G. Edwards、Jonathan M. J. Williams

  DOI：10.1002/ejoc.200600070

  日期：2006.10

  development of an indirect three-step domino sequence for the formation of C-C bonds from alcohol substrates is described. An iridium-catalysed dehydrogenation of alcohol I affords the intermediate aldehyde 2. The desired C-C bond can then be formed by a facile Wittig olefination, yielding the intermediate alkene 3. In the final step the alkene is hydrogenated to afford the indirect Wittig product, the

  描述了从醇底物形成 CC 键的间接三步多米诺骨牌序列的成功开发。醇 I 的铱催化脱氢得到中间体醛 2。然后可以通过简单的 Wittig 烯化形成所需的 CC 键，产生中间体烯烃 3。在最后一步中，烯烃被氢化以提供间接的 Wittig 产物，即烷烃 4. 这个过程的关键是借氢的概念；在最初的脱氢步骤中除去的氢气被铱催化剂简单地借用。作为储氢器，催化剂促进 CC 键的形成，然后在最后一步返回借用的氢。在此，我们将详细介绍我们对底物和反应范围以及催化循环的局限性的研究。((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)。
• [EN] PROCESS FOR PREPARATION OF ALUMINUM SALT OF PHOSPHONIC ACID ESTER<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN SEL D'ALUMINIUM D'UN ESTER D'ACIDE PHOSPHONIQUE
  申请人：ICL IP AMERICA INC

  公开号：WO2013077989A1

  公开（公告）日：2013-05-30

  There is provided herein a process for the preparation of aluminum salts of phosphonic acid esters by reacting phosphonic acid diesters with aluminum hydroxide in the presence of a catalyst. The catalyst is selected from the group consisting of a phase transfer catalyst, a thermally stable tertiary amine having a boiling point higher than about 140°C, a thermally stable tertiary phosphine having a boiling point higher than 140°C and combinations thereof. The aluminum phosphonates prepared can be used for making flame retarded thermoplastic polymers.

  本文提供了一种制备磷酸酯铝盐的方法，通过在催化剂存在下将磷酸二酯与氢氧化铝反应。催化剂选自相转移催化剂、热稳定的沸点高于约140°C的三级胺、热稳定的沸点高于140°C的三级膦和它们的组合。制备的铝磷酸盐可用于制备阻燃热塑性聚合物。
• Process for the preparation of 1-(3-dimethylaminopropyl)-1-(4-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
  申请人：ORION CORPORATION FERMION

  公开号：US20020115872A1

  公开（公告）日：2002-08-22

  Method for the preparation of 1-(3-dimethylaminopropyl)-1-(4-fluoro-phenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (citalopram) comprising the reaction of a compound of formula 1 wherein X is a halogen, with organometallic dimethylaminopropyl halide. Other aspects of the invention are new compounds of formula II and formula III and their preparation.

  制备1-(3-二甲基氨基丙基)-1-(4-氟苯基)-1,3-二氢异苯并呋喃-5-羧腈（西酞普兰）的方法包括将式1的化合物与有机金属二甲基氨基丙基卤化物反应。该发明的其他方面是式II和式III的新化合物及其制备。
• Process for the preparation of threo-methylphenidate hydrochloride
  申请人：ISP INVESTMENTS INC.

  公开号：US20040176412A1

  公开（公告）日：2004-09-09

  The present invention provides a process for the preparation of threo-methylphenidate hydrochloride. According to a preferred embodiment, the process comprises the following steps: (a) contacting 1-(phenylglyoxylyl)piperidine arenesulfonylhydrazone of the formula 1 wherein Ar denotes an aryl group, where the aryl group may be substituted by a C 1 -C 6 alkyl, halo or nitro group; with an inorganic base in the presence of a water immiscible organic solvent and a phase transfer catalyst to obtain (R*,R*)-enriched 7-phenyl-1-azabicyclo[4.2.0]octan-8-one of the formula: 2 (b) reacting the (R*,R*)-enriched 7-phenyl-1-azabicyclo[4.2.0]octan-8-one prepared in step (a) with a solution of hydrogen chloride in methanol to obtain threo-enriched methylphenidate hydrochloride; (c) crystallizing the threo-enriched methylphenidate hydrochloride prepared in step (b) to give the desired threo-methylphenidate hydrochloride. Preferably, the threo-methylphenidate hydrochloride produced by the process of the present invention contains no more than 1% of the erythro-isomer.

  本发明提供了一种制备左旋甲基苯丙胺盐酸盐的方法。根据一个优选实施例，该方法包括以下步骤：(a)将式1中Ar代表芳基的1-(苯基甘氧基基)哌啶芳磺酰肼与一种无机碱在水不相溶有机溶剂和相转移催化剂的存在下接触，以获得(R*,R*)-富集的7-苯基-1-氮杂双环[4.2.0]辛酮的化合物：2(b)将步骤(a)中制备的(R*,R*)-富集的7-苯基-1-氮杂双环[4.2.0]辛酮与甲醇中的盐酸氢溶液反应，以获得左旋富集的甲基苯丙胺盐酸盐；(c)结晶步骤(b)中制备的左旋富集的甲基苯丙胺盐酸盐，以得到所需的左旋甲基苯丙胺盐酸盐。最好，本发明的方法生产的左旋甲基苯丙胺盐酸盐不含多于1%的对映异构体。