二正丁基(i-丙基)膦 | 25032-49-9

• 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 - 有机磷化合物 - 有机膦及其衍生物
• 中文名称: 二正丁基(i-丙基)膦
• 中文别名: 二正丁基(异丙基)膦；二-叔-丁基(异丙基)膦
• 英文名称: di-tert-butylisopropylphosphine
• 英文别名: DI-T-Butyl(I-propyl)phosphine；ditert-butyl(propan-2-yl)phosphane
• CAS: 25032-49-9
• 化学式: C₁₁H₂₅P
• mdl: MFCD06798293
• 分子量: 188.293
• InChiKey: QXTCJLPZCUKMDX-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

SDS

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Section 1: Product Identification
Chemical Name: Di-t-butyl(i-propyl)phosphine, min. 98%
CAS Registry Number: 25032-49-9
Formula: C11H25P
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: Bis-tert-butyl(isopropyl)phosphane

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 25032-49-9 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Harmful by inhalation, in contact with skin and if swallowed. Irritating to skin, eyes and respiratory tract.
Primary Routes of Exposure: Ingestion, inhalation, skin, eyes
Eye Contact: Causes mild to severe irritation of the eyes.
Skin Contact: Harmful in contact with skin. Causes mild irritation or thermal burns if ignited.
Inhalation: Harmful by inhalation. Irritating to the nose, mucous membranes and respiratory tract.
Ingestion: Harmful if swallowed. May cause vomiting and diarrhea.
Acute Health Affects: Harmful by inhalation, in contact with skin and if swallowed. 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: pyrophoric
Autoignition Temperature: no data
Explosion Limits: pyrophoric
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 toxic organic fumes and phosphorus pentoxide.
Decomposion Products:
Unusual Fire or Explosion Hazards: Spontaneously flammable in air.

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SECTION 6: Accidental Release Measures
This material may ignite spontaneously in air. Burning material may release toxic fumes. In case of poor
Spill and Leak Procedures: ventilation, leave the area unless fitted with a self-contained breathing apparatus. Small spills can be mixed
with ground limestone, sodium bicarbonate or other suitable adsorbents, swept up and held in a closed metal
can.

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SECTION 7: Handling and Storage
Store in a tightly sealed container under an inert atmosphere of nitrogen or argon. Keep away from heat.
Handling and Storage: Material should be transferred under an inert atmosphere of nitrogen or argon in an efficient fume hood. Fire
may occur in empty container and transfer lines.

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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: colorless liq.
Molecular Weight: 118.29
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: stench
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: air-sensitive, pyrophoric liquid
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: Contact with air. Material may spontaneously ignite.
Incompatibility: oxidizing agents, halogens, air, halocarbons.
Decomposition Products: carbon monoxide, carbon dioxide, phosphorus oxides and organic fumes.

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

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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): Pyrophoric liquid, Organic, N.O.S.
Hazard Class (CFR): 4.2
Additional Hazard Class (CFR): NA
Packaging Group (CFR): I
UN ID Number (CFR): UN# 2845
Shipping Name (IATA): Forbidden
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：

  二正丁基(i-丙基)膦 在 sodium t-butanolate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.0h， 生成 C₁₈H₃₉NP⁽¹⁺⁾*CF₃O₃S^(1-)
  参考文献：
  名称：

  瞬态稳定C-氨基磷叶立德的合成及其裂解成瞬态稳定卡宾

  摘要：

  只有碱性膦，如三（二甲氨基）膦，才能合成稳定的无环 β-氨基鏻盐 1c，在与丁基锂去质子化后，得到相应的稳定 C-氨基磷叶立德 2c。相比之下，尽管存在弱碱性三芳基膦片段，但环状 β-氨基鏻盐 5a 和 5b 是稳定的。它们是通过将（氨基）（膦基）卡宾的卡宾中心插入到磷取代基的 CH 键中来制备的。5a 的去质子化导致相应的环状 C-氨基磷叶立德 6a，其已被充分表征，包括 X 射线衍射研究。5b 的去质子化得到烯胺 8，这可能是通过将叶立德 6b 裂解为瞬态卡宾 7b 和随后的 1,2-氢位移。瞬态环状 C-氨基磷叶立德 6c 和 6d 已通过分子内加成由磷取代基的去质子化产生的碳负离子来制备。三元杂环 6c 重排成烯烃 9，而四元环系统开环得到稳定的卡宾 7d。后者的结果为合成各种混合卡宾-膦双齿配体铺平了道路。

  DOI：

  10.1021/ja055863c
• 作为产物：
  描述：

  三叔丁基膦 在 sodium amide 作用下， 以 氨 、 正戊烷 为溶剂， 反应 120.0h， 生成 二正丁基(i-丙基)膦
  参考文献：
  名称：

  Schmidbaur, Hubert; Blaschke, Guenther; Zimmer-Gasser, Beate, Chemische Berichte, 1980, vol. 113, # 4, p. 1612 - 1622

  摘要：

  DOI：
• 作为试剂：
  描述：

  对氯苯酚 在 potassium fluoride 、 bis(di-tert-butylisopropylphosphine)palladium⁽⁰⁾ 、 二正丁基(i-丙基)膦 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 129.0h， 生成 1-氯-4-(2-甲基苯基)苯
  参考文献：
  名称：

  Combining the Reactivity Properties of PCy₃ and PtBu₃ into a Single Ligand, P(iPr)(tBu)₂. Reaction via Mono- or Bisphosphine Palladium(0) Centers and Palladium(I) Dimer Formation

  摘要：

  Trialkylphosphine ligands are ubiquitous in catalysis. Via modulation of the steric bulk of these ligands, two central aspects that dictate reactivity and selectivity in catalysis can be controlled: i.e., the coordination sphere and favored oxidation state of the reactive metal center. Within this class of ligands, tricyclohexylphosphine (PCy3) and tri-tert-butylphosphine (PtBu3) are most widely used in catalysis. While the smaller PCy3 favors reactivity via Pd bisphosphine species with the test substrate 4-chlorophenyl triflate 1 and does not form dinuclear Pd(I) complexes upon oxidation of Pd(0), PtBu3 reacts via a monophosphine-ligated Pd complex with 1 and forms dinuclear Pd(I) complexes on oxidation. We herein report that the hybrid ligand P(iPr)(tBu)(2), characterized by a cone angle that is between those of PCy3 and PtBu3, features all of these reactivity properties in a single scaffold. This is exemplified in chemoselectivity studies with test system 1, in which the site selectivity could be readily modulated. The novel Pd(I) dimer {[P(iPr)(tBu)(2)]PdI}(2) has also been synthesized

  DOI：

  10.1021/om5009605

文献信息

• Single component cationic palladium proinitiators for the latent polymerization of cycloolefins
  申请人：Bell Andrew

  公开号：US20050187398A1

  公开（公告）日：2005-08-25

  Palladium compound compositions are provided in accordance with Formulae [((R) 3 E) a Pd(Q)(LB) b ] p [WCA] r , where ((R) 3 E) is a Group 15 electron donor ligand, Q is an anionic ligand, LB is a Lewis base, WCA is a weakly coordinating anion, a is 1, 2 or 3, b is 0, 1 or 2, the sum of a and b is 1, 2 or 3 and each of p and r is an integer such that the molecular charge is zero, or [(E(R) 3 )(E(R) 2 R*)Pd(LB)] p [WCA] r where E(R) 2 R* represents a Group 15 neutral electron donor ligand and where R* is an anionic hydrocarbyl containing moiety, bonded to the Pd and having a β hydrogen with respect to the Pd center. Such compound composition exhibits latent polymerization activity in the presence of polycyclic olefins.

  钯化合物组成按照以下公式提供：[((R)3E)aPd(Q)(LB)b]p[WCA]r，其中((R)3E)是第15族电子供体配体，Q是阴离子配体，LB是路易斯碱，WCA是弱配位阴离子，a为1、2或3，b为0、1或2，a和b的总和为1、2或3，p和r各自为整数，使得分子电荷为零，或[(E(R)3)(E(R)2R*)Pd(LB)]p[WCA]r，其中E(R)2R*代表第15族中性电子供体配体，R*是与Pd键合的含有阴离子烃基的部分，并且相对于Pd中心具有β氢。这种化合物组成在多环烯烃存在时表现出潜在的聚合活性。
• PROCESS FOR PRODUCING PHENYL-SUBSTITUTED HETEROCYCLIC DERIVATIVE THROUGH COUPLING USING TRANSITION METAL CATALYST
  申请人：Komiyama Masato

  公开号：US20110313169A1

  公开（公告）日：2011-12-22

  A process for efficiently producing, through few steps either a xanthine oxidase inhibitor, which is a therapeutic agent for hyperuricemia, or an intermediate therefore. The process is a novel coupling process which comprises subjecting a compound represented by formula (1) to coupling reaction with a compound represented by formula (2) in the presence of a transition metal compound to thereby obtain a compound represented by formula (3).

  一种高效生产黄嘌呤氧化酶抑制剂或其中间体的方法，该抑制剂是治疗高尿酸血症的药物。该方法是一种新型偶联过程，包括将式（1）表示的化合物与式（2）表示的化合物在过渡金属化合物存在下进行偶联反应，从而获得式（3）表示的化合物。
• METHOD FOR PRODUCING FLUOROVINYL ETHER COMPOUND
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：US20210284593A1

  公开（公告）日：2021-09-16

  An object of the present invention is to provide, for example, a novel method for synthesizing a fluorovinyl ether compound from a fluorine-containing vinyl compound. This problem is solved by a method for producing a compound represented by formula (1): wherein R a1 is a hydrogen atom, a halogeno group, an alkyl group, a fluoroalkyl group, or an aromatic group optionally having one or more substituents, Rf is a fluoro group or a perfluoroalkyl group, R a2 is a hydrogen atom, a halogeno group, an alkyl group, a fluoroalkyl group, or an aromatic group optionally having one or more substituents, or (i) R a1 and R a2 , (ii) R a1 and Rf, or (iii) Rf and R a2 may be linked to each other, R b1 is R S , R b2 is a hydrogen atom or R S , R b3 is a hydrogen atom or R S , or two or three of R b1 , R b2 , and R b3 , taken together with the adjacent carbon atom, may form a ring optionally having one or more substituents, and R S , in each occurrence, is the same or different and represents a hydrocarbon group optionally having one or more substituents, the method comprising step A of reacting a compound represented by formula (2): wherein R x is a leaving group, and other symbols are as defined above, with a compound represented by formula ( 3 ): wherein the symbols in the formula are as defined above, in the presence of a transition metal catalyst.

  本发明的一个目标是提供一种从含氟乙烯化合物合成氟乙烯醚化合物的新方法。这个问题通过以下方法解决：生产一个由以下式表示的化合物的方法(1)：其中Ra1是氢原子、卤素基团、烷基基团、氟烷基基团或可能具有一个或多个取代基的芳香基团，Rf是氟基团或全氟烷基基团，Ra2是氢原子、卤素基团、烷基基团、氟烷基基团或可能具有一个或多个取代基的芳香基团，或(i) Ra1和Ra2、(ii) Ra1和Rf或(iii) Rf和Ra2可能连接在一起，Rb1是RS，Rb2是氢原子或RS，Rb3是氢原子或RS，或者Rb1、Rb2和Rb3中的两个或三个，与相邻的碳原子一起，可以形成一个可能具有一个或多个取代基的环，RS在每次出现时相同或不同，表示一个可能具有一个或多个取代基的碳氢基团，该方法包括以下步骤：步骤A，将由以下式表示的化合物(2)：其中Rxis是一个离去基团，和上述其他符号的定义相同，与由以下式表示的化合物(3)：其中式中的符号与上述定义相同，在过渡金属催化剂存在下反应。
• Preparation of polyisocyanates containing uretdione groups using phosphine catalysts
  申请人：Richter Frank

  公开号：US20080262262A1

  公开（公告）日：2008-10-23

  The invention provides a process for isocyanate dimerization (uretdione formation) and a process for preparing polyisocyanates having a high content of uretdione groups, using specific phosphines as catalysts. The phosphines have one or two tertiary alkyl radicals bound directly to phosphorus.

  该发明提供了一种异氰酸酯二聚化（尿素二酮形成）的过程以及一种利用特定膦作为催化剂制备含有高含量尿素二酮基团的多异氰酸酯的过程。这些膦具有一个或两个直接结合到磷的三级烷基基团。
• [EN] PROCESSES FOR THE PREPARATION OF PERIPHERAL OPIOID ANTAGONIST COMPOUNDS AND INTERMEDIATES THERETO<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS ANTAGONISTES DES OPIOÏDES PÉRIPHÉRIQUES ET DES INTERMÉDIAIRES DE CEUX-CI
  申请人：ADOLOR CORP

  公开号：WO2013012871A1

  公开（公告）日：2013-01-24

  Novel processes for the preparation of peripheral opioid antagonist compounds and intermediates thereto. The compounds prepared by the present processes may be useful, for example, as antagonists to the mu, kappa and delta opioid receptors, and thereby may be useful in the treatment of gastrointestinal motility disorders, and in preventing peripheral opiate induced side effects. The present processes may offer improved yields, chemical or stereochemical purity, ease of preparation and/or isolation of intermediates and final product, and more industrially useful reaction conditions and workability.

  用于制备外周阿片受体拮抗剂化合物及其中间体的新型工艺。通过本工艺制备的化合物可能可用作mu、kappa和delta阿片受体的拮抗剂，从而可能在治疗胃肠动力障碍和预防外周阿片诱导的副作用方面有用。本工艺可能提供更高的产率、化学或立体化纯度、中间体和最终产品的制备和分离的便利性，以及更具工业应用的反应条件和可操作性。