二异丙基磷化氢 | 20491-53-6

• 物质功能分类: 化学试剂 - 有机试剂 - 含磷化合物
• 分子结构分类: 有机化合物 - 有机磷化合物
• 中文名称: 二异丙基磷化氢
• 中文别名: 二异丙基膦
• 英文名称: di-isopropylphosphine
• 英文别名: diisopropylphosphane；Diisopropylphosphine；di(propan-2-yl)phosphane
• CAS: 20491-53-6
• 化学式: C₆H₁₅P
• 分子量: 118.159
• InChiKey: WDIIYWASEVHBBT-UHFFFAOYSA-N

物化性质

• 沸点：
  118 °C
• 密度：
  0.800
• 闪点：
  -22 °C
• 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)：
  1.5
• 重原子数：
  7
• 可旋转键数：
  2
• 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

安全信息

• 危险品标志：
  N-C-F,F,C,N
• 安全说明：
  S16,S26,S33,S45,S61,S62,S9
• 危险类别码：
  R67
• 海关编码：
  2931900090
• 储存条件：
  存放于阴凉干燥处

SDS

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Section 1: Product Identification
Chemical Name: Di-i-propylphosphine, 98% (10 wt% in hexanes)
CAS Registry Number: 20491-53-6
Formula: (C3H7)2PH
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: Di-iso-propylphosphane

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 20491-53-6 10% no data no data
Hexane 73513-42-5 90% 50ppm 1800mg/m3

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Section 3: Hazards Identification
Harmful by inhalation, in contact with skin and if swallowed. Inhalation of vapors may depress central nervous
Emergency Overview:
system. Possible risk of harm to the unborn child and impaired fertility.
Primary Routes of Exposure: Ingestion, inhalation, skin, eyes
Eye Contact: Contact will cause irritation, redness and a burning sensation.
Skin Contact: Causes irritation of the skin. Repeated contact causes defatting of the skin.
Harmful by inhalation. Inhalation of vapors may depress the central nervous system causing dizziness, and
Inhalation:
irritation to the lungs.
Ingestion: Harmful if swallowed. May cause gastrointestinal irritation, nausea, vomiting and headache.
Harmful by inhalation, in contact with skin and if swallowed. Ingestion may cause nausea and vomiting.
Acute Health Affects:
Inhalation may cause headache and dizziness. Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: Prolonged exposure to high vapor concentrations may cause nerve damage and sensory loss.
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: -14.8°F (hexane)
Autoignition Temperature: no data
Explosion Limits: LEL (1.7%) UEL (7.7%)
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: Highly flammable.

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SECTION 6: Accidental Release Measures
If spilled, all personnel must be immediately evacuated and the area sealed off. The material may self-ignite
Spill and Leak Procedures: releasing toxic and corrosive fumes of phosphorus pentoxide. Ventilation should be available. If entry into the
area is required, personnel should be fitted with self-contained breathing apparatus.

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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.

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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. Consult glove manufacturer to determine the proper type of glove.
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: 118.62
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: pungent and noxious odor
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: air sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: contact with air
Incompatibility: oxidizing agents, alkyl halides, and halogens
Decomposition Products: carbon monoxide, carbon dioxide, phosphorus oxides and organic fumes.

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SECTION 11: Toxicological Information
No information available on title compound. For hexane--Standard Draize Test(rabbit); 10mg(mild).
Inhalation(human); TCLo: 190ppm/8W. Oral(rat); ld50: 28710mg/kg. Inhalation(rat); LC50: 48000ppm/4H.
RTECS Data: Intraperitoneal(rat); LDLo: 9100mg/kg. Intravenous(mouse); LDLo: 831mg/kg. Inhalation(rat); TCLo:
2000ppm/12H/24W-I. TDLo: 38g/kg oral(mouse) fetotoxicity: TCLo: 10,000ppm/7H. Inhalation(rat)
reproductive, behavioral, newborn; TCLo: 1000ppm/6H. Inhalation(rat) reproductive, newborn, wt. loss; TCLo:
5000ppm/20H.
Carcinogenic Effects: Hexane: Insufficient data
Mutagenic Effects: Hexane: Possible mutagen
Tetratogenic Effects: Hexane: Possible reproductive effector

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SECTION 12: Ecological Information
Ecological Information: Toxic to aquatic organisms. May cause long-term adverse effects in the aquatic environment.

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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): Flammable liquid, N.O.S.
Hazard Class (CFR): 3
Additional Hazard Class (CFR): NA
Packaging Group (CFR): I
UN ID Number (CFR): UN# 1993
Shipping Name (IATA): Flammable liquid, N.O.S.
Hazard Class (IATA): 3
Additional Hazard Class (IATA): NA
Packaging Group (IATA): I
UN ID Number (IATA): UN# 1993

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SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory
SARA (Title 313): Title compound not listed. Hexane: reportable under SARA 313.
Second Ingredient: Listed in the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  二异丙基磷化氢 在 三乙烯二胺 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 4.5h， 生成 羰基氯氢[双（2-二-异丙基膦酰基乙基）胺]钌（II）
  参考文献：
  名称：

  N,N-BIS(2-DIALKYLPHOSPHINOETHYL)AMINE-BORANE COMPLEX AND PRODUCTION METHOD THEREFOR, AND METHOD FOR PRODUCING RUTHENIUM COMPLEX CONTAINING N,N-BIS(2-DIALKYLPHOSPHINOETHYL)AMINE AS LIGAND

  摘要：

  本发明的目的是提供一种N,N-双(2-二烷基膦基乙基)胺硼烷配合物，它是一种在氢化反应中表现出优异催化活性的钌配合物等，以及其生产方法，以及一种有效生产含有N,N-双(2-二烷基膦基乙基)胺作为配体的钌配合物的方法。本发明能够通过在碱存在下将噁唑烷酮化合物(1)与二烷基膦硼烷化合物(2)反应来有效生产胺硼烷配合物(3)。本发明还能够通过在胺存在下将胺硼烷配合物(3)与钌化合物(4)反应来有效生产钌配合物(5)。

  公开号：

  US20190040090A1
• 作为产物：
  描述：

  methyl diisopropylphosphinate 在 二异丁基氢化铝 作用下， 以 乙醚 为溶剂， 反应 4.5h， 以0.772 g的产率得到二异丙基磷化氢
  参考文献：
  名称：

  一级，二级和三级膦的革兰氏级合成的通用方法

  摘要：

  尽管有机膦的合成在一个世纪的上半叶已广为人知，但是即使对于资深的合成化学家来说，膦的合成仍然代表着艰巨的任务。膦作为一类化合物，其对空气的敏感性差异很大，并且误以为新手化学家尝试看似简单的合成是微不足道的，甚至是容易的，这会带来灾难性的结果。为了简化任务，我们之前已经开发出一种使用台式中间体访问各种氧化膦（膦的直接前体）的方法。这种合成方法可以节省无空气的处理，直到最后一步（还原并分离出膦）。本文介绍了将膦酸酯，次膦酸酯和膦氧化物轻松还原为伯，仲，和叔膦使用氢化铝还原剂。亲电还原剂（i Bu） 2 AlH和AlH 3在还原选择性和反应性方面被确定大大优于LiAlH 4。值得注意的是，即使LiAlH 4和（ i Bu） 2 AlH不能，AlH 3仍能还原具有极强抗性的三环己基氧化膦。使用这种新方法，可以以克级反应合成出代表性范围的伯，仲和叔膦（包括挥发性膦），而无需纯化步骤，可实现出色的收率和无与伦比的纯度。

  DOI：

  10.1021/acs.organomet.7b00684
• 作为试剂：
  描述：

  二氯(萘-1-基)膦 在 二异丙基磷化氢 作用下， 以 氘代苯 为溶剂， 反应 0.17h， 生成 、 1,2,3,4-tetranaphthalen-1-yltetraphosphetane 、 1-naphthylphosphine
  参考文献：
  名称：

  用于快速形成环多膦的膦的氢/卤素交换

  摘要：

  膦的氢/卤素交换已被用于建立真正可用的底物范围和形成环多膦的直接方法。从单一的二氯膦开始，牺牲质子“供体膦”使环多膦的快速、温和合成成为可能：反应在室温下 10 分钟内完成。新的（芳基）环五膦（ArP）5已经以良好的转化率形成，并具有晶体结构。在二膦 (Ar 2 P) 2和烷基取代的环四或环五膦（(AlkylP) n，其中n= 4 或 5) 形成。无铁和铁介导的反应都对一种特定的环尺寸显示出高水平的选择性。最后，对 Fe(acac) 3反应性的研究表明，铁物质充当了反应副产物盐酸的汇。

  DOI：

  10.1021/acs.inorgchem.1c02734

文献信息

• Rapid Metal-Free Formation of Free Phosphines from Phosphine Oxides
  作者：Cei B. Provis-Evans、Emma A. C. Emanuelsson、Ruth L. Webster

  DOI：10.1002/adsc.201800723

  日期：2018.10.18

  A rapid method for the reduction of secondary phosphine oxides under mild conditions has been developed, allowing simple isolation of the corresponding free phosphines. The methodology involves the use of pinacol borane (HBpin) to effect the reduction while circumventing the formation of a phosphine borane adduct, as is usually the case with various other commonly used borane reducing agents such as

  已经开发出一种在温和条件下还原仲膦氧化物的快速方法，可以简单地分离相应的游离膦。该方法涉及使用频哪醇硼烷（HBpin）的，以实现同时避免膦硼烷加合物的形成的减少，如通常与各种其它常用的甲硼烷还原剂的情况下，如硼烷四氢呋喃复合物（BH 3 ⋅THF）和硼烷二甲硫醚复合物（BH 3 ⋅SMe 2）。此外，这种方法只需要少量过量的还原剂，因此不仅可以与不需要金属助催化剂的其他硼烷还原剂进行比较，而且可以与硅烷和铝基试剂进行比较。
• Convenient Methods for the Synthesis of a Library of Hemilabile Phosphines
  作者：M. Jiménez、Jesús Pérez-Torrente、M. Bartolomé、Luis Oro

  DOI：10.1055/s-0028-1088060

  日期：2009.6

  A series of novel functionalized phosphines of hemi­labile character, R2P(CH2)nZ, have been prepared from diaryl­phosphines using several synthetic methodologies. The synthetic methods include the alkylation of lithium diarylphosphide or (di­arylphosphino)borane adducts with functionalized halogenoalkanes, X(CH2)nZ, and the photochemical hydrophosphination of suitable functionalized allyl or vinyl

  一系列hemilabile字符的新的官能化的膦的，R 2 P（CH 2）Ñ Z，已经从使用几种合成方法二芳基膦制备。合成方法包括用官能化的卤代烷烃X（CH 2）n Z对二芳基磷酸锂或（二芳基膦基）硼烷加合物进行烷基化，以及合适的官能化烯丙基或乙烯基衍生物的光化学加氢磷酸化，H 2 C = CHZ或H 2 C = CHCH 2 Z，使用白光。甲范围R 2 PH（R = BN，4-MeOC 6 H ^ 4，4-MEC 6 ħ 4，2-MEC为了调节磷供体原子上的电子密度，已经使用了6 H 4，Ph，4-F 3 CC 6 H 4）。通过选择供体基团（Z = OMe，OEt，OBu，NMe 2）或柔性碳链的长度（n = 2、3），可以改变半不稳定片段的配位能力。由二芳基氯膦和烯丙基溴化镁制备了半不稳定的氟化烯丙基膦，R 2 PCH 2 CH ＝ CH 2（R ＝ 4-FC 6 H 4，C 6 F 5）。
• New cyclic phosphonium salts derived from the reaction of phosphine-aldehydes with acid
  作者：Alexandre A. Mikhailine、Paraskevi O. Lagaditis、Peter E. Sues、Alan J. Lough、Robert H. Morris

  DOI：10.1016/j.jorganchem.2010.04.016

  日期：2010.6

  Various cyclic phosphonium structures are formed in high yield by the deprotection of unstable phosphine-aldehydes in acidic solution. When there is a methylene spacer between the phosphine and the aldehyde, a phosphonium ion [PHR2CH2CH(OEt)2]Br2, R=iPrOH, Et is obtained. Reaction of these phosphonium salts with water produces the dimers [–PR2CH2CH(OH)–]2[Br]2 R = iPr, Et. When there is an ethylene

  通过将不稳定的膦醛在酸性溶液中脱保护，可以高产率形成各种环状结构。当在膦和醛之间存在亚甲基间隔基时，获得ion离子[PHR 2 CH 2 CH（OEt）2 ] Br 2，R ＝ iPrOH，Et。这些phospho盐与水反应生成二聚体[–PR 2 CH 2 CH（OH）–] 2 [Br] 2  R =  i Pr，Et。如PPh 2 CH 2 CH 2 CH（OCH 2 CH 2O），一种具有16元环[-PPh 2 CH 2 CH 2 CH（OH）–] 4 [Cl] 4的显着四聚体，在盐酸溶液中形成为一种非对映异构体。HCl与受保护的膦醛与丙烯间隔基（PPh 2 CH 2 CH 2 CH 2 CH（OCH 2 CH 2 O））的反应导致形成单体phospho盐[–PPh 2 CH 2 CH 2 CH 2具有5元环的CH（OH）–] Cl。使用X射线衍射实验确定了不同环类型的固态结构。
• N-(PHOSPHINOALKYL)-N-(THIOALKYL)AMINE DERIVATIVE, METHOD FOR PRODUCING SAME, AND METAL COMPLEX THEREOF
  申请人：TAKASAGO INTERNATIONAL CORPORATION

  公开号：US20170233418A1

  公开（公告）日：2017-08-17

  The purpose of the present invention is to provide: a ligand that is useful in a catalytic organic synthetic reaction; a method for producing said ligand; and a metal complex that is useful as a catalyst in an organic synthetic reaction. The present invention provides a compound represented by general formula (1 A ), a method for producing said compound, and a metal complex including said compound as a ligand. (In the formula, H, N, P, S, L, R 1 , R 2 , R 3 , Q 1 , and Q 2 have the meaning as defined in the Description.)

  本发明的目的是提供：在催化有机合成反应中有用的配体；制备所述配体的方法；以及在有机合成反应中作为催化剂有用的金属配合物。本发明提供了由通式（1A）表示的化合物，制备所述化合物的方法，以及包括所述化合物作为配体的金属配合物。（在该式中，H、N、P、S、L、R1、R2、R3、Q1和Q2的含义如描述中所定义。）
• Hydrogenation of Esters to Alcohols with a Well-Defined Iron Complex
  作者：Svenja Werkmeister、Kathrin Junge、Bianca Wendt、Elisabetta Alberico、Haijun Jiao、Wolfgang Baumann、Henrik Junge、Fabrice Gallou、Matthias Beller

  DOI：10.1002/anie.201402542

  日期：2014.8.11

  We present the first base‐free Fe‐catalyzed ester reduction applying molecular hydrogen. Without any additives, a variety of carboxylic acid esters and lactones were hydrogenated with high efficiency. Computations reveal an outer‐sphere mechanism involving simultaneous hydrogen transfer from the iron center and the ligand. This assumption is supported by NMR experiments.

  我们展示了第一个使用分子氢的无碱铁催化的酯还原反应。在没有任何添加剂的情况下，各种羧酸酯和内酯被高效地氢化。计算揭示了一种外球机理，涉及同时从铁中心和配体转移氢。NMR实验支持这一假设。