1-二异丙基膦基-2-（N，N-二甲基氨基）-1H-茚 | 540492-51-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 中文名称: 1-二异丙基膦基-2-（N，N-二甲基氨基）-1H-茚
• 中文别名: 1-二异丙基膦-2-(N,N-二甲氨)-1H-茆(含乙烯基异构体)；1-二-异丙基膦基-2-(N,N-二甲基氨基)-1H-茚
• 英文名称: 1-diisopropylphosphino-2-dimethylaminoindene
• 英文别名: C9H6(N(methyl)2)P(isopropyl)2；1-P(i-Pr)2-2-NMe2-indene；1-P(i)Pr2-2-NMe2-indene；1-PiPr2-2-NMe2-indene；C6H4CHPiPr2CHCNMe2；1H-Inden-2-amine, 1-[bis(1-methylethyl)phosphino]-N,N-dimethyl-；1-di(propan-2-yl)phosphanyl-N,N-dimethyl-1H-inden-2-amine
• CAS: 540492-51-1
• 化学式: C₁₇H₂₆NP
• 分子量: 275.374
• InChiKey: AXHDIGXWRNPNMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

SDS

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Section 1: Product Identification
Chemical Name: 1-Di-i-propylphosphino-2-(N,N-dimethylamino)-1H-indene, 99%
CAS Registry Number: 540492-51-1
Formula: C17H26NP
EINECS Number: none
Chemical Family: phosphine ligand
Synonym: (1-Diisopropylphosphanyl-1H-inden-2-yl)-dimethyl-amine

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 540492-51-1 100% 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: Inhalation, skin, eyes
Eye Contact: Causes slight to mild irritation of the eyes.
Skin Contact: Causes irritation to the skin
Inhalation: Causes irritation to the nose, mucous membranes and respiratory tract
Ingestion: No information on the physiological effects of ingestion. May be harmful if swallowed.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information available 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 chemical 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 organic fumes
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards

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SECTION 6: Accidental Release Measures
Small spills can be mixed with vermiculite, sodium carbonate or other suitable non-combustible adsorbent and
Spill and Leak Procedures:
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,
Handling and Storage:
well-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: off-white xtl
Molecular Weight: 275.37
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: not determined
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: air sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: prolonged exposure to air
Incompatibility: oxidizing agents
Decomposition Products: carbon dioxide, carbon monoxide, 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
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：

  1-二异丙基膦基-2-（N，N-二甲基氨基）-1H-茚 以 氘代苯 、 甲苯 为溶剂， 生成 六苯基二锡
  参考文献：
  名称：

  Synthesis and Reactivity of New κ²-[P,N]Pt(II) Complexes of Diisopropylphosphino-Substituted 2-Dimethylaminoindene

  摘要：

  Treatment of 1-(PPr2)-Pr-i-2-NMe2-indene (1a[H]) with either cis/trans-(SMe2)(2)PtCl2 or PtCl2 provided ((2)(K) -P,N-2-NMe2-3-(PPr2)-Pr-i-indene)PtCl2 (2) in 84% and 55% yield, respectively, while the reaction of la[H] with (eta(4)-COD)PtClMe afforded ((2)(K)-P, N-2-NMe2-3-(PPr2)-Pr-i-indene)PtClMe (3) in 91% yield. Whereas in the formation of 2 and 3 the ligand precursor la[H] undergoes a rearrangement to give a coordinated 2-NMe2-3-(PPr2)-Pr-i-indene (1b[H]) ligand, la[H] reacted cleanly with 0.5 equiv of [(mu-SMe2)PtMe2](2) to give ((2)(K) -P,N-1a[H])PtMe2 (4a) in 97% yield. The isomerization of 4a to ((2)(K) -P,N-1b[H])PtMe2 (4b) in a THF/(PrOH)-Pr-i mixture is rapid and allowed for the isolation of 4b in 99% yield. Heating of 4a in CH2Cl2 resulted in the quantitative formation of 3, while the thermolysis of 4a in toluene in the presence of SMe2 afforded 5, the apparent product of intramolecular C-H activation of an NMe group. The reactivity of 4a with a variety of other two-electron donors, as well as E-H-containing substrates (E = main group fragment), is reported. Although NMR spectroscopic evidence indicated the formation of an intermediate of the type ((2)(K)-P,N-1[H])Pt(SnPh3)(Me), as well as Ph6Sn2, in the reaction of 4a with 10 equiv of Ph3SnH, negligible conversion of Ph3SnH to Ph6Sn2 was obtained when employing 1 mol % 4a as a catalyst. Single-crystal X-ray diffraction data for 2 and 5 are reported.

  DOI：

  10.1021/om049034w
• 作为产物：
  描述：

  氯二异丙基膦 、 2-Dimethylamino-inden 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.0h， 以93%的产率得到1-二异丙基膦基-2-（N，N-二甲基氨基）-1H-茚
  参考文献：
  名称：

  A Catalytically Active, Charge-Neutral Rh(I) Zwitterion Featuring a P,N-Substituted “Naked” Indenide Ligand

  摘要：

  The synthesis and characterization of a new class of cationic and zwitterionic Rh(I) complexes, which feature multidentate ligands comprised of donor-functionalized indene or indenide units, are reported. This unusual new ligation strategy provides access to the first charge-neutral [kappa2-P,N]Rh(I) zwitterion, a complex that functions as a catalyst for the C-H/Si-H dehydrogenative coupling of styrene and triethylsilane.

  DOI：

  10.1021/ja034543v

文献信息

• New bidentate cationic and zwitterionic relatives of Crabtree's hydrogenation catalyst
  作者：Judy Cipot、Robert McDonald、Mark Stradiotto

  DOI：10.1039/b510253g

  日期：——

  Inspired by the monodentate P,N ligation strategy featured in Crabtree's catalyst [(COD)Ir(PCy3)(Py)]+PF6-([1]+PF6-), a new class of bidentate cationic ([2]+X-) and zwitterionic (3) Ir complexes have been developed, which are capable of mediating the hydrogenation of alkenes under mild conditions and in a wider range of solvents than is possible for [1]+PF6-.

  受到Crabtree催化剂[（COD）Ir（PCy3）（Py）] + PF6-（[1] + PF6-）（一种新型的双齿阳离子（[2] + X- ）和两性离子（3）Ir络合物已被开发出来，它们能够在温和的条件下，在比[1] + PF6-可能的溶剂范围更大的溶剂中介导烯烃的氢化反应。
• Cationic and Formally Zwitterionic Rhodium(I) and Iridium(I) Derivatives of a P,N-Substituted Indene:  A Comparative Synthetic, Structural, and Catalytic Investigation
  作者：Judy Cipot、Robert McDonald、Michael J. Ferguson、Gabriele Schatte、Mark Stradiotto

  DOI：10.1021/om060758c

  日期：2007.1.1

  A family of neutral, cationic, and formally zwitterionic Rh(I) and Ir(I) complexes featuring 1-PiPr2-2-NMe2-indene (3a), 3-PiPr2-2-NMe2-indene (3b), or 3-PiPr2-2-NMe2-indenide (3c) ligands have been prepared and structurally characterized. Whereas treatment of 3a with 0.5 equiv of [(COD)RhCl]2 afforded (COD)RhCl(κ1-P,N-3a) (4a) in 96% isolated yield, [(COD)M(κ2-P,N-3a)]+X- ([5a]+PF6-, M = Rh; [6a]+SO3CF3-

  具有1-P i的中性，阳离子和正式两性离子Rh（I）和Ir（I）配合物家族Pr 2 -2-NMe 2-茚（3a），3-P iPr 2 -2-NMe 2-茚（3b）或3-P iPr 2 -2-NMe 2-茚化物（3c）配体已经被制备并在结构上被表征。而治疗的图3a用0.5当量[（COD）的RhCl]的2得到（COD）的RhCl（κ 1 - P，N- 3A）（图4a）在96％分离产率，[（COD）M（κ 2 - P，ñ -图3a）] + X -（[ 5A ] + PF 6 -，M = RH; [图6A ] + SO 3 CF 3 -在14％和41％，获得M = Ir）的配合物从分离产3A和原位制备的[（COD）M（THF）的适当2 ] + X -的前体。同分异构的配合物[（COD）M（κ 2 - P，ñ -图3b）] + X -（[图5b ] + X -，M = RH; [图6B ] + X -，M
• Synthesis and Crystallographic Characterization of New Manganese(I) Complexes of Donor-Functionalized Indenes
  作者：Judy Cipot、Dominik Wechsler、Robert McDonald、Michael J. Ferguson、Mark Stradiotto

  DOI：10.1021/om0490435

  日期：2005.3.1

  - (6) was prepared in 30% yield by treating BrMn(CO)5 with AgBF4, followed by the addition of 2[H]. The benzocymantrene η5-[2]Mn(CO)3 was prepared in 56% yield via reduction of η5-(2-NMe2-3-P(S)iPr2-indenyl)Mn(CO)3 with Cl3SiSiCl3. Compound 2[Li] reacts with BrMn(CO)5 to give a complex product mixture, from which 4 and [κ2-P,N-(2-NMe2-3-PiPr2-indene)Mn(CO)4]+[Mn2(CO)8(μ-PiPr2)]- (7) were isolated.

  1-P i的治疗PR 2 -2-NME 2 -茚（2 [H]）与BrMn（CO）5 κ提供2 - P，ñ - （2-NME 2 -3-P我Pr 2-茚）Mn（CO）3 Br（4）的产率为73％。将AgBF 4或AgSO 3 CF 3加到4分别得到相应的内球四氟硼酸酯（5a）和三氟甲磺酸酯（5b）配合物，产率分别为62％和65％。去质子化4，图5a，或5b中产生的产品的一个棘手的混合物。阳离子络合物[κ 2 - P，ñ - （2-NME 2 -3-P我PR 2 -茚）的Mn（CO）4 ] + BF 4 - （6）通过处理BrMn（CO）在30％的产率制备5用的AgBF 4，然后通过加入2 [H]。η的benzocymantrene 5 - [ 2 ]的Mn（CO）3经还原的56％产率制备η 5 - （2-NME 2 -3-P（S）我Pr 2-茚基）Mn（CO）3与Cl 3 SiSiCl 3。化合物2
• Exploring the Influence of Ancillary Ligand Charge and Geometry on the Properties of New Coordinatively Unsaturated Cp*(κ²-<i>P</i>,<i>N</i>)Ru⁺ Complexes:  Linkage Isomerism, Double C−H Bond Activation, and Reversible α-Hydride Elimination
  作者：Matthew A. Rankin、Robert McDonald、Michael J. Ferguson、Mark Stradiotto

  DOI：10.1021/om050534e

  日期：2005.10.1

  apparent cyclometalation of 4b to give 4e is reversible. While the base-stabilized zwitterion 5a·CH3CN was successfully prepared (83%), attempts to generate the coordinatively unsaturated zwitterion Cp*Ru(κ2-P,N-1) (5a) instead resulted in the formation of the isomeric hydridocarbenes 5b (80%) and 5c (84%). The apparent rearrangement of 5a to a hydridocarbene is noteworthy, as it represents a remarkably facile

  的合成，表征，和反应性新的Cp * Ru配合物支持的属性由κ 2 - P，Ñ -1-P我PR 2 -2-NME 2 -茚（1A），κ 2 - P，Ñ -2- NME 2 -3-P我PR 2 -茚（1B），和κ 2 - P，Ñ -2- NME 2 -3-P我PR 2 -indenide（1）中有所描述（CP * =η 5 -C 5我5）。加入1A至（CP *的RuCl）4得到的Cp *的Ru（Cl）的（κ 2 - P，ñ - 1A）（图2a，92％），这反过来又转化的Cp *的Ru（Cl）的（κ 2 - P，N - 1b）（2b，85％）。用乙腈中的AgBF 4处理2a或2b可提供相应的18电子，碱稳定的阳离子[Cp * Ru（CH3 CN）（κ 2 - P，Ñ - 1A，b）] + BF 4 - （图3a，89％;图3b，91％）。为了追求类似的不含乙腈的16电子物种（4a或4b），将复合物2a或2b用Li（Et
• A Formally Zwitterionic Ruthenium Catalyst Precursor for the Transfer Hydrogenation of Ketones that Does Not Feature an Ancillary Ligand NH Functionality
  作者：Rylan J. Lundgren、Matthew A. Rankin、Robert McDonald、Gabriele Schatte、Mark Stradiotto

  DOI：10.1002/anie.200700345

  日期：2007.6.18