双[2-（二-叔丁基膦基)乙基]胺 | 944710-34-3

• 物质功能分类: 有机原料 - 氨基化合物
• 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: 双[2-（二-叔丁基膦基)乙基]胺
• 中文别名: 双[2-(二-叔丁基膦基)乙基]胺
• 英文名称: bis[2-(di-tert-butylphosphino)ethyl]amine
• 英文别名: Bis[2-(DI-T-butylphosphino)ethyl]amine；2-ditert-butylphosphanyl-N-(2-ditert-butylphosphanylethyl)ethanamine
• CAS: 944710-34-3
• 化学式: C₂₀H₄₅NP₂
• 分子量: 361.532
• InChiKey: MJYKYLNPIGDVEF-UHFFFAOYSA-N

物化性质

• 沸点：
  419.2±30.0 °C(Predicted)
• 密度：
  0.911 g/mL at 25 °C
• 闪点：
  -17 °C
• 暴露限值：
  ACGIH: TWA 50 ppm; STEL 100 ppm (Skin)OSHA: TWA 200 ppm(590 mg/m3)NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  3
• 储存条件：
  室温、密闭保存，并保持干燥。

SDS

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Section 1: Product Identification
Chemical Name: Bis[2-(di-t-butylphosphino)ethyl]amine, min. 97% (10wt% in hexanes)
CAS Registry Number: 944710-34-3
Formula: C20H45NP2
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: none

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 944710-34-3 10% no data no data
Hexane 73513-42-5 90% 50ppm 1800mg/m3

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Section 3: Hazards Identification
Extremely flammable liquid. Vapors irritating to skin, eyes and respiratory tract. Inhalation of vapors may
Emergency Overview:
depress central nervous system causing dizziness, headache and nausea.
Primary Routes of Exposure: Ingestion, inhalation
Eye Contact: Contact will cause irritation, redness and a burning sensation.
Skin Contact: Contact with skin can result in local irritation. May be absorbed through skin.
Inhalation of vapors may depress the central nervous system causing dizziness, difficulty in walking and
Inhalation:
irritation to the lungs.
Ingestion may cause gastrointestinal irritation, nausea, vomiting and headache. May cause lung damage if
Ingestion:
swallowed.
Irritating to skin, eyes and respiratory tract. Harmful by inhalation. Ingestion may cause gastrointestinal
Acute Health Affects:
irritation, nausea, vomiting and headache. Possible risk of harm to the unborn child.
Chronic Health Affects: No information on long-term chronic effects. Possible risk of impaired fertility.
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%) hexane
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 and irritating fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: Highly flammable. Vapors can form explosive mixtures in air.

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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 a 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.
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 liquid
Molecular Weight: 361.53
Melting Point: no data
Boiling Point: 68°C (hexane)
Vapor Pressure: no data
Specific Gravity: no data
Odor: pungent and noxious
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 oxidizing agents, ignition sources and prolonged exposure to air
Incompatibility: strong oxidizing agents and halogens
Decomposition Products: carbon monoxide, carbon dioxide, phosphorous oxides and organic fumes

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SECTION 11: Toxicological Information
Title compound: No information available in the RTECS files. Hexane: Inhalation(humane); TCLo:
190ppm/8W. Inhalation(rat); LC50: 48000ppm/4H. Intraperitoneal(rat); LDLo: 9100mg/kg. Inhalation(mouse);
LCLo: 120g/m3. Intravenous(mouse); LDLo: 831mg/kg. Intravenous(rabbit); LDLo: 132mg/kg. Oral(rat); TDLo:
RTECS Data:
20000mg/kg. Oral(rat); LD50: 15840mg/kg. Inhalation(rat); TCLo: 1000ppm/4H/59W
(intermittent)-Tumorigenic-carcinogenic by RTECS criteria. Inhalation(rat); TCLo: 10000ppm/7H; female-1-18
days after conception-behavorial effects on newborn.
Carcinogenic Effects: Hexane: Insufficient data
Mutagenic Effects: Hexane: Possible mutagen
Tetratogenic Effects: Hexane: Possible reproductive effector

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SECTION 12: Ecological Information
Hexane is very toxic to aquatic organisms. May cause long-term adverse effects in the aquatic environment.
Ecological Information:
Avoid release to the 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 liquids, 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): Not reportable under SARA 313.
Second Ingredient: Hexane: Listed in the TSCA inventory. Reportable under SARA 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  双[2-（二-叔丁基膦基)乙基]胺 在 2,4,5-tri(tertbutyl)phenoxy 作用下， 以 四氢呋喃 、 氯苯 、 苯 为溶剂， 反应 2.08h， 生成
  参考文献：
  名称：

  脂肪族PNP夹配体的化学纯性

  摘要：

  报道了二乙烯基酰胺基PNP镍（II）配合物[NiBr {N（CHCHP t Bu 2）2 }]的合成。该化合物表现出可逆的，以配体为中心的氧化和质子化反应。所产生的夹杂化学无毒可用于苄基CH氢原子的提取。检查了氢原子转移的热化学和动力学。

  DOI：

  10.1002/chem.201604407
• 作为产物：
  描述：

  二叔丁基氯化膦 、 N,N-bis(2-chloroethyl)-1,1,1-trimethylsilanamine 在 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 75.0h， 以22.2 g的产率得到双[2-（二-叔丁基膦基)乙基]胺
  参考文献：
  名称：

  [EN] TRANSITION METAL ISONITRILE CATALYSTS
  [FR] CATALYSEURS D'ISONITRILE À MÉTAUX DE TRANSITION

  摘要：

  本公开涉及新的过渡金属异腈化合物，制备这些化合物的方法以及将这些化合物用作催化剂的用途。该公开还涉及将金属异腈化合物用作催化剂，用于含有一个或多个碳-氧、碳-氮和/或碳-碳双键的化合物的加氢和转移加氢。

  公开号：

  WO2018193401A1
• 作为试剂：
  描述：

  5-(2-fluorophenyl)-1-(pyridin-3-yl-sulfonyl)-1H-pyrrole-3-carbonitrile 、 盐酸甲胺 、 富马酸 在 光气 、 sodium tetrahydroborate 、 双[2-（二-叔丁基膦基)乙基]胺 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 以90.2%的产率得到5-(2-氟苯基)-N-甲基-1-(3-吡啶基磺酰基)-1H-吡咯-3-甲胺富马酸盐
  参考文献：
  名称：

  一种富马酸沃诺拉赞的制备方法

  摘要：

  本发明提供一种富马酸沃诺拉赞(I)的制备方法，选用易得的5‑(2‑氟苯基)‑1‑(3‑吡啶基磺酰基)‑3‑氰基‑1H‑吡咯(II)为原料，一步反应得到沃诺拉赞，再与富马酸成盐即可得到目标产物。该方法路线新颖，操作简单可控，产品收率高，环境友好，适于工业规模化放大生产。

  公开号：

  CN110452222B

文献信息

• Additive‐Free Isomerization of Allylic Alcohols to Ketones with a Cobalt PNP Pincer Catalyst
  作者：Brian Spiegelberg、Andrea Dell'Acqua、Tian Xia、Anke Spannenberg、Sergey Tin、Sandra Hinze、Johannes G. de Vries

  DOI：10.1002/chem.201901148

  日期：2019.6.12

  Catalytic isomerization of allylic alcohols in ethanol as a green solvent was achieved by using air and moisture stable cobalt (II) complexes in the absence of any additives. Under mild conditions, the cobalt PNP pincer complex substituted with phenyl groups on the phosphorus atoms appeared to be the most active. High rates were obtained at 120 °C, even though the addition of one equivalent of base

  通过在不存在任何添加剂的情况下使用空气和湿气稳定的钴（II）配合物，可以实现烯丙醇在乙醇中的催化异构化（绿色溶剂）。在温和的条件下，被磷原子上的苯基取代的钴PNP钳形络合物似乎是活性最高的。即使加入一当量的碱可大大提高反应速度，但在120°C时仍可获得较高的反应速率。尽管获得了支持脱氢-加氢机理的一些证据，但已证明这不是主要机理。取而代之的是，乙醇脱氢形成的氢化钴配合物能够通过烯烃插入-消除反应实现双键异构化。
• Selective Construction of C−C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides
  作者：Xin Liu、Thomas Werner

  DOI：10.1002/adsc.202001209

  日期：2021.2.16

  manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon‐carbon single (C−C) and carbon‐carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C−C vs. C=C bonds can be controlled by the

  在本文中，我们报道了锰与磷酰化物的锰催化偶联。伯醇与磷酰化物偶联形成碳碳单键（CC）和碳碳双键（C = C）的选择性可以通过配体控制。在更具挑战性的仲醇与磷酰化物的转化中，通过反应条件，即碱的量，可以控制形成CC与C = C键的选择性。偶联反应的范围和局限性通过21种醇和15种烷基化物的转化得到了彻底评估。值得注意的是，与基于贵金属络合物作为催化剂的现有方法相比，本催化体系基于富含稀土的锰催化剂。该反应也可以在顺序的一锅法反应中进行，该反应在锰催化的C-C和C = C键形成后就地生成磷叶立德。机理研究表明，CC键是通过借位氢途径生成的，而C = C键的形成遵循无受体的脱氢偶联途径。
• Synthesis and characterisation of ruthenium dihydrogen complexes and their reactivity towards B–H bonds
  作者：Jong-Hoo Choi、Nils E. Schloerer、Josefine Berger、Martin H. G. Prechtl

  DOI：10.1039/c3dt52037d

  日期：——

  In this paper the synthesis and characterisation of ruthenium dihydrogen complexes bearing rigid aliphatic PNP pincer-type ligands are described. As one result hydride complexes were synthesised in good to high yields by a one-pot direct hydrogenation reaction. As another finding the dihydrogen complex, stabilised with a N–Me group in the ligand frame, can be converted with dimethylamine borane into

  本文描述了带有刚性脂肪族PNP钳型配体的钌二氢配合物的合成和表征。结果，通过一锅法直接氢化反应以良好至高产率合成了氢化物配合物。另一个发现是，在配体框架中用N–Me基团稳定的二氢配合物可以与二甲胺硼烷一起转化为具有快速B–N的稀有σ-硼配合物[RuH 2（BH 3）（Me-PNP）]。去耦。此外，我们介绍了通过液体注入场解吸/电离技术（LIFDI-MS）对合成的σ复合物进行的首次质谱分析。
• Efficient and selective hydrogenation of amides to alcohols and amines using a well-defined manganese–PNN pincer complex
  作者：Veronica Papa、Jose R. Cabrero-Antonino、Elisabetta Alberico、Anke Spanneberg、Kathrin Junge、Henrik Junge、Matthias Beller

  DOI：10.1039/c7sc00138j

  日期：——

  Novel manganese NNP and PNP pincer complexes have been synthesized. The active catalyst allows the efficient hydrogenation of a wide range of amides under relatively mild conditions to afford alcohols and amines in high yields.

  已经合成了新型的锰NNP和PNP钳形配合物。活性催化剂允许在相对温和的条件下有效氢化各种酰胺，从而以高收率提供醇和胺。
• Manganese-catalyzed direct C–C coupling of α-C–H bonds of amides and esters with alcohols <i>via</i> hydrogen autotransfer
  作者：Jagannath Rana、Virendrakumar Gupta、Ekambaram Balaraman

  DOI：10.1039/c8dt05020a

  日期：——

  Mn-catalyzed C-alkylation of amides and tert-butyl acetate using alcohols as alkylating agents is reported. This approach exhibits a broad substrate scope providing the C(α)-alkylated amides in good yields via hydrogen auto-transfer strategy.

  锰催化的酰胺和叔丁基醋酸酯的C-烷基化反应使用醇作为烷基化试剂。这种方法具有广泛的底物范围，通过氢自动转移策略提供良好产率的C(α)-烷基化酰胺。