叔丁基膦 | 2501-94-2

• 分子结构分类: 有机化合物 - 有机磷化合物
• 中文名称: 叔丁基膦
• 英文名称: tert-butylphosphine
• 英文别名: Phosphine, (1,1-dimethylethyl)-；tert-butylphosphane
• CAS: 2501-94-2
• 化学式: C₄H₁₁P
• mdl: MFCD00761891
• 分子量: 90.1051
• InChiKey: ZGNPLWZYVAFUNZ-UHFFFAOYSA-N

物化性质

• 熔点：
  -85 °C
• 沸点：
  54°C
• 密度：
  0.7

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  5
• 可旋转键数：
  0
• 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

ADMET

毒理性

• 副作用

Dermatotoxin - 皮肤烧伤。

Dermatotoxin - Skin burns.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• 危险等级：
  4.2
• 危险类别码：
  R17,R34,R26
• 危险品运输编号：
  UN 2845
• 包装等级：
  I
• 危险类别：
  4.2
• 安全说明：
  S43,S45,S9

SDS

---

Section 1: Product Identification
Chemical Name: t-Butylphosphine, min. 95% TBP
CAS Registry Number: 2501-94-2
Formula: (C4H9)PH2
EINECS Number: none
Chemical Family: organophosphorus ligand
Synonym: tert-Butylphosphane; (1,1-dimethylethyl)phosphane; 1,1-dimethylethylphosphine

---

Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 2501-94-2 100% no data no data

---

Section 3: Hazards Identification
Material has an intensely pungent odor. Toxic by inhalation, in contact with skin and if swallowed. Inhalation of
Emergency Overview:
vapors may lead to headache and dizziness. Irritating to skin, eyes and respiratory tract.
Primary Routes of Exposure: Ingestion, skin, inhalation
Eye Contact: Causes mild to severe irritation of the eyes.
Skin Contact: Liquid may burst into flame in air causing thermal burns to skin.
Toxic by inhalation. Inhalation may lead to headaches and dizziness. Irritating to nose and mucous
Inhalation:
membranes.
Ingestion: Toxic if swallowed. May cause vomiting and diarrhea.
Acute Health Affects: Toxic 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

---

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.

---

SECTION 5: Fire Fighting Measures
Flash Point: no data
Autoignition Temperature: pyrophoric
Explosion Limits: no data
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 vapors of phosphorus pentoxide.
Decomposion Products:
Material is pyrophoric. May spontaneously ignite if exposed to air, especially when in contact with organic
Unusual Fire or Explosion Hazards:
matter.

---

SECTION 6: Accidental Release Measures
Small spills can be mixed with vermiculite or other suitable adsorbents. Spillage in areas not adequately
Spill and Leak Procedures: ventilated will require an evacuation site. Material may spontaneously ignite. Avoid static electricity.
Emergency response teams will require self-contained breathing apparatus.

---

SECTION 7: Handling and Storage
Handling and Storage: Material must be handled and stored under an inert atmosphere of nitrogen or argon.

---

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.

---

SECTION 9: Physical and Chemical Properties
Color and Form: colorless liquid
Molecular Weight: 90.1
Melting Point: no data
Boiling Point: 54C°
Vapor Pressure: no data
Specific Gravity: 0.7
Odor: intensely pungent odor
Solubility in Water: insoluble

---

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

---

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

---

SECTION 12: Ecological Information
Ecological Information: No information available

---

SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations.

---

SECTION 14: Transportation
Shipping Name (CFR): Pyrophoric liquids, 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): UN# 2845

---

SECTION 15: Regulatory Information
TSCA: Listed in the TSCA inventory
SARA (Title 313): Title compound not listed
Second Ingredient: none

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  叔丁基膦 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以99%的产率得到t-butylphosphine-borane
  参考文献：
  名称：

  Reactions oft-Butylphosphine–Borane with Various Electrophiles and Synthesis of Optically Activet-Butylmethylphosphine–Borane

  摘要：

  对t-丁基磷烷-硼烷与各种电亲核试剂的反应性进行了研究，重点关注烷基化。这种化合物的单烷基化过程顺利进行，产率良好（61-85%）。还合成了二取代衍生物，产率也很好（86-99%）。通过分离中间反式异构体(1S)-内源-2-硼酸酯(t-丁基)甲基磷烷-硼烷，制备了光学活性的t-丁基甲基磷烷-硼烷。

  DOI：

  10.1246/bcsj.75.1359
• 作为产物：
  描述：

  叔丁基(二氟)膦 在 三甲基乙氧基硅烷 作用下， 反应 1.0h， 以65%的产率得到叔丁基膦
  参考文献：
  名称：

  Reaction of tert-butyldifluorophosphine with trimethylethoxysilane

  摘要：

  DOI：

  10.1007/bf00958373
• 作为试剂：
  描述：

  白杨素 在 吡啶 、 4-二甲氨基吡啶 、 叔丁基膦 、 硫酸 、 5%-palladium/activated carbon 、 水 、 氢气 、 palladium diacetate 、 碳酸氢钠 、 potassium carbonate 、 caesium carbonate 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 sodium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 乙腈 、 二乙二醇 为溶剂， 反应 203.82h， 生成 (1R,2R,3S,3aR,8bS)-methyl 6-(dimethylamino)-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1Hbenzo[b]cyclopenta[d]furan-2-carboxylate
  参考文献：
  名称：

  合成Silvestrol类似物作为有效的和选择性的蛋白质合成抑制剂

  摘要：

  蛋白质翻译失调在人类癌症发病机理的许多层面上都起着至关重要的作用。西尔维斯托尔，环戊达[ b]苯并呋喃天然产物通过干扰eIF4F翻译复合物的组装，在起始步骤阻止翻译。Silvestrol具有复杂的化学结构，其官能团的要求尚未得到系统的研究。而且，由于药物样性质差，silvestrol具有有限的发展潜力。在本文中，我们寻求开发Silvestrol关键中间体的实用合成方法，并探索C6位置周围的构效关系。相对于简单的5'UTR，silvestrol和类似物选择性抑制蛋白质翻译的能力（相对于简单的5'UTR，对翻译起始机制（即复杂的5'-非翻译区UTR）有很高的要求）。Silvestrol的简化类似物，例如化合物74与silvestrol相比，它们中的76种和76种具有相似的细胞毒性作用和更好的ADME特性。

  DOI：

  10.1021/jm3011542

文献信息

• 碳水化合物单膦、它们的制备方法和用途
  申请人：东莞市均成高新材料有限公司

  公开号：CN111018923A

  公开（公告）日：2020-04-17

  本发明提供具有通式Ia、Ib、IIa或IIb的碳水化合物单膦，包括磷原子构型不同的Ia和Ib的混合物或者磷原子构型不同的IIa和IIb的混合物，和它们的制备方法；本发明描述了碳水化合物单膦的硼烷加合物、氧化物、硫化物或硒化物；此外，本发明还提供了碳水化合物单膦配位的钯络合物；碳水化合物单膦与钯盐或络合物组成的催化体系、或碳水化合物单膦配位的钯络合物在催化有机反应中的用途亦是本发明的一部分，特别是在催化（拟）卤代芳烃去形成新的C‑C、或C‑N键的偶联反应中的用途。
• Exploring the Reactivity of Donor-Stabilized Phosphenium Cations: Lewis Acid-Catalyzed Reduction of Chlorophosphanes by Silanes
  作者：Kyle G. Pearce、Andryj M. Borys、Ewan R. Clark、Helena J. Shepherd

  DOI：10.1021/acs.inorgchem.8b01578

  日期：2018.9.17

  Phosphane-stabilized phosphenium cations react with silanes to effect either reduction to primary or secondary phosphanes, or formation of P–P bonded species depending upon counteranion. This operates for in situ generated phosphenium cations, allowing catalytic reduction of P(III)–Cl bonds in the absence of strong reducing agents. Anion and substituent dependence studies have allowed insight into

  磷稳定的阳离子与硅烷反应，以还原为伯或仲膦，或形成P–P键合物种（取决于抗衡阴离子）。这适用于原位生成的阳离子，可在没有强还原剂的情况下催化还原P（III）-Cl键。阴离子和取代基依赖性研究已使人们深入了解了所涉及的竞争机制。
• Practical P-Chiral Phosphane Ligand for Rh-Catalyzed Asymmetric Hydrogenation
  作者：Duan Liu、Xumu Zhang

  DOI：10.1002/ejoc.200400690

  日期：2005.2

  conformationally rigid P-chiral bis(trialkylphospholane) ligand 2 (DuanPhos) has been prepared in both enantiomeric forms through a concise syn-thesis. Rh-2 complex has exhibited remarkably high enantio-selectivities (up to >99% ee) and reactivities (up to 10,000 TON) for the hydrogenation of a wide variety of functionalized prochiral alkenes (5 different types), which provides a very practical catalytic system

  已经通过简洁的合成以两种对映体形式制备了高度供电子和构象刚性 P-手性双（三烷基磷烷）配体 2 (DuanPhos)。Rh-2 络合物对多种官能化前手性烯烃（5 种不同类型）的氢化表现出非常高的对映选择性（高达 99% ee）和反应性（高达 10,000 吨），提供了一种非常实用的催化用于制备各种合成有用的手性化合物的系统。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Laser‐induced homoepitaxy of GaP
  作者：R. Solanki、U. Sudarsan、J. C. Johnson

  DOI：10.1063/1.99273

  日期：1988.3.14

  Laser‐induced pyrolytic process is utilized to ‘‘direct write’’ epitaxial GaP structures. The precursors used were trimethylgallium and tertiarybutylphosphine, a new phosphorus donor. Dependence of the epitaxial growth on several deposition parameters is examined.

  激光诱导热解工艺用于“直接写入”外延 GaP 结构。使用的前体是三甲基镓和叔丁基膦，一种新的磷供体。检查了外延生长对几个沉积参数的依赖性。
• BISPHOSPHONIUM SALT AND PROCESS FOR PRODUCING THE SAME
  申请人：——

  公开号：US20040138504A1

  公开（公告）日：2004-07-15

  A bis-phosphonium salt represented by the following formula (1) is provided: 1 wherein R 1 , R 2 , R 3 , and R 4 each represent a linear or branched alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group; A represents an alkylene group; Y represents an anion; R 1 and R 2 may form a ring; R 3 and R 4 may form a ring; and R 1 , R 2 , R 3 , and R 4 may be the same or different. A process for producing such a bis-phosphonium salt includes a step of allowing a first secondary phosphine and second secondary phosphine to react with a compound in an alcohol solvent selected from a secondary alcohol and tertiary alcohol. The compound is represented by the following formula (5): Y—A—Y  (5)

  提供以下式（1）所代表的双磷銨鹽：其中R1、R2、R3和R4分别代表直链或支链烷基、环烷基、芳基或芳基烷基；A代表烷基；Y代表阴离子；R1和R2可以形成环；R3和R4可以形成环；R1、R2、R3和R4可以相同也可以不同。制备这种双磷銨鹽的方法包括让第一次二级膦和第二次二级膦在选择自二级醇和三级醇的醇溶剂中与以下式（5）所代表的化合物反应的步骤：Y—A—Y（5）。