ALPHA,ALPHA'双(二叔丁基膦)邻二甲苯 | 121954-50-5

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: ALPHA,ALPHA'双(二叔丁基膦)邻二甲苯
• 中文别名: Alpha,Alpha-双(二叔丁基磷氢基)-邻二甲苯；1,2-双(二叔丁基膦甲基)苯
• 英文名称: 1,2-bis[di(t-butyl)phosphinomethyl]benzene
• 英文别名: 1,2-bis(di-tert-butylphosphinomethyl)benzene；dtbpx；DTBPMB；1,2-bis((di-tert-butylphosphanyl)methyl)benzene；1,2-bis(di-tert-butylphosphino)xylene；α,α'-bis(di-t-butylphosphino)-o-xylene；1,2-dtbpmb；ditert-butyl-[[2-(ditert-butylphosphanylmethyl)phenyl]methyl]phosphane
• CAS: 121954-50-5
• 化学式: C₂₄H₄₄P₂
• 分子量: 394.561
• InChiKey: SFCNPIUDAIFHRD-UHFFFAOYSA-N

物化性质

• 熔点：
  59-62°C
• 沸点：
  456.7±38.0 °C(Predicted)
• 稳定性/保质期：

  如果按照规格正确使用和储存，则不会发生分解，且没有已知的危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  保持贮藏器密封，并将其存放在阴凉、干燥处。确保工作环境有良好的通风或排气设施。

SDS

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Section 1: Product Identification
Chemical Name: alpha,alpha'-Bis(di-t-butylphosphino)-o-xylene, min. 97%
CAS Registry Number: 121954-50-5
Formula: C6H4[CH2P(C4H9)2]2
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: 1,2-Bis(di-t-butylphosphinomethyl)benzene

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 121954-50-5 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract. May be harmful if swallowed.
Primary Routes of Exposure: Ingestion, inhalation
Eye Contact: Causes slight to mild irritation of the eyes
Skin Contact: Causes slight to mild irritation of the skin.
Inhalation: Irritating to the nose, mucous membranes and respiratory tract.
Ingestion: No specific information is available 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 the effects of long-term exposure.
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: none
Explosion Limits: none
Extinguishing Medium: carbon dioxide, dry powder or foam
If this material 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.
Decomposion Products:
Unusual Fire or Explosion Hazards: Flammable solid. No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Spill and Leak Procedures: Small spills can be mixed with vermiculite or sodium carbonate and swept up.

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SECTION 7: Handling and Storage
Handling and Storage: Material will degrade on exposure to air. Handle and store under an inert atmosphere of nitrogen or argon.

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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: Material may form a fine dust. If possible, 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: Material may form a fine dust. If possible, 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: white xtl.
Molecular Weight: 394.56
Melting Point: 59-62°
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: no data
Solubility in Water: no data

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SECTION 10: Stability and Reactivity
Stability: air-sensitive solid
Hazardous Polymerization: none
Conditions to Avoid: none
Incompatibility: oxidizing agents, halogens
Decomposition Products: carbon dioxide, carbon monoxide, organic fumes, and phosphorus oxides.

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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): 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): Not reportable under SARA Title 313
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  ALPHA,ALPHA'双(二叔丁基膦)邻二甲苯 以 氘代吡啶 、 乙醚 、 正己烷 为溶剂， 生成
  参考文献：
  名称：

  具有β-Pt-HC键的铂乙基络合物

  摘要：

  质子化与所述复合物非协调酸[PT（η 2 -C 2 H ^ 4）（L-L）] [L-L =（H 11 C ^ 6）2 P（CH 2）2 P（C 6 ħ 11）2，1A，卜吨2 P（CH 2）2 PBU吨2，1B，（H 11 C ^ 6）2 P（CH 2）3 P（C 6 H ^ 11）2，1C，卜吨2 P（CH 2）3 PBU吨2，1D或ö -Bu吨2 PCH 2 ç 6 ħ 4 CH 2 PBU吨2，1E ]和[PTET 2（L-L）]图2a - 2d中，得到一系列阳离子铂（II）配合物3a - 3e，在3a - 3c的情况下采用顺式乙烯/氢化物基态，而在3d和3e中，缺电子的金属中心通过与乙基配体的β-CH键的两个电子，三个中心的胶态相互作用而得以稳定。配合物13由进行了表征1个H，13 C和31 P NMR光谱和用于2D和3D通过单晶X射线晶体学。螯合二膦配体对原子键强度的影响通过NM

  DOI：

  10.1039/dt9920002653
• 作为产物：
  描述：

  二叔丁基氯化膦 、 Grignard reagent of o-xylylene dichloride 以 四氢呋喃 为溶剂， 反应 8.0h， 以55%的产率得到ALPHA,ALPHA'双(二叔丁基膦)邻二甲苯
  参考文献：
  名称：

  Method of manufacturing phosphine compound

  摘要：

  一种制备通式（R3—C）2P—L1—X—L2—P—（C—R3）2的化合物（I）的方法，其中R独立地是一个吊挂的、可选择取代的有机基团，通过该基团与三级碳原子C相连；L1和L2分别是选择自可选择取代的较低烷基链连接到X基团的磷原子的连接基团，X是一个桥接基团，包括一个可选择取代的芳基部分，磷原子与相邻的碳原子连接；包括：（i）将通式为A—L1—X—L2—A的化合物（II）与金属M在适当的溶剂中反应，形成中间化合物（III）的步骤：A—M—L1—X—L2—M—A；（ii）将所述中间化合物（III）与通式为（R3—C）2P—A1的化合物（IV）反应，其中A1是一种卤素原子，可以与A相同也可以不同，形成所述的化合物（I）。

  公开号：

  US06335471B1
• 作为试剂：
  描述：

  4-溴-1,2-亚甲二氧基苯 在 三氟甲磺酸 、 palladium diacetate 、 magnesium 、 lithium chloride 、 ALPHA,ALPHA'双(二叔丁基膦)邻二甲苯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.83h， 生成 5-(1-(heptylthio)propyl)benzo[d][1,3]dioxole
  参考文献：
  名称：

  钯催化烯丙基芳烃的串联异构化/氢硫醇化

  摘要：

  本文中，我们报告了由原位生成的氢化钯促进的烯丙基苯的串联烯烃迁移/氢硫基化。由乙酸钯和二齿配体dtbpx（1,2-双（二叔丁基膦基甲基）苯组成的催化剂体系在催化量的三氟甲磺酸存在下导致了串联转化，提供了苄基硫醚，该反应具有较高的区域选择性催化剂的坚固性通过与配位硫醇的反应得以体现。

  DOI：

  10.1021/acs.orglett.9b00504

文献信息

• Homogeneous Palladium-Catalyzed Transfer Hydrogenolysis of Benzylic Alcohols Using Formic Acid as Reductant
  作者：Benjamin Ciszek、Ivana Fleischer

  DOI：10.1002/chem.201801466

  日期：2018.8.22

  We report the first homogeneous palladium‐based transfer hydrogenolysis of benzylic alcohols using an in situ formed palladium‐phosphine complex and formic acid as reducing agent. The reaction requires a catalyst loading as low as only 1 mol % of palladium and just a slight excess of reductant to obtain the deoxygenated alkylarenes in good to excellent yields. Besides demonstrating the broad applicability

  我们报道了使用原位形成的钯膦配合物和甲酸作为还原剂的苄基醇的第一个基于钯的均相钯转移氢解反应。该反应需要低至仅1mol％的钯的催化剂负载和仅略微过量的还原剂以良好至优异的产率获得脱氧的烷基芳烃。除了证明其广泛适用于伯，仲和叔苄醇外，还可以鉴定出一种反应中间体。另外，可以证明所施加的膦配体的部分氧化对于反应过程是有益的，大概是通过稳定活性催化剂。使用反应曲线和催化剂中毒实验来表征催化剂，
• PALLADIUM CATALYST SYSTEM COMPRISING ZWITTERION AND/OR ACID-FUNCTIONALYZED IONIC LIQUID
  申请人：Riisager Anders

  公开号：US20110065950A1

  公开（公告）日：2011-03-17

  The present invention concerns a catalyst system in particular a catalyst system comprising Palladium (Pd), a zwitterion and/or an acid-functionalized ionic liquid, and one or more phosphine ligands, wherein the Pd catalyst can be provided by a complex precursor, such as Pd(CH 3 COO) 2 , PdCl 2 , Pd(CH 3 COCHCOCH 3 ), Pd(CF 3 COO) 2 , Pd(PPh 3 ) 4 or Pd 2 (dibenzylideneacetone) 3 . Such catalyst systems can be used for e.g. alkoxycarbonylation reactions, carboxylation reactions, and/or in a co-polymerization reaction, e.g. in the production of methyl propionate and/or propanoic acid, optionally in processes forming methyl methacrylate and/or methacrylic acid. Catalyst systems according to the invention are suitable for reactions forming separable product and catalyst phases and supported ionic liquid phase SILP applications.

  本发明涉及一种催化剂体系，特别是包括钯（Pd）、一个伪离子和/或酸功能化离子液体，以及一个或多个膦配体的催化剂体系，其中Pd催化剂可以由复合前体提供，例如Pd(CH3COO)2、PdCl2、Pd(CH3COCHCOCH3)、Pd(CF3COO)2、Pd(PPh3)4或Pd2(dibenzylideneacetone)3。这种催化剂体系可用于例如烷氧羰基化反应、羧化反应和/或在共聚反应中，例如在生产甲基丙酸丙酯和/或丙酸中，可选地在形成甲基丙烯酸甲酯和/或甲基丙烯酸的过程中。根据本发明的催化剂体系适用于形成可分离产品和催化剂相以及支持的离子液体相SILP应用的反应。
• [EN] PROCESS FOR PREPARING MONO AND DICARBOXYLIC ACIDS<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ACIDES MONO ET DICARBOXYLIQUES
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2017135898A1

  公开（公告）日：2017-08-10

  The present application relates to a process for preparing a dicarboxylic acid or dicarboxylic ester according to general formula (IV) R1OOC-(CH2)m-CH2CH2-(CH2)y-COOR4 (IV), comprising the steps of subjecting alkenoic acid or alkenoate of formula (II) R1OOC-(CH2)m-CH=CH-(CH2)x-H (II) to a metathesis reaction in the presence of a metathesis catalyst to form a longer-chain alkenoic acid or alkenoate of formula (III) R1OOC-(CH2)m-CH=CH-(CH2)y-H (III) where x

  本申请涉及一种根据通式（IV）R1OOC-(CH2)m- -( )y-COOR4（IV）制备二羧酸或二羧酸酯的方法，包括以下步骤：将通式（II）R1OOC-( )m-CH=CH-( )x-H（II）的烯酸或烯酸酯在存在烯烃交换催化剂的情况下进行交换反应，形成通式（III）R1OOC-( )m-CH=CH-( )y-H（III）的长链烯酸或烯酸酯，其中x羧酸酯、醚或醇的方法。
• A Comprehensive Mechanistic Picture of the Isomerizing Alkoxycarbonylation of Plant Oils
  作者：Philipp Roesle、Lucia Caporaso、Manuel Schnitte、Verena Goldbach、Luigi Cavallo、Stefan Mecking

  DOI：10.1021/ja508447d

  日期：2014.12.3

  olefin substrates, but virtually no effect of the double bond position within the substrate. Compared to higher olefins, ethylene carbonylation under identical conditions is much faster, likely due not just to the occurrence of reactive linear acyls exclusively but also to an intrinsically favorable insertion reactivity of the olefin. The alcoholysis reaction is slowed down for higher alcohols, evidenced

  对异构化烷氧基羰基化的整个催化循环的理论研究表明，二膦配位的 Pd 中心周围的空间拥挤是选择性和生产率的决定性因素。异构化的能量分布对于可变空间体积的二膦是平坦的，但是对于空间要求高的二膦更倾向于形成直链 Pd-烷基物种。对于所有研究的 Pd-烷基物质，CO 插入是可行和可逆的，并且受二膦影响很小。与最高能量屏障相关的总体限速步骤是 Pd-酰基物质的甲醇分解。考虑到线性 Pd-酰基物质的甲醇分解，其能量势垒在所有研究的 Pd-酰基物质中最低，计算出的势垒对于更拥挤的二膦更低。计算表明，对于体积更大的二膦，线性与支化 Pd-酰基的甲醇分解能量差异更为明显，这是由于在过渡态中涉及不同数量的甲醇分子。在压力反应器条件下的实验研究表明，较短链烯烃底物的转化速度更快，但底物内的双键位置几乎没有影响。与高级烯烃相比，相同条件下的乙烯羰基化速度要快得多，这可能不仅是由于反应性线性酰基的出现，而且还因为烯
• PLATINUM COMPLEXES HAVING BENZYL-BASED DIPHOSPHINE LIGANDS FOR THE CATALYSIS OF THE ALKOXYCARBONYLATION OF ETHYLENICALLY UNSATURATED COMPOUNDS
  申请人：EVONIK OPERATIONS GMBH

  公开号：US20210299645A1

  公开（公告）日：2021-09-30

  Platinum complexes having benzyl-based diphosphine ligands for the catalysis of the alkoxycarbonylation of ethylenically unsaturated compounds.

  具有苄基二膦配体的铂配合物用于催化乙烯不饱和化合物的羧酸醇酯化反应。