氯[2-二环己基(2',4',6'-三异丙基联苯基)膦]金(I) | 854045-94-6

• 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: 氯[2-二环己基(2',4',6'-三异丙基联苯基)膦]金(I)
• 中文别名: 氯[2-二环己基(2′,4′,6′-三异丙基联苯基)膦]金(I)
• 英文名称: XPhosAuCl
• 英文别名: dicyclohexyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane;gold(1+);chloride
• CAS: 854045-94-6
• 化学式: C₃₃H₄₉AuClP
• 分子量: 709.145
• InChiKey: AFVLNRJUCUDBHP-UHFFFAOYSA-M

物化性质

• 熔点：
  243-250 °C

计算性质

• 辛醇/水分配系数(LogP)：
  11.18
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 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：
  室温

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: Chloro[2-dicyclohexyl(2′,4′,6′-
Product name
trisopropylbiphenyl)phosphine]gold(I)
CAS-No. : 854045-94-6

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
: 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl gold(I) chloride
Synonyms
Formula : C33H49AuClP
Molecular Weight : 709,14 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Oxides of phosphorus, Hydrogen chloride gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Air, light, and moisture sensitive. Handle and store under inert gas.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 243 - 250 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
resulting from handling or from contact with the above product. See reverse side of invoice or packing
slip for additional terms and conditions of sale.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  氯[2-二环己基(2',4',6'-三异丙基联苯基)膦]金(I) 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  金和钯介导的双金属催化：通过隔离有机金（I）中间体的机理研究。

  摘要：

  基于Au-Pd的催化系统是独特的一对，这归因于Au的嗜碳路易斯酸度和Pd的氧化还原特性。为了深入了解这对双金属材料，进行了合成和机械研究。作为关键底物，使用乙酰胺（N-炔基烯丙氧基氨基甲酸酯和N-炔基乙氧基氨基甲酸酯）。机械部分必不可少的是有机金（I）中间体的分离，以验证所提出的机理。总共合成了18个多取代的恶唑酮和12个有机金（I）配合物。

  DOI：

  10.1021/acscatal.9b02275
• 作为产物：
  描述：

  (tetrahydrothiophene)gold(I) chloride 、 2-二环己基磷-2,4,6-三异丙基联苯 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 氯[2-二环己基(2',4',6'-三异丙基联苯基)膦]金(I)
  参考文献：
  名称：

  人血清白蛋白传递的[Au（PEt3）] +是T细胞增殖的有效抑制剂。

  摘要：

  使用模块化库格式结合细胞生存力（MTS）和流式细胞术分析，研究了90种阳离子复合物[AuPL] n +（P =膦配体； L =硫脲衍生物或氯化物）在CD8 + T淋巴细胞中的抗增殖活性。化合物的活性与膦配体的空间体积有关。硫脲是一个离去基团，很容易被半胱氨酸巯基取代（NMR，ESI-MS）。利用选择性硫脲配体交换，化合物1和2中的[Au（PEt3）] +和[Au（JohnPhos）] +（JohnPhos = 1,1'-联苯-2-基）二叔丁基膦的片段将其转移至重组人血清白蛋白（rHSA）。PEt3促进了HSA（HSA-1）中Cys34的有效修饰，而使用庞大的JohnPhos作为载体配体会导致血清蛋白被多个金加合物（HSA-2）进行非特异性修饰（Ellman检验，ESI-TOF MS）。HSA-1（而不是HSA-2）以纳摩尔剂量强烈抑制T细胞增殖。讨论了HSA作为递送载体在基于黄金的自身免疫性疾病治疗中的潜在作用。

  DOI：

  10.1021/acsmedchemlett.7b00142
• 作为试剂：
  描述：

  1-乙炔基-2-氟苯 、 咔唑 在 氯[2-二环己基(2',4',6'-三异丙基联苯基)膦]金(I) 、 四(3,5-二(三氟甲基)苯基)硼酸钠 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以70%的产率得到9-(1-(2-fluorophenyl)vinyl)-9H-carbazole
  参考文献：
  名称：

  金催化炔烃的咔唑化反应。

  摘要：

  在本文中，我们报道了炔烃与咔唑的Au（I）催化反应，该反应能够一步合成乙烯基咔唑，而乙烯基咔唑是用作光致发光材料的重要分子。该反应在室温下在温和条件下进行，不需要外部碱，并且可用于单加氢胺化和多加氢胺化反应中的各种芳族和脂族炔烃。我们以乙烯基咔唑产品的光物理研究作为结束，该产品具有独特的荧光特性。

  DOI：

  10.1021/acs.orglett.0c01719

文献信息

• A Gold Carbene Manifold to Prepare Fused γ-Lactams by Oxidative Cyclisation of Ynamides
  作者：Fernando Sánchez-Cantalejo、Joshua D. Priest、Paul W. Davies

  DOI：10.1002/chem.201804378

  日期：2018.11.22

  in γ‐lactam synthesis but are limited by preferential over‐oxidation to form α‐keto imides. Evaluating the factors that might limit N‐cyclisation pathways led to effective gold‐catalysed conditions that allow access to different fused γ‐lactams on changing the ynamide N‐substituent and accommodate previously incompatible substitution patterns. New and efficient methods for the synthesis of functionalised

  金催化的炔酰胺氧化环化反应在γ-内酰胺合成中具有广阔的前景，但受到优先过度氧化形成α-酮酰亚胺的限制。评估可能限制N环化途径的因素导致了有效的金催化条件，允许在改变 ynamide N取代基时获得不同的稠合 γ-内酰胺，并适应以前不相容的取代模式。提出了合成功能化 3-芳基吲哚和环庚[c]吡咯-1-酮衍生物的新且有效的方法。这些条件说明了金催化与其他金属的互补性。
• Gold Catalyzed Synthesis of Substituted Furan by Intermolecular Cascade Reaction of Propargyl Alcohol and Alkyne
  作者：Seyedmorteza Hosseyni、Yijin Su、Xiaodong Shi

  DOI：10.1021/acs.orglett.5b02980

  日期：2015.12.18

  Using a combination of triazole-gold (TA-Au) and copper catalysts, the substituted furan was achieved in one pot through a three-step reaction cascade. The reaction tolerates a large substrate scope with simple starting materials. The desired di-, tri-, and tetrasubstituted furans were prepared in good to excellent yields.

  使用三唑金（TA-Au）和铜催化剂的组合，通过三步反应级联，在一个反应​​釜中获得了取代的呋喃。该反应用简单的起始原料就可耐受大范围的底物。所需的二，三和四取代的呋喃以良好至优异的产率制备。
• Cyclization of Gold Acetylides: Synthesis of Vinyl Sulfonates via Gold Vinylidene Complexes
  作者：Janina Bucher、Thomas Wurm、Kumara Swamy Nalivela、Matthias Rudolph、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1002/anie.201310280

  日期：2014.4.7

  Differently substituted terminal alkynes that bear sulfonate leaving groups at an appropriate distance were converted in the presence of a propynyl gold(I) precatalyst. After initial formation of a gold acetylide, a cyclization takes place at the β‐carbon atom of this species. Mechanistic studies support a mechanism that is related to that of dual gold‐catalyzed reactions, but for the new substrates

  在丙炔基金（I）预催化剂的存在下，将具有适当距离的磺酸盐离去基团的不同取代的末端炔烃进行了转化。乙炔化金最初形成后，在该物种的β-碳原子上发生环化。机理研究支持一种与双重金催化反应相关的机制，但对于新的底物，仅需一个金原子即可激活底物。形成亚乙烯基金络合物后，它与磺酸盐的离去基团形成紧密的接触离子对，这两个部分的重组产生了乙烯基磺酸盐，这是有价值的目标，可以用作例如交叉偶联反应的前体。
• Synthesis of Polysubstituted Fused Pyrroles by Gold-Catalyzed Cycloisomerization/1,2-Sulfonyl Migration of Yndiamides
  作者：Philip J. Smith、Yubo Jiang、Zixuan Tong、Helena D. Pickford、Kirsten E. Christensen、Jeremy Nugent、Edward A. Anderson

  DOI：10.1021/acs.orglett.1c02360

  日期：2021.8.20

  be achieved using Au(I) catalysis that proceeds at ambient temperature, and a thermally promoted process. The utility of the products is demonstrated by a range of reactions to functionalize the fused pyrrole core.

  炔二酰胺（双 N 取代的炔烃）是氮杂环的宝贵前体。在这里，我们报告了炔基-炔二酰胺的环异构化/1,2-磺酰基迁移以形成四氢吡咯并吡咯，这是前所未有的与药物化学相关的杂环支架。这种耐受官能团的转化可以使用在环境温度下进行的 Au(I) 催化和热促进过程来实现。通过一系列反应来使稠合吡咯核功能化，证明了这些产品的实用性。
• Triazole–gold promoted intermolecular propargyl alcohol addition to alkyne: the reaction cascade toward substituted allenes
  作者：Seyedmorteza Hosseyni、Shengtao Ding、Yijin Su、Novruz G. Akhmedov、Xiaodong Shi

  DOI：10.1039/c5cc08233a

  日期：——

  Gold-catalyzed intermolecular propargyl alcohol addition to alkyne was achieved. Reaction of propargyl alcohol with typical gold catalyst gave almost exclusively hydration product. Triazole gold catalyst (TA-Au) successfully prevented the hydration,...

  实现了金催化的炔烃间分子炔丙醇的加成反应。炔丙醇与典型的金催化剂反应几乎只得到水合产物。三唑金催化剂（TA-Au）成功地防止了水合，...