1,1'-dibromoferrocene | 1293-65-8

• 物质功能分类: 有机原料 - 有机金属类化合物 - 有机铁
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 1,1'-dibromoferrocene
• 英文别名: 1,1′-dibromoferrocene；1,1’-dibromoferrocene；dibromoferrocene；2-Bromocyclopenta-1,3-diene;iron(2+)；2-bromocyclopenta-1,3-diene;iron(2+)
• CAS: 1293-65-8
• 化学式: C₁₀H₈Br₂Fe
• 分子量: 343.829
• InChiKey: ANUJXWUVZHMJDL-UHFFFAOYSA-N

物化性质

• 熔点：
  52-55 °C
• 溶解度：
  溶于甲醇
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，没有已知的危险反应。请避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• TSCA：
  No
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29319090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将贮藏器密封保存，并存放在阴凉干燥处。同时，确保工作环境具有良好的通风或排气设施。

SDS

1,1'-Dibromoferrocene Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 1,1'-Dibromoferrocene

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 1,1'-Dibromoferrocene
Percent: >98.0%(LC)(T)
CAS Number: 1293-65-8
Chemical Formula: C10H8Br2Fe

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
1,1'-Dibromoferrocene

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a refrigerator.
Store away from incompatible materials such as oxidizing agents.
Heat-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Protective gloves.
Hand protection:
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
Reddish yellow - Deep yellow red
Colour:
1,1'-Dibromoferrocene

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents]
Soluble: Methanol

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Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Chemical stability:
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Hydrogen bromide
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
No data available
Crustacea:
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
No data available
Henry's Law
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
1,1'-Dibromoferrocene

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

1,1'-二溴二茂铁主要用作有机合成中的中间体。

反应信息

• 作为反应物：
  描述：

  1,1'-dibromoferrocene 在 n-BuLi 、 CuCN 、 oxygen 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到dibromobiferrocene
  参考文献：
  名称：

  含杂原子的混合价二茂钛鎓盐中的分子内电子转移：制备，结构和57 FeMössbauer特性

  摘要：

  开发了一种方便的新方法来制备1'，1'''-二取代的二茂铁，该二茂铁可以用碘氧化成一系列新的混合价化合物。1'，1'''-二甲氧基甲基，1'，1'''-二乙氧基，1'，1'''-二甲基，1'，1'''-二羟甲基，1'，1的X射线结构'''-二苯甲酰氧基甲基，1'，1'''-二甲硫基和1'，1'''-二乙硫基中性二茂铁和混合价1'，1'''-二乙氧基，1'，1''' -二甲基，1'，1'''-二苯甲酰氧基甲基和1'，1'''-二苯硫基二碘化三碘鎓盐已在298 K下测定。温度为57 FeMössbauer实验。

  DOI：

  10.1021/om970746e
• 作为产物：
  描述：

  二茂铁 在 正丁基锂 、 四甲基乙二胺 、 1,2-二溴四氯乙烷 作用下， 以 正己烷 、 四氢呋喃 为溶剂， 反应 32.0h， 以81%的产率得到1,1'-dibromoferrocene
  参考文献：
  名称：

  通过流动化学实现了功能化二茂铁叠氮化物和胺的可扩展合成。

  摘要：

  在流动中已经实现了对官能化的二茂铁基叠氮化物的可扩展访问。通过卤素-锂交换二茂铁基卤化物并用甲苯磺酰基叠氮化物捕集，可以高收率获得各种官能化的二茂铁基叠氮化物。为使这些潜在爆炸性化合物的制备规模可扩展，开发了一种流动方案，可将反应时间缩短至数分钟，并避免潜在危险中间体的积累。然后通过可靠的还原方法制备相应的二茂铁胺。

  DOI：

  10.1021/acs.orglett.9b04450

文献信息

• Iodoferrocene as a partner in<i>N</i>-arylation of amides
  作者：Lingaswamy Kadari、William Erb、Thierry Roisnel、Palakodety Radha Krishna、Florence Mongin

  DOI：10.1039/d0nj03470c

  日期：——

  Optimization of the reaction was first performed from acetamide on the basis of the achievements in the benzene series. Next, the identified conditions (use of copper(I) iodide, N,N′-dimethylethylenediamine, tripotassium phosphate in dioxane at 90 °C for 14 h) were applied to different aliphatic/aromatic primary and cyclic/acyclic secondary amides in order to determine the scope of the reaction, thus easily

  在这项研究中，我们开发了一个方便的方法ñ各种乙酰胺，苯酰胺和iodoferrocene相关化合物的-arylation。首先根据乙苯系列的成果，从乙酰胺进行反应的优化。接下来，将确定的条件（在二恶烷中于90°C下使用碘化铜（I），N，N'-二甲基乙二胺，磷酸三钾14小时）以用于不同的脂族/芳族伯酰胺和环状/无环仲酰胺。确定反应的范围，从而容易生成小的二茂铁酰胺库。
• (Spectro)electrochemical investigations on (ferrocenyl)thiophenes modified by tungsten Fischer carbenes
  作者：Belinda van der Westhuizen、J. Matthäus Speck、Marcus Korb、Daniela I. Bezuidenhout、Heinrich Lang

  DOI：10.1016/j.jorganchem.2014.08.025

  日期：2014.12

  A series of thiophene tungsten Fischer carbene complexes of type [(CO)5W=C(OMe)R] (1, R = 2-Th; 4, R = fcthFc) and [(CO)5W=C(OMe)-R′-(OMe)C=W(CO)5] (2, R′ = th; 5, R′ = fcthfc) was synthesized for investigating low energy charge transfer interactions between the carbene substituents and the transition metal carbonyl fragment incorporating the thiophene heterocyclic system (Th = Thienyl; th = 2,5-thiendiyl;

  [（CO）5 W = C（OMe）R]（1，R = 2-Th; 4，R = fcthFc）和[（CO）5 W = C（OMe） -R'-（OMe）C = W（CO）5 ]（2，R'= th; 5，R'= fcthfc）合成用于研究卡宾取代基与掺入过渡金属羰基片段之间的低能电荷转移相互作用噻吩杂环系统（Th =噻吩基； th = 2,5-噻吩二基； Fc =二茂铁基； fc = 1,1'-二茂铁基）。电化学调查进行了这些配合物得到仔细洞察的电子性质1，2，4和5。对于所有金属卡宾配合物中的卡宾还原本身和羰基钨氧化过程，可以发现典型的电极反应。然而，对于复杂的噻吩2 2分离良好的观察单电子还原的事件，这表明该费卡宾部分的相互作用在2 - ，在噻吩桥。还观察到配合物4和5中二茂铁基部分的可逆单电子氧化还原事件。在UV-Vis-NIR光谱电化学研究期间，混合价α，α的典型低能量吸收发现这两种配合物
• Synthesis, crystal structures, electrochemical properties, and complexation of ferrocene-based compounds: 1,2-bis(dimethyldithiocarbamate)ferrocene and 1,2-bis(benzothiazol-2-ylthio)ferrocene
  作者：Ryo Horikoshi、Ryo Sumitani、Tomoyuki Mochida

  DOI：10.1016/j.jorganchem.2019.120928

  日期：2019.11

  Ferrocene-based metalloligands have various applications in material sciences due to their stability in air and redox active properties. Two ferrocene-based compounds, 1,2-bis(dimethyldithiocarbamate)ferrocene (1) and 1,2-bis(benzothiazol-2-ylthio)ferrocene (2), were synthesized from 1,1′-dibromoferrocene and the corresponding disulfides via two steps. The reaction of 1 with PdCl2(PhCN)2 formed a 1:1

  基于二茂铁的金属配体由于其在空气中的稳定性和氧化还原活性特性而在材料科学中具有多种应用。由1,1'-二溴二茂铁和相应的二硫化物通过1'-二溴二茂铁合成了两种基于二茂铁的化合物1,2-双（二甲基二硫代氨基甲酸酯）二茂铁（1）和1,2-双（苯并噻唑-2-基硫基）二茂铁（2）。两步。1与PdCl 2（PhCN）2的反应形成1：1金属：配体络合物[PdCl 2（1）]。化合物1，2，和[的PdCl 2（1）]通过单晶X射线衍射进行结构表征，并通过循环伏安法测量其氧化还原电位。通过从乙醇重结晶获得两种假多晶型物，即乙醇溶剂化的1（C 2 H 5 OH）0.33和非溶剂化的1。[PdCl 2（1）]的X射线结构表明，Pd（II）中心被两个硫代酮硫原子螯合了1个。图1在0.17和0.41 V（vs. Fe（Cp）2 / Fe（Cp）2 +），分别对应于两个取代基和二茂铁的氧化。相反地​​，2 在二价茂铁部分显示出在E
• Diastereoselective Synthesis of P‐Chirogenic and Atropisomeric 2,2′‐Bisphosphino‐1,1′‐binaphthyls Enabled by Internal Phosphine Oxide Directing Groups
  作者：Qingquan Xue、Shangfei Huo、Tingyi Wang、Zeming Wang、Jianli Li、Meifang Zhu、Weiwei Zuo

  DOI：10.1002/anie.202001561

  日期：2020.5.18

  Diphosphine ligands that merge both axial and P‐centered chirality may exhibit superior or unique properties. Herein we report the diastereoselective introduction of P‐centered chirality at the 2‐position of the axially chiral 2′‐(phosphine oxide)‐1,1′‐binaphthyl scaffold. A lithium–bromide exchange reaction of a 2‐bromo‐2′‐(phosphine oxide)‐1,1′‐binaphthyl and treatment with dichlorophosphines followed

  兼具轴向和P中心手性的二膦配体可能表现出优异的或独特的性能。在此，我们报道了在轴向手性2'-（氧化膦）-1,1'-联萘骨架的2位上非中心选择性引入P-中心手性。2-溴2'-（氧化膦）-1,1'-联萘的溴化锂交换反应并用二氯膦处理，然后用亲核有机金属试剂处理，得到不对称的2-膦-2'-（氧化膦）-具有双萘基轴向手性的1,1'-萘基和一个或两个带有多个P取代基的磷立体中心。最终的非对映异构纯的2,2'-双膦基-1,1'-联萘基是通过氧化膦直接基团的还原而获得的。
• Kinetic Resolution of Planar-Chiral Ferrocenylphosphine Derivatives by Molybdenum-Catalyzed Asymmetric Ring-Closing Metathesis and Their Application in Asymmetric Catalysis
  作者：Masamichi Ogasawara、Sachie Arae、Susumu Watanabe、Kiyohiko Nakajima、Tamotsu Takahashi

  DOI：10.1021/acscatal.5b02692

  日期：2016.2.5

  preparing planar-chiral ferrocenylphosphines by catalytic asymmetric reactions. The single-enantiomer planar-chiral ferrocenylphosphines were applied as chiral ligands in the rhodium-catalyzed asymmetric 1,4-addition reaction (the Hayashi–Miyaura conjugate addition reaction) of phenylboronic acid to 2-cyclohexenone to show excellent enantioselectivity and high yields. The NMR studies clarified that

  外消旋平面-手性金属茂基膦硫化物的高对映选择性动力学拆分是通过钼与k rel催化的不对称闭环复分解反应实现的如此获得的对映体富集的1,4-丁-2-烯基桥联的二茂铁膦膦硫化物可通过从热甲醇中简单重结晶而纯化成对映体纯形式，随后还原膦膦提供相应的平面-保留对映异构体同质性的手性膦。这是通过催化不对称反应制备平面手性二茂铁基膦的罕见例子。单对映体平面手性二茂铁基膦被用作手性配体，用于苯基硼酸向2-环己烯酮的铑催化的不对称1,4-加成反应（Hayashi-Miyaura共轭加成反应），表现出出色的对映选择性和高收率。