1,1'-二乙基二茂铁 | 1273-97-8

• 物质功能分类: 催化剂及助剂 - 贵金属催化剂
• 分子结构分类: 有机化合物 - 碳氢化合物 - 芳香烃
• 中文名称: 1,1'-二乙基二茂铁
• 中文别名: 二乙基二茂铁；双乙基二茂铁；1,1’-二乙基二茂铁
• 英文名称: 1,1'-diethylferrocene
• 英文别名: Ferrocene, 1,1'-diethyl-；1-ethylcyclopenta-1,3-diene;iron(2+)
• CAS: 1273-97-8
• 化学式: C₁₄H₁₈Fe
• 分子量: 242.144
• InChiKey: CJCVWCLJWGEOOG-UHFFFAOYSA-N

物化性质

• 沸点：
  284 °C(lit.)
• 密度：
  1.18 g/mL at 25 °C(lit.)
• 闪点：
  230 °F
• 稳定性/保质期：

  如果按照规格使用和储存，则不会发生分解，目前没有已知的危险反应，应避免与氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  T
• WGK Germany：
  3
• RTECS号：
  YT9000000
• 海关编码：
  2931900090
• 危险类别：
  6.1
• 安全说明：
  S24/25
• 危险类别码：
  R25
• 包装等级：
  II
• 危险品运输编号：
  UN 2811 6.1/PG 2
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  请将贮藏器密封，并存放在阴凉、干燥处。确保工作区域有良好的通风或排气设施。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
: 1,1′-Diethylferrocene
Product name
CAS-No. : 1273-97-8

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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.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C14H18Fe
Molecular Weight : 242,14 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, Iron oxides
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 breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
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
Normal measures for preventive fire protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Handle and store under inert gas. Air sensitive. Moisture sensitive.
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
impervious clothing, 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 not required. For nuisance exposures use type OV/AG (US) or type ABEK
(EU EN 14387) respirator cartridges. 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: liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 284 °C - lit.
boiling range
g) Flash point 110 °C - closed cup
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 1,18 g/mL at 25 °C
n) Water solubility insoluble
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
Air Avoid moisture.
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
no data available
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
no data available
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
and is applicable to the product with regard to appropriate safety precautions. It does not represent any

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：1,1'-二乙基二茂铁可用作有机合成，在实验室研发和化工医药合成过程中发挥重要作用。

反应信息

• 作为反应物：
  描述：

  1,1'-二乙基二茂铁 在 1,4-二氧六环 、 氧气 、 苯甲酸 作用下， 以 1,4-二氧六环 、 甲苯 、 叔丁醇 为溶剂， 生成 (EtCp₎₂Fe⁺
  参考文献：
  名称：

  Specific Features of the Oxidation of Ferrocenylacetic Acid and 1,1'-Diethylferrocene with Molecular Oxygen in Organic Solvents

  摘要：

  DOI：

  10.1023/b:rugc.0000016043.25718.0a
• 作为产物：
  描述：

  1,1'-diacetylferrocene 在 Zn 、 HCl 作用下， 以50%的产率得到1,1'-二乙基二茂铁
  参考文献：
  名称：

  一些二茂铁衍生物的热力学和分子动力学

  摘要：

  采用低温绝热量热法在5~300 K范围内研究了乙酰二茂铁、1,1'-二乙酰二茂铁和1,1'-二乙基二茂铁的热容并计算了它们的热力学函数。物质的燃烧焓由燃烧量热法测定，其形成的热力学函数由量子化学方法计算。还通过分子力学和分子动力学方法研究了二茂铁衍生物的分子间和分子内相互作用。

  DOI：

  10.1007/bf02494807

文献信息

• Simple reduction of ferrocenyl aldehydes and ketones by sodium boranuide in trifluoroacetic acid: new, efficient, general preparation of alkylferrocenes
  作者：Sukanta Bhattacharyya

  DOI：10.1039/p19960001381

  日期：——

  Alkylferrocenes are obtained in excellent yields by ionic hydrogenation of ferrocenyl aldehydes and ketones using sodium boranuide and trifluoroacetic acid.

  通过使用硼氢化钠和三氟乙酸，对二茂铁基醛和酮进行离子氢化反应，可以以极佳的产率获得烷基二茂铁化合物。
• Efficient regio- and diastereo-controlled synthesis of 1,1′- and 1,1′,2,2′-functionalised ferrocenes and the formation of 2-oxa[3]ferrocenophanes
  作者：Michael A. Carroll、Andrew J. P. White、David A. Widdowson、David J. Williams

  DOI：10.1039/b000833h

  日期：——

  A synthesis of a C2 symmetric 1,1′,2,2′-tetrasubstituted ferrocene system is described. The route involves the reduction of ferrocenyl carbonyl compounds which give access to a range of alcohols, alkenes, alkanes, ethers and 2-oxa[3]ferrocenophanes depending on the precise conditions used.

  描述了一种 C2 对称的 1,1'，2,2' 四取代铁烯系统的合成。该路线涉及对铁烯基羰基化合物的还原，根据使用的具体条件，可获得一系列醇、烯烃、烷烃、醚和 2-氧-3-铁烯甙。
• Ionic Hydrogenation of Acylferrocenes Using Zinc Borohydride:  An Efficient, Mild Method for the Preparation of Alkylferrocenes
  作者：Sukanta Bhattacharyya

  DOI：10.1021/om950751n

  日期：1996.2.6

  An effective mild procedure for the reductive deoxygenation of α-ferrocenyl aldehydes, ketones, and alcohols into the corresponding alkylferrocenes is described using a combination of zinc borohydride and zinc chloride. This is the first example of such reactivity of zinc borohydride. The present method allows the synthesis of alkylferrocenes bearing terminally functionalized pendant chains.

  描述了使用硼氢化锌和氯化锌的组合将α-二茂铁基醛，酮和醇还原脱氧为相应的烷基二茂铁的有效温和程序。这是硼氢化锌的这种反应性的第一个例子。本方法允许合成带有末端官能化的侧链的烷基二茂铁。
• The reactions of acylferrocenes with samarium diiodide: reduction, deoxygenation, reductive coupling and rearrangement
  作者：Shean-Jeng Jong、Jim-Min Fang、Chun-Hsu Lin

  DOI：10.1016/s0022-328x(99)00411-8

  日期：1999.11

  Acylferrocenes reacted with samarium diiodide in the presence of water to give the corresponding (α-hydroxyalkyl)ferrocenes or alkylferrocenes depending on the reaction time and temperature. On treatment with samarium diiodide in the absence of water, ferrocenecarbaldehyde underwent a reductive coupling to give pinacols, whereas acetylferrocene yielded 3,3-diferrocenyl-2-butanone and 2,3-diferrocenyl-2-butene

  在水的存在下，酰基二茂铁与二碘化sa反应生成相应的（α-羟烷基）二茂铁或烷基二茂铁，具体取决于反应时间和温度。在不存在水的情况下用二碘化sa处理时，二茂铁甲醛经还原偶联生成频哪醇，而乙酰基二茂铁经随后的重排和脱氧反应生成3,3-二茂铁基-2-丁酮和2,3-二茂铁基-2-丁烯。
• Highly efficient reduction of ferrocenyl derivatives by borane
  作者：Lucie Routaboul、Jérôme Chiffre、Gilbert G.A. Balavoine、Jean-Claude Daran、Eric Manoury

  DOI：10.1016/s0022-328x(01)00936-6

  日期：2001.12

  Borane, as a DMS or a THF complex, can efficiently reduce a large range of ferrocenyl derivatives (aldehydes, ketones, ethers, acetals, carboxylic acids, esters,…) if they bear at least one oxygen at a carbon at the α position. On the contrary, similar molecules, which contain nitrogen instead of oxygen, do not react with borane.

  硼烷作为DMS或THF络合物，如果它们在α位置的碳原子上带有至少一个氧，则可以有效地还原各种二茂铁基衍生物（醛，酮，醚，缩醛，羧酸，酯等）。相反，含有氮而不是氧的相似分子不会与硼烷反应。