lithium cyclopentadienide | 16733-97-4

• 物质功能分类: 有机原料 - 有机金属类化合物 - 有机锂
• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: lithium cyclopentadienide
• 英文别名: cyclopentadienyl lithium；lithium cyclopentadienyl；CpLi；Cyclopentadienyllithium；lithium;cyclopenta-1,3-diene
• CAS: 16733-97-4
• 化学式: C₅H₅*Li
• 分子量: 72.0357
• InChiKey: DBKDYYFPDRPMPE-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  常温常压下稳定，避免与水分、潮湿、氧化物、酸和空气接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -1.59
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• 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：
  1

安全信息

• 危险等级：
  4.1
• 危险品标志：
  C
• 安全说明：
  S26
• 危险类别码：
  R34
• WGK Germany：
  3
• 危险品运输编号：
  UN 3263 8/PG 2
• 海关编码：
  2902199090
• 包装等级：
  II
• 危险类别：
  4.1
• 危险标志：
  GHS05
• 危险性描述：
  H314
• 危险性防范说明：
  P280,P305 + P351 + P338,P310
• 储存条件：
  常温下应密闭避光、存于通风干燥的环境中，并在惰性气体保护下保存。

SDS

---

Section 1: Product Identification
Chemical Name: Lithium cyclopentadienide, 97%
CAS Registry Number: 16733-97-4
Formula: C5H5Li
EINECS Number: none
Chemical Family: metallocene
Synonym: Cyclopentadienyl lithium

---

Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 16733-97-4 100% no data no data

---

Section 3: Hazards Identification
Dust or vapors are corrosive and may be toxic if inhalaed, swallowed or contacted with the skin. Lithium
Emergency Overview:
compounds are toxic to the central nervous system and may damage kidneys and act as a teratogen.
Primary Routes of Exposure: Ingestion, inhalation, skin, eyes.
Eye Contact: Causes burns to the eyes.
Skin Contact: Causes burns to the skin.
Inhalation: Dust corrosive to mucous membranes and respiratory tract. Vapors may be toxic.
Ingestion: Ingestion may cause burns to the mouth, throat, and esophagus. May be toxic.
Corrosive to skin, eyes and respiratory tract. Ingestion may cause vomiting, diarrhea, kidney injury and central
Acute Health Affects:
nervous system depression.
Chronic effects of exposure to lithium compounds include kidney damage, gastrointestinal disturbances,
Chronic Health Affects:
fatigue, and thyroid damage. May be a teratogen.
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: Unknown
Explosion Limits: Unknown
Extinguishing Medium: dry chemical only.
Fire fighters should be equipped with a NIOSH approved positive pressure self-contained breathing apparatus
Special Fire Fighting Procedures:
and full protective clothing.
Hazardous Combustion and Flammable. If involved in a fire this material may release toxic and corrosive fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: Water liberates cyclopentadiene, a toxic, flammable liquid

---

SECTION 6: Accidental Release Measures
Remove ignition sources. Small spills can be mixed with vermiculite, sodium carbonate or other suitable non
Spill and Leak Procedures:
combustible adsorbent and swept up.

---

SECTION 7: Handling and Storage
Handling and Storage: Handle and store the material under an inert dry atmosphere of nitrogen or argon. Keep away from heat.

---

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. Consult with glove manufacturer to determine the proper type of glove.
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: off-white pwdr.
Molecular Weight: 72.04
Melting Point: no data
Boiling Point: no data
Vapor Pressure: not applicable
Specific Gravity: no data
Odor: Irritating pine oil odor
Solubility in Water: reacts with water

---

SECTION 10: Stability and Reactivity
Stability: air sensitive, moisture sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: Contact with moisture or mineral acids.
Incompatibility: water, alcohols, oxidizers and mineral acids
Decomposition Products: carbon monoxide, carbon dioxide, and lithium hydroxide

---

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

---

SECTION 12: Ecological Information
Ecological Information: No information available

---

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

---

SECTION 14: Transportation
Shipping Name (CFR): Corrosive Solids, N.O.S.
Hazard Class (CFR): 8
Additional Hazard Class (CFR): NA
Packaging Group (CFR): II
UN ID Number (CFR): UN# 1759
Shipping Name (IATA): Corrosive Solid, N.O.S.
Hazard Class (IATA): 8
Additional Hazard Class (IATA): NA
Packaging Group (IATA): II
UN ID Number (IATA): UN# 1759

---

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

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：可用于制备茂金属和环戊二烯基衍生物。

反应信息

• 作为反应物：
  描述：

  lithium cyclopentadienide 在 氨 作用下， 以 四氢呋喃 为溶剂， 生成 [(CpLi)2(NH3)3]
  参考文献：
  名称：

  Unprecedented CpLi Ammoniacates

  摘要：

  CpLi aggregates from ammonia: [(CpLi)(2)(NH3)(3)] (1) contains syn-arranged lithocene with an additional eta(1) coordination of Li(NH3)(3), and[Li(NH3)(4)][Cp](2)features naked Cp anions and [Li(NH3)(4)](+) cations arranged to channel walls generated from cationic meshes.

  DOI：

  10.1021/om100831v
• 作为产物：
  描述：

  环戊二烯 在 正丁基锂 作用下， 以 正己烷 为溶剂， 反应 18.0h， 以78%的产率得到lithium cyclopentadienide
  参考文献：
  名称：

  半夹心复合物FeCl（dppe）Cp *，FeCl（dppe）Cp，RuCl（dppe）Cp *和RuCl（dppe）Cp的优化合成

  摘要：

  由于其合成的多功能性，半夹心金属氯化物的MC1（DPPE）（η 5 -C 5 - [R 5）[M =铁，钌; dppe = 1,2-双（二苯基膦基）乙烷，R = H（环戊二烯，Cp），CH 3（五甲基环戊二烯，Cp *）]是许多有机金属实验室的主要原料。在这里，我们概述了目前可用于FeCl（dppe）Cp *，FeCl（dppe）Cp，RuCl（dppe）Cp *和RuCl（dppe）Cp的合成方法，并详细描述了所有方法的更新和优化的多谱图合成四种化合物。

  DOI：

  10.1071/ch16322
• 作为试剂：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 在 lithium cyclopentadienide 、 lithium bromide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以100%的产率得到3-Brom-3-desoxy-1,2;5,6,-di-O-isopropyliden-α-D-glucofuranose
  参考文献：
  名称：

  Influence of the stereochemistry of sugars on the selectivity of formation of carbohydrate-derived cyclopentadienyl and indenyl ligands

  摘要：

  环戊二烯锂与适当的部分受保护的 α-D-allofuranose triflate（4，葡萄糖 C3 的缩合物）相互作用，除了得到预期的葡萄糖-环戊二烯（5）外，还得到葡萄糖-二取代环戊二烯（6）作为主要产物。α-D-呋喃葡萄糖和其他糖类不会出现这种前所未有的现象，初步解释是 LiCp 与 4 和 5 分子中一个分子的异亚丙基官能团的氧原子发生了络合反应，从而产生了作为模板效应结果的三分子结构。其他实验的结果，如使用 MgCp2 代替 LiCp 或用三酸锂络合氧原子，在很大程度上改变了反应的选择性，有利于单取代产物 5，也支持了这一假设。当茚化锂与 4 反应时，分别生成葡萄糖一取代茚和葡萄糖二取代茚，即 8 和 9，并以几乎完全的非对映选择性得到 9。这一结果也可以通过锂的立体选择性络合得到合理解释，正如单独的实验和分子力学计算所显示的那样。以葡萄糖一取代的 5 环戊二烯和葡萄糖二取代的 6 环戊二烯为原料，合成了甲基三羰基钼（II）配合物，并对其进行了表征。

  DOI：

  10.1039/b517146f

文献信息

• Novel Cyclopentadienyl Tricarbonyl ^99mTc Complexes Containing 1-Piperonylpiperazine Moiety: Potential Imaging Probes for Sigma-1 Receptors
  作者：Xia Wang、Dan Li、Winnie Deuther-Conrad、Jie Lu、Ying Xie、Bing Jia、Mengchao Cui、Jörg Steinbach、Peter Brust、Boli Liu、Hongmei Jia

  DOI：10.1021/jm5009488

  日期：2014.8.28

  We report the design, synthesis, and evaluation of a series of novel cyclopentadienyl tricarbonyl 99mTc complexes as potent σ1 receptor radioligands. Rhenium compounds 3-(4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl)propylcarbonylcyclopentadienyl tricarbonyl rhenium (10a) and 4-(4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl)butylcarbonylcyclopentadienyl tricarbonyl rhenium (10b) possessed high in vitro

  我们报告的设计，合成，以及一系列新颖环戊二烯三羰基的评价99米锝配合物作为有力的σ 1受体的放射性。compounds化合物3-（4-（1,3-苯并二恶唑-5-基甲基）哌嗪-1-基）丙基羰基环戊二烯基三羰基en（10a）和4-（4-（1,3-苯并二恶唑-5-基甲基）哌嗪-1基）三羰基butylcarbonylcyclopentadienyl铼（10B）在体外亲和力具有较高的对σ 1受体和中度到高选择性σ 2受体和囊泡乙酰胆碱转运。小鼠的生物分布研究表明，相应的99m Tc衍生物[ 99m Tc注射后2分钟，Tc] 23和[ 99m Tc] 24分别为2.94和2.13％注射剂量（ID）/ g。氟哌啶醇的预处理显着降低了脑中[ 99m Tc] 23或[ 99m Tc] 24的放射性示踪剂蓄积。对C6和DU145肿瘤细胞中[ 99m Tc] 23的细胞吸收研究表明，与氟哌啶醇，1-（3,4-二
• Crossing Organolithium Compounds with Organolithium Compounds: Molecular Squares and a Cage-Encapsulating Reaction
  作者：Andrew A. Fyfe、Alan R. Kennedy、Jan Klett、Robert E. Mulvey

  DOI：10.1002/anie.201103027

  日期：2011.8.16

  extraordinary crossing reaction involving three popular utility organolithium reagents nBuLi, LiTMP (TMP=2,2,6,6‐tetramethylpiperidide), and LiC5H5 leads to the unexpected deprotonation of C5H5− anions to C5H42− dianions, which was manifested through the trapping of the hexameric nBuLi cage by a [Li(μ‐TMP)Li(μ‐C5H5)}4] molecular square ring (see picture).

  三重交叉：涉及三个流行效用有机锂试剂的非凡交叉反应Ñ丁基锂，LiTMP（TMP = 2,2,6,6-四甲基）和LiC 5 ħ 5所导致C的意外脱质子5 ħ 5 -阴离子ç 5 ħ 4个2-二价阴离子，将其通过六聚体的捕获表现ñ丁基锂笼由[栗（μ-TMP）栗（μ-C 5 H ^ 5）} 4 ]分子方形环（见图）。
• Synthesis and reactivity of five- and six-coordinate hydrido(vinyl) iridium(III) complexes
  作者：Thomas Dirnberger、Helmut Werner

  DOI：10.1016/j.ica.2006.03.020

  日期：2007.3

  Abstract The reaction of the dihydrido iridium(III) precursor [IrH2(Cl)(PiPr3)2] (5) with internal alkynes RC C(CO2Me) (R = Me, CO2Me) afforded the five-coordinate hydrido(vinyl) complexes [IrH(Cl)(E)-C(R) CH(CO2Me)}(PiPr3)2] (6, 7), via insertion of the alkyne into one of the Ir H bonds. Compounds 6 and 7 are also accessible by careful hydrogenation of the alkyne iridium(I) derivatives trans-[IrClRC C(CO2Me)}(PiPr3)2]

  摘要二氢铱（III）前体[IrH2（Cl）（PiPr3）2]（5）与内部炔烃RC C（CO2Me）（R = Me，CO2Me）的反应得到了五配位的氢化（乙烯基）络合物[ IrH（Cl）（E）-C（R）CH（CO2Me）}（PiPr3）2]（6，7），是通过将炔烃插入Ir H键之一来实现的。也可以通过对炔烃铱（I）衍生物反式[[IrCl RC C（CO2Me）}（PiPr3）2]（9、10）进行仔细加氢来获得化合物6和7，后者是由原位生成的反式- [IrCl（C8H14）（PiPr3）2]和RC C（CO2Me）。紫外线6（R = CO2Me）导致形成具有乙烯基的异构体[IrH（Cl）κ2（C，O）-C（CO2Me）CHC（OMe）O}（PiPr3）2]（3）配体以双齿形式配合。当6与乙腈和CO反应生成六配位铱（III）化合物[IrH（Cl）（E）-C（CO2Me）CH（CO2Me）
• Bulky metal aryloxides, arylamides, and sulphur and phosphorus analogues. Part 1. Synthetic and chemical studies of titanium and zirconium aryloxides
  作者：Alan W. Duff、Rose A. Kamarudin、Michael F. Lappert、Reginald J. Norton

  DOI：10.1039/dt9860000489

  日期：——

  complexes are of types [TiCl(OR)2}n] and [Ti(η-C5H5)2(OR)]; the ZrIII complexes are of seven types: [ZrCl2(OR)2] and [Zr(η-C5H5)2(OR)X], with X = OR, Cl, NMe2, OMe, OC(O)NMe2, or N(Ph)C(O)NMe2; the new lithium aryloxides have formula [Li(OR)(OEt2)]n. Most of the results relate to the ligands 2,6-Me2C6H3O–, 2,6-Pri2C6H3O–, 2,6 But2C6H3O–, 4-Me-2,6-But2C6H2O–, 2,4,6-But3C6H2O–, 3,5-But2C6H3O and 2,4-But2C6H3O–

  描述了Ti IV，Ti III，Zr IV和Li的几种芳基氧化物（OR​​）的合成和表征。Ti IV的有八类：[Ti（OR）4 ]，[TiCl 2（OR）2 ]，[TiCl 2（OR）2（thf）2 ]，[Ti（NMe 2）2（OR）2 ]，钛[Ti（OME）2（OR）2 ]，[的TiCl（OR'）（OR）2 ]，[的TiCl（R'）（OR）2 ]和[的TiCl（η-C 5 H ^ 5） （或）2]（R'＝烷基，thf ＝四氢呋喃）；在Ti III复合物的类型[的TiCl（OR）2 } Ñ ]和钛[Ti（η-C 5 H ^ 5）2（OR）]; Zr的III络合物七种类型的：[的ZrCl 2（OR）2 ]和[Zr的（η-C 5 H ^ 5）2（OR）X]，其中X = OR，氯，NME 2，青梅，OC（O ）NMe 2，或N（Ph）C（O）NMe 2；新的芳氧基锂具有式[Li（OR）（OEt
• Amido-tert-butylimido-vanadium(V)-Verbindungen. Darstellung, Reaktionen und ⁵¹V-NMR-spektroskopische Untersuchungen / Amido-tert-butylimidovanadium(V) Compounds. Synthesis, Reactions and ⁵¹V NMR Spectroscopic Studies
  作者：Fritz Preuss、Monika Vogel、Uwe Fischbeck、Jens Pemer、Gerhard Overhoff、Edith Fuchslocher、Frank Tabellion、Barbara Geiger、Gotthelf Wolmershäuser

  DOI：10.1515/znb-2001-1102

  日期：2001.11.1

  amido tert-butylimido-vanadium(V) complexes as well as of the binuclear complexes [μ-NtBu)2V2(NtBu)2Cl2] and [(μ-0)V2(NtBu)2Cp2Cl2] are also described. All compounds obtained have been characterized by 51V NMR spectroscopy. tBuN=V(OMe)3 was investigated by X-ray diffraction analysis; the molecular structure has been found to be that of a binuclear vanadium(V) complex with two bridging methoxo ligands.

  已经研究了 tBuN = VCl2·DME 与 LiX（X = NHtBu、NR2、OSiPh3、SR、烷基、Cp）的反应。LiNHtBu 和 LiCH3 提供双核抗磁性叔丁基亚氨基钒 (IV) 化合物 [(μ-NtBu)2V2X4]；在所有其他情况下，只能分离通过钒（IV）的歧化反应形成的钒（V）化合物 tBuN=VX3 和 tBuN=VCpCl2。还描述了各种单核酰氨基叔丁基亚氨基钒 (V) 配合物以及双核配合物 [μ-NtBu)2V2(NtBu)2Cl2] 和 [(μ-0)V2(NtBu)2Cp2Cl2] 的合成。获得的所有化合物均已通过51V NMR光谱表征。tBuN=V(OMe)3通过X射线衍射分析；已发现分子结构是具有两个桥接甲氧基配体的双核钒 (V) 络合物。