Bis(cyclopentadienyl)iron 二茂铁

CAS 102-54-5 MFCD00001427

化学结构图

102-54-5
SMILES: [Fe+2].c1cc[cH-]c1.c1cc[cH-]c1

化学属性

Mol. FormulaC10H10Fe
Mol. Weight186.04
Density1.49
Boiling Point249 °C at 760 mmHg
Vapor Pressure0.03 mmHg ( 40 °C)
Melting Point173.0 to 177.0 deg-C
TSCAYes
Solubility难溶
Stability对空气,湿度和热敏感
Flash Point100°C
Appearance 桔黄色针状结晶。熔点172.5-173℃,100℃以上升华,沸点249℃。溶于稀硝酸、浓硫酸、苯、乙醚、石油醚和四氢呋喃,在稀硝酸和浓硫酸中生成带蓝色荧光的深红色溶液。不熔于水、10%氢氧化钠和热的浓盐酸,这些溶剂的沸液中,二茂铁既不溶解也不分解,能随水蒸气挥发,有类似樟脑的气味,在空气中稳定,具有强烈吸收紫外线的作用,对热相当稳定,可耐470℃高温加热。

别名和识别编码

Chemical NameBis(cyclopentadienyl)iron
MDL NumberMFCD00001427
CAS Number102-54-5
EC Number203-039-3
Beilstein Registry Number2384789
Synonym Ferrocene {LY} Ferrocene {} {LY} Ferrocene {} {} {LY} Ferrocene {} {} {} {LY} Ferrocene {} {} {} {} {LY} Ferrocene {} {} {} {} {} {LY} Ferrocene {} {} {} {} {} {} {LY} Ferrocene {} {} {} {} {} {} {} {LY} Ferrocene {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Ferrocene {} {} {} {} {} {} {} {} {} {LY} Ferrocene {} {} {} {} {} {} {} {} {} {} {LY} Ferrocene {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {LY} Ferrocene {} {} {} {} {} {} {} {} {} {} {} {} {LY} Ferrocene {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Ferrocene {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Ferrocene {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Ferrocene {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Ferrocene {} {} {} {} {} {} {} {} {} {}
PubChem Substance ID7611
Merck Number4037
Chemical Name Translation二茂铁
Wiswesser Line NotationL50TJ 0-FE-- 0L50TJ
LabNetwork Molecule IDLN01344276
InChIInChI=1S/2C5H5.Fe/c2*1-2-4-5-3-1;/h2*1-5H;/q2*-1;+2
Canonical SMILES[][Fe][].c1cccc1.c2cccc2
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分类

  • {SA} Analytical Reagents, Analytical/Chromatography, Catalysis and Inorganic Chemistry, Chemical Synthesis, Derivatization Reagents, Derivatization Reagents HPLC, Electrochemical, Iron
  • {SNA} Catalysis and Inorganic Chemistry, Chemical Synthesis, Iron Catalysts
  • {uni_hamburg} no charge; metal-organic; other heterocycle; carbocycle; alicycle; fused rings; 3ring; 4ring; 5ring; 6ring; 1fragment; zwitterion
  • {SNA} Catalysis a

产品应用

  • 二茂铁是一种具有夹心结构的金属有机化合物。二茂铁及其衍生物因其本身的特点,如疏水性、生物可氧化性、芳香性、稳定性、低性、生物活性等,而被广泛应用。如作催化剂。汽油的抗爆添加剂。高温润滑剂。高温聚合物中间体。紫外光吸收剂。

相关文献及参考

  • For Mannich reaction using tetramethylmethylenediamine as the source of the Mannich intermediate, see: Org. Synth. Coll., 5, 434 (1973).
  • Short: II/25D
  • Short: II/27C
  • Promotes the Pschorr cyclization of stilbene derivatives in acetone to give phenanthrenes: J. Org. Chem., 60, 196 (1995).
  • Readily undergoes electrophilic substitution reactions such as acylation, formylation, Mannich reaction, etc. For a review, see: Org. React., 17, 1 (1969).
  • Merck:14,4037
  • In combination with TFA anhydride, reduces sulfoxides to sulfides at room temperature: Chem. Lett., 400 (2000).
  • Reacts with chlorobenzenes to give ferrocenium salts, which can be used to arylate diethyl malonate: Synth. Commun., 18, 291 (1988); J. Chem. Soc., Perkin 1, 469 (1989).
  • Merck:14,4037 Beilstein: 16,IV,1783

安全信息

Signal word Danger Warning
GHS Symbol
WGK Germany2
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘;
  • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免释放到环境中,参考特别指示/安全收据说明书;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置;
  • S57 Use appropriate containment to avoid environmental contamination 使用适当容器避免环境污染;
  • S36 Wear suitable protective clothing 穿戴适当的防护服;
  • S16 Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R51/53
  • R22 Harmful if swallowed 吞咽有害
  • R11 Highly flammable 非常易燃
Precautionary statements
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P332+P313
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
  • P314 Get medical advice/attention if you feel unwell. 获取医疗咨询/就医,如果你觉得不舒服
  • P301+P312+P330
  • P337+P313
  • P241 Use explosion-proof electrical/ventilating/lighting/…/equipment. 使用防爆电气/通风/照明/ .../设备。
  • P403+P233
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
  • P304+P340
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
Hazard statements
  • H228 Flammable solid 易燃固体
  • H302 Harmful if swallowed 吞食有害
  • H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害
  • H410 Verytoxictoaquaticlifewithlonglastingeffects 对水生生物毒性非常大并具有长期影响。
  • H302+H332
  • H373 May causes damage to organs through prolonged or repeated exposure 长期或频繁接触可能会损伤器官
Personal Protective Equipment Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
RTECSLK0700000
Packing GroupII
UN Number UN1325 UN 1325 4.1/PG 2 1325
Storage condition 2-8°C, protect from light, stored under nitrogen {LY} 2-8°C, protect from light, stored under nitrogen Air & Moisture Sensitive Flammables area {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored und
Hazard Codes F,Xn F;Xn;N F,Xn,N
Hazard Class4.1
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intramuscular
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 5175 mg/kg/2Y-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Tumorigenic - tumors at site of application
REFERENCE :
   NCIUS* Progress Report for Contract No. PH-43-64-886, Submitted to the
   National Cancer Institute by The Institute of Chemical Biology, University
   of San Francisco.  (San Francisco, CA 94117)  Volume(issue)/page/year:
   PH43-64-886

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 335 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NCIUS* Progress Report for Contract No. PH-43-64-886, Submitted to the
   National Cancer Institute by The Institute of Chemical Biology, University
   of San Francisco.  (San Francisco, CA 94117)  Volume(issue)/page/year:
   PH43-64-886

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 500 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NCIUS* Progress Report for Contract No. PH-43-64-886, Submitted to the
   National Cancer Institute by The Institute of Chemical Biology, University
   of San Francisco.  (San Francisco, CA 94117)  Volume(issue)/page/year:
   PH43-64-886

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1320 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   SCCUR* Shell Chemical Company.  Unpublished Report.  (2401 Crow Canyon Rd.,
   San Romon, CA 94583)  Volume(issue)/page/year: -,5,1961

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 178 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems
   Laboratory, NIOSH Exchange Chemicals.  (Aberdeen Proving Ground, MD 21010)
   Volume(issue)/page/year: NX#023

TYPE OF TEST            : Heritable translocation test
ROUTE OF EXPOSURE       : Parenteral
TEST SYSTEM             : Insect - Drosophila melanogaster
DOSE/DURATION           : 100 ppm
REFERENCE :
   ENMUDM Environmental Mutagenesis.  (New York, NY)  V.1-9, 1979-87.  For
   publisher information, see EMMUEG.  Volume(issue)/page/year: 7,87,1985

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 10 ug/plate
REFERENCE :
   ENMUDM Environmental Mutagenesis.  (New York, NY)  V.1-9, 1979-87.  For
   publisher information, see EMMUEG.  Volume(issue)/page/year: 5(Suppl
   1),3,1983

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 130 ug/L
REFERENCE :
   ENMUDM Environmental Mutagenesis.  (New York, NY)  V.1-9, 1979-87.  For
   publisher information, see EMMUEG.  Volume(issue)/page/year: 7,1,1985

TYPE OF TEST            : Sex chromosome loss and nondisjunction
ROUTE OF EXPOSURE       : Parenteral
TEST SYSTEM             : Insect - Drosophila melanogaster
DOSE/DURATION           : 100 ppm
REFERENCE :
   ENMUDM Environmental Mutagenesis.  (New York, NY)  V.1-9, 1979-87.  For
   publisher information, see EMMUEG.  Volume(issue)/page/year: 7,87,1985

其他信息

  • Acros Organics:二茂铁/二环戊二烯铁 Ferrocene, 98%(102-54-5)
  • 蒸气压:0.03 mm Hg ( 40 °C)
  • Alfa Aesar:Ferrocene, 99%(102-54-5)
  • Sigma Aldrich:102-54-5(sigmaaldrich)
  • 方法一:由铁粉与环戊二烯在300℃的氮气氛中加热,或以无水氯化亚铁与环戊二烯合钠在四氢呋喃中反应而得,也可采用电解合成法,采用环戊二烯、氯化亚铁、二乙胺为原料合成二茂铁可按下法操作。搅拌下,向四氢呋喃中分次投入无水氯化铁(FeCL3),再加入铁粉,在氮气保护下加热回流4.5h,得到氯化亚铁溶液。减压蒸除溶剂四氢呋喃,得近干的残留物。在冰浴冷却下,加入环戊二烯和二乙胺的混合液,在室温下猛烈搅拌6-8h,减压蒸除多余的胺,残留物用石油醚回流萃取。将萃取液趁热过滤,蒸除溶剂后,即得二茂铁粗品。用戊烷或环已烷重结晶,或采用升华法提出纯,即为精制品收率73-84%。
  • 用途一:用作节能消烟助燃添加剂:可用于各种燃料,如柴油、汽油、重油、煤炭等。车用柴油中加入0.1%的二茂铁,可节约燃料油10-14%,提高率10-13%,尾气中烟度下降30-80‰。另外,在重油中加入0.3‰,煤
  • 用途四:二茂铁可用作火箭燃料添加剂,汽油的抗爆剂和橡胶及硅树脂的熟化剂,也可作紫外线吸收剂。二茂铁的乙烯基衍生物能发生烯键聚合,得到碳链骨架的含金属高聚物,可作航天飞船的外层涂料。二茂铁的消烟助燃作用发现较早,无讼是添加在固体燃料、液体燃料或气体燃料中,都能发挥这种效应,尤其对于在燃烧时产生烟大的烃类,其效果更为显著。其添加在汽油中有很好的抗震作用,但是由于氧化铁沉积到火花塞上影响发火而受到限制,为此,也有人使用排铁混合物以减少铁的沉积现象。二茂铁添加在煤油或柴油中,由于该发动机不用点火装置,所以不良的影响较少,在燃烧中除了消烟助燃外,其还有促使一氧化碳较化为二氧化碳的作用。另外,它在燃烧中可提高燃烧热、增加功率而达到节能和减少大气污染的效果,二茂铁添加到锅炉燃料油中,可减少烟的生成和喷嘴积碳。在柴油中添加0.1%,可消烟30-70%,节油10-14%,功率提高10%。二茂铁用在固体火箭燃料中的使用报道更多,甚至还有掺在煤粉中作减速烟剂使用。在以高分子聚合物废料作燃料时,添加二茂铁后可降烟数倍,还可作塑料的减烟添加剂。除上述用途以外,二茂铁还有其他应用,作为铁肥料,有益于植物吸收,增长率加作物的含铁量,它的衍生物可作杀虫剂。二茂铁的工业和有机合成方面的用途也很多,例如,它的衍生物可作为橡胶或聚乙烯的抗氧剂、聚脲酯的稳定剂、异丁烯痉甲基化催化剂、高分子过氧化物的分解催化剂,增加甲苯氯化中对位氯甲苯的产率,在其他方面又可作为润滑油抗负荷添加剂、研磨材料的促进剂等。
  • 有樟脑气味。最大吸收波长358mm。易燃。能随水蒸气挥发。易溶于苯、乙醇,乙醚、汽油、柴油等有机溶剂。也溶于稀硝酸和浓硫酸而成深红色,同时有蓝色荧光,几乎不溶于水、11%氢氧化钠和沸的浓盐酸。
  • 有樟脑气味。最大吸收波长358mm。易燃。能随水蒸气挥发。易溶于苯、乙醇,乙醚、汽油、柴油等有机溶剂。也溶于稀硝酸和浓硫酸而成深红色,同时有蓝色荧光,几乎不溶于水、10%氢氧化钠和沸的浓盐酸。
  • 用途二:用作催化剂及汽油抗爆添加剂
  • 图谱信息:二茂铁(102-54-5)核磁图( 1 HNMR) 二茂铁(102-54-5)质谱(MS) 二茂铁(102-54-5)红外图谱(IR2) 二茂铁(102-54-5)核磁图( 13 CNMR) 二茂铁(102-54-5)红外图谱(IR1)
  • TC
  • 储运特性:库房低温, 通风, 干燥; 与氧化剂分开存放
  • MOL 文件:102-54-5.mol
  • 用途五:二茂铁是一
  • 二茂铁价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 30198170 二茂铁;环戊二烯铁 1kg 150元 2011/08/23 30198173 二茂铁;环戊二烯铁 500g 76元 2011/
  • 下游产品:二甲基二茂铁 --> 二氯[1,1'-双(耳叔丁基膦)二茂铁钯(II) ]PALLADIUM
  • {C

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