三羰基环己二烯基铁 | 12152-72-6

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 中文名称: 三羰基环己二烯基铁
• 中文别名: 环己二烯三羰基铁
• 英文名称: (cyclohexa-1,3-diene)iron tricarbonyl
• 英文别名: (η⁴-1,3-cyclohexadiene) iron tricarbonyl；tricarbonyl(η(4)-cyclohexa-1,3-diene)iron；tricarbonyl(η-cyclohexa-1,3-diene)iron；cyclohexadiene iron tricarbonyl；1,3-cyclohexadienetricarbonyliron；tricarbonyl[(1-4-η)-cyclohexa-1,3-diene]iron；(η4-cyclohexa-1,3-diene)Fe(CO)3；carbon monoxide;cyclohexa-1,3-diene;iron
• CAS: 12152-72-6
• 化学式: C₉H₈FeO₃
• 分子量: 220.008
• InChiKey: OVNCEUCQDGRASI-UHFFFAOYSA-N

物化性质

• 熔点：
  8°C
• 沸点：
  55 °C(Press: 0.7 Torr)
• 稳定性/保质期：

  在常温常压下稳定，应避免接触氧化物、卤素和热空气。

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  6.1
• 安全说明：
  S16,S26,S36
• 危险类别码：
  R36/37/38,R11
• 包装等级：
  II
• 危险类别：
  6.1
• 危险品运输编号：
  UN 1993

SDS

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Section 1: Product Identification
Chemical Name: Cyclohexadiene iron tricarbonyl, 98%
CAS Registry Number: 12152-72-6
Formula: C6H8Fe(CO)3
EINECS Number: None
Chemical Family: metal carbonyl complexes
Synonym: 1,4-Cyclohexadiene iron tricarbonyl

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title Compound 12152-72-6 100% no data no data

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Section 3: Hazards Identification
Harmful by inhalation, in contact with skin and if swallowed. May be irritating to skin, eyes and respiratory
Emergency Overview:
tract.
Primary Routes of Exposure: Ingestion, inhalation, skin, eyes.
Eye Contact: May cause slight to mild irritation of the eyes.
Skin Contact: May cause slight to mild irritation of the skin. Harmful in contact with skin.
Inhalation: Harmful by inhalation. may be irritating to the nose, mucous membranes and respiratory tract.
Ingestion: harmful if swallowed.
Acute Health Affects: Harmful by inhalation, in contact with skin and if swallowed.
The toxicological properties of this compound have not been thoroughly investigated. Unrecognized hazards
Chronic Health Affects:
may be present.
NTP: No
IARC: No
OSHA: No

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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.

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SECTION 5: Fire Fighting Measures
Flash Point: not applicable
Autoignition Temperature: none
Explosion Limits: none
Extinguishing Medium: carbon dioxide, foam or dry powder
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self- contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit irritating fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: Flammable. No unusual fire or explosion hazards.

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

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SECTION 7: Handling and Storage
Keep material in a tightly sealed container. Prolonged exposure to the air will result in degradation of the
Handling and Storage:
product. Handle and store material under an inert atmosphere of nitrogen or argon.

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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.
Ventilation: Material may form a vapor. If possible, 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: Material may form a vapor. If possible, handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: yellow to orange liq.
Molecular Weight: 220.01
Melting Point: 8°
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: none
Solubility in Water: insoluble

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SECTION 10: Stability and Reactivity
Stability: air sensitive, (store cold)
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: Contact with air
Incompatibility: Oxidizing agents and halogens
Decomposition Products: carbon dioxide, carbon monoxide, organic fumes, and iron oxide

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files.
Carcinogenic Effects: No data
Mutagenic Effects: No data
Tetratogenic Effects: No data

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SECTION 12: Ecological Information
Ecological Information: No information available

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

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SECTION 14: Transportation
Shipping Name (CFR): Flammable liquids, N.O.S.
Hazard Class (CFR): 3
Additional Hazard Class (CFR): NA
Packaging Group (CFR): II
UN ID Number (CFR): UN# 1993
Shipping Name (IATA): Flammable liquids, N.O.S.
Hazard Class (IATA): 3
Additional Hazard Class (IATA): NA
Packaging Group (IATA): II
UN ID Number (IATA): UN# 1993

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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  三羰基环己二烯基铁 在 CO 、 AlCl₃ 、 H₂O 作用下， 以 二氯甲烷 为溶剂， 以24%的产率得到tricarbonyl(η4-dihydrotropone)iron
  参考文献：
  名称：

  Eilbracht, Peter; Jelitte, Ruediger; Walz, Leonhard, Chemische Berichte, 1984, vol. 117, # 12, p. 3473 - 3489

  摘要：

  DOI：
• 作为产物：
  描述：

  tricarbonyl(η4-1,4-cyclohexadiene)iron 以 正己烷 为溶剂， 生成 三羰基环己二烯基铁
  参考文献：
  名称：

  三羰基双（eta.2-顺式-环辛烯）铁：用于烯烃异构化和制备应用的多功能三羰基铁源的光化学合成

  摘要：

  制备标准反应photochimique a -40°C。La 反应热反应 戊烯-1 结果 en une isomerisation de l'alcene

  DOI：

  10.1021/ja00319a021

文献信息

• Synthesis, Molecular Structure, Fluxional Behavior, and Tricarbonyliron Transfer Reactions of (η4-1-Azabuta-1,3-diene)tricarbonyliron Complexes
  作者：Hans-Joachim Knölker、Gerhard Baum、Norbert Foitzik、Helmut Goesmann、Peter Gonser、Peter G. Jones、Herbert Röttele

  DOI：10.1002/(sici)1099-0682(199807)1998:7<993::aid-ejic993>3.0.co;2-6

  日期：1998.7

  (η4-1-azabuta-1,3-diene)tricarbonyliron complexes 10 are easily prepared in high yield by condensation of the corresponding arylamines 7 with the cinnamaldehydes 8 and subsequent ultrasound-promoted complexation of the resulting 1-azabuta-1,3-dienes 9 with nonacarbonyldiiron. The complexes 10 are shown to represent excellent reagents for the transfer of the tricarbonyliron fragment onto cyclohexa-1

  (η4-1-azabuta-1,3-diene)tricarbonyliron 配合物 10 很容易通过相应的芳胺 7 与肉桂醛 8 的缩合和随后产生的 1-azabuta-1,3 的超声促进络合以高产率制备-二烯 9 与九羰基二铁。显示复合物 10 代表了用于将三羰基铁片段转移到环己-1,3-二烯 (1a) 上的极好试剂。配合物 10 的结构表征是通过 IR、1H-NMR 和 13C-NMR 光谱以及 10b、10c 和 10l 的 X 射线晶体学来实现的。使用变温 13C-NMR 光谱研究了配合物 10a、10b、10c、10e 和 2 的流动性，并确定了三羰基铁碎片旋转门旋转的激活势垒。
• 단핵 철 착체 및 그것을 사용한 유기 합성 반응
  申请人：KYUSHU UNIVERSITY, NATIONAL UNIVERSITY CORPORATION 고쿠리쓰다이가쿠호진 규슈다이가쿠(520070190503)

  公开号：KR20150125983A

  公开（公告）日：2015-11-10

  식 (1)로 표시되는 철-규소 결합을 갖는 단핵 철 착물은 하이드로실릴화 반응, 수소화 반응, 카본일 화합물의 환원 반응의 3 반응에 우수한 촉매 활성을 발휘할 수 있다. (식 중, R∼R은, 서로 독립하여, 수소 원자, X로 치환되어 있어도 되는 알킬기, 아릴기, 아르알킬기 등을 나타내거나, R∼R 중 어느 하나와 R∼R 중 어느 하나의 적어도 1쌍이 하나로 합쳐진 가교 치환기를 나타내고, X는 할로젠 원자, 오가노옥시기 등을 나타내고, L은 CO 이외의 2전자 배위자를 나타내고, L이 복수 존재하는 경우, 그것들은 서로 동일해도 상이해도 되고, L이 2개인 경우, 그것들은 서로 결합하고 있어도 되며, n 및 m은 서로 독립하여 1∼3의 정수를 나타내지만, n+m은 3 또는 4를 충족시킨다.)

  具有铁-硅键合的单核铁配合物可以在氢硅化反应、氢化反应和碳碳化合物的还原反应中表现出优异的催化活性。 （在方程中，R〜R表示独立的氢原子，或者可以被取代为烷基，芳基，芳基烷基等，R〜R中的任何一个和R〜R中的任何一个至少一对表示为一个桥接取代基，X表示卤素原子，有机氧基等，L表示除CO之外的二电子受体，如果L存在多个，则它们可以相同也可以不同，如果L为2个，则它们可以相互结合，n和m是独立的整数1-3，但n+m等于3或4。）
• Catalyst design for iron-promoted reductions: an iron disilyl-dicarbonyl complex bearing weakly coordinating η2-(H–Si) moieties
  作者：Yusuke Sunada、Hironori Tsutsumi、Keisuke Shigeta、Ryota Yoshida、Toru Hashimoto、Hideo Nagashima

  DOI：10.1039/c3dt52598h

  日期：——

  Iron disilyl dicarbonyl complex 1, in which two H–Si moieties of the 1,2-bis(dimethylsilyl)benzene ligand were coordinated to the iron center in an η2-(H–Si) fashion, was synthesized by the reaction of (η4-C6H8)Fe(CO)3 with 2 equiv. of 1,2-bis(dimethylsilyl)benzene under photo-irradiation. Complex 1 demonstrated high catalytic activity toward the hydrogenation of alkenes, the hydrosilylation of alkenes and the reduction of carbonyl compounds.

  铁二硅基二羰基配合物1通过(η⁴-C6H8)Fe(CO)3与2当量1,2-双(二甲基硅基)苯在光照射下反应合成，其中1,2-双(二甲基硅基)苯配体的两个H-Si部分以η²-(H-Si)方式与铁中心配位。配合物1对烯烃的氢化、烯烃的氢硅化以及羰基化合物的还原表现出高效的催化活性。
• Kinetics and mechanism of mono- and di-olefin exchange at five-co-ordinate iron(0)
  作者：Philip M. Burkinshaw、Denis T. Dixon、James A. S. Howell

  DOI：10.1039/dt9800000999

  日期：——

  Exchange of various mono-olefins with styrene in [Fe(CO)4(PhCHCH2)] proceeds via a dissociative process, involving an Fe(CO)4 intermediate. Ligand exchange in system (i)(enone = benzylideneacetone, cinnamaldehyde, chalcone, or dypnone; polyene = cyclohexa- and cyclohepta-1,3-diene, cycloheptatriene, cycle-octatetraene, [Fe(CO)3(η4-enone)]+ polyene ⇌[Fe(CO)3(η4-polyene)]+ enone (i) or 1,4-diphenylbuta-1

  各种单烯烃与苯乙烯在[Fe（CO）4（PhCH CH 2）]中的交换通过离解过程进行，涉及Fe（CO）4中间体。配体交换系统（ⅰ）（烯酮=亚苄基丙酮，肉桂醛，查耳酮，或dypnone;多烯= cyclohexa-和环庚-1,3-二烯，环庚三烯，循环octatetraene，的[Fe（CO）3（η 4 -enone） ] +多烯⇌的[Fe（CO）3（η 4-多烯）] +烯酮（i）或1，4-二苯基丁-1，3-二烯）是逐步的，包括速率确定的π-键合的CO部分的脱螯作用。缔合和解离途径都被发现。讨论了二烯结构和烯酮取代基的影响。
• The kinetics and mechanism of diene exchange in (η4-enone) Fe(CO)2L complexes (L = phosphine, phosphite)
  作者：James A.S. Howell、John C. Kola、Denis T. Dixon、Philip M. Burkinshaw、Marion J. Thomas

  DOI：10.1016/0022-328x(84)80113-8

  日期：1984.4

  Kinetic data for the exchange of 1,3-cyclohexadiene with (η4-benzylideneacetone)Fe(CO)2L complexes (L = CO, PPh3-xMex (x = 0-2) or P(OPh)3) to give (η4-1,3-cyclohexadiene)Fe(CO)2L derivatives indicate a mechanism involving stepwise competing D and Id opening of the ketonic M-CO π-bond. Rates increase in the order CO ⪢ PPh3 ≈ P(OPh)3 > PPh2Me ⪢ PPhMe2, and both steric and electronic factors appear to

  为1,3-环己二烯与交换动力学数据（η 4 -benzylideneacetone）的Fe（CO）2个大号络合物（L = CO，PPH 3-x我X（X = 0-2）或者P（OPH）3）以得到（η 4 -1,3-环己二烯）的Fe（CO）2大号衍生物表明涉及逐步竞争的机制d和我ð的酮M-COπ键的开口。率的顺序CO⪢PPH增加3 ≈P（OPH）3 > PPH 2我⪢PPhMe 2，并且两个空间和电子因素似乎是重要的。（η 4 -1,3-环己二烯）的Fe（CO）2在对映选择性合成的潜在用途L的复合物（L =（+） - pH 2 P（薄荷基）或（+） - pH 2 PCH 2 CH（Me）中的Et）可以通过制备它们的（η 4 -benzylideneacetone）的Fe（CO ）2个大号络合物。