四氢二环戊二烯 | 6004-38-2

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 环烃
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 四氢二环戊二烯
• 中文别名: 四氢二聚环戊二烯
• 英文名称: endo-octahydro-4,7-methano-1H-indene
• 英文别名: endo-tricyclo[5.2.1.0^2,6]decane；exo-tetrahydrodicyclopentadiene；Tetrahydrodicyclopentadiene；tricyclo[5.2.1.02,6]decane
• CAS: 6004-38-2
• 化学式: C₁₀H₁₆
• 分子量: 136.237
• InChiKey: LPSXSORODABQKT-UHFFFAOYSA-N

物化性质

• 熔点：
  75°C
• 沸点：
  185.55°C (rough estimate)
• 密度：
  0.8455 (estimate)
• 溶解度：
  可溶于氯仿（少量）、DMSO（少量）
• LogP：
  4.220 (est)
• 物理描述：
  Liquid
• 保留指数：
  1077.6;1078

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险等级：
  3
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38

SDS

Name:	Tricyclo(5.2.1.0/2 6)decane 98% Material Safety Data Sheet
Synonym:	Tetrahydrodicyclopentadien
CAS:	6004-38-2

Section 1 - Chemical Product MSDS Name:Tricyclo(5.2.1.0/2 6)decane 98% Material Safety Data Sheet
Synonym:Tetrahydrodicyclopentadien

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
6004-38-2	Tricyclo[5.2.1.0/2,6]decane, 98%	98	227-851-2

Hazard Symbols: F
Risk Phrases: 11

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable.
Potential Health Effects
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Water Reactive. Material will react with water and may release a flammable and/or toxic gas.
Extinguishing Media:
Do NOT use water directly on fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Keep away from water. Flammables-area.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 6004-38-2: Personal Protective Equipment Eyes: Wear safety glasses and chemical goggles if splashing is possible.
Skin:
Wear appropriate protective gloves and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
Wear a NIOSH/MSHA or European Standard EN 149 approved full-facepiece airline respirator in the positive pressure mode with emergency escape provisions.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Not available.
Color: colorless
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: 172 20.00 deg C
Boiling Point: 193 deg C @ 769.00mm Hg
Freezing/Melting Point: 77.00 - 79.00 deg C
Autoignition Temperature: 275 deg C ( 527.00 deg F)
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H16
Molecular Weight: 136.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 6004-38-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Tricyclo[5.2.1.0/2,6]decane, 98% - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: FLAMMABLE SOLID, ORGANIC, N.O.S.*
Hazard Class: 4.1
UN Number: 1325
Packing Group: II
IMO
Shipping Name: FLAMMABLE SOLID, ORGANIC, N.O.S.
Hazard Class: 4.1
UN Number: 1325
Packing Group: II
RID/ADR
Shipping Name: FLAMMABLE SOLID, ORGANIC, N.O.S.
Hazard Class: 4.1
UN Number: 1325
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: F
Risk Phrases:
R 11 Highly flammable.
Safety Phrases:
S 16 Keep away from sources of ignition - No
smoking.
WGK (Water Danger/Protection)
CAS# 6004-38-2: No information available.
Canada
CAS# 6004-38-2 is listed on Canada's DSL List.
CAS# 6004-38-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 6004-38-2 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  四氢二环戊二烯 在 PtReCo 、 RE-Y zeolite 盐酸 、 氢气 作用下， 250.0 ℃ 、1.62 MPa 条件下， 反应 2.0h， 以31%的产率得到金刚烷
  参考文献：
  名称：

  Y-沸石上四氢环戊二烯向金刚烷的催化重排

  摘要：

  双功能稀土交换Y型沸石，在固定床流动系统中，在氢气和氯化氢存在下，对四氢双环戊二烯合成金刚烷具有高催化活性。因沉积烃堵塞孔隙而失活的催化剂几乎可以通过加氢裂化完全再生。

  DOI：

  10.1246/cl.1986.315
• 作为产物：
  描述：

  dicyclopentadiene 在 sodium tetrahydroborate 、 氢气 、 nickel dichloride 作用下， 以 异丙醇 为溶剂， 40.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以95%的产率得到四氢二环戊二烯
  参考文献：
  名称：

  Hydrogenation of alkenes over nickel nanoparticles under atmospheric pressure of hydrogen

  摘要：

  Nickel nanoparticles have been shown to be an accessible catalyst which allows hydrogenation of unsaturated compounds to be accomplished under atmospheric pressure of hydrogen at relatively low temperatures. Linear and cyclic alkenes, styrene and norbornene derivatives, as well as pinenes and camphene have been smoothly hydrogenated under these conditions. In some cases, selective hydrogenation of unsaturated carbon-carbon bond is possible with the other functional group remaining intact.

  DOI：

  10.1134/s1070428016030040

文献信息

• The NiCl2-Li-Arene (cat.) Combination as Reducing System, Part 9: Catalytic Hydrogenation of Organic Compounds using the NiCl2-Li-(Naphthalene or Polymer-Supported Naphthalene) (cat.) Combination
  作者：Francisco Alonso、Pablo Candela、Cecilia Gómez、Miguel Yus

  DOI：10.1002/adsc.200390022

  日期：2003.1

  polymer-supported naphthalene, and anhydrous nickel(II) chloride, in THF at room temperature, generates a finely divided and very reactive nickel(0) which has been efficiently applied to the catalytic hydrogenation of different organic compounds such as alkenes, alkynes, carbonyl compounds, imines, organic halides, aromatic compounds, hydrazines, azoxy compounds, and N-oxides.

  锂粉，催化量的萘或聚合物负载的萘与无水氯化镍（II）在室温下于THF中的反应生成细分且反应性强的镍（0），已被有效地应用于催化氢化不同的有机化合物，例如烯烃，炔烃，羰基化合物，亚胺，有机卤化物，芳族化合物，肼，a氧基化合物和N-氧化物。
• Catalyst-Free Hydrogenation of Alkenes and Alkynes with Hydrazine in the Presence of Oxygen
  作者：Metin Balci、Nurettin Menges

  DOI：10.1055/s-0033-1340554

  日期：——

  A series of alkenes and alkynes was subjected to reduction with hydrazine hydrate in ethanol in the presence of oxygen. An efficient method was developed for the reduction of C–C double bonds and C–C triple bonds with diimide, generated in situ from hydrazine hydrate by oxidation with oxygen. The reduction process proceeded for 24–48 hours with high chemoselectivity and excellent yields. This reduction

  在氧气存在下，一系列烯烃和炔烃在乙醇中用水合肼还原。开发了一种用二亚胺还原 C-C 双键和 C-C 三键的有效方法，二亚胺是由水合肼通过氧氧化原位生成的。还原过程持续 24-48 小时，具有高化学选择性和优异的产率。与金属催化氢化以及其他系统相比，这种还原过程具有合成优势。
• Dendrimer‐Encapsulated Pd Nanoparticles, Immobilized in Silica Pores, as Catalysts for Selective Hydrogenation of Unsaturated Compounds
  作者：Edward A. Karakanov、Anna V. Zolotukhina、Andrey O. Ivanov、Anton L. Maximov

  DOI：10.1002/open.201800280

  日期：2019.3

  on the presence of Si(OEt)4, while dendrimer molecules acting as both anchored ligands and template, demonstrated the maximum activity in the hydrogenation of terminal linear alkynes and conjugated dienes, reaching TOF values up to 400000 h−1. Herein the total selectivity on alkene in the case of terminal alkynes and conjugated dienes reached 95–99 % even at hydrogen pressure of 30 atm. The catalysts

  通过原位共水解获得​​的基于固定在二氧化硅孔和网络中的聚（丙烯亚胺）树枝状聚合物的多相含钯纳米催化剂已被合成并在各种不饱和化合物的氢化中进行了检验。发现催化剂活性和选择性强烈依赖于载体结构以及底物电子和几何特征。因此，在聚合物模板和四乙氧基硅烷存在下合成的介孔催化剂显示出在各种苯乙烯（包括大体积和刚性的二苯乙烯及其异构体）的氢化中具有最大活性，达到约230000 h -1的TOF值。在聚合物模板存在下合成的其他介孔催化剂，但不添加 Si(OEt) 4，提供了反式环辛烯形成的选择性为 90-95%，与基于均相树枝状聚合物的催化剂相似。仅在 Si(OEt) 4存在下获得的微孔催化剂，同时充当锚定配体和模板的树枝状聚合物分子，在末端直链炔烃和共轭二烯的氢化中表现出最大活性，TOF 值高达 400000 h -1。在此，即使在 30 atm 的氢气压力下，对于末端炔烃和共轭二烯，烯烃的总选择性也达到
• The first one-pot amidation of alkanes and cycloalkanes
  作者：Irena S. Akhrem、Dzul’etta V. Avetisyan、Lyudmila Afanas’eva、Sergei V. Vitt、Pavel V. Petrovskii、Alexander Orlinkov

  DOI：10.1016/j.tetlet.2007.12.070

  日期：2008.2

  Alkanes (or cycloalkanes) and CO in the presence of superelectrophilic systems CX4·2AlBr3 (X = Cl, Br) have been applied for the first time as equivalents of acylium salts in one-pot selective syntheses of amides from amines.

  在超亲电体系CX 4 ·2AlBr 3（X = Cl，Br）存在下，烷烃（或环烷烃）和CO首次作为acy盐的等同物首次应用于胺类胺的一锅选择性合成中。
• Colloidal and nanosized catalysts in organic synthesis: XV. Gas-phase hydrogenation of alkenes catalyzed by supported nickel nanoparticles
  作者：Yu. V. Popov、V. M. Mokhov、D. N. Nebykov、S. E. Latyshova、A. O. Panov、A. A. Dontsova、P. M. Shirkhanyan、K. V. Shcherbakova

  DOI：10.1134/s1070363216120033

  日期：2016.12

  Gas-phase hydrogenation of alkenes and their derivatives, catalyzed by nickel nanoparticles supported on zeolite or silica gel support occurs at 150–250°С and an atmospheric hydrogen pressure and results in a high conversion. The selectivity of the hydrogenation depends on the amount of hydrogen: at a low diene (triene)–hydrogen ratio, selective hydrogenation of one multiple bond in the substrate is

  在沸石或硅胶载体上负载的镍纳米颗粒催化的烯烃及其衍生物的气相加氢反应在150-250°С和大气压的氢气压力下进行，并导致高转化率。氢化的选择性取决于氢的量：在低的二烯（三烯）-氢比率下，可以对底物中的一个多重键进行选择性氢化。

表征谱图