2,7-二碘-9,9-二辛基-9H-芴 | 278176-06-0

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类卤化物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 2,7-二碘-9,9-二辛基-9H-芴
• 中文别名: 2,7-二碘-9,9-二辛基-9-芴
• 英文名称: 2,7-diiodo-9,9-dioctylfluorene
• 英文别名: 2,7-diiodo-9,9-dioctyl-9H-fluorene
• CAS: 278176-06-0
• 化学式: C₂₉H₄₀I₂
• 分子量: 642.446
• InChiKey: AZXJTFHMYPUMPP-UHFFFAOYSA-N

物化性质

• 熔点：
  55-57 °C (lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• WGK Germany：
  3
• 海关编码：
  2903999090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 2,7-Diiodo-9,9-dioctyl-9H-fluorene
CAS-No. : 278176-06-0
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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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
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C29H40I2
Molecular Weight : 642,44 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
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, Hydrogen iodide
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 dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. 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
Provide appropriate exhaust ventilation at places where dust is formed.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.
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., 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 is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. 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: solid
Colour: light yellow
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 55 - 57 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
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 no data available
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
no data available
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.
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
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  2,7-二碘-9,9-二辛基-9H-芴 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 2,7-diethynyl-9,9-dioctyl-9H-fluorene
  参考文献：
  名称：

  通过改变基于棒状芴基-炔基的π-共轭低聚物及其双核金（i）炔基络合物的供体/受体单元来实现黄色发射†

  摘要：

  芴基的炔基的π共轭棒状低聚物轴承不同的中心芳族结构部分和官能化的二炔基的末端，如H- -Fl- -Fl- -Fl- -H（OH1），H- -Fl- -Btz- –Fl– –H（OH2）和H– –Fl– –Btd– –Fl– –H（OH3），其中Fl = 9,9-二辛基芴，Btz = N-己基苯并三唑和Btd =苯并噻二唑是通过Pd（0）催化的Stille偶联方案成功合成的。引入了吸电子至强至中性受体的苯并噻二唑和苯并三唑，以及与施主一样的芴，以调节施主-受体（D-A）的强度来微调带隙（E g）和发射波长。相应的digold（I）σ络合物（PPh 3）Au– –Fl– –Fl– –Fl– –Au（PPh 3）（OM1），（PPh 3）Au– –Fl– –Btz– –Fl– – Au（PPh 3）（OM2）和（PPh 3还通过Au（PPh 3）Cl和甲醇NaOMe在DCM中与相应的炔基官能化的低聚物反应制备了Au-

  DOI：

  10.1039/c7dt00895c
• 作为产物：
  描述：

  芴 在 四丁基溴化铵 、 碘 、 高碘酸 、 sodium hydroxide 作用下， 以 硫酸 、 水 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 2,7-二碘-9,9-二辛基-9H-芴
  参考文献：
  名称：

  新型per双酰亚胺衍生物的合成及其光物理性质，用作OLED的发光材料

  摘要：

  成功设计并合成了三种新型的per二酰亚胺衍生物，它们具有庞大的芳族部分（芴，咔唑基芴和蒽基芴），它们通过三键与triple芯连接。制备的化合物的化学结构通过1 H和13确认13 C NMR和质谱。基于密度泛函理论从理论上估计了它们的优化基态几何和前沿分子轨道。这些化合物经历了可逆的电化学还原过程，并且显示出非常低的能带隙（1.56-1.98 eV），有望用于电子应用。它们还显示出优异的溶解性，高的热稳定性和在溶液中以及在固态时呈红色光谱区域中的薄膜的发光性。对于带有per二酰亚胺的芴单元，发现了最高的光致发光量子产率（溶液中为79％，薄膜中为28％）。所有分子在施加电压下均具有发光能力。制成的结构为ITO / PEDOT：PSS /化合物/ Al的二极管表现出电致发光，其最大发射带位于685至732 nm之间。

  DOI：

  10.1016/j.dyepig.2018.07.006

文献信息

• Synthesis and Properties of Extended π-Conjugated Compounds with 9,10-Bis(phenylethynyl)anthracene Units
  作者：Shinji Toyota、Sayaka Karashima、Tetsuo Iwanaga

  DOI：10.1246/bcsj.20140279

  日期：2015.1.15

  New extended π-conjugated compounds with two 9,10-bis(phenylethynyl)anthracene units and various linkers were synthesized by one-shot double-elimination reactions and Sonogashira coupling. Their UV...

  通过一次性双消除反应和 Sonogashira 偶联合成了具有两个 9,10-双（苯乙炔基）蒽单元和各种接头的新型扩展 π 共轭化合物。他们的紫外线...
• One-pot synthesis of benzofluorene fused aromatic hydrocarbons
  作者：Wendan Dong、Zhun Hu、Ziqi Wang、Bing Sun、Xueqiong Zhang、Fang-Lin Zhang

  DOI：10.1016/j.tetlet.2019.151299

  日期：2019.12

  A new and efficient synthetic approach for the one-pot construction of benzofluorene fused aromatic hydrocarbons was developed via a transient-directing group strategy. The palladium-catalyzed cascade reaction proceeded via consecutive arylation, cyclization and aromatization steps. Moderate to good yields along with broad functional group tolerance were achieved under mild reaction conditions.

  通过过渡导向基团策略，开发了一种新的有效的合成方法，用于一锅法建造苯并芴稠合的芳烃。钯催化的级联反应通过连续的芳基化，环化和芳构化步骤进行。在温和的反应条件下，获得了中等至良好的收率以及广泛的官能团耐受性。
• Synthesis and tunable chiroptical properties of chiral BODIPY-based D–π–A conjugated polymers
  作者：Xiao Ma、Eman Abdel Azeem、Xiaolin Liu、Yixiang Cheng、Chengjian Zhu

  DOI：10.1039/c3tc32029d

  日期：——

  structures, the three chiral BODIPY-based conjugated polymers can exhibit a red fluorescent emission centered at around 624–650 nm, with tunable band gaps in the range 1.56–1.96 eV, respectively. Interestingly, compared with the anisotropy (r = 0.005) and the CPL dissymmetry factor (glum < 0.01) of the chiral BODIPY small molecule as the counterpart, the three chiral polymers can exhibit a high r (up

  可以用具有2,7-二乙炔基-的二碘取代的手性硼-二吡咯亚甲基（BODIPY）衍生物（M-1）合成三种新型的供体-π-受体（D-π-A）型手性聚合物P1，P2和P3。 9,9-二辛基9 ħ芴（M-2 ），3,6-二乙炔基-9-辛基- 9 ħ咔唑（M-3 ），和3,7-二乙炔基10十二烷基10 ħ -吩噻嗪（M-4）通过Pd催化的Sonogashira偶联反应。从三种不同的供体结构中选择，三种基于手性BODIPY的共轭聚合物可以显示红色荧光发射，中心波长在624-650 nm左右，可调节的带隙分别在1.56-1.96 eV的范围内。有趣的是，与手性BODIPY小分子的各向异性（r = 0.005）和CPL不对称因子（g lum <0.01）相比，这三种手性聚合物可以表现出较高的r（P1最高为0.10 ）和a。大摹LUM（高达0.32 P2），这可归因于链间π–π堆积效应以及沿这些聚合物主链的明确手性排列。
• Synthesis of S-Acetyl Oligo-p-aryleneethynylene Tetrathiols
  作者：Omar Hassan Omar、Francesco Babudri、Gianluca M. Farinola、Francesco Naso、Alessandra Operamolla

  DOI：10.1002/ejoc.201001049

  日期：2011.1

  A novel class of tetrathiolated aryleneethynylene oligomers was obtained by the Cassar-Heck-Sonogashira coupling between S,S'-(5-ethynyl-1,3-phenylene) bis(methylene) diethanethioate (1) and aryl diiodides or dibromides. Although standard coupling conditions are effective in the case of iodo derivatives, the addition of free triphenylphosphane to the reaction mixture was required to overcome the slower

  通过 S,S'-(5-乙炔基-1,3-亚苯基) 双 (亚甲基) 二乙硫酸酯 (1) 和芳基二碘化物或二溴化物之间的 Cassar-Heck-Sonogashira 偶联获得了一类新的四硫代亚芳基乙炔基低聚物。尽管标准偶联条件在碘衍生物的情况下是有效的，但需要向反应混合物中加入游离三苯基膦以克服二溴芳烃较慢的反应速率。通过应用相同的合成方法，可以从更高的同源物 1 开始获得具有扩展共轭系统的低聚物。这些低聚物代表了有趣的分子线，可能能够在各种基材上自组装，包括薄膜或纳米颗粒形式的金和其他贵金属。
• Direct Sequential C3 and C1 Arylation Reaction of Imidazo[1,5-<i>a</i>]pyridine Catalyzed by a 1,10-Phenanthroline–Palladium Complex
  作者：Eiji Yamaguchi、Fumitoshi Shibahara、Toshiaki Murai

  DOI：10.1246/cl.2011.939

  日期：2011.9.5

  The direct sequential arylation reaction at the C3 and C1 positions of imidazo[1,5-a]pyridines with a variety of aryl iodides catalyzed by [Pd(phen)2](PF6)2 is described. The reaction of unsubstitu...

  描述了在 [Pd(phen)2](PF6)2 催化下，咪唑并 [1,5-a] 吡啶与各种芳基碘化物在 C3 和 C1 位置的直接连续芳基化反应。未取代的反应...