菲-9-甲酸 | 837-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 菲-9-甲酸
• 中文别名: 9-甲酸菲
• 英文名称: phenanthrene-9-carboxylic acid
• 英文别名: 9-phenanthrenecarboxylic acid
• CAS: 837-45-6
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: LMFJKKGDLAICPF-UHFFFAOYSA-N

物化性质

• 熔点：
  249-251℃
• 沸点：
  323.41°C (rough estimate)
• 密度：
  1.305
• 溶解度：
  DMSO（微溶）、甲醇（微溶、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存于室温、干燥且密封的环境中。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 9-Phenanthrenecarboxylic acid
CAS-No. : 837-45-6
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 : C15H10O2
Molecular Weight : 222,23 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
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
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing 253 - 255 °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 no data available
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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  菲-9-甲酸 在 喹啉 、 copper(l) iodide 作用下， 反应 4.0h， 以46 mg的产率得到菲
  参考文献：
  名称：

  邻乙烯基溴苯与芳族溴化物的顺序交叉偶联/环化反应，用于合成多环芳族化合物。

  摘要：

  实现了邻乙烯基溴苯与芳族溴的顺序交叉偶联/环化反应，这提供了直接和模块化的方法来获得多环芳族化合物。乙烯基配位的palladacycle被提议为该顺序过程的关键中间体。在该转化中观察到优异的化学选择性和区域选择性。该方法的实用性因其广泛的底物范围，出色的官能团耐受性以及与所得产物相关的丰富转化而突出。

  DOI：

  10.1002/anie.201910792
• 作为产物：
  描述：

  2,2,2-三氯-1,1-二乙氧基-1-(9-菲基)-乙烷 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 以25%的产率得到菲-9-甲酸
  参考文献：
  名称：

  二氯卡宾的正式插入成C的Ar S键

  摘要：

  相转移生成的二氯卡宾与9-硫代甲基菲（4）的反应生成6，而不是预期的加成产物5。6是从卡宾插入C，S键的形式得出的。13 C-标记表明，CH 3 4基在反应过程中丢失。

  DOI：

  10.1016/s0040-4039(00)82214-5

文献信息

• Conformation-Dependent Intramolecular Electron Transfer in <i>N-</i>(Aminoalkyl)-9-phenanthrenecarboxamides
  作者：Frederick D. Lewis、Eric L. Burch

  DOI：10.1021/jp9526758

  日期：1996.1.1

  photophysical behavior of several secondary and tertiary N-(aminoalkyl)phenanthrenecarboxamides have been investigated. Secondary (aminoalkyl)amides exist predominantly in the Z conformation, whereas tertiary amides exist as mixtures of Z and E conformers and semirigid piperazines as mixtures of chair conformers. Rate constants for endergonic intramolecular electron transfer are found to be highly dependent

  已经研究了几种仲和叔N-（氨基烷基）菲碳酰胺的分子结构和光物理行为。仲（氨基烷基）酰胺主要以Z构象存在，而叔酰胺以Z和E构象异构体的混合物形式存在，而半刚性哌嗪则以椅子构象异构体的混合物形式存在。发现正电子分子内电子转移的速率常数高度依赖于分子结构。叔酰胺的芳族和酰胺基团基本上是正交的，因此，E氨基烷基可采用低能构象，其中芳族基和胺基之间存在空间重叠，而Z氨基烷基或哌嗪则不可能重叠。观察到在E vs Z构象中通过附加的三烷基胺对菲单峰进行更快速的分子内电子转移淬灭的原因是这种重叠的差异。还发现菲-酰胺二面角的增加导致通过Z氨基烷基的分子内电子转移猝灭的速率常数降低。在附加叔苯胺的情况下，Z和Z均发生有效的电子转移猝灭E构形者。的ž构象形成荧光激发络合物，提供在不存在直接的π-π重叠的激基复合物型发射的一个新实例。由E构象子形成的激基复合物是非荧光的，显然经历了快速的系统间杂交。在溶液和冷冻
• Photochemical and Photophysical Behavior of<i>p</i>-Methoxyphenyl alkenyl Phenanthrenecarboxylates. I. Structure and Competitive Formation of Intramolecular Cycloaddition Products
  作者：Hirochika Sakuragi、Katsumi Tokumaru、Hiroki Itoh、Kohki Terakawa、Katsuo Kikuchi、R. A. Caldwell、Chien-Chung Hsu

  DOI：10.1246/bcsj.63.1049

  日期：1990.4

  entenyl, (E)-4-(p-methoxyphenyl)-4-hexenyl, and (E)-5-(p-methoxyphenyl)-5-heptenyl 9-phenanthrenecarboxylates (B-2E, B-3E, and B-4E, respectively) in benzene gave intramolecular [2+2] cycloadducts, cyclobutane derivatives (CB-2, CB-3, and CB-4, respectively) possessing the same conformation as an intermolecular [2+2] cycloadduct (CB-0) between methyl 9-phenanthrenecarboxylate (9-MCP) and trans-anethole

  (E)-3-(对甲氧基苯基)-3-戊烯基、(E)-4-(对甲氧基苯基)-4-己烯基和(E)-5-(对甲氧基苯基)-5-庚烯基的辐照苯中的 9-菲羧酸盐（分别为 B-2E、B-3E 和 B-4E）产生分子内 [2+2] 环加合物，环丁烷衍生物（分别为 CB-2、CB-3 和 CB-4）具有与 9-菲羧酸甲酯 (9-MCP) 和反式茴香脑 (t-AN) 以及氧杂环丁烷衍生物 (OX-2、OX-3 和 OX) 之间的分子间 [2+2] 环加合物 (CB-0) 的构象相同-4，分别）由羰基和烯烃双键之间的分子内环加成产生。然而，(E)-4-(对甲氧基苯基)-3-丁烯基和(E)-5-(对甲氧基苯基)-4-戊烯基9-菲羧酸酯(分别为A-2E和A-3E)仅提供产物衍生自氧杂环丁烷前体。
• 二核化配位子又は二核金属錯体
  申请人：学校法人同志社

  公开号：JP2021042186A

  公开（公告）日：2021-03-18

  【課題】高いがん細胞毒性を有する、ＤＮＡ標的とｃｙｃｌｅｎを持つ金属錯体の提供。【解決手段】下記式（ＩV）で示される二核金属錯体。【選択図】なし

  提供具有高癌细胞毒性、DNA靶向和环状结构的金属配合物。采用以下式（IV）所示的双核金属配合物。【选择图】无
• Method for preparing aromatic compounds
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0825173A1

  公开（公告）日：1998-02-25

  A method for synthesizing aromatic compounds by selectively dehalogenating aromatic starting materials is provided. Compounds may be prepared which are substituted with fluoro, chloro or bromo. The method may be used to remove halogen atoms from sites at which halogenation is not desired, and to form substantially pure halogenated compounds from mixtures of starting materials. The method uses a copper containing dehalogenation agent and an acid with the dehalogenation being controlled by a substituent such as a carboxylic acid, amide, ester, aldehyde, ketone or cyano on the aromatic ring.

  提供了一种通过选择性地脱卤芳香族起始材料来合成芳香族化合物的方法。可以制备被氟、氯或溴取代的化合物。该方法可用于从不需要卤素化的位置去除卤素原子，并从起始材料的混合物中形成基本上纯净的卤代化合物。该方法使用含有铜的脱卤素剂和酸，脱卤素作用通过芳香环上的取代基如羧酸、酰胺、酯、醛、酮或腈来控制。
• Direct Carboxylation of Arenes and Halobenzenes with CO₂ by the Combined Use of AlBr₃ and R₃SiCl
  作者：Koji Nemoto、Hiroki Yoshida、Naoki Egusa、Naoya Morohashi、Tetsutaro Hattori

  DOI：10.1021/jo101808z

  日期：2010.11.19

  Ph3SiCl, which suggests that the silyl chlorides activate CO2 in cooperation with AlBr3. 1H NMR analysis of unworked-up reaction mixtures reveals that the products merge as aluminum carboxylates. The mass balance concerning silicon indicates that the silyl chlorides are recycled during the reaction sequence. On the basis of these observations, a feasible mechanism is proposed for the present carboxylation

  通过添加在硅原子上总共带有三个烷基和/或芳基取代基的甲硅烷基氯，有效地促进了路易斯酸介导的芳香族化合物与CO 2的直接羧化。因此，甲苯，二甲苯，均三甲苯和一些其他烷基苯在室温下于CO 2压力（3.0 MPa）下，在纯净的底物中用AlBr 3和Ph 3 SiCl的1：1混合物处理，从而得到60基于AlBr 3，产率-97％。借助1摩尔当量的AlBr 3和Ph 3将多环芳烃（包括萘，菲和联苯）区域选择性地羧化，产率为91-98％在适当的溶剂中的SiCl，该溶剂选自苯，氯苯和氟苯。这些溶剂以及溴苯都能抵抗羧化反应。然而，当在高温下用AlBr 3和i PrSiCl的1：5混合物处理时，它们也以中等收率被羧化。通过将AlBr 3和Ph 3 SiCl的悬浮液在环己烷中暴露于CO 2制备的混合物的FT-IR光谱显示约1650 cm -1的吸收带，该吸收带归属于由CO 2组成的物质的C═O拉伸振动，AlBr