10-氯-9-蒽甲醛 | 10527-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 10-氯-9-蒽甲醛
• 中文别名: 10-氯蒽-9-甲醛；1-氯-9-蒽甲醛
• 英文名称: 10-chloro-9-anthraldehyde
• 英文别名: 10-chloro-9-anthracenecarboxaldehyde；10-Chlor-9-anthraldehyd；10-chloro-9-anthracenecarbaldehyde；10-chloroanthracene-9-carbaldehyde
• CAS: 10527-16-9
• 化学式: C₁₅H₉ClO
• mdl: MFCD00001255
• 分子量: 240.689
• InChiKey: SHYBXXMECBHHFH-UHFFFAOYSA-N

物化性质

• 熔点：
  215-218 °C (lit.)
• 沸点：
  435.9±18.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规定使用和储存，则不会分解，未有已知危险发生。 应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  3
• 海关编码：
  2913000090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  请将药品存放在密闭、阴凉干燥的地方，并确保通风良好。

SDS

Name:	10-Chloro-9-Anthraldehyde 97% Material Safety Data Sheet
Synonym:	None known
CAS:	10527-16-9

Section 1 - Chemical Product MSDS Name:10-Chloro-9-Anthraldehyde 97% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
10527-16-9	10-Chloro-9-Anthraldehyde	97	234-086-8

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. 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. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 10527-16-9: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: yellow
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 215.00 - 218.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C15H9ClO
Molecular Weight: 240.69

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Strong bases, strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 10527-16-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
10-Chloro-9-Anthraldehyde - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 10527-16-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 10527-16-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 10527-16-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  10-氯-9-蒽甲醛 在 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以15%的产率得到蒽醌
  参考文献：
  名称：

  合成，细胞毒性评价的人类细胞系和异Arylidene-9（10H）-蒽酮的体外DNA相互作用

  摘要：

  异亚芳基-9（10 H）-蒽酮在人细胞系中的合成，细胞毒性评估和体外DNA相互作用

  DOI：

  10.1002/ejoc.201701500
• 作为产物：
  描述：

  10-氯蒽-9-甲醇 在 2-碘酰基苯甲酸 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以91%的产率得到10-氯-9-蒽甲醛
  参考文献：
  名称：

  IBX在球磨过程中在无溶剂条件下有效工作†

  摘要：

  IBX（2-碘氧基苯甲酸），发现于1893年，是合成化学中的一种氧化剂，由于其在高温下的爆炸性以及在除DMSO之外的普通有机溶剂中的溶解性差而被广泛使用而受到阻碍。自1983年发现Dess-Martin Periodinane以来，已经报道了几种改进的IBX系统。但是，在球磨条件下，IBX可以在环境温度和无溶剂条件下有效地利用各种有机功能。另外，反应产生的废IBA（2-碘代苯甲酸）也就地在接下来的步骤中，使用过硫酸氢钾将其氧化成IBX，因此通过保持其效率（在15个循环后仅损失约6％）而重复用于多个循环。这项工作概述了一种非常经济的合成方法，该方法克服了使用IBX的问题，可以有效地以克为单位且以非爆炸方式进行。

  DOI：

  10.1039/c4ra00415a

文献信息

• Highly efficient carbazolyl-derived phosphine ligands: application to sterically hindered biaryl couplings
  作者：Sheung Chun To、Fuk Yee Kwong

  DOI：10.1039/c1cc10708a

  日期：——

  A new family of phosphine ligands bearing a bulky carbazolyl scaffold is described. With the combination of ligand 2a and Pd(OAc)2, difficult tri-ortho-substituted biaryl couplings are accomplished smoothly. In particular, the catalyst loading as low as 0.02 mol% of Pd for non-activated 2,6-disubstituted aryl chloride coupling can be achieved.

  描述了一类新型膦配体，这些配体含有一个庞大的咔唲基骨架。通过结合配体2a和Pd(OAc)2，成功实现了难以进行的三邻位取代联苯偶联反应。特别是，对于非活化的2,6-二取代芳基氯偶联反应，可以实现低至0.02mol%的钯催化剂负载量。
• In Silico Driven Design and Synthesis of Rhodanine Derivatives as Novel Antibacterials Targeting the Enoyl Reductase InhA
  作者：Liudas Slepikas、Gianpaolo Chiriano、Remo Perozzo、Sébastien Tardy、Agata Kranjc、Ophélie Patthey-Vuadens、Hajer Ouertatani-Sakouhi、Sébastien Kicka、Christopher F. Harrison、Tiziana Scrignari、Karl Perron、Hubert Hilbi、Thierry Soldati、Pierre Cosson、Eduardas Tarasevicius、Leonardo Scapozza

  DOI：10.1021/acs.jmedchem.5b01620

  日期：2016.12.22

  computational studies. Their antimicrobial activity was assessed against Mycobacterium marinum (Mm) (a model for Mtb), Pseudomonas aeruginosa (Pa), Legionella pneumophila (Lp), and Enterococcus faecalis (Ef) by using anti-infective, antivirulence, and antibiotic assays. Nineteen out of 34 compounds reduced Mm virulence at 10 μM. 33 exhibited promising antibiotic activity against Mm with a MIC of 0.21 μM and showed

  在这里，我们报告针对结核分枝杆菌结核（Mtb）反-2-烯酰基酰基载体蛋白还原酶（InhA）的4-噻唑烷酮（若丹宁）衍生物的设计，合成和生物学评估。在罗丹宁环第5位具有庞大芳族取代基且在N -3位具有色氨酸残基的化合物对InhA的活性最高，IC 50值为2.7至30μM。实验数据显示与计算研究一致的相关性。他们的抗菌活性评估了对结核分枝杆菌（Mm）（铜绿假单胞菌（Mtb）的模型）。Pa），嗜肺军团菌（Lp）和粪肠球菌（Ef），方法是使用抗感染，抗毒力和抗生素检测方法。34种化合物中有19种降低了10μM的Mm毒力。33的MIC为0.21μM，对Mm表现出有希望的抗生素活性，在30μM的抗感染试验中，Lp的生长降低了89％。32显示对Ef的高抗生素活性，MIC为0.57μM。
• Nucleophilic difluoromethylation and difluoromethylenation using bromodifluoromethyl phenyl sulfone
  作者：G.K. Surya Prakash、Ying Wang、Jinbo Hu、George A. Olah

  DOI：10.1016/j.jfluchem.2005.07.011

  日期：2005.10

  found to be an effective electron-transfer agent that promoted the reactions of bromodifluoromethyl phenyl sulfone with aldehydes to give structurally diverse (benzenesulfonyl)difluoromethylated alcohols in good yield, which can be further transformed into difluoromethyl alcohols and 1,1-difluoro-1-alkenes via reductive desulfonylation and Julia olefination, respectively.

  已发现四（二甲基氨基）乙烯（TDAE）是一种有效的电子转移剂，可促进溴二氟甲基苯基砜与醛的反应，从而以高收率获得结构多样的（苯磺酰基）二氟甲基化醇，可将其进一步转化为二氟甲基醇和1,1-二氟-1-烯烃分别通过还原性脱磺酰基反应和朱莉娅烯化反应。
• Catalytic α-Selective Deuteration of Styrene Derivatives
  作者：Thomas R. Puleo、Alivia J. Strong、Jeffrey S. Bandar

  DOI：10.1021/jacs.8b12874

  日期：2019.1.30

  We report an operationally simple protocol for the catalytic α-deuteration of styrenes. This process proceeds via the base-catalyzed reversible addition of methanol to styrenes in DMSO -d6 solvent. The concentration of methanol is shown to be critical for high yields and selectivities over multiple competing side reactions. The synthetic utility of α-deuterated styrenes for accessing deuterium-labeled

  我们报告了一个操作简单的苯乙烯催化 α-氘化协议。该过程通过碱催化将甲醇可逆加成到 DMSO -d6 溶剂中的苯乙烯中进行。甲醇的浓度显示出对于多个竞争副反应的高产率和选择性至关重要。证明了 α-氘代苯乙烯在获取氘标记的手性苄基立体中心方面的合成效用。
• CuIBiOI is an efficient novel catalyst in Ullmann-type CN couplings with wide scope—A rare non-photocatalyic application
  作者：Gábor Varga、Marianna Kocsis、Ákos Kukovecz、Zoltán Kónya、Igor Djerdj、Pál Sipos、István Pálinkó

  DOI：10.1016/j.mcat.2020.111072

  日期：2020.9

  Ullmann-type CN coupling reactions between aryl halides and aqueous ammonia, its catalytic capabilities were tested. The effects of solvents, added base and catalyst loading as well as reaction time and reaction temperature were scrutinized, and a green way for the reaction was identified. The recyclability of the catalyst without the loss of activity and its general applicability for a wide range of aryl halides

  制备了新的混合阳离子层状Cu I BiOI，并探索了其非光催化催化性能。该固体物质由于在Bi 2 O 2层中掺入Cu I离子而具有BiOI状，层状和挠曲结构。所制备的物质已通过XRD，拉曼，远红外，UV DR，XP光谱，热（TG-DTG）和分析（ICP-MS，SEM-EDX）方法，电子显微镜（SEM，TEM）进行了全面表征作为BET表面积测量值。通过执行乌尔曼型CN测试了芳基卤化物与氨水之间的偶联反应，并对其催化能力进行了测试。考察了溶剂，添加碱和催化剂的量以及反应时间和反应温度的影响，并确定了绿色反应方式。还证明了催化剂的可回收性而不丧失活性，并且证明了其广泛适用于各种芳基卤化物。

表征谱图