2-乙基-1,3-氢化茚二酮 | 1133-72-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 2-乙基-1,3-氢化茚二酮
• 中文别名: 2-乙酰基-1,3-茚二酮
• 英文名称: 2-acetyl-indan-1,3-dione
• 英文别名: 2-acetyl-1,3-indandione；2-acetylindane-1,3-dione；2-acetyl-1,3-indanedione；2-Acetyl-1H-indene-1,3(2H)-dione；2-acetylindene-1,3-dione
• CAS: 1133-72-8
• 化学式: C₁₁H₈O₃
• mdl: MFCD00466278
• 分子量: 188.183
• InChiKey: SGLKFWMIZOJHCL-UHFFFAOYSA-N

物化性质

• 熔点：
  109-112 °C (lit.)
• 稳定性/保质期：

  在常温常压下，该物质保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• RTECS号：
  NK5075000
• 海关编码：
  2914399090
• 储存条件：
  常温、避光、存放在通风干燥处。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 2-Acetyl-1,3-indanedione
CAS-No. : 1133-72-8
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
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C11H8O3
Molecular Weight : 188,18 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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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.
Air sensitive.
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 Melting point/range: 109 - 112 °C - lit.
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
Air
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.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: NK5075000

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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-乙基-1,3-氢化茚二酮 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 N-<β-(1,3-dioxo-2-indanyl)carbonylethyl>glycine
  参考文献：
  名称：

  Hammouda, M.; Hamama, W. S.; Kandeel, E. M., Pharmazie, 1988, vol. 43, # 8, p. 529 - 531

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-3-(2-oxopropylidene)-3H-isobenzofuran-1-one 在 sodium methylate 作用下， 生成 2-乙基-1,3-氢化茚二酮
  参考文献：
  名称：

  Buelow; Deseniss, Chemische Berichte, 1906, vol. 39, p. 2279

  摘要：

  DOI：

文献信息

• Molecular Tweezers: Synthesis and Formation of Host-Guest Complexes
  作者：Béatrice Legouin、Maud Gayral、Philippe Uriac、Jean-François Cupif、Nicolas Levoin、Loic Toupet、Pierre van de Weghe

  DOI：10.1002/ejoc.201000729

  日期：——

  A chiral molecular tweezer obtained from (+)-usnic acid placed in solution in the presence of various aromatic compounds afforded complexes with low association constants. Thus, the X-ray structure of assembly 3i is presented, where the guest is sandwiched between the two pincers of the tweezer. The association constants for various guests were determined through different methods. Finally, other tweezers

  在各种芳香族化合物存在的情况下，从 (+)-usnic 酸溶液中获得的手性分子镊子提供了具有低缔合常数的复合物。因此，呈现组件 3i 的 X 射线结构，其中客体夹在镊子的两个钳子之间。各种客人的关联常数是通过不同的方法确定的。最后，由 (1R,2R)-1,2-二氨基环己烷制备了其他带有富电子芳香醛和酮的镊子。最有趣的配合物也通过结构分析得到证实，并且以 10-羟基菲-9-甲醛 (5i) 作为芳香部分获得了最好的结果。
• Synthesis and Antimicrobial Activity of Some 1,3-Disubstituted Indeno[1,2-<i>c</i>]pyrazoles
  作者：Rajni Mohil、Devinder Kumar、Satbir Mor

  DOI：10.1002/jhet.1081

  日期：2014.1

  Synthesis of new 3‐alkyl indeno[1,2‐c]pyrazoles, possessing 4‐substituted thiazole moiety at position‐1 derived from 2‐acyl indane‐1,3‐diones, has been described. These compounds and their precursor were screened for their antibacterial (Staphylococcus aureus, Bacillus subtilis, Escherichia coli) and antifungal (Aspergillus niger, Candida albicans) activities.

  已经描述了新的3-烷基茚并[1,2- c ]吡唑的合成，该衍生物在2-位茚满-1,3-二酮衍生自位置1处具有4-取代的噻唑部分。筛选了这些化合物及其前体的抗菌活性（金 黄色葡萄球菌，枯草芽孢杆菌，大肠杆菌）和抗真菌活性（黑曲霉，白色念珠菌）。
• Synthesis, Type II diabetes inhibitory activity, antimicrobial evaluation and docking studies of indeno[1,2-c]pyrazol-4(1H)-ones
  作者：Satbir Mor、Suchita Sindhu

  DOI：10.1007/s00044-019-02457-8

  日期：2020.1

  We report a convenient and efficient synthesis of indeno[1,2-c]pyrazol-4(1H)-ones (4a‒o) by the reaction of a variety of 2-acyl-(1H)-indene-1,3(2H)-diones (1) and 2-hydrazinylbenzo[d]thiazole/2-hydrazinyl-6-substitutedbenzo[d]thiazoles (2) in the presence of glacial acetic acid in good yields. The structure of the compounds thus prepared were confirmed by analytical and spectral (FT-IR, 1H NMR, 13C

  我们报告了通过各种2-酰基-（1 H）-茚-1的反应，方便高效地合成茚并[1,2 - c ]吡唑-4（1 H）-ones（4a‒o），在冰乙酸存在下，以高收率得到3（2 H）-二酮（1）和2-肼基苯并[ d ]噻唑/ 2-肼基-6-取代的苯并[ d ]噻唑（2）。通过分析和光谱（FT-IR，1 H NMR，13 C NMR和HRMS）技术确认了由此制备的化合物的结构。所有合成的茚并[1,2 - c ]吡唑-4（1 H）-ones（4a‒o通过使用阿卡波糖（Acarbose）作为标准药物测定其体外II型糖尿病抑制活性，并以链霉素和氟康唑为参考药物测定其体外抗菌活性。在合成的衍生物中，发现4e（IC 50  = 6.71μg/ mL）与标准阿卡波糖（IC 50  = 9.35μg/ mL）和4i（IC 50  = 11.90μg / mL）相比，对α-葡萄糖苷酶的抑制作用更强。与标准阿卡波糖（IC
• Synthesis, Characterization and DNA Binding Studies of Some Hydrazide Derivatives Schiff Base Metal Complexes of Mn(II), Co(II/III), Ni(II), Cu(II) and Zn(II) Metal Ions
  作者：Ramina、Rajkumar Bhubon Singh、Oinam U-wang

  DOI：10.14233/ajchem.2021.23408

  日期：——

  carbohydrazide (L4). Characterization of the metal complexes were carried out by using various physico-chemical techniques. Complexes 1, 3, 4, 6, 11, 14, 15, 16, 17 and 18 have been found octahedral structures while the metal complexes 2, 5, 8, 10 and 13 have tetrahedral structures. And, complexes 7, 9 and 12 have square planar structures. Thermal study has revealed the presence of lattice and coordinated

  使用四种不同的席夫碱配体合成了十八种金属配合物，(1E)-1-((6-甲基-4-氧代-4H-苯并-3-基)亚甲基)碳酰肼(L1)、6-[2-(水杨基)肼基]-N'-(水杨基)烟酰肼(HL2)、6-肼基-N'-(6-甲基-4-氧代-4H-苯并-3-基-亚甲基)烟酰肼(HL3)和(E) -6-肼基-N'-(1-(2,3-二氢-1,3-二氧代-1H-茚-2-基)-亚乙基)吡啶-3-碳酰肼(L4)。通过使用各种物理化学技术对金属配合物进行表征。配合物1、3、4、6、11、14、15、16、17和18被发现具有八面体结构，而金属配合物2、5、8、10和13具有四面体结构。并且，配合物7、9和12具有正方形平面结构。热研究揭示了复合物中晶格和配位水分子的存在。粉末X射线衍射研究表明配合物2和14为单斜晶系，而配合物3、4、5、9、11、13和15为三斜晶系。配体与其金属配合物的相互作用通过电子吸收法、循环伏安法和粘度法对小牛胸腺
• Reactions of 2-Acyl-1,3-indandiones with Nitrogen Nucleophiles
  作者：Pavel Hrnčiar、Eva Švanygová

  DOI：10.1135/cccc19942734

  日期：——

  Reactions of 2-acyl-1,3-indandiones with nitrogen nucleophiles were studied rarely. The question, if they react with carbonyl carbon of acyl group or indandione skeleton, has not been answered unambiguously. To make clear the question which carbonyl carbon of 2-acyl-1,3-indandiones enters the reaction with nitrogen nucleophiles we carried out the reactions with 2-acetyl- (Ia), 2-propionyl- (Ib), 2-pivaloyl- (Ic), and 2-benzoyl-1,3-indandione (Id). We used different 2-acyl-1,3-indandiones with the aim to find out if the character of acyl group affects the course of reaction. We used ethoxyamine, primary amines, phenylhydrazine, hydrazine and methylhydrazine as nucleophile reactants. The reactions were carried out in methanol at reflux at 10% excess of nitrogen base. The reactions with phenylhydrazine, hydrazine and methylhydrazine were performed with twofold excess of nitrogen base. The separation of reaction products was carried out by chromatography on silica gel. We found that 2-acyl-1,3-indandiones I react with ethoxyamine both at the acylcarbonyl carbon to produce 2-(1-ethoxyiminoalkyl)-1,3-indandiones II and the carbonyl carbon of indandione skeleton to give rise 3-(ethoxyimino)-2-acyl-1-indanones III. In all cases, the carbonyl carbon of acyl group was preferred (the observed ratio of products II to III was 6 - 8 : 1). From the reaction of 2-acyl-1,3-indandiones with primary amines only the products IV of reaction with the acylcarbonyl carbon were isolated. The hydrazines used reacted with 2-acyl-1,3-indandiones also at carbonyl carbon of acyl group in the first step to produce hydrazones. However, the products isolated in most cases were formed by the attack of hydrazone nitrogen at carbonyl carbon of indandione skeleton giving rise to derivatives of indeno[2,3-d]pyrazole-4-one V. It is interesting that 2-acetyl-1,3-indandione and 2-propionyl-1,3-indandione, reacting with phenylhydrazine and hydrazine, yielded only corresponding hydrazones VI.

  2-酰基-1,3-茚酮与氮亲核试剂的反应很少被研究。问题是，它们是与酰基羰基还是茚酮骨架上的羰基碳反应，尚未明确回答。为了澄清2-酰基-1,3-茚酮的哪个酰基碳与氮亲核试剂进入反应，我们进行了与2-乙酰-（Ia）、2-丙酰-（Ib）、2-戊酰-（Ic）和2-苯甲酰-1,3-茚酮（Id）的反应。我们使用不同的2-酰基-1,3-茚酮，旨在找出酰基群的性质是否影响反应的过程。我们使用乙氧胺、一级胺、苯基肼、肼和甲基肼作为亲核试剂。反应在甲醇中以10%的氮碱过量进行。苯基肼、肼和甲基肼的反应是在氮碱的两倍过量下进行的。反应产物的分离是通过硅胶色谱法进行的。我们发现，2-酰基-1,3-茚酮I与乙氧胺反应，既在酰基羰基碳上产生2-(1-乙氧亚胺烷基)-1,3-茚酮II，又在茚酮骨架的羰基碳上产生3-(乙氧亚胺)-2-酰基-1-茚酮III。在所有情况下，酰基羰基碳被优先选择（观察到的产物II与III的比例为6-8：1）。从2-酰基-1,3-茚酮与一级胺的反应中，只分离出与酰基羰基碳反应的产物IV。使用的肼也在首步与2-酰基-1,3-茚酮的酰基羰基碳反应，产生肼酮。然而，在大多数情况下，分离出的产物是由肼酮氮原子攻击茚酮骨架的羰基碳形成的，形成吲哚[2,3-d]吡唑-4-酮衍生物V。有趣的是，2-乙酰-1,3-茚酮和2-丙酰-1,3-茚酮与苯基肼和肼反应，只产生相应的肼酮VI。