2-苯甲酰-1,3-茚满二酮 | 1785-95-1

• 物质功能分类: 化学农药原药 - 杀虫剂 - 杀鼠剂
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-苯甲酰-1,3-茚满二酮
• 中文别名: 2-苯甲酰基-1,3-茚二酮
• 英文名称: 2-benzoyl-1,3-indanedione
• 英文别名: 2-Benzoyl-indan-1,3-dion；2-benzoyl-1,3-indandione；2-benzoyl-indandion-(1,3)；2-benzoyl-1H-indene-1,3(2H)-dione；2-Benzoyl-1,3-indandion；2-benzoylindene-1,3-dione
• CAS: 1785-95-1
• 化学式: C₁₆H₁₀O₃
• mdl: MFCD00051929
• 分子量: 250.254
• InChiKey: UURMMRCWXJLUKF-UHFFFAOYSA-N

物化性质

• 熔点：
  108-112 °C
• 沸点：
  455.4±45.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  常温常压下稳定，可与强化剂发生反应。

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S36/37
• 危险类别码：
  R22
• 海关编码：
  2914399090
• RTECS号：
  NK5105000
• 储存条件：
  密封贮藏，存放在阴凉干燥处，并远离氧化剂。

SDS

Name:	2-Benzoyl-1 3-indanedione 98% Material Safety Data Sheet
Synonym:
CAS:	1785-95-1

Section 1 - Chemical Product MSDS Name:2-Benzoyl-1 3-indanedione 98% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1785-95-1	2-Benzoyl-1,3-indanedione	98%	unlisted

Hazard Symbols: XN
Risk Phrases: 22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with 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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical 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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1785-95-1: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 108 - 112 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density:
Molecular Formula: C16H10O3
Molecular Weight: 250.25

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1785-95-1: NK5105000 LD50/LC50:
CAS# 1785-95-1: Oral, mouse: LD50 = 350 mg/kg.
Carcinogenicity:
2-Benzoyl-1,3-indanedione - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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: XN
Risk Phrases:
R 22 Harmful if swallowed.
Safety Phrases:
WGK (Water Danger/Protection)
CAS# 1785-95-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1785-95-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1785-95-1 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

制备方法与用途

概述

3-茚满二酮类杀鼠剂是一种重要的抗凝血杀鼠剂。由于其适口性好且对非靶动物安全，多次口服的毒力远大于急性口服毒力，因此具有明显的累计毒力效果和良好的灭鼠效果，已成为杀灭鼠类的主要药物之一。常见的1,3-茚满二酮类杀鼠剂有敌鼠、敌鼠钠盐、氯鼠酮等。

近年来，基于抗凝血杀鼠剂结构的改进及增加特异性官能团的研究一直是国内外研究的热点。

应用

2-苯甲酰-1,3-茚满二酮是一种可用于医药合成中间体的化合物。如果吸入了2-苯甲酰-1,3-茚满二酮，应立即将患者移至新鲜空气处；若皮肤接触到该物质，请先脱去污染的衣物，并用肥皂水和清水彻底冲洗皮肤；如出现不适症状，请及时就医。

反应信息

• 作为反应物：
  描述：

  2-苯甲酰-1,3-茚满二酮 在 甲醇 、 sodium 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (4Z,6Z)-2,2-diethyl-7-phenyl-4-(p-tolyl)-8H-indeno[2,1-H][1,3,5,6,2]dioxadiazastannonin-8-one
  参考文献：
  名称：

  衍生自2-苯甲酰基-1H-茚-1,3（2H）-二酮和4-取代的苯甲酸酰肼的席夫碱的二有机锡（IV）配合物的合成，表征，体外抗菌，DNA结合活性和QSAR研究

  摘要：

  （2021年）。衍生自2-苯甲酰基-1H-茚-1,3（2H）-二酮和4-取代的苯甲酸酰肼的席夫碱的二有机锡（IV）配合物的合成，表征，体外抗菌，DNA结合活性和QSAR研究。磷，硫和硅及相关元素：196，第2号，第133-145页。

  DOI：

  10.1080/10426507.2020.1821026
• 作为产物：
  描述：

  2-(3-Oxo-3-phenylpropanoyl)benzoyl chloride 在 samarium(III) chloride 、 三乙胺 作用下， 以 甲苯 为溶剂， 以86%的产率得到2-苯甲酰-1,3-茚满二酮
  参考文献：
  名称：

  SmCl3催化1,3-二羰基化合物和丙二腈的C-酰化。

  摘要：

  已开发出一种可回收，方便且有效的催化体系，用于用酰氯对1，3-二羰基化合物和丙二腈进行C-酰化，在温和条件下产生中等至极好的收率。这是这种反应的第一个催化实例。另外，通过将该方案用作关键步骤，可以轻松地以一锅法高收率合成3,5-二取代-1H-吡唑-4-羧酸酯。

  DOI：

  10.1021/ol701961z

文献信息

• Palladium-Catalyzed Carbonylative Annulation Reactions Using Aryl Formate as a CO Source: Synthesis of 2-Substituted Indene-1,3(2<i>H</i>)-dione Derivatives
  作者：Ying Zhang、Jing-Lei Chen、Zhen-Bang Chen、Yong-Ming Zhu、Shun-Jun Ji

  DOI：10.1021/acs.joc.5b01758

  日期：2015.11.6

  An efficient synthesis of 2-substituted indene-1,3(2H)-diones from stable and readily available 1-(2-halophenyl)-1,3-diones by employing phenyl formate as a CO source has been developed. The reaction occurred via palladium-catalyzed intramolecular carbonylative annulation using K3PO4 as a base and DMSO as a solvent at 95 °C. In this protocol, the reaction showed a broad substrate scope with good to

  已经开发了通过使用甲酸苯酯作为CO源从稳定且容易获得的1-（2-卤代苯基）-1,3-二酮有效合成2-取代的茚-1,3（2 H）-二酮的方法。该反应通过在95°C下使用K 3 PO 4为碱和DMSO作为溶剂的钯催化的分子内羰基环化反应进行。在该方案中，反应显示出广泛的底物范围，具有良好或优异的产率。
• 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。
• Unraveling Structure−Reactivity Relationships in S_NV Reactions: Kinetics of the Reactions of Methoxybenzylidenemalononitrile, 2-(Methylthiobenzylidene)-1,3-indandione, 2-(Benzylthiobenzylidene)-1,3-indandione, and Methyl β-Methylthio-α-nitrocinnamate with OH^- and Thiolate Ions in Aqueous DMSO
  作者：Claude F. Bernasconi、Rodney J. Ketner、Mark L. Ragains、Xin Chen、Zvi Rappoport

  DOI：10.1021/ja003536t

  日期：2001.3.1

  The kinetics of the title reactions were determined in 50% DMSO-50% water (v/v) at 20 degrees C; n-BuS-, HOCH2CH2S-, and MeO2CCH2S- were used as thiolate ions. The reactions with the thiolate ions gave rise to two separate kinetic processes. The first refers to rapid, reversible attachment of RS- to the substrate leading to a tetrahedral intermediate (k1RS), k(-1)RS, the second to the conversion of

  标题反应的动力学在 50% DMSO-50% 水 (v/v) 中于 20 摄氏度进行测定；n-BuS-、HOCH2CH2S- 和 MeO2CCH2S- 用作硫醇盐离子。与硫醇盐离子的反应产生两个独立的动力学过程。第一个是指 RS- 与底物的快速、可逆连接，导致四面体中间体 (k1RS)，k(-1)RS，第二个是中间体转化为产物 (k2RS)。在大多数情况下，可以确定所有速率常数（k1RS、k(-1)RS 和 k2RS。结合先前研究的结果，详细讨论了活化取代基和离去基团对速率常数和平衡常数的影响与本征速率常数一样，与 OH- 的反应仅允许测定 k1OH 对底物的亲核攻击；
• Fused Tetrazolo[1,5-<i>a</i>]pyrimidines and 2-Azidopyrimidines from 2-Acyl-1,3-indandiones and 5-Aminotetrazole
  作者：Thomas Russ、Jan W Bats、Walter Ried

  DOI：10.1055/s-1990-26994

  日期：——

  Cyclocondensations of 2-acyl-1,3-indandiones 1a-e and 5-amino-tetrazole monohydrate (2) in ethanol in the presence of catalytic amounts of acetic acid afford indeno[1,2-d]tetrazolo[1,5-a]pyrimidin-6-ones 3a-c or 2-azidoindeno[1,2-d]pyrimidin-5-ones 4a,b in a single step depending on the nature of the acyl substituent R. The structure of 3c was confirmed by X-ray analysis.

  2-酰基-1,3-茚满二酮 1a-e 和 5-氨基-四唑一水合物 (2) 在乙醇中在催化量的乙酸存在下环缩合得到茚并[1,2-d]四唑[1,5- a]嘧啶-6-酮 3a-c 或 2-叠氮茚并[1,2-d]嘧啶-5-酮 4a,b 根据酰基取代基 R 的性质，一步完成。 3c 的结构通过以下方式确认X 射线分析。
• Photochemical synthesis of isomeric (E/Z)-3-alkylidene-3H-isobenzofuranones
  作者：Satbir Mor、Som N. Dhawan、Mona Kapoor、Devinder Kumar

  DOI：10.1016/j.tet.2006.11.021

  日期：2007.1

  The synthesis of isomeric (E/Z)-3-alkylidene-3H-isobenzofuranones by photoisomerization of 2-aroyl-2-methyl/benzylindan-1,3-diones in high yields is described.

  描述了通过高产率地2-芳酰基-2-甲基/苄基茚满-1，3-二酮的光异构化合成异构体（E / Z）-3-亚烷基-3 H-异苯并呋喃酮。

表征谱图