6-氯-5-(2-氯乙基)羟吲哚 | 118289-55-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 6-氯-5-(2-氯乙基)羟吲哚
• 中文别名: 5-(2-氯乙基)-6-氯-1,3-二氢-吲哚-2-(2H)-酮；6-氯-5-(2-氯乙氧基)-2-吲哚二酮；5-(2-氯乙基)-6-氯-1,3-二氢(2H)-吲哚-2-酮；5-(2-氯乙基)-6-氯-1,3-二氢-2H-吲哚-2-酮；5-氯乙基-6-氯-2-氧嗓
• 英文名称: 6-chloro-5-(2-chloroethyl)-2-oxindole
• 英文别名: 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one；6-Chloro-5-(2-chloroethyl)indolin-2-one；6-chloro-5-(2-chloroethyl)-1,3-dihydroindol-2-one
• CAS: 118289-55-7
• 化学式: C₁₀H₉Cl₂NO
• mdl: MFCD03411598
• 分子量: 230.094
• InChiKey: ZTQQXEPZEYIVDK-UHFFFAOYSA-N

物化性质

• 熔点：
  218-221℃
• 沸点：
  393.8±42.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基甲酰胺
• LogP：
  2.93 at 20℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  9
• 危险品标志：
  N
• 危险类别码：
  R50/53
• 危险品运输编号：
  3077
• 海关编码：
  2933790090
• 包装等级：
  III
• 危险类别：
  9
• 安全说明：
  S60,S61
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P310,P330,P362+P364,P403+P233,P501
• 危险性描述：
  H302,H315,H318,H335,H410
• 储存条件：
  | 冰箱 |

SDS

6-Chloro-5-(2-chloroethyl)oxindole
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 6-Chloro-5-(2-chloroethyl)oxindole

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS
Category 1
Acute aquatic hazard
Long-term aquatic hazard Category 1
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements
Very toxic to aquatic life
Very toxic to aquatic life with long lasting effects
Precautionary statements:
[Prevention] Avoid release to the environment.
Collect spillage.
[Response]
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 6-Chloro-5-(2-chloroethyl)oxindole
Percent: >98.0%(GC)
CAS Number: 118289-55-7
Synonyms: 6-Chloro-5-(2-chloroethyl)-2-indolinone
Chemical Formula: C10H9Cl2NO

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
6-Chloro-5-(2-chloroethyl)oxindole

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Section 4. FIRST AID MEASURES
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Dry chemical, foam, water spray, carbon dioxide.
Suitable extinguishing
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Be careful not to let it flow into rivers, etc., since adverse effects on the environment
are concerned.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a refrigerator.
Store away from incompatible materials such as oxidizing agents.
Heat-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: Very pale yellow - Pale reddish yellow
No data available
Odour:
6-Chloro-5-(2-chloroethyl)oxindole

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:225°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents]
Soluble: Dimethylformamide(DMF)

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Hydrogen chloride
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: 9: Miscellaneous dangerous goods.
UN-No: 3077
Proper shipping name: Environmentally hazardous substance, solid, n.o.s.
6-Chloro-5-(2-chloroethyl)oxindole

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Section 14. TRANSPORT INFORMATION
Packing group: III
Marine pollutant Y

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

齐拉西酮中间体：5-(2-氯乙基)-6-氯-1,3-二氢-吲哚-2-(2H)-酮，5-氯乙酰-6-氯-1,3-二氢-2H-吲哚-2-酮，3-(1-哌嗪基)-1,2-苯并异噻唑盐酸盐

齐哌西酮是一种非典型抗精神病药，属苯并噻唑哌嗪类化合物。体外实验表明，其对多巴胺D2、D3、5-HT2A、5-HT2C、5-HT1A、5-HT1D和α1肾上腺素受体的亲和力很强；对组胺H1受体的亲和力中等。它对多巴胺D1、D2、5-HT2A、5-HT1D具拮抗作用，而对5-HT1A受体起激动作用。齐哌西酮还抑制突触前膜对5-HT和去甲肾上腺素的再摄取，但其作用机制尚不明确，可能通过对多巴胺D2和5-HT2的联合拮抗产生抗精神分裂症疗效。其阻断强度类似于利培酮和氟哌啶醇，比奥氮平、奎硫平和氯氮平更强，主要用于治疗急性或慢性初发或复发的精神分裂症，对阴性和阳性症状均有效，尤其在改善阴性症状方面效果更佳。它能减轻幻觉、妄想、思维和行动异常等阳性症状；同时改善情绪单调、意志性行为减少等阴性症状。

非典型抗精神病药又称为新一代抗精神病药，指对多巴胺D2受体的阻断弱于对5-HT2A受体的阻断的药物。目前临床上使用的氯氮平、利培酮、奥氮平、奎硫平和齐拉西酮等均属此类。除氯氮平临床应用较早外（70年代），其他药物的应用时间较晚。

非典型抗精神病药不仅阻断多巴胺D2受体，还具有更强地阻断5-HT2A受体的作用。当阻断中脑-边缘通路的多巴胺D2受体时，可改善患者的阳性症状；而当阻断中脑-皮质通路突触前膜上的5-HT2A受体时，则会引起多巴胺脱抑制性释放，激动前额皮质背外侧的多巴胺D1受体，改善阴性和认知症状；激动前额皮质背内侧部和眶部的多巴胺D1受体，可改善抑郁症状。当阻断黑质-纹状体通路突触前膜上的5-HT2A受体时，则会引起多巴胺脱抑制性释放，部分抵消药物对多巴胺D2受体的阻断作用，从而减轻锥体外系反应（长期使用也不易引起迟发性运动障碍）。同样地，当阻断下丘脑-漏斗部突触前膜上的5-HT2A受体时，则会引起多巴胺脱抑制性释放，部分抵消药物对多巴胺D2受体的阻断作用，从而减少高催乳素血症的发生。

化学性质：浅褐色粉末

用途：齐拉西酮中间体。

反应信息

• 作为反应物：
  描述：

  6-氯-5-(2-氯乙基)羟吲哚 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  镍（II）催化α-重氮吡唑酰胺与硫吲哚的不对称硫代克莱森重排。

  摘要：

  用修饰的手性N，N'-二氧化物配体实现了镍（II）催化的α-重氮吡唑酰胺与硫吲哚的对映体硫克莱森重排反应，高收率（高达95％）提供了多种C3取代的吲哚衍生物。在温和的反应条件下具有出色的对映选择性（高达96％ee）。基于先前的报道和催化剂的X射线晶体结构，提出了可能的过渡态模型。

  DOI：

  10.1039/d0cc04590j
• 作为产物：
  描述：

  2,5-二氯硝基苯 在 盐酸 、 aluminum (III) chloride 、 tin 、 potassium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 16.25h， 生成 6-氯-5-(2-氯乙基)羟吲哚
  参考文献：
  名称：

  [EN] A SHORT PROCESS FOR THE PREPARATION OF ZIPRASIDONE AND INTERMEDIATES THEREOF
  [FR] PROCÉDÉ COURT POUR LA PRÉPARATION DE ZIPRASIDONE ET DE SES INTERMÉDIAIRES

  摘要：

  一种制备氧化吲哚衍生物（盐酸齐拉西酮）的方法，包括将式（II）的化合物与金属或金属化合物矿酸反应，以一步得到式（III）的化合物，该化合物转化为式IV的化合物，后者是制备式（I）的化合物的关键中间体。

  公开号：

  WO2012020424A1
• 作为试剂：
  描述：

  6-氯-5-(2-氯乙基)羟吲哚 、 7-bromo-3-piperazinyl-1,2-benzisothiazole 在 6-氯-5-(2-氯乙基)羟吲哚 作用下， 以89的产率得到5-(2-(4-(7-bromo-1,2-benzisothiazol-3-yl)piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  J. Labelled Compd. Rad. 1994, 34, 117-125

  摘要：

  DOI：

文献信息

• Discovery of a Tetracyclic Quinoxaline Derivative as a Potent and Orally Active Multifunctional Drug Candidate for the Treatment of Neuropsychiatric and Neurological Disorders
  作者：Peng Li、Qiang Zhang、Albert J. Robichaud、Taekyu Lee、John Tomesch、Wei Yao、J. David Beard、Gretchen L. Snyder、Hongwen Zhu、Youyi Peng、Joseph P. Hendrick、Kimberly E. Vanover、Robert E. Davis、Sharon Mates、Lawrence P. Wennogle

  DOI：10.1021/jm401958n

  日期：2014.3.27

  We report the synthesis and structure–activity relationships of a class of tetracyclic butyrophenones that exhibit potent binding affinities to serotonin 5-HT2A and dopamine D2 receptors. This work has led to the discovery of 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H,7H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8-yl)-1-(4-fluorophenyl)-butan-1-one 4-methylbenzenesulfonate (ITI-007), which

  我们报告了一类四环丁苯酮的合成与结构-活性关系，这些四环丁酮显示了对5-羟色胺5-HT 2A和多巴胺D 2受体的强结合亲和力。这项工作导致了4-（（6b R，10a S）-3-methyl-2,3,6b，9,10,10 a -hexahydro -1 H，7 H -pyrido [3'，4 ′：4,5]吡咯并[1,2,3- de ]喹喔啉-8-基）-1-（4-氟苯基）-丁-1-酮4-甲基苯磺酸盐（ITI-007），其有效值为5 -HT 2A拮抗剂，突触后D 2素和5-羟色胺转运蛋白的抑制剂。该多功能候选药物具有口服生物利用度，并且在体内表现出良好的抗精神病功效。目前，这种正在研究中的新药正在临床开发中，用于治疗神经精神疾病和神经疾病。
• [EN] OXINDOLE SUBSTITUTED PIPERAZINE DERIVATIVES<br/>[FR] DERIVES DE PIPERAZINE SUBSTITUES PAR UN OXINDOLE
  申请人：WARNER LAMBERT CO

  公开号：WO2004037820A1

  公开（公告）日：2004-05-06

  The invention relates to compounds of the formula (I), wherein Ar, A, R, R?1, R2, R3, R4 and R5¿ are defined as in the specification, pharmaceutical compositions containing them and their use in the treatment of central nervous system disorders.

  这项发明涉及公式（I）的化合物，其中Ar，A，R，R1，R2，R3，R4和R5在规范中定义，包含它们的药物组合物以及它们在治疗中枢神经系统疾病中的用途。
• Facile synthesis of pyrroloindoles <i>via</i> a rhodium(<scp>ii</scp>)-catalyzed annulation of 3-benzylidene-indolin-2-ones and α-imino carbenes
  作者：Xueji Ma、Xuemei Xie、Li Liu、Ran Xia、Tongyu Li、Hangxiang Wang

  DOI：10.1039/c7cc08438b

  日期：——

  A novel carbenoid strategy to construct pyrrole-fused indole alkaloids.

  一种新颖的碳亚甲基策略用于构建咔唑并融合吲哚生物碱。
• HETEROCYCLIC COMPOUNDS, PROCESS FOR PREPARATION OF THE SAME AND USE THEREOF
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES

  公开号：US20170158680A1

  公开（公告）日：2017-06-08

  The present invention provides a heterocyclic compound represented by the formula (I), its stereoisomers, or a pharmaceutically acceptable salt thereof, pharmaceutical compositions thereof, and their use in preparing a medicament for the prevention and/or treatment of central nervous system disease.

  本发明提供了一种由公式（I）表示的杂环化合物，其立体异构体，或其药用可接受的盐，其药物组合物，以及它们用于制备预防或治疗中枢神经系统疾病的药物。
• METHOD OF TREATING GLAUCOMA AND ISCHEMIC RETINOPATHY
  申请人：——

  公开号：US20020004504A1

  公开（公告）日：2002-01-10

  A method for treating glaucoma and ischemic retinopathy in a mammal, comprising administering to said mammal a therapeutically effective amount of a compound of the formula 1 or a pharmaceutically acceptable acid addition salt thereof, wherein n, X, Y and Ar are as defined in the specification.

  在哺乳动物中治疗青光眼和缺血性视网膜病的方法，包括向所述哺乳动物施用公式1的化合物或其药学上可接受的酸盐的治疗有效量，其中n、X、Y和Ar如规范中定义。