5-氯吲哚啉 | 25658-80-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 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: 5-氯吲哚啉
• 中文别名: 5-氯-2,3-二氢-1H-吲哚；5-氯-2,3二氢吲哚
• 英文名称: 5-chloro-2,3-dihydroindole
• 英文别名: 5-chloroindoline；5-chloro-2,3-dihydro-1H-indole；2,3-dihydro-5-chloroindole
• CAS: 25658-80-4
• 化学式: C₈H₈ClN
• mdl: MFCD01941330
• 分子量: 153.611
• InChiKey: YMCIVAPEOZDEGH-UHFFFAOYSA-N

物化性质

• 沸点：
  93-98°C 0,3mm
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 海关编码：
  2933990090
• WGK Germany：
  3
• 储存条件：
  存储条件：2-8°C，避光保存。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 5-Chloroindoline
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
P273: Avoid release to the environment
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician

---

Section 3. Composition/information on ingredients.
Ingredient name: 5-Chloroindoline
CAS number: 25658-80-4

---

Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H8ClN
Molecular weight: 153.6

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen chloride.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
UN Number: UN2811 Class: 6.1 Packing group: III
Proper shipping name: TOXIC SOLIDS, ORGANIC, N.O.S. (5-Chloroindoline)

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  吲哚啉	1-indoline	496-15-1	C8H9N	119.166
  ——	5-Chloro-2,3-dihydroindole-1-carbaldehyde	——	C9H8ClNO	181.622
  ——	1-(5-chloroindolin-1-yl)ethan-1-one	25630-01-7	C10H10ClNO	195.648
  5-氯-2-吲哚啉羧酸	5-chloroindoline-2-carboxylic acid	10241-98-2	C9H8ClNO2	197.621

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5-chloro-1-methylindoline	26663-50-3	C9H10ClN	167.638
  ——	2-(5-chloroindolin-1-yl)ethanamine	——	C10H13ClN2	196.68
  ——	5-Chloro-1-nitroso-indolenin	34851-18-8	C8H7ClN2O	182.609
  ——	2-(5-Chloro-2,3-dihydroindol-1-yl)acetic acid	1366246-42-5	C10H10ClNO2	211.648
  ——	1-(5-chloroindolin-1-yl)ethan-1-one	25630-01-7	C10H10ClNO	195.648
  5-氯靛红	5-chloroindole 2,3-dione	17630-76-1	C8H4ClNO2	181.578
  ——	5-chloro-1-(4-piperidyl)indoline	1571907-72-6	C13H17ClN2	236.744
  ——	3-(5-chloro-1-indolinylmethyl)benzenemethanamine	92083-54-0	C16H17ClN2	272.777
  ——	3-(5-chloro-2,3-dihydro-1H-indol-1-yl)-benzenemethanamine	92083-26-6	C15H15ClN2	258.75
  ——	3-(5-chloro-1-indolinyl)benzonitrile	92083-25-5	C15H11ClN2	254.719

反应信息

• 作为反应物：
  描述：

  5-氯吲哚啉 在 2-亚碘酰基苯甲酸 、 氧气 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以81%的产率得到5-氯靛红
  参考文献：
  名称：

  碘代苯甲酸 (IBA) 催化的苄基和芳族 C-H 氧化

  摘要：

  摘要 采用一种不含金属的可重复使用的高价碘 (III) 试剂作为稳定的催化剂，用于将活性亚甲基、吲哚和苯乙烯的 C-H 键选择性氧化为相应的羰基化合物。从经济和环境的角度来看，使用 2-碘代苯甲酸代替金属进行氧化，使反应变得有趣。图形摘要一种无金属可重复使用的高价碘 (III) 试剂被用作活性亚甲基选择性氧化的稳定催化剂，吲哚和苯乙烯 C-H 键合到相应的羰基化合物上。从经济和环境的角度来看，使用氧气作为氧化剂，使反应变得有趣。

  DOI：

  10.1007/s10562-017-2050-4
• 作为产物：
  描述：

  仲丁醇 在 sodium hydroxide 作用下， 以 氯仿 、 水 、 异丙醇 为溶剂， 以76%的产率得到5-氯吲哚啉
  参考文献：
  名称：

  5-Chloro-indole preparation

  摘要：

  一种改进的制备5-氯吲哚的过程，包括在氯惰性有机溶剂中将吲哚与有机羧酸的酰化剂反应以获得相应的1-酰基吲哚，将后者在水和碱性试剂的存在下与氯反应形成5-氯-1-酰基吲哚，将后者经皂化得到5-氯吲哚，并将后者在不溶于水的有机溶剂中加热与芳香族硝基化合物在粉末状钌催化剂的存在下反应，以获得优良产率的5-氯吲哚。

  公开号：

  US04377699A1

文献信息

• Ruthenium-Catalyzed C7 Amidation of Indoline CH Bonds with Sulfonyl Azides
  作者：Changduo Pan、Ablimit Abdukader、Jie Han、Yixiang Cheng、Chengjian Zhu

  DOI：10.1002/chem.201304236

  日期：2014.3.24

  A ruthenium‐catalyzed direct C7 amidation of indoline CH bonds with sulfonyl azides was developed. This procedure allows the synthesis of a variety of 7‐amino‐substituted indolines, which are useful in pharmaceutical. The good functional tolerances, as well as the mild conditions, are prominent feature of this method.

  开发了钌催化的二氢吲哚CH键与磺酰叠氮化物的C7酰胺化反应。该程序可合成多种7-氨基取代的二氢吲哚，可用于制药。良好的功能公差以及温和的条件是该方法的突出特点。
• [EN] GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE<br/>[FR] INHIBITEURS DE GLYCOLATE OXYDASE POUR LE TRAITEMENT D'UNE MALADIE
  申请人：BIOMARIN PHARM INC

  公开号：WO2020257487A1

  公开（公告）日：2020-12-24

  Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

  本文描述了化合物、制备这种化合物的方法、含有这种化合物的药物组合物和药物，以及使用这种化合物治疗或预防与甘氧酸代谢缺陷相关的疾病或紊乱的方法，例如与甘氧酸氧化酶（GO）或草酸代谢变化相关的疾病或紊乱。这些疾病或紊乱包括与产生过多草酸相关的甘氧酸代谢紊乱，例如原发性高草酸尿症。
• [EN] VASOPRESSIN RECEPTOR ANTAGONISTS AND PRODUCTS AND METHODS RELATED THERETO<br/>[FR] ANTAGONISTES DU RÉCEPTEUR DE LA VASOPRESSINE, PRODUITS ET PROCÉDÉS ASSOCIÉS
  申请人：BLACKTHORN THERAPEUTICS INC

  公开号：WO2019050988A1

  公开（公告）日：2019-03-14

  Compounds are provided that antagonize vasopressin receptors, particularly the V1a receptor products containing such compounds, as well as to methods of their use and synthesis. Such compounds have the structure of Formula (I), or a pharmaceutically acceptable isomer, racemate, hydrate, solvate, isotope, or salt thereof: (I) wherein Q1, Q2, Q3, R2a, R2b, R3 and X are as defined herein.

  提供了拮抗加压素受体的化合物，特别是含有这些化合物的V1a受体产品，以及它们的使用和合成方法。这些化合物具有以下结构的结构（I），或其药学上可接受的异构体、消旋体、水合物、溶剂合物、同位素或盐：（I）其中Q1、Q2、Q3、R2a、R2b、R3和X如本文所定义。
• Design, synthesis and biological evaluation of novel 2-aminobenzamides containing dithiocarbamate moiety as histone deacetylase inhibitors and potent antitumor agents
  作者：Rui Xie、Yan Li、Pingwah Tang、Qipeng Yuan

  DOI：10.1016/j.ejmech.2017.08.041

  日期：2018.1

  HDAC2 selective inhibitors. We also rationalize the high potency and selectivity of compound M122 by molecular docking. Further investigation showed that M101, M122 and M133 could inhibit colony formation of human hepatocellular carcinoma cell line SMMC7721. Furthermore, M101, M122 and M133 remarkably induced apoptosis in SMMC7721 cancer cells. M101 and M133 were found to potently induce SMMC7721 cancer

  设计并合成了一系列以二硫代氨基甲酸酯为帽基的新型2-氨基苯甲酰胺，作为组蛋白脱乙酰基酶（HDAC）抑制剂。大多数新合成的化合物对多种人类肿瘤细胞系均显示出强大的抗增殖活性。最有效的化合物M101，M122和M133在IC 50的作用下，对6种癌细胞系表现出显着增强的抗癌能力与CS055（2.28〜> 26μM）和MS275（0.47–6.74μM）相比，该值低至0.54–2.49μM。HDAC同工型选择性测定表明M101，M122和M133是HDAC1和HDAC2选择性抑制剂。我们还通过分子对接合理化了化合物M122的高效价和选择性。进一步的研究表明，M101，M122和M133可以抑制人肝癌细胞SMMC7721的集落形成。此外，M101，M122和M133显着诱导SMMC7721癌细胞的凋亡。发现M101和M133在G2 / M期有效诱导SMMC7721癌细胞周期停滞。这项研究表明，引入
• [EN] ANTIBACTERIAL BENZOIC ACID DERIVATIVES<br/>[FR] DERIVES D'ACIDES BENZOIQUES ANTIBACTERIENS
  申请人：UPJOHN CO

  公开号：WO2004018428A1

  公开（公告）日：2004-03-04

  The invention provides antimicrobial agents and methods of using the agents for sterilization, sanitation, antisepsis, disinfection, and treatment of infections in mammals.

  这项发明提供了抗菌剂和使用这些剂进行哺乳动物的消毒、卫生、防腐、消毒和治疗感染的方法。