1,2,3,4-四氢咔唑 | 942-01-8

• 物质功能分类: 化学试剂 - 有机试剂 - 三环化合物
• 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: 1,2,3,4-四氢咔唑
• 中文别名: 2,3,4,9-四氢-1H-咔唑；四氢咔唑
• 英文名称: 1,2,3,4-tetrahydrocarbazole
• 英文别名: 2,3,4,9-tetrahydro-1H-carbazole；tetrahydrocarbazole；1,2,3,4-tetrahydro-9H-carbazole；6,7,8,9-tetrahydrocarbazole；1,2,3,4,10,11-hexahydrocarbazole
• CAS: 942-01-8
• 化学式: C₁₂H₁₃N
• mdl: MFCD00004959
• 分子量: 171.242
• InChiKey: XKLNOVWDVMWTOB-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120 °C (lit.)
• 沸点：
  325-330 °C (lit.)
• 密度：
  1.1459 (rough estimate)
• 闪点：
  325-330°C
• 保留指数：
  1809;1775.8
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与氧化物直接接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  2
• 海关编码：
  2933990090
• RTECS号：
  FE6300000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥的地方。

SDS

Name:	1 2 3 4-Tetrahydrocarbazole 99% Material Safety Data Sheet
Synonym:	2,3-Tetramethyleneindole; 1H-Carbazole, 2,3,4,9-Tetrahydro- (9CI); 5,6,7,8-Tetrahydrocarbazole
CAS:	942-01-8

Section 1 - Chemical Product MSDS Name:1 2 3 4-Tetrahydrocarbazole 99% Material Safety Data Sheet
Synonym:2,3-Tetramethyleneindole; 1H-Carbazole, 2,3,4,9-Tetrahydro- (9CI); 5,6,7,8-Tetrahydrocarbazole

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
942-01-8	1,2,3,4-Tetrahydrocarbazole	99%	213-385-7

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. Runoff from fire control or dilution water may cause pollution.
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:
Keep container closed when not in use. 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# 942-01-8: 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:
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: beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 325 - 330 deg C @ 760.00mmHg
Freezing/Melting Point: 118.00 - 120.00 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:
Specific Gravity/Density:
Molecular Formula: C12H13N
Molecular Weight: 171.24

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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:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 942-01-8: FE6300000 LD50/LC50:
CAS# 942-01-8: Oral, rat: LD50 = 2650 mg/kg.
Carcinogenicity:
1,2,3,4-Tetrahydrocarbazole - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 942-01-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 942-01-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 942-01-8 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

1,2,3,4-四氢咔唑可用作医药合成的中间体。它可以由苯肼盐酸盐与环己酮反应制备，也可以通过吲哚反应物、1,4-二溴丁烷、PdCl2(MeCN)2以及降冰片烯进行反应来制备。

制备

在100毫升三口瓶中，将苯肼盐酸盐（1.44克，10毫摩尔）在30分钟内分批加入到环己酮（1.00克，10毫摩尔）的30毫升乙酸溶液中。随后回流8小时，直至反应完全。冷却至室温后，将反应液倒入冰水中并过滤收集固体。然后用甲醇进行重结晶，得到白色固体中间体1,2,3,4-四氢咔唑，总产率为85％。

反应信息

• 作为反应物：
  描述：

  1,2,3,4-四氢咔唑 在 氨 、 sodium 、 ferric nitrate 作用下， 生成 2,3,4,9-四氢-9-甲基-1H-咔唑
  参考文献：
  名称：

  Nakazaki; Isoe, Nippon Kagaku Zasshi, 1955, vol. 76, p. 1159,1167

  摘要：

  DOI：
• 作为产物：
  描述：

  环己酮 2-苯基腙 在 zinc(II) chloride 作用下， 以 三乙二醇 为溶剂， 反应 0.08h， 生成 1,2,3,4-四氢咔唑
  参考文献：
  名称：

  费歇尔合成困难的新方法：在受控的微波辐射下在三甘醇中使用氯化锌催化剂。

  摘要：

  [反应：请参见文字]。三乙二醇与催化量的氯化锌（ZnCl2 / TEG）的应用被描述为一种难于进行费歇尔合成的新型高效反应介质，可导致敏感的吲哚。3-乙酰基-1-甲基硫代环烷基[c]吡啶苯基和对甲氧基苯基hydr转化为2-（2-吡啶基）吲哚和5-甲氧基-2-（2-吡啶基）吲哚，这是我们总的合成子sempervirine型生物碱的合成，是在受控的微波辐射下，在TEG中的干燥氯化锌溶液（0.16 M）中进行的。该方案以优异的收率通过苯乙酮或苯乙酮从苯乙酮或环己酮生产吲哚。

  DOI：

  10.1021/ol052255t
• 作为试剂：
  描述：

  呋喃 、 间氨基苯甲酸 在 tetrafluoroboric acid 、 sodium nitrite 、 1,2,3,4-四氢咔唑 作用下， 以 水 、 丙酮 、 二甲基亚砜 为溶剂， 反应 15.0h， 生成 3-(2-呋喃基)苯甲酸
  参考文献：
  名称：

  咔唑基电子给体受体（EDA）催化合成联芳基和芳基-杂芳基化合物

  摘要：

  描述了一种高度区域选择性的，基于咔唑的电子给体受体（EDA）催化的联芳基和芳基-杂芳基化合物的合成。筛选了各种吲哚和咔唑衍生物进行均相芳香取代（HAS）反应。四氢咔唑（THC）对于HAS转化非常有效，并通过重氮盐与富电子的四氢咔唑之间的络合物形成进行。紫外-可见光谱技术已用于确认复合物的形成。在原位发现即使催化量也能生成的EDA络合物对于单电子转移（SET）过程非常有效，并且没有任何光活化作用。联芳基化合物，2-苯基呋喃，2-苯基噻吩和2-苯基吡咯以及生物活性化合物（例如丹特林和canagliflozin）的合成产率中等至优异。

  DOI：

  10.1039/d0ob00282h

文献信息

• [EN] METHODS OF TREATMENT OF AMYLOIDOSIS USING ASPARTYL-PROTEASE INIHIBITORS<br/>[FR] PROCEDES DE TRAITEMENT D'AMYLOIDOSE UTILISANT DES INHIBITEURS DE PROTEASE ASPARTYLE
  申请人：ELAN PHARM INC

  公开号：WO2005070407A1

  公开（公告）日：2005-08-04

  The invention relates to acetyl 2-hydroxy-1,3-diaminospirocyclohexanes and derivatives thereof that are useful in treating diseases, disorders, and conditions associated with amyloidosis. Amyloidosis refers to a collection of diseases, disorders, and conditions associated with abnormal deposition of A-beta protein.

  这项发明涉及乙酰2-羟基-1,3-二氨基螺环己烷及其衍生物，可用于治疗与淀粉样变性相关的疾病、疾病和症状。淀粉样变性是指与A-beta蛋白异常沉积相关的一系列疾病、疾病和症状。
• Methods of treatment of amyloidosis using bi-aryl aspartyl protease inhibitors
  申请人：John Varghese

  公开号：US20060014737A1

  公开（公告）日：2006-01-19

  The invention relates to novel compounds and methods of treating diseases, disorders, and conditions associated with amyloidosis. Amyloidosis refers to a collection of diseases, disorders, and conditions associated with abnormal deposition of A-beta protein.

  这项发明涉及新型化合物和治疗与淀粉样变性相关的疾病、紊乱和症状的方法。淀粉样变性指与A-beta蛋白异常沉积相关的一系列疾病、紊乱和症状。
• One-pot synthesis of polysubstituted indoles from aliphatic nitro compounds under mild conditions
  作者：Christopher A. Simoneau、Alexis M. Strohl、Bruce Ganem

  DOI：10.1016/j.tetlet.2007.01.031

  日期：2007.3

  Polysubstituted indoles can be prepared directly from functionalized nitroalkanes under very mildly acidic conditions in a simple, one-pot, two-stage procedure.

  多取代吲哚可以在非常温和的酸性条件下通过简单的一锅两步程序直接从官能化硝基烷烃制备。
• TROPAN COMPOUND
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1785421A1

  公开（公告）日：2007-05-16

  The conventional anticholinergic drugs for administration through inhalation have been considered to have the possibility of aggravating dysuria associated with prostatic hyperplasia mediated by blood, and it has been demanded that the conventional anticholinergic drugs for administration through inhalation will have to show reduced side effects or adverse ractions. The present invention relates to a compound represented by the general formula (I): (wherein A represents; and R1, R2, R3 and R1 each a hydrogen atom or a substituent; R5 is a substituent; X- is an anion;the symbol: denotes an exo-form or endo-form, or their mixture), its salt or solvation product thereof. They are useful as a prophylactic and/or therapeutic agent with reduced side effects or adverse reactions for the diseases mediated by the muscarinic receptor.

  传统的抗胆碱药物通过吸入给药被认为可能加重与前列腺增生相关的排尿困难，并要求传统的抗胆碱药物通过吸入给药必须显示减少副作用或不良反应。 本发明涉及一种由通式（I）表示的化合物： （其中A代表; 和R1、R2、R3和R1分别是氢原子或取代基; R5是取代基; X-是阴离子;符号: 表示外向型或内向型，或它们的混合物），其盐或溶剂化产物。它们可用作通过胆碱受体介导的疾病的预防和/或治疗剂，具有减少副作用或不良反应。
• Enantioconvergent Alkylations of Amines by Alkyl Electrophiles: Copper-Catalyzed Nucleophilic Substitutions of Racemic α-Halolactams by Indoles
  作者：Agnieszka Bartoszewicz、Carson D. Matier、Gregory C. Fu

  DOI：10.1021/jacs.9b07875

  日期：2019.9.18

  classic SN2 reaction of an amine with an alkyl electrophile, both with respect to reactivity and to enantioselectivity. In this study, we describe the development of a user-friendly method (reaction at room temperature, with commercially available catalyst components) for the enantioconvergent nucleophilic substitution of racemic secondary alkyl halides (α-iodolactams) by indoles. Mechanistic studies are

  过渡金属催化有可能解决胺与烷基亲电试剂的经典 SN2 反应在反应性和对映选择性方面的缺点。在这项研究中，我们描述了一种用户友好的方法（在室温下反应，与市售的催化剂组分）的开发，用于由吲哚对外消旋仲烷基卤化物（α-碘内酰胺）的对映聚合亲核取代。机理研究与铜 (I)-吲哚基复合物的形成一致，该复合物与亲电子试剂的两种对映异构体以不同的速率反应，它们在反应条件下相互转化（动态动力学拆分）。这项研究补充了早期光诱导对映会聚 N-烷基化的工作，

表征谱图