2,3,7-三甲基吲哚 | 27505-78-8

• 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: 2,3,7-三甲基吲哚
• 英文名称: 2,3,7-trimethyl-1H-indole
• 英文别名: 2,3,7-trimethylindole；2,3,7-Trimethyl-indol
• CAS: 27505-78-8
• 化学式: C₁₁H₁₃N
• 分子量: 159.231
• InChiKey: USKKDNORVCJALM-UHFFFAOYSA-N

物化性质

• 沸点：
  274.74°C (rough estimate)
• 密度：
  1.0293 (rough estimate)
• 稳定性/保质期：
  遵循规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2933990090
• WGK Germany：
  3
• 储存条件：
  存储于0至6°C的阴凉干燥环境当中。

SDS

Name:	2 3 7-Trimethylindole Material Safety Data Sheet
Synonym:
CAS:	27505-78-8

Section 1 - Chemical Product MSDS Name:2 3 7-Trimethylindole Material Safety Data Sheet
Synonym:

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
27505-78-8	2,3,7-trimethylindole		unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

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.

---

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:

---

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.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

---

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:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

---

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 process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 27505-78-8: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Granules
Color: brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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: C11H13N
Molecular Weight: 159.23

---

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.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 27505-78-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,3,7-trimethylindole - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

---

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# 27505-78-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 27505-78-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 27505-78-8 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,3,7-三甲基吲哚 在 硫酸 、 镍 、 一水合肼 、 potassium nitrate 作用下， 以 乙醇 为溶剂， 生成 5-amino-2,3,7-trimethylindole
  参考文献：
  名称：

  硝基和氨基吲哚的合成

  摘要：

  DOI：

  10.1007/bf02251816
• 作为产物：
  描述：

  α-hydroxy-β-o-toluidino-isovaleric acid ethyl ester 在 硫酸 作用下， 生成 2,3,7-三甲基吲哚
  参考文献：
  名称：

  Martynow, Zhurnal Obshchei Khimii, 1953, vol. 23, p. 999,1001;engl.Ausg.S.1047

  摘要：

  DOI：

文献信息

• BCL-XL Inhibitory Compounds and Antibody Drug Conjugates Including the Same
  申请人：Ackler Scott L.

  公开号：US20160158377A1

  公开（公告）日：2016-06-09

  Small molecule Bcl-xL inhibitors and Antibody Drug Conjugates (ADCs) comprising small molecule Bcl-xL inhibitors are disclosed herein. The Bcl-xL inhibitors and ADCs of the disclosure are useful for, among other things, inhibiting anti-apoptotic Bcl-xL proteins as a therapeutic approach towards the treatment of diseases that involve a dysregulated apoptosis pathway.

  小分子Bcl-xL抑制剂和包括小分子Bcl-xL抑制剂的抗体药物结合物（ADCs）在此披露。披露的Bcl-xL抑制剂和ADCs可用于抑制抗凋亡Bcl-xL蛋白，作为治疗涉及失调凋亡途径的疾病的治疗方法之一。
• Fischer Indole Synthesis in Brønsted Acidic Ionic Liquids: A Green, Mild, and Regiospecific Reaction System
  作者：Dan-Qian Xu、Wen-Long Yang、Shu-Ping Luo、Bing-Tao Wang、Jian Wu、Zhen-Yuan Xu

  DOI：10.1002/ejoc.200600886

  日期：2007.2

  A novel one-pot Fischer indole synthesis approach has been developed by using Bronsted acidic ionic liquids as dual solvent-catalysts. Yields of 83–97 % were obtained after reaction in BMImHSO4 at 70–110 °C in 0.5–6 h, and exclusive formation of 2,3-disubstituted indoles was observed in the reaction of alkyl methyl unsymmetrical ketones. The indoles produced could be conveniently separated from the

  通过使用布朗斯台德酸性离子液体作为双溶剂催化剂开发了一种新的单锅 Fischer 吲哚合成方法。在 BMImHSO4 中在 70–110 °C 下反应 0.5–6 小时后，产率为 83–97%，并且在烷基甲基不对称酮的反应中观察到了 2,3-二取代吲哚的独特形成。生成的吲哚可以方便地从反应混合物中分离出来，无需任何挥发性有机溶剂，而且 BMImHSO4 可以很容易地重复使用，只需 1 当量的简单处理后效率不会降低。HCl 中和，然后过滤。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007）
• Palladium-Catalyzed Dearomative Allylic Alkylation of Indoles with Alkynes To Synthesize Indolenines with C3-Quarternary Centers
  作者：Shang Gao、Zijun Wu、Xinxin Fang、Aijun Lin、Hequan Yao

  DOI：10.1021/acs.orglett.6b01947

  日期：2016.8.5

  A palladium-catalyzed dearomative allylic alkylation of indoles with alkynes to construct indolenines with C3-quarternary centers was reported. The in situ formed arylallene intermediate omitted the need to install leaving groups on the allylic compounds and employ extra oxidants to oxidize the allylic C–H bonds. The reaction exhibited good functional group tolerance and high atom economy. Moreover

  报道了钯与炔烃的钯催化的吲哚脱芳香基烯丙基烷基化反应，以构建具有C 3四元中心的吲哚。原位形成的芳基亚芳基中间体无需在烯丙基化合物上安装离去基团，并使用额外的氧化剂氧化烯丙基CH键。该反应表现出良好的官能团耐受性和高原子经济性。此外，反应进一步扩大以合成吡咯并吲哚啉和呋喃并吲哚啉。
• Fe-Catalyzed Sequential C(sp³)–H/N–H Annulation of 2-Methylindoles with Ethyl Trifluoropyruvate at Room Temperature: Construction of Pyrrolo[1,2-α]indoles
  作者：Le Wang、Jia Zhou、Han-Qia Chen、Dong-Li Li、Jun-Bing Lin、Ke Li、Tong-Mei Ding、Shu-Yu Zhang

  DOI：10.1021/acs.orglett.0c01522

  日期：2020.6.19

  An efficient and benign iron-catalyzed room-temperature method was developed for direct sequential C(sp3)–H/N–H annulation to construct pyrroloindole scaffolds. This strategy features cheap and readily available raw materials and mild room-temperature reaction conditions and provides a green and practical method for the one-pot rapid synthesis of a wide range of diversely functionalized pyrrolo[1,2-α]indoles

  开发了一种有效且良性的铁催化室温方法，用于直接连续C（sp 3）–H / N–H环空法构建吡咯并吲哚支架。该策略以廉价且容易获得的原料为特征，并具有温和的室温反应条件，并为一锅快速合成多种多样的官能化吡咯并[1,2-α]吲哚提供了绿色实用的方法。
• Stereoselective Synthesis of 2,3-Disubstituted Indoline Diastereoisomers by Chemoenzymatic Processes
  作者：María López-Iglesias、Eduardo Busto、Vicente Gotor、Vicente Gotor-Fernández

  DOI：10.1021/jo301307q

  日期：2012.9.21

  structural motifs such as C-2 and C-3 substitutions (alkyl or aryl), cis/trans relative stereochemistry and functionalization of the aromatic ring (fluoro, methyl or methoxy groups) have been efficiently prepared through Fischer indolization and subsequent diastereoselective reduction of the unprotected indoles. Combination of Candida antarctica lipase type A and allyl 3-methoxyphenyl carbonate has been

  通过Fischer吲哚化已有效制备了外消旋二氢吲哚，包括各种结构基序，例如C-2和C-3取代（烷基或芳基），顺/反相对立体化学和芳香环（氟，甲基或甲氧基）的官能化以及随后的非保护吲哚的非对映选择性还原。的组合南极假丝酵母脂肪酶A型和烯丙基3-甲氧基苯基碳酸酯已经被鉴定为对他们的动力学拆分最好串联，观察对于大多数所测试的二氢吲哚的优良stereodiscriminations。