3-(2-溴乙基)吲哚 | 3389-21-7

• 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: 3-(2-溴乙基)吲哚
• 中文别名: 3-(2-溴乙烷)哚吲
• 英文名称: 3-(2-bromoethyl)-1H-indole
• 英文别名: 3-(2-bromoethyl)indole；tryptophyl bromide
• CAS: 3389-21-7
• 化学式: C₁₀H₁₀BrN
• mdl: MFCD00130155
• 分子量: 224.1
• InChiKey: NTLAICDKHHQUGC-UHFFFAOYSA-N

物化性质

• 熔点：
  97-99 °C (lit.)
• 沸点：
  343.5±17.0 °C(Predicted)
• 密度：
  1.515±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿：可溶,25mg/mL，澄清，黄色
• 稳定性/保质期：

  如果按照规格正确使用和储存，则不会发生分解，且目前没有已知的危险情况。

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• WGK Germany：
  3
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P264,P271,P280,P301+P330+P331,P303+P361+P353,P304+P340,P305+P351+P338,P310,P363,P403+P233,P501
• 危险品运输编号：
  3261
• 危险性描述：
  H314
• 储存条件：
  密闭、阴凉干燥处保存。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 3-(2-Bromoethyl)indole
CAS-No. : 3389-21-7

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
Causes skin irritation.
Causes serious eye irritation.
May cause respiratory irritation.
Precautionary statement(s)
Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S37/39 Wear suitable gloves and eye/face protection.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C10H10BrN
Molecular Weight : 224,1 g/mol
Component Concentration
3-(2-Dromoethyl)-1H-indole
CAS-No. 3389-21-7 -
EC-No. 222-219-2

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Hydrogen bromide gas
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end use(s)
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: flakes
Colour: orange
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 97 - 99 °C - lit.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine Pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-(2-溴乙基)吲哚 在 sodium dithionite 、 碳酸氢钠 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 22.0h， 生成 1-(2-indol-3-yl-ethyl)-1,4-dihydro-pyridine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  手性四氢-β-咔啉的构建：吲哚基二氢吡啶的不对称Pictet-Spengler反应

  摘要：

  通过使用手性磷酸催化吲哚基二氢吡啶的Pictet-Spengler反应，开发了对映体富集的四氢-β-咔啉的高效合成方法。反应在温和的反应条件下进行，以良好的产率（高达96％）和高的对映选择性（高达99％ee）提供所需的手性四氢-β-咔啉。用这种方法，可以高效地完成橘皮苷的正式合成和十氢萘烷的全部合成。

  DOI：

  10.1002/anie.201703178
• 作为产物：
  描述：

  1-(4-bromobut-1-en-2-yl)-2-nitrobenzene 在 盐酸 、 titanium(III) chloride 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 以64%的产率得到3-(2-溴乙基)吲哚
  参考文献：
  名称：

  三氯化钛水溶液促进邻硝基苯乙烯还原成吲哚的环化反应：利扎曲普坦和曲霉精的合成开发及应用

  摘要：

  在室温下用TiCl 3水溶液处理邻硝基苯乙烯，通过正式的还原性C（sp 2）–H胺化过程获得了吲哚。可以耐受多种功能，例如卤化物（Cl，Br），羰基（酯，氨基甲酸酯），氰基，羟基和氨基。通过多米诺还原/环化/迁移过程，由β，β-二取代的邻-硝基苯乙烯形成2,3-二取代的吲哚。温和的条件，简单的实验程序，易于接近的起始原料以及良好至极佳的收率是目前转化的特征。该方法学被用作简明合成利扎曲普坦和正式全合成阿斯哌啶的关键步骤。

  DOI：

  10.1002/anie.201505713
• 作为试剂：
  描述：

  、 叠氮化钠 、 3-(2-溴乙基)吲哚 、 丙炔酸甲酯 在 甲醇 、 chloroform methanol 、 desired product 、 3-(2-溴乙基)吲哚 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 188.0h， 生成 Methyl 1-(2-(1H-indol-3-yl)ethyl)-1H-1,2,3-triazole-4-carboxylate
  参考文献：
  名称：

  SUBSTITUTED HETEROARYL DERIVATIVES

  摘要：

  本发明涉及取代杂环芳基衍生物，其生产方法，包含该化合物的药物以及利用取代杂环芳基衍生物制备药物的用途。

  公开号：

  US20100009986A1

文献信息

• Peptidomimetic analogues of an Arg-Trp-x-x-Trp motif responsible for interaction of translocase MraY with bacteriophage ϕX174 lysis protein E
  作者：Rachel V. Kerr、Julia A. Fairbairn、Andrew T. Merritt、Timothy D.H. Bugg

  DOI：10.1016/j.bmc.2021.116502

  日期：2021.12

  also found in several cationic antimicrobial peptides. Analogues of Arg-Trp-octyl ester, found previously to show antimicrobial activity, were tested for antimicrobial activity, with Lys-Trp-oct (MIC50 P. fluorescens 5 µg/mL) and Arg-Trp-decyl ester (MIC50 P. fluorescens 3 µg/mL) showing enhanced antimicrobial activity. Synthesis and testing of α-helix peptidomimetic analogues for this motif revealed

  Translocase MraY 是噬菌体 φX174 裂解蛋白 E 的靶标，它通过大肠杆菌MraY的 Phe-288 和 Glu-287 介导的蛋白质-蛋白质相互作用以及蛋白质 E 上的 Arg-Trp-xx-Trp 基序进行相互作用，在几种阳离子抗菌肽中发现。先前发现显示抗微生物活性的 Arg-Trp-辛酯类似物用 Lys-Trp-oct（MIC 50 P. fluorescens 5 µg/mL）和 Arg-Trp-癸酯（MIC 50 P . fluorescens 3 µg/mL) 显示出增强的抗菌活性。该基序的 α-螺旋拟肽类似物的合成和测试表明其抗菌活性有所提高（MIC 50 大肠杆菌4–7 µg/mL) 用于含有两个芳香族取代基的类似物，模拟 Arg-Trp-xx-Trp 基序，以及一种此类肽模拟物的 MraY 抑制 (IC 50 140 µM)。使用 Alamar Blue
• Free and Polymer-Bound Tricyclic Azaphosphatranes HP(RNCH₂CH₂)₃N⁺:  Procatalysts in Dehydrohalogenations and Debrominations with NaH
  作者：Xiaodong Liu、John G. Verkade

  DOI：10.1021/jo990217f

  日期：1999.6.1

  efficient procatalyst for these reactions and also for the debromination of vicinal dibromides using NaH as a relatively inexpensive stoichiometric hydride source in CH(3)CN at room temperature. In dehydrohalogenations requiring more than ca. 10 h, the CH(2)CN(-) ion also acts as a base. By itself, NaH does not function well or at all under the same conditions. A catalytic cycle is proposed in which hydride

  较早显示，市售的非离子碱P（CH（3）NCH（2）CH（2））（3）N（1a）优于DBU作为化学计量试剂，可将伯烷基卤化物和仲烷基卤化物转化为烯烃（Arumugam，S。； Verkade，JGJ Org.Chem.1997，62，4827）。本文报道前体阳离子HP（CH（3）NCH（2）CH（2））（3）N（+）（2）至1a更稳定，价格更低，是这些反应的有效前催化剂并且还用于在室温下使用NaH作为CH（3）CN中相对便宜的化学计量的氢化物源，使用邻位二溴化物脱溴。在脱卤化氢中需要超过约 10小时后，CH（2）CN（-）离子也充当碱。就其本身而言，NaH不能很好地发挥作用，或者根本不能在相同条件下发挥作用。提出了一种催化循环，其中氢化物使质子2去质子化，从而释放出催化1a。阳离子HP（HNCH（2）CH（2））（3）N（+）（3）和HP [N（聚合物）CH（2）CH（2）] N（CH（2）CH（2）NH
• Nickel-Catalyzed Reductive Thiolation of Unactivated Alkyl Bromides and Arenesulfonyl Cyanides
  作者：Fei Wang、Weidong Rao、Shun-Yi Wang

  DOI：10.1021/acs.joc.1c00903

  日期：2021.7.2

  alkyl bromides with arenesulfonyl cyanides catalyzed by Ni(acac)2 under reductive conditions to form unsymmetrical sulfides is developed. This approach for sulfide synthesis is practical, relies on available, unfunctionalized materials such as alkyl (pseudo)halides, and is scalable. This catalytic strategy provides a complementary method for the preparation of unsymmetrical alkyl–aryl sulfides under

  开发了未活化的烷基溴与芳烃磺酰氰在还原条件下由 Ni(acac) 2催化形成不对称硫化物的交叉亲电偶联。这种硫化物合成方法是实用的，依赖于可用的非官能化材料，例如烷基（伪）卤化物，并且具有可扩展性。这种催化策略为在温和条件下制备具有良好官能团耐受性的不对称烷基-芳基硫化物提供了一种补充方法。
• Late-Stage Photoredox C–H Amidation of N-Unprotected Indole Derivatives: Access to <i>N</i>-(Indol-2-yl)amides
  作者：Yue Weng、Bo Ding、Yunqing Liu、Chunlan Song、Lo-Ying Chan、Chien-Wei Chiang

  DOI：10.1021/acs.orglett.1c00609

  日期：2021.4.2

  carboxamides are valuable in pharmaceutical applications, the preparation N-(indol-2-yl)amides with similar structures continues to be challenging. Herein we report on visible-light-induced late-stage photoredox C–H amidation with N-unprotected indoles and tryptophan-containing peptides, leading to the formation of N-(indol-2-yl)amide derivatives. N-Unprotected indoles and aryloxyamides that contain an electron-withdrawing

  N-未保护的吲哚的后期功能化可用于修饰低分子量药物和生物活性肽。吲哚羧酰胺在医药应用中很有价值，而具有相似结构的N-（吲哚-2-基）酰胺的制备仍然具有挑战性。本文中我们报道了可见光诱导的后期光氧化还原C–H酰胺化与N-未保护的吲哚和含色氨酸的肽，导致N的形成-（吲哚-2-基）酰胺衍生物。通过在室温下用绿色发光二极管照射，可以将含有吸电子基团的N-未保护的吲哚和芳氧基酰胺直接偶联至曙红Y作为光催化剂。机理研究和密度泛函理论计算表明，这种转变可能通过吲哚从PS *到PS •–循环的C–H氧化功能化而进行。该协议为N-未保护的吲哚衍生物的后期修饰标记和肽-药物结合提供了一个新的工具包。
• [EN] NAPHTHYL ETHER COMPOUNDS AND THEIR USE<br/>[FR] COMPOSES DE NAPHTYL ETHER ET LEUR UTILISATION
  申请人：ASTRAZENECA AB

  公开号：WO2004022539A1

  公开（公告）日：2004-03-18

  Compounds having the following structure wherein R1, R2, R3, R4, R5, R6, R7 m and n are as defined in the specification, in vivo-hydrolysable precursors thereof, pharmaceutically-acceptable salts thereof, the use in therapy and pharmaceutical compositions and methods of treatment using the same.

  具有以下结构的化合物，其中R1、R2、R3、R4、R5、R6、R7、m和n如规范中定义，其体内可水解的前体，其药用盐，以及在治疗中的使用、制药组合物和使用相同的治疗方法。