1-乙酰基-5-溴吲哚 | 61995-52-6

• 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: 1-乙酰基-5-溴吲哚
• 英文名称: N-acetyl-5-bromoindole
• 英文别名: 1-(5-bromo-1H-indol-1-yl)ethanone；1-(5-bromo-1H-indol-1-yl)ethan-1-one；1-acetyl-5-bromoindole；1-(5-bromoindol-1-yl)ethanone
• CAS: 61995-52-6
• 化学式: C₁₀H₈BrNO
• 分子量: 238.084
• InChiKey: BOMKWHSZGCMFEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H302,H319
• 储存条件：
  存储条件：2-8°C，密封保存，并保持干燥。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 1-Acetyl-5-Bromo-1H-Indole
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
Eye irritation (Category 2), H319
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22
R36
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H319 Causes serious eye irritation.
Precautionary statement(s)
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
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 238,08 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
1-Acetyl-5-Bromo-1H-Indole
Acute Tox. 4; Eye Irrit. 2; <= 100 %
H302, H319
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
1-Acetyl-5-Bromo-1H-Indole
Xn, R22R36 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting 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 vapours, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
For personal protection see section 8.
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.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): Non Combustible Solids
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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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
Complete suit protecting against chemicals, 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).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour No data available
c) Odour Threshold No data available
d) pH No data available
e) Melting point/freezing No data available
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
Stable under recommended storage conditions.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
In the event of fire: see section 5

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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 sensitisation
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
No data available
Specific target organ toxicity - repeated exposure
No data available
Aspiration hazard
No data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
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. 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
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
Eye Irrit. Eye irritation
H302 Harmful if swallowed.
H319 Causes serious eye irritation.
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R22 Harmful if swallowed.
R36 Irritating to eyes.
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  1-乙酰基-5-溴吲哚 在 MoO5*HMPA 、 四氯化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 168.5h， 生成 1-乙酰基-5-溴吲哚-3-酮
  参考文献：
  名称：

  Chien, Chun-Sheng; Hasegawa, Atsushi; Kawasaki, Tomomi, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 4, p. 1493 - 1496

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴吲哚 以80%的产率得到
  参考文献：
  名称：

  GRIBBLE G. W.; REILLY L. W. JR.; JOHNSON J. L., ORG. PREP. PROCED INT., 1977, 9, NO 6, 271-276

  摘要：

  DOI：

文献信息

• Metal-Reductant-Free Electrochemical Nickel-Catalyzed Couplings of Aryl and Alkyl Bromides in Acetonitrile
  作者：Robert J. Perkins、Alexander J. Hughes、Daniel J. Weix、Eric C. Hansen

  DOI：10.1021/acs.oprd.9b00232

  日期：2019.8.16

  attractive approach for the synthesis of complex molecules at both small and large scale, two barriers for large-scale applications have remained: the use of stoichiometric metal reductants and a need for amide solvents. In this communication, new conditions that address these challenges are reported. The nickel-catalyzed reductive cross-coupling of aryl bromides with alkyl bromides can be conducted in a

  尽管还原性交叉电化学偶联是小规模和大规模合成复杂分子的一种有吸引力的方法，但仍存在大规模应用的两个障碍：化学计量的金属还原剂的使用和对酰胺溶剂的需求。在本通信中，报告了应对这些挑战的新条件。镍催化的芳基溴化物与烷基溴化物的交叉还原偶联反应可以在分开的电化学槽中进行，使用乙腈作为溶剂，二异丙基胺作为牺牲性还原剂，以提供合成有用的收率（22-80％）。另外，使用配体4,4'，4''-三叔丁基-2,2'：6'，2'-叔吡啶和4,4'-二叔丁基的组合-丁基-2,2'-联吡啶对于实现高收率至关重要。
• Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent
  作者：Mincong Su、Xia Huang、Chuanhu Lei、Jian Jin

  DOI：10.1021/acs.orglett.1c04018

  日期：2022.1.14

  nickel-catalyzed reductive cross-coupling has been achieved using (hetero)aryl bromides and vinyl acetate as the coupling partners. This mild, applicable method provides a reliable access to a variety of vinyl arenes, heteroarenes, and benzoheterocycles, which should expand the chemical space of precursors to fine chemicals and polymers. Importantly, a sustainable solvent, dimethyl isosorbide, is used

  已经使用（杂）芳基溴化物和乙酸乙烯酯作为偶联伙伴实现了镍催化的还原交叉偶联。这种温和、适用的方法提供了获得各种乙烯基芳烃、杂芳烃和苯并杂环化合物的可靠途径，这将扩大精细化学品和聚合物前体的化学空间。重要的是，使用了一种可持续溶剂二甲基异山梨醇，从绿色化学的角度来看，这使得该协议更具吸引力。
• Cobalt co-catalysis for cross-electrophile coupling: diarylmethanes from benzyl mesylates and aryl halides
  作者：Laura K. G. Ackerman、Lukiana L. Anka-Lufford、Marina Naodovic、Daniel J. Weix

  DOI：10.1039/c4sc03106g

  日期：——

  of aryl halides with alkyl radicals derived from alkyl halides has recently been extended to couplings with carbon radicals generated by a co-catalyst. In this study, a new co-catalyst, cobalt phthalocyanine (Co(Pc)), is introduced and demonstrated to be effective for coupling substrates not prone to homolysis. This is because Co(Pc) reacts with electrophiles by an SN2 mechanism instead of by the electron-transfer

  镍催化的芳基卤化物与衍生自烷基卤化物的烷基的交叉偶联最近已扩展到与助催化剂产生的碳自由基的偶联。在这项研究中，引入了一种新的助催化剂——酞菁钴（Co(Pc)），并被证明对偶联不易均裂的底物有效。这是因为 Co(Pc) 通过 S N 2 机制而不是之前探索的电子转移或卤素抽象机制与亲电子试剂发生反应。研究证明了 (bpy)Ni 和 Co(Pc) 的正交反应性，将这种选择性应用于甲磺酸苄酯与芳基卤的偶联，以及将这些条件适应于反应性较低的磷酸苄酯和对映体收敛反应。
• Replacing Conventional Carbon Nucleophiles with Electrophiles: Nickel-Catalyzed Reductive Alkylation of Aryl Bromides and Chlorides
  作者：Daniel A. Everson、Brittany A. Jones、Daniel J. Weix

  DOI：10.1021/ja301769r

  日期：2012.4.11

  general method is presented for the synthesis of alkylated arenes by the chemoselective combination of two electrophilic carbons. Under the optimized conditions, a variety of aryl and vinyl bromides are reductively coupled with alkyl bromides in high yields. Under similar conditions, activated aryl chlorides can also be coupled with bromoalkanes. The protocols are highly functional-group tolerant (−OH,

  提出了通过两个亲电碳的化学选择性组合合成烷基化芳烃的一般方法。在优化的条件下，各种芳基和乙烯基溴化物以高产率与烷基溴化物还原偶联。在类似条件下，活化的芳基氯也可以与溴代烷烃偶联。该协议具有高度的官能团耐受性（-OH、-NHTs、-OAc、-OTs、-OTf、-COMe、-NHBoc、-NHCbz、-CN、-SO2Me），并且反应在台式上组装，无需排除空气或湿气的特殊预防措施。该反应显示出与传统交叉偶联反应不同的化学选择性，例如铃木-宫浦反应、斯蒂尔反应和日山-丹麦反应。带有亲电和亲核碳的底物导致亲电碳 (R-X) 处的选择性偶联，并且在亲核碳 (R-[M]) 处不发生有机硼 (-Bpin)、有机锡 (-SnMe3) 和有机硅的反应(-SiMe2OH) 含有机卤化物 (X–R–[M])。Hammett 研究表明，σ 和 σ(-) 参数与取代芳基溴化物与溴代烷烃的相对反应速率呈线性相关。这些相关性
• Organophotoredox assisted cyanation of bromoarenes <i>via</i> silyl-radical-mediated bromine abstraction
  作者：Maniklal Shee、Sk. Sheriff Shah、N. D. Pradeep Singh

  DOI：10.1039/d0cc00163e

  日期：——

  The insertion of a nitrile (–CN) group into arenes through the direct functionalization of the C(sp2)–Br bond is a challenging reaction. Herein, we report an organophotoredox method for the cyanation of aryl bromides using the organic photoredox catalyst 4CzIPN and tosyl cyanide (TsCN) as the nitrile source. A photogenerated silyl radical, via a single electron transfer (SET) mechanism, was employed

  通过C（sp 2）-Br键的直接官能化将腈基（–CN）插入芳烃中是一项具有挑战性的反应。本文中，我们报道了使用有机光氧化还原催化剂4CzIPN和甲苯磺酰氰（TsCN）作为腈源的有机光氧化还原方法，用于芳基溴化物的氰化。通过单电子转移（SET）机制，将光生甲硅烷基自由基用于从芳基溴化物中提取溴，以提供芳基基团，该芳基基团同时被TsCN拦截以提供芳族腈。已证明一系列包含给电子和吸电子基团的底物在室温下以良好的产率进行氰化。