2-溴-5-甲基-1-苯并噻吩 | 111860-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 2-溴-5-甲基-1-苯并噻吩
• 英文名称: 2-bromo-5-methylbenzo[b]thiophene
• 英文别名: 2-Bromo-5-methyl-1-benzothiophene
• CAS: 111860-00-5
• 化学式: C₉H₇BrS
• 分子量: 227.125
• InChiKey: HZPBPLLBZYSGBI-UHFFFAOYSA-N

物化性质

• 熔点：
  92 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

SDS

Name:	2-Bromo-5-methyl-1-benzothiophene Material Safety Data Sheet
Synonym:	None Known
CAS:	111860-00-5

Section 1 - Chemical Product MSDS Name:2-Bromo-5-methyl-1-benzothiophene Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
111860-00-5	2-Bromo-5-methyl-1-benzothiophene	97+	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation. Harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
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:
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.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Wash clothing before reuse.
Storage:
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# 111860-00-5: 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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 91.5-92.5 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: C9H7BrS
Molecular Weight: 227.12

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents, acids, bases.
Hazardous Decomposition Products:
Carbon monoxide, oxides of sulfur, carbon dioxide, hydrogen bromide, bromine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 111860-00-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Bromo-5-methyl-1-benzothiophene - Not listed by ACGIH, IARC, or NTP.

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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
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 111860-00-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 111860-00-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 111860-00-5 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

反应信息

• 作为反应物：
  描述：

  2-溴-5-甲基-1-苯并噻吩 在 硝基甲烷 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 2-fluoro-7-methyl-3-(phenylsulfanyl)benzo[b]thieno[2,3-d]thiophene
  参考文献：
  名称：

  通过二硫酯生成的二氟硫杂环丙烷的扩环构建噻吩噻吩和噻吩呋喃环系

  摘要：

  芳基噻吩-2-碳二硫酸酯或噻吩-3-二硫代碳酸酯与由 BrCF 2 CO 2 Li/分子筛 4A 生成的二氟卡宾反应产生芳基硫烷基化 2,2-二氟-3-噻吩基硫杂环丙烷。在锂离子存在的情况下，硫杂丙环中间体经历扩环然后消除HF，产生氟化噻吩并[3,2- b ]噻吩或噻吩并[2,3- b ]噻吩。氧类似物芳基呋喃碳二硫酸酯的反应也进行得到相应的噻吩并[3,2- b]呋喃。生成的芳基硫烷基（氟）噻吩并呋喃中的分子内氟取代允许构建另一个噻吩环，从而合成稠合的五环噻吩并呋喃。

  DOI：

  10.1021/acs.orglett.1c03805
• 作为产物：
  描述：

  2-(2,2-dibromovinyl)-4-methylbenzenethiol 在 potassium phosphate 、 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到2-溴-5-甲基-1-苯并噻吩
  参考文献：
  名称：

  Intramolecular cross-coupling of gem-dibromoolefins: a mild approach to 2-bromo benzofused heterocycles

  摘要：

  采用温和的无配体铜催化交叉偶联程序，从容易获得的二溴烯烃中制备出了非常有用的卤代苯并呋喃和苯并噻吩。

  DOI：

  10.1039/b912093a

文献信息

• Bromide as the Directing Group for β-Arylation of Thiophenes
  作者：Hong-Hai Zhang、Cai-Xia Wang、Fei-Fei Sheng、Kai-Hui Liu、Jian-Guo Gu、Kang Shen、Zheng-Yi Sun、Kunlun Hong

  DOI：10.1055/a-1838-8958

  日期：2022.9

  Direct β-arylation of thiophene derivatives with bromide as directing group is disclosed. The reaction is conducted with PdCl2/(p-tolyl)3P as catalyst, silver carbonate as additive, and aryl iodide as coupling partner, affording brominated biaryl compounds as product. Control experiments indicated that the presence of bromide group enhances the reactivity of the C–H bond, enabling β-arylation. Furthermore

  公开了用溴化物作为导向基团的噻吩衍生物的直接β-芳基化。该反应以PdCl 2 /(对甲苯基) 3 P为催化剂，碳酸银为添加剂，芳基碘化物为偶联剂进行，得到溴代联芳基化合物作为产物。对照实验表明溴化物基团的存在增强了 C-H 键的反应性，使 β-芳基化成为可能。此外，C-Br 键可以通过多种方法轻松转化为许多有用的官能团。机理研究表明，银盐在 C-H 键活化步骤中起关键作用。
• 有机化合物、混合物、组合物和有机电子器件
  申请人：广州华睿光电材料有限公司

  公开号：CN116354998A

  公开（公告）日：2023-06-30

  本申请公开了一种有机化合物及包括所述有机化合物的混合物、组合物和有机电子器件，所述有机化合物具有如通式(1)所示的结构：所述有机化合物用于有机电子器件中，特别是作为发光材料用于有机电子器件的发光层中，用以提高有机电子器件的效率和寿命。
• Construction of Thienothiophene and Thienofuran Ring Systems via Ring Expansion of Difluorothiiranes Generated from Dithioesters
  作者：Kohei Fuchibe、Ibuki Mukohara、Atsushi Yamada、Daisuke Miyazaki、Ryo Takayama、Junji Ichikawa

  DOI：10.1021/acs.orglett.1c03805

  日期：2022.1.14

  The reaction of aryl thiophene-2-carbodithioates or thiophene-3-carbodithioates with difluorocarbene generated from BrCF2CO2Li/molecular sieves 4A produced arylsulfanylated 2,2-difluoro-3-thienylthiiranes. In the presence of lithium ion, the thiirane intermediates underwent ring expansion followed by HF elimination, leading to fluorinated thieno[3,2-b]thiophenes or thieno[2,3-b]thiophenes. The reactions

  芳基噻吩-2-碳二硫酸酯或噻吩-3-二硫代碳酸酯与由 BrCF 2 CO 2 Li/分子筛 4A 生成的二氟卡宾反应产生芳基硫烷基化 2,2-二氟-3-噻吩基硫杂环丙烷。在锂离子存在的情况下，硫杂丙环中间体经历扩环然后消除HF，产生氟化噻吩并[3,2- b ]噻吩或噻吩并[2,3- b ]噻吩。氧类似物芳基呋喃碳二硫酸酯的反应也进行得到相应的噻吩并[3,2- b]呋喃。生成的芳基硫烷基（氟）噻吩并呋喃中的分子内氟取代允许构建另一个噻吩环，从而合成稠合的五环噻吩并呋喃。
• Intramolecular cross-coupling of gem-dibromoolefins: a mild approach to 2-bromo benzofused heterocycles
  作者：Stephen G. Newman、Valentina Aureggi、Christopher S. Bryan、Mark Lautens

  DOI：10.1039/b912093a

  日期：——

  Highly useful halogenated benzofurans and benzothiophenes are prepared from readily available gem-dibromoolefins using a mild, ligand-free copper catalyzed cross-coupling procedure.

  采用温和的无配体铜催化交叉偶联程序，从容易获得的二溴烯烃中制备出了非常有用的卤代苯并呋喃和苯并噻吩。