3-溴噻吩[3,2-b]噻吩 | 25121-83-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 中文名称: 3-溴噻吩[3,2-b]噻吩
• 中文别名: 3-溴噻吩[3,2-B]噻吩
• 英文名称: 3-bromothieno[3,2-b]thiophene
• 英文别名: 3-Bromo-thieno<3,2-b>thiophen；6-bromothieno[3,2-b]thiophene
• CAS: 25121-83-9
• 化学式: C₆H₃BrS₂
• 分子量: 219.126
• InChiKey: YFWCQBIKGWTZQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  288.0±20.0 °C(Predicted)
• 密度：
  1.69

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

3-Bromothieno[3,2-b]thiophene Revision number: 1
SAFETY DATA SHEET

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Section 1. BASE INFORMATION
Product name: 3-Bromothieno[3,2-b]thiophene

Revision number: 1

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS Not classified
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements
None
Pictograms or hazard symbols
Signal word No signal word
None
Hazard statement
Precautionary statements None

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Component(s): 3-Bromothieno[3,2-b]thiophene
Percent: >94.0%(GC)
CAS Number: 25121-83-9
Chemical Formula: C6H3BrS2

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Extinguishing media not to Solid streams of water
be used:
Specific hazards: Take care as it may decompose upon combustion or in high temperatures to
generate poisonous fume.
3-Bromothieno[3,2-b]thiophene

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Section 5. FIRE-FIGHTING MEASURES
Specific methods: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Ensure adequate ventilation. Entry to non-involved personnel should be controlled
emergency procedures: around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Absorb spilled material in a suitable absorbent (e.g. rag, dry sand, earth, saw-dust).
containment and cleaning In case of large amount of spillage, contain a spill by bunding. Adhered or collected
up: material should be promptly disposed of, in accordance with appropriate laws and
regulations.

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Section 7. HANDLING AND STORAGE
Handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent generation of vapor or mist. Wash hands and face thoroughly after handling.
Use a ventilation, local exhaust if vapor or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Storage
Keep container tightly closed. Store in a refrigerator.
Storage conditions:
Store under inert gas.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Law is followed.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Vapor respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Liquid
Physical state (20°C):
Form: clear
Color: Pale yellow - Yellow
Odor: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling Point/Range: No data available
Flash Point: No data available
Explosive limits
Lower: No data available
Upper: No data available
Density: 1.69
Solubility: No data available

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Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Stability:
Reactivity: No special reactivity has been reported.
3-Bromothieno[3,2-b]thiophene

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Section 10. STABILITY AND REACTIVITY
Conditions to avoid: Heat-sensitive, Light-sensitive, Air-sensitive
Incompartible materials: oxidizing agents
Hazardous Decomposition Carbon monoxide, Carbon dioxide, Sulphur oxides, Hydrogen bromide
Products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobillity in soil
log Pow: No data available
No data available
Soil adsorption (Koc):
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to burn in a chemical
incinerator equipped with an afterburner and scrubber system. Observe all federal, state and local regulations when
disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
Not Listed
UN-No:

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26,
2002): Safe use and production, the storage of a dangerous chemical, transport, loading and unloading were
prescribed.
3-Bromothieno[3,2-b]thiophene

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-溴噻吩[3,2-b]噻吩 在 正丁基锂 、 双(苯磺酰)硫醚 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 13.67h， 以41.1%的产率得到bis(3-thieno<3,2-b>thienyl) sulfide
  参考文献：
  名称：

  一种基于线性稠合并五苯并用于场效应晶体管的高度 π 堆叠有机半导体

  摘要：

  我们介绍了稠环化合物二噻吩并[2,3-d:2',3'-d']噻吩并[3,2-b:4,5-b']二噻吩（pentathienoacene，PTA）的合成和表征）。与并五苯相比，PTA 比有机场效应晶体管 (OFET) 中使用的大多数半导体具有更大的带隙，因此预计在空气中是稳定的。PTA 的大 pi 共轭和平面分子结构也将形成更高的分子级，从而有利于载流子传输。在其薄膜上进行的 X 射线衍射和原子力显微镜实验表明，这些分子成层堆叠，其长轴垂直于表面。X 射线光电子能谱表明 PTA/Au 界面没有化学键。已经构建了基于 PTA 的 OFET，并展示了它们作为 p 型半导体的性能。

  DOI：

  10.1021/ja052816b
• 作为产物：
  描述：

  (4-Bromo-2-formyl-thiophen-3-ylsulfanyl)-acetic acid methyl ester 在 sodium ethanolate 、 铜 作用下， 以 喹啉 为溶剂， 生成 3-溴噻吩[3,2-b]噻吩
  参考文献：
  名称：

  Synthesis of tetrathieno-acene and pentathieno-acene: UV-spectral trend in a homologous series of thieno-acenes

  摘要：

  DOI：

  10.1016/s0040-4039(00)99231-1

文献信息

• [EN] NEW THIENOPYRIMIDINE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX DÉRIVÉS DE THIÉNOPYRIMIDINE, PROCÉDÉ POUR LEUR PRÉPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SERVIER LAB

  公开号：WO2015097123A1

  公开（公告）日：2015-07-02

  Compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, R7, R12, X, A and n are as defined in the description.

  式（I）的化合物：其中R1、R2、R3、R4、R5、R6、R7、R12、X、A和n的定义如描述中所述。
• Cyano-Functionalized Bithiophene Imide-Based n-Type Polymer Semiconductors: Synthesis, Structure–Property Correlations, and Thermoelectric Performance
  作者：Kui Feng、Han Guo、Junwei Wang、Yongqiang Shi、Ziang Wu、Mengyao Su、Xianhe Zhang、Jae Hoon Son、Han Young Woo、Xugang Guo

  DOI：10.1021/jacs.0c11608

  日期：2021.1.27

  developed a series of novel acceptor building blocks, CNI, CNTI, and CNDTI, which show substantially higher electron deficiencies than does BTI. On the basis of these novel building blocks, acceptor-acceptor type homopolymers and copolymers were successfully synthesized and featured greatly suppressed LUMOs (-3.64 to -4.11 eV) versus that (-3.48 eV) of the control polymer PBTI. Their deep-positioned LUMOs

  具有深位最低未占分子轨道 (LUMO) 能级的 n 型聚合物对于实现具有高稳定性的 n 型有机薄膜晶体管 (OTFT) 和具有高掺杂效率和前景的 n 型有机热电 (OTE) 至关重要热电性能。联噻吩酰亚胺 (BTI) 及其衍生物已被证明是构建高性能 n 型聚合物的有前途的受体单元。然而，BTI 中富含电子的噻吩部分导致所得聚合物的 LUMO 升高，从而限制了它们的 n 型性能和内在稳定性。在这里，我们通过在 BTI 及其衍生物上引入强吸电子氰基功能来解决这个问题。我们成功地克服了合成挑战并开发了一系列新型受体构建块、CNI、CNTI、和 CNDTI，它们显示出比 BTI 高得多的电子缺陷。在这些新型结构单元的基础上，成功合成了受体-受体型均聚物和共聚物，其 LUMO (-3.64 至 -4.11 eV) 与对照聚合物 PBTI 的 (-3.48 eV) 相比得到了极大的抑制。他们的深定位 LUMO
• [EN] PHOTOCHROMIC THIENOCHROMENE COMPOUNDS<br/>[FR] COMPOSÉS THIÉNOCHROMÈNE PHOTOCHROMIQUES
  申请人：TRANSITIONS OPTICAL INC

  公开号：WO2016144324A1

  公开（公告）日：2016-09-15

  The present invention relates to photochromic compounds, such as thienochromene compounds represented by the following Formulas (la) and/or (lb). The present invention also relates to photochromic compositions and articles containing one or more such photochromic thienochromene compounds.

  本发明涉及光致变色化合物，例如由以下式（Ia）和/或（Ib）表示的噻吩基色烯化合物。本发明还涉及含有一种或多种此类光致变色噻吩基色烯化合物的光致变色组合物和制品。
• Donor–Acceptor Conjugated Polymers Based on Dithieno[3,2-<i>b</i>:3′,2′-<i>b</i>′]naphtho[1,2-<i>b</i>:5,6-<i>b</i>′]dithiophene: Synthesis and Semiconducting Properties
  作者：Mu He、Weili Li、Yao Gao、Hongkun Tian、Jidong Zhang、Hui Tong、Donghang Yan、Yanhou Geng、Fosong Wang

  DOI：10.1021/acs.macromol.5b02583

  日期：2016.2.9

  A polycyclic aromatic unit comprising six rings, i.e., 5,11-bis(2-octyldodecyl)dithieno[3,2-b:3′,2′-b′]naphtho[1,2-b:5,6-b′]dithiophene (DTNDT), was developed. Four donor–acceptor (D–A) conjugated polymers, which are named P-BT, P-2FBT, P-IID, and P-DPP, were synthesized with DTNDT as the D-unit and 2,1,3-benzothiadiazole (BT), 5,6-difluorobenzo[c][1,2,5]thiadiazole (2FBT), isoindigo (IID), and diketopyrrolopyrrole

  包含六个环的多环芳族单元，即5,11-双（2-辛基十二烷基）二硫基[3,2- b：3'，2'- b ']萘[1,2- b：5,6- b开发了']二噻吩（DTNDT）。四个供体-受体（d-A）共轭聚合物，其被命名为P-BT，P-2FBT，P-IID，和P-DPP，用DTNDT作为d-单元和2,1,3-苯并噻二唑（合成BT），5,6-二氟苯并[ c] [1,2,5]噻二唑（2FBT），异靛蓝（IID）和二酮吡咯并吡咯（DPP）作为A单元。所有四种聚合物均具有热稳定性，分解温度高于390°C，并显示出伪直形骨架。它们的有序薄膜是通过溶液旋铸制备的，其中共轭骨架主要在基板上采用边对边对齐。用底栅和顶接触（BGTC）有机薄膜晶体管（OTFT）来表征聚合物的半导体性能。所有四种聚合物均表现出p型传输行为，并且对于P-BT，P-2FBT，P-IID和P-DPP，空穴迁移率分别为0.023、0.078、0
• Selective Multiple Magnesiations of the Thieno[3,2-b]thiophene Scaffold
  作者：Thomas Kunz、Paul Knochel

  DOI：10.1002/chem.201002506

  日期：2011.1.17

  A full functionalization of all four positions of the thieno[3,2‐b]thiophene scaffold was achieved. Starting from 2,5‐dichlorothieno[3,2‐b]thiophene, magnesiation of the 3‐ and 6‐position using tmpMgCl⋅LiCl furnishes, after trapping with various electrophiles, 3,6‐difunctionalized dichlorothieno[3,2‐b]thiophenes. Subsequent dechlorination and regioselective metalation or regioselective magnesium insertion

  噻吩并[3,2- b ]噻吩支架的所有四个位置都实现了完全功能化。从2,5-二氯噻吩并[3,2- b ]噻吩开始，在被各种亲电试剂捕获后，使用tmpMgCl⋅LiCl放大3和6-位，使3,6-二官能化的二氯噻吩并[3,2- b ]噻吩。随后的脱氯和区域选择性金属化或区域选择性镁插入CCl键可提供完全功能化的噻吩并[3,2- b ]噻吩。此外，已经制备了这些化合物的新的稠合杂环和小的低聚物，它们在材料化学中具有潜在的应用。

表征谱图