3,4-二溴噻吩-2,5-二甲醛 | 25373-20-0

• 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 - 有机氧化合物
• 中文名称: 3,4-二溴噻吩-2,5-二甲醛
• 英文名称: 3,4-dibromothiophene-2,5-dicarbaldehyde
• 英文别名: 3,4-dibromothiophene-2,6-dicarbaldehyde；3,4-Dibromothiophene-2,5-dicarboxaldehyde
• CAS: 25373-20-0
• 化学式: C₆H₂Br₂O₂S
• 分子量: 297.955
• InChiKey: UIIQKZFRHPLSLU-UHFFFAOYSA-N

物化性质

• 熔点：
  227 °C
• 沸点：
  376.3±42.0 °C(Predicted)
• 密度：
  2.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险品运输编号：
  UN 2811 6.1/PG 3
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P301+P330+P331+P310,P305+P351+P338
• 危险性描述：
  H301,H319
• 储存条件：
  2-8°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 3,4-Dibromothiophene-2,5-dicarboxaldehyde
CAS-No. : 25373-20-0

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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]
Acute toxicity, Oral (Category 3)
Eye irritation (Category 2)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
Toxic if swallowed.
Causes serious eye irritation.
Precautionary statement(s)
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
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)
R22 Harmful if swallowed.
S-phrase(s) none
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C6H2Br2O2S
Molecular Weight : 297,95 g/mol
Component Concentration
3,4-Dibromothiophene-2,5-dicarboxaldehyde
CAS-No. 25373-20-0 -

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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. Take victim immediately to hospital. 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, Sulphur oxides, 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
Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate
ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Prevent further leakage or spillage if safe to do so. 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.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Store under inert gas.
Specific end uses
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
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling
the product.
Personal protective equipment
Eye/face protection
Face shield and safety glasses 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
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N99 (US) or type P2 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. 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: 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) Autoignition 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
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion Toxic if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes Causes 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. 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: 2811 IMDG: 2811 IATA: 2811
UN proper shipping name
ADR/RID: TOXIC SOLID, ORGANIC, N.O.S. (3,4-Dibromothiophene-2,5-dicarboxaldehyde)
IMDG: TOXIC SOLID, ORGANIC, N.O.S. (3,4-Dibromothiophene-2,5-dicarboxaldehyde)
IATA: Toxic solid, organic, n.o.s. (3,4-Dibromothiophene-2,5-dicarboxaldehyde)
Transport hazard class(es)
ADR/RID: 6.1 IMDG: 6.1 IATA: 6.1
Packaging group
ADR/RID: III IMDG: III IATA: III
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：

  3,4-二溴噻吩-2,5-二甲醛 在 calcium hydroxide 、 水 作用下， 生成 3,4-dibromo-thiophene-2-carboxylic acid-(3,4-dibromo-[2]thienylmethyl ester)
  参考文献：
  名称：

  Steinkopf; Eger, Justus Liebigs Annalen der Chemie, 1938, vol. 533, p. 270,274

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二甲基噻吩 在 溴 、 silver nitrate 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 33.33h， 生成 3,4-二溴噻吩-2,5-二甲醛
  参考文献：
  名称：

  有效地合成双（二溴甲基）芳烃作为合成有用的二醛的重要前体

  摘要：

  摘要 这项工作提出了在各种反应条件下，通过溴化二甲基取代的芳烃，有效合成作为芳香族二醛前体的双（二溴甲基）苯和双（二溴甲基）噻吩（产率高达99％）。此反应的几个新变体，包括使用N还测试了溴代琥珀酰亚胺（NBS）和溴，以及用于替代四氯化碳，苯和二硫化碳的各种溶剂。在优化方案中，将不方便的溶剂替换为1,2-二氯乙烷（DCE）和/或乙腈。在DCE协议中，相对于文献协议，我们将反应时间缩短了24-32倍，将NBS的数量减少了几倍，并降低了功耗。该程序还可以消除持久的白炽灯辐射（100–500 W）。用溴代替NBS导致溴化剂用量进一步减少。将获得的溴代衍生物有效地转化为相应的二醛（90-96％），这反过来又可用于材料化学中。 这项工作提出了在各种反应条件下，通过溴化二甲基取代的芳烃，有效合成作为芳香族二醛前体的双（二溴甲基）苯和双（二溴甲基）噻吩（产率高达99％）。此反应的几个新变体，包括使用N还测

  DOI：

  10.1055/s-0035-1561651

文献信息

• Fluorescent Flipper Probes: Comprehensive Twist Coverage
  作者：Karolina Strakova、Amalia I. Poblador‐Bahamonde、Naomi Sakai、Stefan Matile

  DOI：10.1002/chem.201903604

  日期：2019.11.22

  substantial multistep organic synthesis, yields excitation maxima that shift over +100 nm to the red in response to increasing order of the surrounding membrane. This record redshift comes with record changes in fluorescence intensity and lifetime, high push-pull transition dipoles and higher rotational barriers. Supported by distinct dependence on viscosity and twist of the push-pull probes, kinetic

  为了成像活细胞中的膜张力，已经引入了可平面化的推挽式探针。第一个可操作探针围绕两个二噻吩并[3,2-b：2'，3'-d]噻吩（DTT）构筑而成，这些噻吩不共平面地扭曲，并在任一端与施主和受主极化。在此报告中，全面评估了可用于“翻转探针”扭曲的化学空间。毫不奇怪，结果是每个原子都很重要：去除扭曲区域中的一个甲基会产生探针，这些探针已经在溶液中平坦化，因此对膜张力的敏感性降低。在相同区域中添加一个或多个碳会阻碍沿脂质尾部的无干扰探针排列，从而阻碍其进入脂质双层膜以及机械敏感性。然而，通过相当大量的多步有机合成，可以在扭曲区域中的等排三氟甲基取代一个甲基，从而产生最大的激发峰，响应周围膜的顺序增加，其跃迁在+100 nm处变为红色。这种记录的红移伴随着荧光强度和寿命的变化，高推挽跃迁偶极子和更高的旋转势垒。推挽式探针对粘度和扭曲的独特依赖性支持了黑暗，完全扭曲和明亮，完全平坦化的松弛激发态之间的
• 신규한 싸이오펜 유도체, 그 제조방법 및 이를 포함하는 유기태양전지
  申请人：Industry-Academic Cooperation Foundation, Dankook University 단국대학교 산학협력단(220050166344) BRN ▼106-82-12299

  公开号：KR20150041434A

  公开（公告）日：2015-04-16

  작은 밴드갭을 갖는 싸이오펜 단위와 비닐렌 단위로 이루어진 전자주게 블록과 전자받게 블록을 공중합함으로써 태양광의 효과적인 흡수를 통한 고효율의 태양전지를 제조할 수 있는 신규한 싸이오펜 유도체, 그 제조방법 및 이를 포함하는 유기태양전지가 제공된다. 본 발명에 따르면, 작은 밴드갭을 가지는 신규한 싸이오펜 유도체를 통하여 태양광을 효과적으로 흡수할 수 있고, 용해도를 증가시킬 수 있으며, 성능이 향상된 유기태양전지를 제공할 수 있다.

  通过聚合含有小带隙的噻吩单元和苯乙烯单元的电子受体块和电子给体块，制备了一种新型的噻吩衍生物，可通过有效吸收太阳能实现高效率太阳能电池的制造。该发明提供了一种新型的噻吩衍生物，可有效吸收太阳能，增加溶解度，并提供性能更好的有机太阳能电池。
• 유기염료 및 이를 포함하는 광전소자, 염료감응 태양전지
  申请人：SFC CO., LTD. 에스에프씨 주식회사(120060087061) Corp. No ▼ 135511-0105889BRN ▼134-81-54429

  公开号：KR101791161B1

  公开（公告）日：2017-10-30

  본 발명은 광흡수율 및 광전변환 효율이 우수한 유기염료 및 그 광전소자, 염료감응 태양전지를 제공할 수 있다.

  这项发明可以提供具有优异光吸收率和光电转换效率的有机染料及其光电器件、染料敏化太阳能电池。
• Improved synthesis of dithieno[3,2-b:2′,3′-d]thiophene (DTT) and derivatives for cross coupling
  作者：Joseph Frey、Andrew D. Bond、Andrew B. Holmes

  DOI：10.1039/b207403f

  日期：——

  An improved synthesis of dithieno[3,2-b:2',3'-d]thiophene (DTT) and its 2,6- and 3,5-dibromo derivatives has been devised; Stille cross coupling of 2,5-(bistrimethylstannyl)-DTT afforded the oligomer 12.

  已设计出一种改进的二噻吩并[3，2-b：2′，3′-d]噻吩（DTT）及其2，6-和3，5-二溴衍生物的合成方法。2,5-（双三甲基锡烷基）-DTT的Stille交叉偶联提供了低聚物12。
• Effect of the π-linker on the performance of organic photovoltaic devices based on push–pull D–π–A molecules
  作者：Hong Chul Lim、Jang-Joo Kim、Jyongsik Jang、Jong-In Hong

  DOI：10.1039/c8nj00915e

  日期：——

  Two push–pull D–π–A molecules, 3T and DTT as donor materials, were synthesized and characterized for solution-processed bulk heterojunction (BHJ) organic photovoltaic (OPV) devices. The π-linker plays a vital role not only in electrochemical and thermal properties but also affects the thin film morphology of 3T and DTT. 3T showed the high electrochemical stability with a faster electrode reaction rate

  合成了两个推挽式D–π–A分子，即3T和DTT作为供体材料，并对其进行了固溶异质结（BHJ）有机光伏（OPV）器件的表征。π-连接基不仅在电化学和热学性质方面起着至关重要的作用，而且还影响3T和DTT的薄膜形态。3T表现出较高的电化学稳定性，电极反应速度更快。基于3T的固溶处理的OPV器件比基于DTT的器件具有更高的功率转换效率，因为它具有出色的电化学性能。