4,5-二溴噻吩-2-甲醛 | 38071-22-6

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 4,5-二溴噻吩-2-甲醛
• 英文名称: 4,5-dibromothiophene-2-carbaldehyde
• 英文别名: 4,5-dibromothiophene-2-carboxaldehyde
• CAS: 38071-22-6
• 化学式: C₅H₂Br₂OS
• mdl: MFCD00225242
• 分子量: 269.944
• InChiKey: CHRAVDVWAPGZOY-UHFFFAOYSA-N

物化性质

• 熔点：
  79-83 °C
• 沸点：
  306.1±37.0 °C(Predicted)
• 密度：
  2.195±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  常规情况下不会分解，也没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• 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：
  密封、阴凉、干燥保存

SDS

Name:	4 5-Dibromothiophene-2-carboxaldehyde Material Safety Data Sheet
Synonym:	None Known
CAS:	38071-22-6

Section 1 - Chemical Product MSDS Name:4 5-Dibromothiophene-2-carboxaldehyde Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
38071-22-6	4,5-Dibromothiophene-2-carboxaldehyde	98	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: 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.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. 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 chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 38071-22-6: Personal Protective Equipment Eyes: Wear chemical splash goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: off-white to light beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 79 - 81 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: C5H2Br2OS
Molecular Weight: 269.94

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong reducing agents, strong bases.
Hazardous Decomposition Products:
Sulfur dioxide, carbon monoxide, carbon dioxide, hydrogen bromide, sulfuric acid.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 38071-22-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4,5-Dibromothiophene-2-carboxaldehyde - 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: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 38071-22-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 38071-22-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 38071-22-6 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

制备方法与用途

4,5-二溴噻吩-2-甲醛是一种高度官能团化的噻吩类化合物，可溶于常见的有机溶剂但不溶于水。

在有机合成化学中，这种化合物可用于合成具有高度官能团化的噻吩类功能有机分子。其结构中的醛基可以通过Wittig烯基化反应与磷酰卤化物（如三甲基膦溴化物）反应，生成α,β-不饱和醛化合物。此反应可以用于构建双键结构，以扩展分子的π-共轭体系。

反应信息

• 作为反应物：
  描述：

  4,5-二溴噻吩-2-甲醛 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 1.0h， 生成 (4,5-dibromothiophen-2-yl)methanol
  参考文献：
  名称：

  黄病毒 NS2B-NS3 蛋白酶变构抑制剂的合成、构效关系和抗病毒活性

  摘要：

  黄病毒，包括寨卡病毒、登革热病毒和西尼罗河病毒，是重要的人类病原体。黄病毒的高度保守的 NS2B-NS3 蛋白酶对于病毒复制是必不可少的，因此是一个有前途的药物靶点。通过化合物筛选和药物化学研究，发现一系列新型 2,5,6-三取代吡嗪化合物是有效的寨卡病毒蛋白酶 (ZVpro) 变构抑制剂，IC 50值低至 130 nM。讨论了它们的结构-活性关系。ZVpro 抑制剂还抑制登革热病毒和西尼罗河病毒的同源蛋白酶，并且它们的抑制活性是相关的。最有效的化合物47和103有效抑制寨卡病毒在 EC 68细胞中的复制值 300-600 nM 和在寨卡病毒感染的小鼠模型中。这些化合物代表了针对黄病毒感染的药物开发的新药理学线索。

  DOI：

  10.1021/acs.jmedchem.0c02070
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 4,5-二溴噻吩-2-甲醛
  参考文献：
  名称：

  Rojahn; Schulten, Archiv der Pharmazie, 1926, p. 350

  摘要：

  DOI：

文献信息

• 5-Membered heterocyclic compound
  申请人：Nishida Haruyuki

  公开号：US20090156642A1

  公开（公告）日：2009-06-18

  The present invention provides 5-membered heterocycle compounds represented by the following general formula (I): The present compounds have a superior acid secretion inhibitory effect, and shows an antiulcer activity and the like.

  本发明提供了以下通式(I)表示的5元杂环化合物： 本化合物具有优异的抑制胃酸分泌效果，并显示出抗溃疡活性等。
• Synthesis and Analgesic Activity of 4,7-Dimethyl-3,4,4a,5,8,8a-Hexahydro-2H-Chromen-4,8-Diols Containing Thiophene Substituents
  作者：A. V. Pavlova、E. V. Nazimova、O. S. Mikhal’chenko、I. V. Il’ina、D. V. Korchagina、O. V. Ardashov、E. A. Morozova、T. G. Tolstikova、K. P. Volcho、N. F. Salakhutdinov

  DOI：10.1007/s10600-016-1785-2

  日期：2016.9

  Hexahydro-2H-chromenes with thiophene fragments were synthesized via reactions of a p-menthane monoterpenoid diol with several thiophenecarboxaldehydes. Most of the synthesized compounds with an additional thiophene fragment displayed analgesic activity in vivo tests at a dose of 10 mg/kg. It was found that the activity in either an acetate-writhing test or a hot-plate test depended on the type and location of substituent in the heteroaromatic ring.

  通过几种噻吩甲醛与对孟烷单萜二醇的反应合成了含噻吩片段的六氢-2H-色烯。在体内测试中，大多数带有额外噻吩片段的合成化合物在10 mg/kg剂量下显示出镇痛活性。研究发现，无论是醋酸扭体实验还是热板实验中，活性都取决于杂芳环中取代基的类型和位置。
• Dichloro-Bis(aminophosphine) Complexes of Palladium: Highly Convenient, Reliable and Extremely Active Suzuki-Miyaura Catalysts with Excellent Functional Group Tolerance
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.1002/chem.200903309

  日期：2010.4.6

  systems, is a highly convenient, reliable, and extremely active Suzuki catalyst with excellent functional group tolerance that enables the quantitative coupling of a wide variety of activated, nonactivated, and deactivated and/or sterically hindered functionalized and heterocyclic aryl and benzyl bromides with only a slight excess (1.1–1.2 equiv) of arylboronic acid at 80 °C in the presence of 0.2 mol % of

  二氯双（氨基膦）配合物是稳定的长相形式的钯纳米颗粒，并已证明是出色的Suzuki-Miyaura催化剂。配体的简单修饰（和/或向反应混合物中加水）可以控制它们的形成。二氯双[1-（二环己基膦酰基）哌啶]钯（3）是研究体系中最活跃的催化剂，是高度便捷，可靠且极具活性的Suzuki催化剂，具有出色的官能团耐受性，可实现多种活化，非活化和失活和/或位阻功能化的定量偶联以及芳烃和苄基溴的杂环化合物，在工业用甲苯中，在0.2°C的催化剂中，在80°C时，芳基硼酸仅略有过量（1.1-1.2当量）芳基硼酸，对大气开放。通常仅在几分钟内即可实现> 95％的转化率。本文提出的反应方案是普遍适用的。副产品很少被发现。与基于膦的膦类似物相比，基于氨基膦的体系的催化活性被显着提高，这是由于钯纳米颗粒形成明显加快的结果。催化剂的分解产物是二环己基次膦酸酯，环己基膦酸酯和磷酸盐，它们很容易从偶联产物中分离出来，与非水溶性膦基体系相比，具有很大的优势。
• Synthesis of functionalized benzothiophenes and dibenzothiophenes by twofold Heck and subsequent 6π-electrocyclization reactions of 2,3-dibromothiophenes and 2,3-dibromobenzothiophenes
  作者：Serge-Mithérand Tengho Toguem、Imran Malik、Munawar Hussain、Jamshed Iqbal、Alexander Villinger、Peter Langer

  DOI：10.1016/j.tet.2012.10.050

  日期：2013.1

  Benzothiophenes and dibenzothiophenes were prepared by twofold Heck reactions of 2,3-dibromothiophene and 2,3-dibromobenzothiophene, respectively, and subsequent thermal 6π-electrocyclization. The Heck reaction of 2,3-dibromothiophene and 2,3-dibromobenzothiophene with 1 equiv of alkenes proceeded with different regioselectivities and afforded 2-alkenylthiophenes and 3-alkenylbenzothiophenes.

  苯并噻吩和二苯并噻吩分别通过2,3-二溴噻吩和2,3-二溴苯并噻吩的两次Heck反应，然后进行热6π-电环化来制备。2，3-二溴噻吩和2，3-二溴苯并噻吩与1当量的烯烃的Heck反应以不同的区域选择性进行，得到2-烯基噻吩和3-烯基苯并噻吩。
• Quinolones used as MRS inhibitors and bactericides
  申请人：SmithKline Beecham plc

  公开号：US06320051B1

  公开（公告）日：2001-11-20

  Compounds of formula (I) are inhibitors of the bacterial enzyme S aureus methionyl tRNA synthetase and are of use in treating bacterial infections.

  化合物的化学式（I）是细菌酶S aureus甲硫氨酰tRNA合成酶的抑制剂，并可用于治疗细菌感染。

表征谱图