4,5-二溴-1H-吡咯-2-甲醛 | 932-82-1

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4,5-二溴-1H-吡咯-2-甲醛
• 中文别名: 4,5-二溴-1H-吡咯-2-羧醛
• 英文名称: 4,5-dibromo-1H-pyrrole-2-carbaldehyde
• 英文别名: 4,5-dibromo-2-formylpyrrole；4,5-dibromopyrrole-2-carboxaldehyde；4,5-Dibrom-2-formyl-pyrrol
• CAS: 932-82-1
• 化学式: C₅H₃Br₂NO
• 分子量: 252.893
• InChiKey: IJBMHOCPMBSRPX-UHFFFAOYSA-N

物化性质

• 熔点：
  144-148
• 沸点：
  341.9±37.0 °C(Predicted)
• 密度：
  2.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 储存条件：
  储存温度：2-8°C，密封保存，并保持干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4,5-Dibromo-1H-pyrrole-2-carboxaldehyde
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 4,5-Dibromo-1H-pyrrole-2-carboxaldehyde
CAS number: 932-82-1

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C5H3Br2NO
Molecular weight: 252.9

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4,5-二溴-1H-吡咯-2-甲醛 在 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 MoO5*pyridine*HMPA 、 三溴化硼 、 sodium carbonate 、 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 2-甲基四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 75.25h， 生成 discoipyrrole C
  参考文献：
  名称：

  通过MoOPH介导的2,3,5-三取代的吡咯的氧化反应，全过程合成海洋生物碱DiscoipyrroleC。

  摘要：

  描述了海洋生物碱盘二吡咯C（3）的全合成。在关键步骤中，在MeOH的存在下用MoOPH处理2,3,5-三取代的吡咯19，并使所得的甲氧基化的1,2-二氢-3 H-吡咯-3-酮20与碳酸钾反应在MeOH中然后在三氟乙酸和H 2 O中洗脱。这得到目标3及其脱水产物的混合物，并且通过单晶X射线分析确认了前一种化合物的结构。

  DOI：

  10.1021/acs.jnatprod.7b00872
• 作为产物：
  描述：

  2-吡咯甲醛 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以83%的产率得到4,5-二溴-1H-吡咯-2-甲醛
  参考文献：
  名称：

  通过MoOPH介导的2,3,5-三取代的吡咯的氧化反应，全过程合成海洋生物碱DiscoipyrroleC。

  摘要：

  描述了海洋生物碱盘二吡咯C（3）的全合成。在关键步骤中，在MeOH的存在下用MoOPH处理2,3,5-三取代的吡咯19，并使所得的甲氧基化的1,2-二氢-3 H-吡咯-3-酮20与碳酸钾反应在MeOH中然后在三氟乙酸和H 2 O中洗脱。这得到目标3及其脱水产物的混合物，并且通过单晶X射线分析确认了前一种化合物的结构。

  DOI：

  10.1021/acs.jnatprod.7b00872

文献信息

• Electron-withdrawing group effect in aryl group of allyl bromides for the successful synthesis of indolizines via a novel [3+3] annulation approach
  作者：Sujin Park、Ikyon Kim

  DOI：10.1016/j.tet.2015.02.013

  日期：2015.4

  A new synthetic approach to 6,7-disubstituted indolizines has been developed from pyrrole-2-carboxaldehydes and allyl bromides via two successive base-mediated reactions. As three-carbon units for formation of pyridine moiety of indolizines, allyl bromides easily derived from Morita–Baylis–Hillman (MBH) adducts were employed. We found that positioning electron-withdrawing group(s) at the aromatic ring

  通过两个连续的碱介导的反应，由吡咯-2-羧醛和烯丙基溴开发了一种新的合成方法来合成6,7-二取代的吲哚嗪。作为形成吲哚嗪吡啶部分的三碳单元，采用了容易从森田-贝利斯-希尔曼（MBH）加合物衍生的烯丙基溴。我们发现，在烯丙基溴的芳香环上放置吸电子基团是成功闭环的关键，以允许获得具有独特取代方式的吲哚嗪。同样通过该方法组装结构上相关的咪唑并[1,2- a ]吡啶和吡啶并[1,2- a ]吲哚。
• One-Pot Evolution of Ageladine A through a Bio-Inspired Cascade towards Selective Modulators of Neuronal Differentiation
  作者：Takayuki Iwata、Satoshi Otsuka、Kazuki Tsubokura、Almira Kurbangalieva、Daisuke Arai、Koichi Fukase、Yoichi Nakao、Katsunori Tanaka

  DOI：10.1002/chem.201602651

  日期：2016.10.4

  A bio‐inspired cascade reaction has been developed for the construction of the marine natural product ageladine A and a de novo array of its N1‐substituted derivatives. This cascade features a 2‐aminoimidazole formation that is modeled after an arginine post‐translational modification and an aza‐electrocyclization. It can be effectively carried out in a one‐pot procedure from simple anilines or guanidines

  已开发出一种受生物启发的级联反应，用于构建海洋天然产物ageladine A及其从头开始的N1取代衍生物阵列。该级联具有2-氨基咪唑的形成，该结构是在精氨酸的翻译后修饰和氮杂-电环化之后建模的。它可以通过简单的苯胺或胍的一锅法有效地进行，从而导致原本无法通过合成获得的法拉定A的结构类似物。我们发现该结构新颖的文库中的某些化合物在调节神经分化方面显示出显着的活性。即，这些化合物选择性地激活或抑制神经干细胞向神经元的分化，而向星形胶质细胞的分化可忽略不计。
• Phosphonium salt-catalysed synthesis of nitriles from in situ activated oximes
  作者：Ross M. Denton、Jie An、Petra Lindovska、William Lewis

  DOI：10.1016/j.tet.2012.01.067

  日期：2012.4

  A metal-free catalytic method for the conversion of aromatic and aliphatic aldoximes to nitriles at room temperature using oxalyl chloride (1.2 equiv) in combination with 5 mol % of triphenylphosphine oxide is reported. Of the many potential pathways leading from oxime to nitrile a manifold involving chlorophosphonium salt-catalysed decomposition of oxime chlorooxalates formed in situ is shown to be

  报道了一种无金属催化方法，该方法在室温下使用草酰氯（1.2当量）结合5摩尔％的三苯基氧化膦将芳族和脂族醛肟转化为腈。在从肟到腈的许多潜在途径中，涉及氯salt盐催化的原位形成的氯代草酸肟的分解的多种方法被证明是有效的。
• Regioselective and Stepwise Syntheses of Functionalized BODIPY Dyes through Palladium-Catalyzed Cross-Coupling Reactions and Direct C–H Arylations
  作者：Zeya Feng、Lijuan Jiao、Yuanmei Feng、Changjiang Yu、Na Chen、Yun Wei、Xiaolong Mu、Erhong Hao

  DOI：10.1021/acs.joc.6b00858

  日期：2016.8.5

  Regioselective and stepwise syntheses of a series of functionalized BODIPY dyes through palladium-catalyzed cross-coupling reactions and direct C–H arylations have been developed. In particular, this method allows the straightforward synthesis of 2,6-dibromo-3,5-diarylBODIPYs and 2-bromo-3-arylBODIPYs from polybrominated BODIPYs. The X-ray structure of intermediates 5a–c indicated that the palladium

  已经开发了通过钯催化的交叉偶联反应和直接的C–H芳基化反应，对一系列功能化的BODIPY染料进行区域选择性和逐步合成的方法。特别地，该方法允许由多溴化的BODIPY直接合成2，6-二溴-3，5-二芳基BODIPY和2-溴-3-芳基BODIPY。中间体5a – c的X射线结构表明，钯首先在溴化BODIPY的3,5-位插入C-Br键中。所得的2，6-二溴取代的BODIPYs是潜在的长波长光敏剂，使用以前的方法不易获得。
• 一种非对称双亚胺钛族金属络合物及其制备方法与应用
  申请人：上海化工研究院有限公司

  公开号：CN111592561B

  公开（公告）日：2023-05-02

  本发明涉及一种非对称双亚胺钛族金属络合物及其制备方法与应用，将非对称双亚胺配体化合物与烷基锂反应后，再与金属氯化物在有机介质中反应，后经过滤、浓缩、重结晶处理，获得非对称双亚胺钛族金属络合物，在烷基铝氧烷或氟硼化合物存在下应用于烯烃聚合。与现有技术相比，本发明原料易得，合成路线简单，产品收率高，性质比较稳定，同时具有较高的催化活性，能获得分子量高、分子量分布窄的烯烃均聚物和乙烯/α‑烯烃共聚物，能够满足工业应用的需要。