1-苄基-2,4,5-三溴-1H-咪唑 | 31250-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-苄基-2,4,5-三溴-1H-咪唑
• 中文别名: 1-苯基-2,4,5-三溴咪唑
• 英文名称: 1-benzyl-2,4,5-tribromo-1H-imidazole
• 英文别名: 1-benzyl-2,4,5-tribromoimidazole；N-benzyl-2,4,5-tribromoimidazole；1-benzyl-2,4,5-tribromo-1H-imidazole；1-benzyl-2,4,5-tribromo-imidazole；2,4,5-Tribrom-imidazol
• CAS: 31250-80-3
• 化学式: C₁₀H₇Br₃N₂
• 分子量: 394.891
• InChiKey: DPVXZXBHQWNJDP-UHFFFAOYSA-N

物化性质

• 熔点：
  60-62°C

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933290090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P310,P330,P361,P403+P233,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H311,H331

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Benzyl-2,4,5-tribromo-1H-imidazole
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: 1-Benzyl-2,4,5-tribromo-1H-imidazole
CAS number: 31250-80-3

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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.
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: C10H7Br3N2
Molecular weight: 394.9

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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：

  1-苄基-2,4,5-三溴-1H-咪唑 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 8.0h， 生成 1-benzyl-2,4,5-triphenyl-1H-imidazole
  参考文献：
  名称：

  Selective Sequential Cross-Coupling Reactions on Imidazole towards Neurodazine and Analogues

  摘要：

  Polysubstituted imidazoles represent a common structural motif in bioactive molecules. A modular and flexible strategy towards 2,4,5-triarylated imidazoles is reported applying a Suzuki-Miyaura cross-coupling protocol. Employing 1-protected 2,4,5-tribromoimidazole as starting material, both stepwise and one-pot protocols towards the title compounds are disclosed. The utility of the approach was demonstrated by synthesizing neurodazine, a biologically active molecule affecting neuronal cell differentiation.

  DOI：

  10.1055/s-0032-1316906
• 作为产物：
  描述：

  2,4,5-三溴咪唑 、 溴甲苯 在 caesium carbonate 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 18.0h， 以90%的产率得到1-苄基-2,4,5-三溴-1H-咪唑
  参考文献：
  名称：

  [EN] BENZIMIDAZOLES AND BENZOTHIAZOLES AS INHIBITORS OF MAP KINASE
  [FR] BENZIMIDAZOLES ET BENZOTHIAZOLES UTILISES COMME INHIBITEURS DE LA MAP KINASE

  摘要：

  本发明提供了一种化合物I的激酶抑制剂：其中W代表咪唑、噁唑、吡唑、噻唑或三唑等，这些化合物被苯基或噻吩基取代。所公开的化合物抑制p-38激酶，在转移或类风湿性关节炎的治疗中很有用。

  公开号：

  WO2004014900A1

文献信息

• [EN] BENZIMIDAZOLES AND BENZOTHIAZOLES AS INHIBITORS OF MAP KINASE<br/>[FR] BENZIMIDAZOLES ET BENZOTHIAZOLES UTILISES COMME INHIBITEURS DE LA MAP KINASE
  申请人：LILLY CO ELI

  公开号：WO2004014900A1

  公开（公告）日：2004-02-19

  The present invention provides kinase inhibitors of Formula I: wherein W represents inter alia imidazol, oxazol, pyrazol, thiazol as triazol, which are substituted by phenyl or thienyl. The disclosed compounds inhibit p-38 kinase and are useful in the treatment of metastasis or rheumatoid arthritis.

  本发明提供了一种化合物I的激酶抑制剂：其中W代表咪唑、噁唑、吡唑、噻唑或三唑等，这些化合物被苯基或噻吩基取代。所公开的化合物抑制p-38激酶，在转移或类风湿性关节炎的治疗中很有用。
• Azoles. part 12. 1 synthesis of thieno-extended purines: First example of the imidazo[4′,5′:4,5]thieno[3,2-d]pyrimidine ring system
  作者：David W. Hawkins、Brian Iddon、Darren S. Longthorne

  DOI：10.1016/0040-4020(95)00845-y

  日期：1995.11

  1 -Benzyl-4-bromoimidazole-5-carbonitriles were synthesised by several methods and shown to be surprisingly resistant to nucleophilic displacement of the bromine atom (e.g. by sulfanylacetamide under various conditions). 1 -Benzyl-4-bromo-2-(methylsulfanyl)imidazole-5-carbonitrile underwent Br → Li exchange with butyllithium (THF/-100 °C) and the resulting 4-lithiated imidazole was treated successively

  通过几种方法合成了1-苄基-4-溴咪唑-5-甲腈，并且显示出令人惊讶地对溴原子的亲核取代有抵抗力（例如，在各种条件下被硫烷基乙酰胺）。将1-苄基-4-溴-2-（甲基硫烷基）咪唑-5-腈与丁基锂（THF / -100°C）进行Br→Li交换，然后依次用元素硫和氯乙酰胺处理所得的4-锂化的咪唑，得到2- [1-苄基-5-氰基-2-（甲基硫烷基）-咪唑-4-基硫基]乙酰胺。用乙醇中的乙醇钠将其环化，得到6-氨基-1-苄基-2-（甲基硫烷基）噻吩并[2,3- d咪唑-5-甲酰胺，用原甲酸三乙酯在乙酸酐中处理后，得到标题化合物的首次报道的衍生物。1-苄基-4-溴咪唑-5-甲醛是由1-苄基-2,4,5-三溴咪唑合成的，方法是将其初始转化为2-TBDMS保护的衍生物，然后通过Br→Li引入5-甲酰基。交换并用N-甲酰基哌啶淬灭所得的5-锂化的咪唑，最后除去2-TBDMS-基团（Bu4NF / THF）。
• A convenient synthesis of thieno[2,3-d]imidazoles
  作者：Brian Iddon、Nazir Khan、Bee Lam Lim

  DOI：10.1039/c39850001428

  日期：——

  1-Protectod and 1,2-diprotected derivatives of 4-bromoimidazole-5-carbaldehyde were prepared from imidazole via 2,4,5-tribiomoimidazole and reacted with ethyl 2-mercaptoethanoate to give the title Compounds.

  由咪唑经2,4,5-三生物基咪唑制备4-溴咪唑-5-甲醛的1-保护和1,2-二保护衍生物，并与2-巯基乙酸乙酯反应，得到标题化合物。
• Exploring the Orthosteric Binding Site of the γ-Aminobutyric Acid Type A Receptor Using 4-(Piperidin-4-yl)-1-hydroxypyrazoles 3- or 5-Imidazolyl Substituted: Design, Synthesis, and Pharmacological Evaluation
  作者：Jacob Krall、Claus H. Jensen、Troels E. Sørensen、Birgitte Nielsen、Anders A. Jensen、Tommy Sander、Thomas Balle、Bente Frølund

  DOI：10.1021/jm4006466

  日期：2013.8.22

  A series of 4-(piperidin-4-yl)-1-hydroxypyrazole (4-PHP) 3- or 5-imidazolyl substituted analogues have been designed, synthesized, and characterized pharmacologically. All analogues showed binding affinities in the low micro- to low nanomolar range at native rat GABAA receptors and were found to be antagonists at the human α1β2γ2s receptor. The structure–activity relationship of the compound series

  已经设计，合成和表征了一系列4-（哌啶-4-基）-1-羟基吡唑（4-PHP）3-或5-咪唑基取代的类似物。所有的类似物表现出结合亲和力的低微以低纳摩尔范围在天然大鼠GABA甲受体和被认为是在人α拮抗剂1 β 2 γ 2S受体。该化合物系列的结构-活性关系表明，在正构结合位点4-PHP支架附近，先前发现的腔在大小和结构上存在明显差异。
• A convenient synthesis of 4(5)-mono-, 4,5-di-, and 2,4,5-tri-substituted imidazoles
  作者：Brian Iddon、Nazir Khan

  DOI：10.1016/s0040-4039(00)84334-8

  日期：1986.1

  A procedure is described for the stepwise introduction of substituents (hydrogen included) into the imidazole ring by FGI of the bromine atoms in 1-protected 2,4,5-tribromoimidazoles in the order 2 → 5 → 4 using halogen-metal exchange techniques.

  描述了一种通过卤素-金属交换技术，通过FGI将2-被保护的2,4,5-三溴咪唑中的溴原子按2→5→4的顺序逐步引入取代基（包括氢）到咪唑环中的方法。