3-溴苄脒盐酸盐 | 16796-52-4

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-溴苄脒盐酸盐
• 中文别名: 3-溴苯甲脒盐酸盐
• 英文名称: 3-bromobenzamidine hydrochloride
• 英文别名: 3-bromobenzimidamide hydrochloride；3-bromobenzene-1-carboximidamide hydrochloride；m-bromobenzamidine hydrochloride；3-bromobenzenecarboximidamide;hydrochloride
• CAS: 16796-52-4
• 化学式: C₇H₇BrN₂*ClH
• mdl: MFCD04114439
• 分子量: 235.511
• InChiKey: XIZFRYIWRFNILW-UHFFFAOYSA-N

物化性质

• 熔点：
  129-131 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  11
• 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：
  49.9
• 氢给体数：
  3
• 氢受体数：
  1

安全信息

• 海关编码：
  2925290090
• 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℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Bromobenzimidamide, HCl
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: 3-Bromobenzimidamide, HCl
CAS number: 16796-52-4

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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: C7H8BrClN2
Molecular weight: 235.5

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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 chloride, 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

制备方法与用途

3-溴苄脒盐酸盐概述

3-溴苄脒盐酸盐是一种医药中间体，可通过一步反应从3-溴苯甲腈制备得到。

制备过程

在氩气保护下，将1.18克（22毫摩尔，过量2倍）的氯化铵悬浮于40毫升干燥甲苯中，并将其冷却至0℃。随后滴加11毫升（22毫摩尔，过量2倍）2M三甲基铝的己烷溶液，反应混合物在室温下搅拌直至不再有气体产生。接着加入2.0克（11毫摩尔，1当量）3-溴苯甲腈，该混合物在80℃水浴中搅拌过夜。

冷却至0℃后，向其中加入50毫升甲醇，然后在室温下继续搅拌1小时。过滤所得固体，用甲醇洗涤数次，并将滤液减压蒸发干燥。最后，残余物再用甲醇洗涤一次。

反应信息

• 作为反应物：
  描述：

  3-溴苄脒盐酸盐 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 生成 3-溴苄脒
  参考文献：
  名称：

  银催化的芳基am与苄基异氰化物的[3 + 2 + 1]环化

  摘要：

  开发了银催化的with与苄基异氰化物向[2,4-二芳基-1,3,5-三嗪]的[3 + 2 + 1]环化反应。以中等到良好的产率获得了各种对称和不对称的产物。这项工作还具有2,4-二取代的三嗪的无氧化剂方法。

  DOI：

  10.1016/j.tetlet.2017.10.032
• 作为产物：
  描述：

  间溴苯甲腈 在 盐酸 、 氨 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 96.0h， 生成 3-溴苄脒盐酸盐
  参考文献：
  名称：

  制备三唑并[1,5-c]嘧啶类药物作为潜在的抗哮喘药。

  摘要：

  通过使用人类嗜碱性粒细胞组胺释放测定法，发现5-芳基-2-氨基[1,2,4]三唑并[1,5-c]嘧啶具有作为介质释放抑制剂的活性。这些化合物是通过使芳酰胺与甲酰乙酸乙酯或丙酸乙酯反应生成嘧啶酮而制备的。用三氯氧磷处理得到氯嘧啶，然后用肼将其转化为肼基嘧啶。在Dimroth重排后，使用溴化氰进行环化，得到三唑并[1,5-c]嘧啶。在进行结构活性评估后，将5- [3-（三氟甲基）苯基] -2-氨基（8-10），5-（3-溴苯基）-2-氨基（8-13），5- [3-发现（二氟甲氧基）-苯基] -2-氨基（8-11）和5-（4-吡啶基）-2-氨基（6-7）化合物具有最佳活性。他们被选择进行进一步的药理和毒理学研究。

  DOI：

  10.1021/jm00166a023

文献信息

• An I₂-mediated aerobic oxidative annulation of amidines with tertiary amines<i>via</i>C–H amination/C–N cleavage for the synthesis of 2,4-disubstituted 1,3,5-triazines
  作者：Yizhe Yan、Zheng Li、Chang Cui、Hongyi Li、Miaomiao Shi、Yanqi Liu

  DOI：10.1039/c8ob00635k

  日期：——

  An iodine-mediated formal oxidative cycloaddition of amidines with tertiary amines was first demonstrated in air. Both symmetrical and unsymmetrical 2,4-disubstituted 1,3,5-triazines were obtained in up to 85% yields. It is noted that a tertiary amine was employed as a one carbon synthon of 1,3,5-triazines and two C–N bonds were formed in one pot. Control experiments revealed that the reaction underwent

  碘在空气中首次证明了碘与叔胺介导的甲醛氧化环加成反应。对称和不对称的2,4-二取代的1,3,5-三嗪均以高达85％的产率获得。注意，叔胺被用作1,3,5-三嗪的一个碳合成子，并且在一个罐中形成了两个C–N键。对照实验表明，该反应经历了由I +促进的自由基途径。该方法是无过渡金属，无过氧化物的，并且操作简便，可在多种基材上实施。
• [EN] PHENYL-HETEROCYCLE-PHENYL DERIVATIVES FOR USE IN THE TREATMENT OR PREVENTION OF MELANOMA<br/>[FR] DÉRIVÉS DE PHÉNYL-HÉTÉROCYCLE-PHÉNYLE DESTINÉS À UNE UTILISATION DANS LE TRAITEMENT OU LA PRÉVENTION D'UN MÉLANOME
  申请人：MAX PLANCK GESELLSCHAFT

  公开号：WO2018206778A1

  公开（公告）日：2018-11-15

  The present invention relates to a compound represented by the formula (E) which is useful for treating or preventing melanoma.

  本发明涉及一种化合物，其化学式表示为（E），用于治疗或预防黑色素瘤。
• [EN] SMALL MOLECULE INHIBITORS OF NF-kB INDUCING KINASE<br/>[FR] INHIBITEURS À PETITE MOLÉCULE DE KINASE INDUISANT NF-KB
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2020239999A1

  公开（公告）日：2020-12-03

  The present invention relates to compounds that inhibit NIK and pharmaceutical compositions comprising such compounds and methods of using the same. These compounds and pharmaceutical compositions are envisaged to be useful for preventing or treating diseases such as cancer (such as B-cell malignancies including leukemias, lymphomas and myeloma), inflammatory disorders, autoimmune disorders, immunodermatologic disorders such as palmoplantar pustulosis and hidradenitis suppurativa, and metabolic disorders such as obesity and diabetes.

  本发明涉及抑制NIK的化合物，以及包含这些化合物的药物组合物和使用方法。这些化合物和药物组合物预期能用于预防或治疗癌症（如包括白血病、淋巴瘤和多发性骨髓瘤的B细胞恶性肿瘤）、炎症性疾病、自身免疫疾病、免疫皮肤病学疾病（如掌跖脓疱病和化脓性汗腺炎）以及代谢紊乱疾病（如肥胖和糖尿病）。
• Iron Catalysis for Modular Pyrimidine Synthesis through β-Ammoniation/Cyclization of Saturated Carbonyl Compounds with Amidines
  作者：Xue-Qiang Chu、Wen-Bin Cao、Xiao-Ping Xu、Shun-Jun Ji

  DOI：10.1021/acs.joc.6b02767

  日期：2017.1.20

  method for the modular synthesis of various pyrimidine derivatives by means of the reactions of ketones, aldehydes, or esters with amidines in the presence of an in situ prepared recyclable iron(II)-complex was developed. This operationally simple reaction proceeded with broad functional group tolerance in a regioselective manner via a remarkable unactivated β-C–H bond functionalization. Control experiments

  开发了一种有效的方法，用于在原位制备的可回收铁（II）络合物存在下，通过酮，醛或酯与am的反应进行模块化合成各种嘧啶衍生物。该操作简单的反应通过显着的未激活的β-C-H键官能化，以区域选择性的方式在宽泛的官能团耐受性下进行。进行了对照实验以加深对机理的了解，并且反应很可能通过设计的TEMPO络合/烯胺添加/瞬时α占据/β-TEMPO消除/环化顺序进行。
• 一种嘧啶类衍生物及其应用
  申请人：华中科技大学

  公开号：CN108285452B

  公开（公告）日：2020-05-19

  本发明公开了一种嘧啶类衍生物及其应用，该嘧啶类衍生物具有如下式式(I)所示的结构；其中，所述R1、R2、R3均为选自碳原子数为1‑60的烷基、取代和无取代的芳香杂环基、以及取代和无取代的芳香环基中的任意一种基团。本发明通过对该嘧啶类衍生物关键的化学结构等进行改进，并将该嘧啶类衍生物作为电致发光层材料应用于有机电致发光器件中，与现有技术相比能够有效解决有机电致发光器件中蓝光材料稳定性差、效率低等问题。