3-溴-2,4,6-三甲基吡啶 | 23079-73-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3-溴-2,4,6-三甲基吡啶
• 中文别名: 2,4,6-三甲基-3-溴吡啶
• 英文名称: 3-bromo-2,4,6-trimethylpyridine
• 英文别名: 3-Brom-2,4,6-trimethyl-pyridin
• CAS: 23079-73-4
• 化学式: C₈H₁₀BrN
• 分子量: 200.078
• InChiKey: HDIJRNSEQXUVPU-UHFFFAOYSA-N

物化性质

• 沸点：
  222 ºC
• 密度：
  1.354
• 闪点：
  88 ºC
• 溶解度：
  可溶于乙腈（少许）、氯仿（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933399090
• 储存条件：
  存储条件：2-8°C，密封保存，并确保环境干燥。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 3-Bromo-2,4,6-trimethylpyridine
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 3-Bromo-2,4,6-trimethylpyridine
CAS number: 23079-73-4

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C8H10BrN
Molecular weight: 200.1

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-溴-2,4,6-三甲基吡啶 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以3.51 g的产率得到3-bromo-2-(bromomethyl)-4,6-dimethylpyridine
  参考文献：
  名称：

  PYRAZOLOQUINOLINE DERIVATIVES

  摘要：

  由以下化学式（I）表示的化合物和/或药理学上可接受的盐具有PDE9抑制作用，因此预期将提高脑内cGMP浓度。PDE9抑制作用和cGMP的增加导致学习和记忆行为的改善，化合物（I）具有作为治疗代理人用于阿尔茨海默病认知功能障碍的适用性。其中R1是氢原子；R2是芳香环基团等；R3是氢原子等；R4是氢原子；R5是氧杂环丙基团等；R6是氢原子。

  公开号：

  US20130143907A1
• 作为产物：
  描述：

  2,4,6-三甲基吡啶 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 作用下， 以 三氟乙酸 为溶剂， 反应 36.0h， 以95%的产率得到3-溴-2,4,6-三甲基吡啶
  参考文献：
  名称：

  固态吡啶3-甲醛的构象控制和光烯化：通过氢键和电子控制稳定光烯醇。

  摘要：

  我们已经研究了广泛的吡啶-3-羧醛1-5的固态光行为。如在醛1中一样，将杂原子引入到三聚甲醛中提出了固态构象上的优先权的问题。通过对两个醛1c和2c的X射线晶体结构分析已明确确定了优选的构象。结果表明，分子内氢键可用于构象控制。与均三聚甲醛在固态下进行有效的光环化成苯并环丁烯醇不同，杂原子类似物1b和1c在紫外线照射下表现出可察觉的颜色变化（从1b变为无色至浅黄色，从1c变为橙黄色）。（E）-烯醇的颜色会持续几个小时。持续照射会导致难以处理的聚合物材料。AM1计算已可靠地应用于木二酚热环化为苯并环丁烯醇，结果表明，相对于其相应的苯并环丁烯醇，1的（E）-烯醇比三聚甲醛的稳定性更高。稳定性被解释为是由于杂原子参与共振离域而产生的。通过形成氟硼酸盐很好地证明了氮原子如此作用的贡献。1a-HBF（4）和1b-HBF（4）暴露于紫外线辐射后，由于光烯醇的稳定化，很容易表现出高度红移的吸收。值得注意

  DOI：

  10.1021/jo026621n

文献信息

• Structure activity relationship studies of natural product chemokine receptor CCR5 antagonist anibamine toward the development of novel anti prostate cancer agents
  作者：Feng Zhang、Christopher K. Arnatt、Kendra M. Haney、Harrison C. Fang、John E. Bajacan、Amanda C. Richardson、Joy L. Ware、Yan Zhang

  DOI：10.1016/j.ejmech.2012.07.049

  日期：2012.9

  Anibamine, a novel pyridine quaternary alkaloid isolated from Aniba sp., was found to effectively compete with 125I-gp120 in binding to the chemokine receptor CCR5, with an IC50 = 1 μM. Anibamine is the first natural product reported as a CCR5 antagonist, and thus provides a novel structural skeleton unique from other lead compounds that have generally been identified from high-throughput screening efforts

  最近的研究表明，CCR5趋化因子受体可能是治疗前列腺癌的潜在靶标。因此，CCR5拮抗剂的开发可以提供新颖的前列腺癌治疗方法。发现Anibamine是一种从Aniba sp。分离的新型吡啶季生物碱，其与趋化因子受体CCR5的结合可有效与125 I-gp120竞争，其IC 50为50 = 1μM。茴香胺是第一个被报道为CCR5拮抗剂的天然产物，因此提供了一种不同于其他先导化合物的新颖结构骨架，而这些先导化合物通常是从高通量筛选工作中鉴定出来的。为了改善先导化合物的结构并提高阿尼巴胺衍生物作为潜在的抗前列腺癌药物的治疗指数，在这项工作的结构-活性关系研究中采用了“解构-重建-精制”的方法。在这里，我们报告阿尼巴明和17类似物的设计，合成和抗前列腺癌活性。从结果在体外和体内在此描述的研究表明，这类化合物有潜力提供新颖的引线作为抗前列腺癌试剂。
• Anibamine and Its Analogues: Potent Antiplasmodial Agents from <i>Aniba citrifolia</i>
  作者：Yongle Du、Ana Lisa Valenciano、Yumin Dai、Yi Zheng、Feng Zhang、Yan Zhang、Jason Clement、Michael Goetz、David G. I. Kingston、Maria B. Cassera

  DOI：10.1021/acs.jnatprod.9b00724

  日期：2020.3.27

  In our continuing search for novel natural products with antiplasmodial activity, an extract of Aniba citrifolia was found to have good activity, with an IC50 value less than 1.25 μg/mL. After bioassay-directed fractionation, the known indolizinium alkaloid anibamine (1) and the new indolizinium alkaloid anibamine B (2) were isolated as the major bioactive constituents, with antiplasmodial IC50 values

  在我们不断寻找具有抗疟原虫活性的新型天然产物的过程中，发现柑橘属植物提取物具有良好的活性，其 IC 50值小于 1.25 μg/mL。经过生物测定定向分离，已知的茚茚生物碱anibamine ( 1 )和新的茚茚生物碱anibamine B( 2 )作为主要生物活性成分被分离出来，抗疟原虫的IC 50值分别为0.170和0.244 μM，对耐药Dd2菌株恶性疟原虫。新香豆素类生物素 A ( 3 )、新的降木脂素 anibignan A ( 5 ) 和六种已知的新木脂素( 7 – 12 )) 也得到了。所有分离出的化合物的结构均基于 1D 和 2D NMR 光谱和质谱数据的分析确定，并从其 ECD 谱中确定了苯丙胺 A ( 5 )的绝对构型。对 28 个阿尼巴胺类似物 ( 13 – 40 )库的评估表明，带四元电荷的类似物的 IC 50值低至 58 nM，而不带电荷的类似物则没有活性或活性显
• A general and efficient method for the synthesis of benzo-(iso)quinoline derivatives
  作者：Victor Mamane、Frédéric Louërat、Julien Iehl、Mohamed Abboud、Yves Fort

  DOI：10.1016/j.tet.2008.09.015

  日期：2008.11

  short and efficient synthesis of substituted benzo-(iso)quinoline derivatives is reported. The methodology is based on a Suzuki or Negishi cross-coupling followed by a cyclization reaction induced by t-BuOK in DMF to form the central ring. This approach allowed the synthesis of all four benzo-(iso)quinoline isomers and the substitution of each ring of the benzo-(iso)quinoline core.

  报道了一种新的，短而有效的取代苯并-（异）喹啉衍生物的合成方法。该方法基于Suzuki或Negishi交叉偶联，然后是在DMF中由t -BuOK诱导形成中心环的环化反应。这种方法可以合成所有四种苯并（异）喹啉异构体，并取代苯并（异）喹啉核心的每个环。
• Importance of a Fluorine Substituent for the Preparation of <i>meta</i> - and <i>para</i> -Pentafluoro-λ⁶ -sulfanyl-Substituted Pyridines
  作者：Mikhail Kosobokov、Benqiang Cui、Andrii Balia、Kohei Matsuzaki、Etsuko Tokunaga、Norimichi Saito、Norio Shibata

  DOI：10.1002/anie.201605008

  日期：2016.8.26

  the trick in this case is the presence on the pyridine ring of at least one fluorine atom, which is essential for the successful transformation of the disulfides into m‐and p‐SF5‐pyridines. After enabling the synthesis of an SF5‐substituted pyridine, ortho‐F groups can be efficiently substituted by C, N, S, and O nucleophiles through an SNAr pathway. This methodology provides access to a variety of

  虽然有一些方法可以合成邻-pentafluoro-λ 6硫烷基（SF 5）吡啶类，间位-和对位-SF 5 -取代的吡啶并不多见。我们在此公开了它们合成的一般路线。基本的合成方法与所报道的邻SF 5取代的吡啶和SF 5取代的芳烃的方法相同，即相应的二硫化物的氧化氯四氟化生成吡啶基硫的氯四氟化物（SF 4Cl-吡啶），然后与氟化物进行氯化物/氟化物交换。然而，在这种情况下的窍门是在吡啶环上存在至少一个氟原子，这对于将二硫键成功转化为m和p SF 5吡啶至关重要。能够合成SF 5-取代的吡啶后，邻-F基团可以通过S N Ar途径被C，N，S和O亲核试剂有效取代。这种方法可以访问各种以前无法使用的SF 5取代吡啶构件。
• “Inherently Chiral” Ionic-Liquid Media: Effective Chiral Electroanalysis on Achiral Electrodes
  作者：Simona Rizzo、Serena Arnaboldi、Voichita Mihali、Roberto Cirilli、Alessandra Forni、Armando Gennaro、Abdirisak Ahmed Isse、Marco Pierini、Patrizia Romana Mussini、Francesco Sannicolò

  DOI：10.1002/anie.201607344

  日期：2017.2.13

  To achieve enantioselective electroanalysis either chiral electrodes or chiral media are needed. High enantiodiscrimination properties can be granted by the “inherent chirality” strategy of developing molecular materials in which the stereogenic element responsible for chirality coincides with the molecular portion responsible for their specific properties, an approach recently yielding outstanding

  为了实现对映选择性电分析，需要手性电极或手性介质。开发分子材料的“固有手性”策略可以赋予高对映异构性能，其中负责手性的立体生成元素与负责其特殊性能的分子部分相吻合，这种方法最近在电极表面产生了出色的性能。现在已经从由廉价试剂合成的对映异构体3,3'-联可力定开始制备固有的手性离子液体（ICIL），无需手性HPLC即可将其拆分为对映体，然后将其转化为熔点低于室温的长链二烷基盐。新的ICIL和较短的系列术语（在室温下为固体）均用作非手性IL中的低浓度添加剂，