2-氯-4,6-二甲基吡啶-3-甲酸 | 66662-48-4

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 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: 2-氯-4,6-二甲基吡啶-3-甲酸
• 中文别名: 2-氯-4,6-二甲基烟酸；2-氯-4,6-二甲基嘧啶-3-甲酸
• 英文名称: 2-chloro-4,6-dimethylnicotinic acid
• 英文别名: 2-chloro-4,6-dimethylpyridine-3-carboxylic acid
• CAS: 66662-48-4
• 化学式: C₈H₈ClNO₂
• mdl: MFCD02110082
• 分子量: 185.61
• InChiKey: CXNWZXGXVPYAST-UHFFFAOYSA-N

物化性质

• 熔点：
  139-140 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  342.3±37.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)
• 溶解度：
  >27.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Chloro-4,6-dimethylnicotinic acid
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: 2-Chloro-4,6-dimethylnicotinic acid
CAS number: 66662-48-4

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H8ClNO2
Molecular weight: 185.6

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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.

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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：

  2-氯-4,6-二甲基吡啶-3-甲酸 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 (2-chloro-4,6-dimethylpyridin-3-yl)-morpholin-4-ylmethanone
  参考文献：
  名称：

  Deracemization of Axially Chiral Nicotinamides by Dynamic Salt Formation with Enantiopure Dibenzoyltartaric Acid (DBTA)

  摘要：

  通过结晶实现了从油性外消旋烟酰胺和对映纯的二苯甲酰酒石酸（DBTA）衍生的手性盐的动态对映选择性分离。通过X射线结构分析确定了轴向手性烟酰胺的绝对结构。通过选择对映纯的DBTA作为手性辅助剂可以控制手性。动态盐形成产生的轴向手性在将手性盐溶解在溶液中后长时间保持，即使在去除手性酸后也是如此。烟酰胺的外消旋化速率可以根据温度和溶剂特性进行控制，且与游离烟酰胺相比，盐的外消旋化速率延长，因为盐中吡啶离子的分子结构与无酸烟酰胺的结构不同。

  DOI：

  10.3390/molecules181114430
• 作为产物：
  描述：

  2-氯-3-氰基-4,6-二甲基吡啶 在 硫酸 、 硝酸 作用下， 以 水 、 甲苯 为溶剂， 以80%的产率得到2-氯-4,6-二甲基吡啶-3-甲酸
  参考文献：
  名称：

  2-Methyl-6-alkyl-11-aminoalkyl-6,11-dihydro-5H-pyrido(2,3-B)(1,5)benzodia

  摘要：

  式##STR1##的化合物，其中R.sub.1--是氢、1到6个碳原子的烷基或苄基；R.sub.2--是1到6个碳原子的烷基、5到7个碳原子的环烷基或者与R.sub.1和相邻的氮原子一起，吡咯啉基、哌啶基、己亚甲基基、吗啉基或N'-甲基哌嗪基，其中每个杂环可能有一个或两个1到3个碳原子的烷基或一个或两个甲氧基取代基连接其中；R.sub.3、r.sub.4和R.sub.5分别是氢或甲基；R.sub.6--是1到4个碳原子的烷基；A--是2到4个碳原子的烷基；以及其非毒性、药理学上可接受的酸盐；这些化合物及其盐可用作支气管痉挛解除剂和支气管分泌物溶解剂。

  公开号：

  US04167570A1

文献信息

• [EN] PYRIDINONE DERIVATIVES AS SELECTIVE CYTOTOXIC AGENTS AGAINST HIV INFECTED CELLS<br/>[FR] DÉRIVÉS DE PYRIDINONE UTILISÉS EN TANT QU'AGENTS CYTOTOXIQUES SÉLECTIFS CONTRE DES CELLULES INFECTÉES PAR LE VIH
  申请人：MERCK SHARP & DOHME

  公开号：WO2020236692A1

  公开（公告）日：2020-11-26

  The present disclosure is directed to pyridinone derivatives of Formula I and their use for selectively killing HIV infected GAG-POL expressing cells without concomitant cytotoxicity to HIV nave cells, and for the treatment of infection by HIV, or for the treatment, prophylaxis or delay in the onset or progression of AIDS or AIDS Related Complex (ARC).

  本公开涉及公式I的吡啶酮衍生物，其用于选择性杀灭HIV感染的GAG-POL表达细胞，而不对HIV原始细胞产生细胞毒性，并用于治疗HIV感染，或用于治疗、预防或延缓艾滋病或艾滋病相关综合征（ARC）的发病或进展。
• Deoxofluorination of (Hetero)aromatic Acids
  作者：Serhii Trofymchuk、Maksym Ya. Bugera、Anton A. Klipkov、Bohdan Razhyk、Sergey Semenov、Karen Tarasenko、Viktoriia S. Starova、Olga A. Zaporozhets、Oksana Yu. Tananaiko、Anatoliy N. Alekseenko、Yurii Pustovit、Oleksandr Kiriakov、Igor I. Gerus、Andrei A. Tolmachev、Pavel K. Mykhailiuk

  DOI：10.1021/acs.joc.9b03011

  日期：2020.3.6

  Diverse trifluoromethyl-substituted compounds were synthesized by deoxofluorination of cinnamic and (hetero)aromatic carboxylic acids with sulfur tetrafluoride. The obtained products were used as starting materials in the preparation of novel fluorinated amino acids, anilines, and aliphatic amines - valuable building blocks for medicinal chemistry and agrochemistry.

  通过用四氟化硫对肉桂酸和（杂）芳族羧酸进行脱氧氟化反应，合成了不同的三氟甲基取代的化合物。所得产物用作制备新型氟化氨基酸，苯胺和脂肪胺的原料，这些氟化物是药物化学和农业化学的重要组成部分。
• Chiral Symmetry Breaking of Axially Chiral Nicotinamide by Crystallization from the Melt
  作者：Fumitoshi Yagishita、Kazuma Okamoto、Norifumi Kamataki、Shota Kanno、Takashi Mino、Yoshio Kasashima、Masami Sakamoto

  DOI：10.1246/cl.130796

  日期：2013.12.5

  One of six 2-alkylamino-4,6-dimethylnicotinamides afforded a conglomerate, and subsequent X-ray crystallographic analysis revealed that the compound crystallized in the monoclinic system, the space...

  六个 2-烷基氨基-4,6-二甲基烟酰胺中的一个提供了一个聚集体，随后的 X 射线晶体学分析显示该化合物在单斜晶系中结晶，空间...
• Attrition‐Enhanced Asymmetric Transformation of Axially Chiral Nicotinamides by Dynamic Chiral Salt Formation
  作者：Takumi Nakamura、Hiroki Ishikawa、Kazuma Ban、Yasushi Yoshida、Takashi Mino、Yoshio Kasashima、Masami Sakamoto

  DOI：10.1002/cplu.202100504

  日期：2022.1

  Attrition-enhanced asymmetric transformation of six axially chiral nicotinamides was performed by dynamic chiral salt formation with L-DBTA. Dynamic crystallization with epimerization of equimolar amounts of nicotinamide salts and L-DBTA converged to the (−)-enantiomer with 87–99 % ee. Changing the ratio of two of the nicotinamides with L-DBTA to 1 : 2 inverted the axial chirality.

  通过与 L-DBTA 动态形成手性盐，对六种轴向手性烟酰胺进行了摩擦增强的不对称转化。等摩尔量的烟酰胺盐和 L-DBTA 进行差向异构化的动态结晶收敛到ee为 87-99% 的 (-)-对映体。将两种烟酰胺与 L-DBTA 的比例更改为 1:2，反转了轴向手性。
• Novel non-nucleoside inhibitors of HIV-1 reverse transcriptase. 1. Tricyclic pyridobenzo- and dipyridodiazepinones
  作者：Karl D. Hargrave、John R. Proudfoot、Karl G. Grozinger、Ernest Cullen、Suresh R. Kapadia、Usha R. Patel、Victor U. Fuchs、Scott C. Mauldin、Jana Vitous、Mark L. Behnke、Janice M. Klunder、Kollol Pal、Jerry W. Skiles、Daniel W. McNeil、Janice M. Rose、Grace C. Chow、Mark T. Skoog、Joe C. Wu、Günther Schmidt、Wolfhard W. Engel、Wolfgang G. Eberlein、Tracy D. Saboe、Scot J. Campbell、Alan S. Rosenthal、Julian Adams

  DOI：10.1021/jm00111a045

  日期：1991.7.1

  Novel pyrido[2,3-b][1,4]benzodiazepinones (I), pyrido[2,3-b][1,5]benzodiazepinones (II), and dipyrido[3,2-b:2',3'-e][1,4]diazepinones (III) were found to inhibit human immunodeficiency virus type 1 (HIV-1) reverse transcriptase in vitro at concentrations as low as 35 nM. In all three series, small substituents (e.g., methyl, ethyl, acetyl) are preferred at the lactam nitrogen, whereas slightly larger

  新型吡啶并[2,3-b] [1,4]苯并二氮杂酮（I），吡啶并[2,3-b] [1,5]苯并二氮杂酮（II）和二吡啶并[3,2-b：2'，3发现在低至35 nM的浓度下，'-e] [1,4]二氮杂酮（III）在体外抑制1型人类免疫缺陷病毒（HIV-1）逆转录酶。在所有三个系列中，在内酰胺氮上优选小的取代基（例如甲基，乙基，乙酰基），而在另一个（N-11）二氮杂庚酮氮上优选稍大的烷基部分（例如乙基，环丙基）。通常，相对于在芳环上没有取代基的相应化合物，在A环上优选亲脂取代基，而在C环上的取代通常会降低效能。在内酰胺氮原子邻位的甲基取代可实现最大效力。然而，在这种情况下，优选未取代的内酰胺氮。A环上的其他取代基很容易被容忍。双吡啶二氮杂庚酮衍生物11-环丙基-5,11-二氢-4-甲基-6H-二吡啶并[3,2-b：2'，3'-e] [1,4]二氮杂-6-1（96，奈韦拉平）是一种有效的（IC50