N,N-二甲基-3-硝基吡啶-2-胺 | 5028-23-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: N,N-二甲基-3-硝基吡啶-2-胺
• 中文别名: 二甲基-(3-硝基-2-吡啶基)胺
• 英文名称: N,N-dimethyl-3-nitropyridin-2-amine
• 英文别名: 2-Dimethylamino-3-nitropyridin
• CAS: 5028-23-9
• 化学式: C₇H₉N₃O₂
• mdl: MFCD00956024
• 分子量: 167.167
• InChiKey: HOESCRDIWBIVCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  62
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090
• WGK Germany：
  3
• 危险标志：
  GHS07
• 危险性描述：
  H302

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N,N-Dimethyl-3-nitropyridin-2-amine
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: N,N-Dimethyl-3-nitropyridin-2-amine
CAS number: 5028-23-9

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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: C7H9N3O2
Molecular weight: 167.2

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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.

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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：

  N,N-二甲基-3-硝基吡啶-2-胺 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 4-((2-(dimethylamino)pyridin-3-yl)amino)-2-((2-methoxy-5-methyl-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidine-5-carbonitrile
  参考文献：
  名称：

  WO2021003417A5

  摘要：

  公开号：

  WO2021003417A5
• 作为产物：
  描述：

  2-二甲氨基吡啶 在 硫酸 、 硝酸 作用下， 生成 N,N-二甲基-5-硝基-2-吡啶胺 、 N,N-二甲基-3-硝基吡啶-2-胺
  参考文献：
  名称：

  Tschitschibabin; Knunjanz, Chemische Berichte, 1928, vol. 61, p. 430

  摘要：

  DOI：

文献信息

• Anti-cancer agents and uses thereof
  申请人：Kelly Martha

  公开号：US20060270686A1

  公开（公告）日：2006-11-30

  The present invention is in the area of novel compounds and salts thereof, their syntheses, and their use as anti-cancer agents. The compounds include compounds of Formula I: and solvates, hydrates and pharmaceutically-acceptable salts thereof, wherein A 1 is N or CR 1 ; A 3 is N or CR 3 ; A 5 is N or CR 5 ; R 1 , R 3 —R 6 and L are defined in the specification; n is 0 or 1; and X is an optionally-substituted aryl group having 6-10 carbons in the ring portion, an optionally-substituted 6-membered heteroaryl group having 1-3 nitrogen atoms in the ring portion, an optionally-substituted 5-membered heteroaryl group having 0-4 nitrogen atoms in the ring portion and optionally having 1 sulfur atom or 1 oxygen atom in the ring portion, or an optionally-substituted heteroaryl group in which a 6-membered ring is fused either to a 5-membered ring or to a 6-membered ring, wherein in each case 1, 2, 3 or 4 ring atoms are heteroatoms independently selected from nitrogen, oxygen and sulfur. They are effective against a broad range of cancers, especially leukemia, non-small cell lung and colon.

  本发明涉及新化合物及其盐，它们的合成以及它们作为抗癌剂的用途。这些化合物包括式I的化合物： 和其溶剂化物、水合物和药用可接受盐，其中A 1 为N或CR 1 ；A 3 为N或CR 3 ；A 5 为N或CR 5 ；R 1 ，R 3 —R 6 和L在说明书中有定义；n为0或1；X为在环部分具有6-10个碳的可选择取代芳基，在环部分具有1-3个氮原子的可选择取代的6元杂芳基，在环部分具有0-4个氮原子且可选择具有1个硫原子或1个氧原子的可选择取代的5元杂芳基，或者在其中6元环与5元环或6元环融合的可选择取代的杂芳基，其中在每种情况下1、2、3或4个环原子是从氮、氧和硫中独立选择的杂原子。它们对广泛范围的癌症，特别是白血病、非小细胞肺癌和结肠癌有效。
• Amination of Aromatic Halides and Exploration of the Reactivity Sequence of Aromatic Halides
  作者：Chu Yang、Feng Zhang、Guo-Jun Deng、Hang Gong

  DOI：10.1021/acs.joc.8b02588

  日期：2019.1.4

  A base-promoted amination of aromatic halides has been developed using a limited amount of dimethylformamide (DMF) or amine as an amino source. Various aryl halides, including F, Cl, Br, and I, have been successfully aminated in good to excellent yields. Although the amination of aromatic halides with amines or DMF is usually considered as an aromatic nucleophilic substitution (SNAr) process, and the

  使用有限量的二甲基甲酰胺（DMF）或胺作为氨基源，已经开发出碱促进的芳香族卤化物胺化。包括F，Cl，Br和I在内的各种芳基卤化物均已成功地以良好或优异的收率胺化。尽管通常将胺或DMF芳香卤化物胺化视为芳香亲核取代（S NAr）过程，芳族卤化物的反应性为F> Cl> Br> I，发现该体系中芳族卤化物的反应性为I> Br≈F> Cl。该方案还显示了对多卤代芳烃的良好区域选择性。由于操作简单，氨基源和芳族卤化物的不受限制的可用性，无过渡金属的条件，不需要溶剂以及可扩展性，该协议对于工业应用很有价值。
• General method for nucleophilic aromatic substitution of aryl fluorides and chlorides with dimethylamine using hydroxide-assisted decomposition of N,N-dimethylforamide
  作者：Juana Garcia、Jacob Sorrentino、Emily J. Diller、Daniel Chapman、Zachary R. Woydziak

  DOI：10.1080/00397911.2016.1147051

  日期：2016.3.3

  and convenient procedure for the nucleophilic aromatic substitution of aryl fluorides and chlorides with dimethylamine was developed using a hydroxide-assisted thermal decomposition of N,N-dimethylforamide. These conditions are tolerant of nitro, nitrile, aldehyde, ketone, and amide groups but will undergo acyl substitution to form amides for methyl esters and acyl chlorides. Isolated yields of the products

  摘要 利用 N,N-二甲基甲酰胺的氢氧化物辅助热分解，开发了一种实用且方便的方法，用于芳基氟化物和氯化物与二甲胺的亲核芳香取代。这些条件耐受硝基、腈、醛、酮和酰胺基团，但会发生酰基取代以形成甲酯和酰氯的酰胺。产品的分离产率范围为 44% 至 98%，其中 17 个实例的大多数产率大于 70%。图形概要
• Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridine and acetamidine hydrochloride
  作者：Yibiao Li、Shuo Huang、Chunshu Liao、Yan Shao、Lu Chen

  DOI：10.1039/c8ob02129e

  日期：——

  Under catalyst-free conditions, an efficient method for the synthesis of 2-aminopyridine derivatives through the nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride has been developed. This amination uses inexpensive acetamidine hydrochloride as the ammonia source and has the advantages of a high yield, high chemoselectivity and wide substrate adaptability. The

  在无催化剂的条件下，已经开发了一种通过2-氟吡啶和乙am盐酸盐的亲核取代和水解来合成2-氨基吡啶衍生物的有效方法。该胺化反应使用廉价的乙am盐酸盐作为氨源，具有收率高，化学选择性高，底物适应性广的优点。结果表明，其他含有氟取代基的N-杂环也可以通过这些反应条件完成反应并产生目标产物。
• Cyanoguanidines as K-channel blockers
  申请人：Pharmacia & Upjohn Company

  公开号：US05668157A1

  公开（公告）日：1997-09-16

  Cyanoguanidine compounds of formula (I) and its pharmaceutically acceptable acid addition salts wherein R.sub.1 is hydrogen or methyl; R.sub.2 is C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.3 -C.sub.5 cycloalkenyl hydroxy methyl, methoxy-C.sub.1 -C.sub.5 alkyl, or R.sub.1 and R.sub.2 are combined to form a C.sub.3 -C.sub.6 carbocyclic ring; R.sub.3 and R.sub.4 are each independently selected to be hydrogen, C.sub.1 -C.sub.4 alkyl, F, Cl, Br, I or CF.sub.3 ; R.sub.5 is hydrogen, F or Cl; R.sub.6 is hydrogen, --NH.sub.2, --NHCH.sub.3, --NHC.sub.2 H.sub.5, --NHCH(CH.sub.3).sub.2, --N(CH.sub.3).sub.2, --N(C.sub.2 H.sub.5).sub.2, NH(CH.sub.2).sub.m, --OC.sub.1 -C.sub.3 alkyl (where m is 2 or 3), --NHC(O)C.sub.1 -C.sub.3 alkyl, Cl or Br; and n is 0 or 1. The compounds of formula (I) are potassium channel blockers useful in the treatment of cardiovascular disorders such as congestive heart failure and hypertension and as a diuretic. ##STR1##

  式(I)的氰脲基化合物及其药学上可接受的酸盐，其中R.sub.1为氢或甲基；R.sub.2为C.sub.1-C.sub.6烷基，C.sub.2-C.sub.6烯基，C.sub.2-C.sub.6炔基，C.sub.3-C.sub.5环烷基，C.sub.3-C.sub.5环烯基羟甲基，甲氧基-C.sub.1-C.sub.5烷基，或R.sub.1和R.sub.2结合形成C.sub.3-C.sub.6碳环；R.sub.3和R.sub.4各自独立选择为氢，C.sub.1-C.sub.4烷基，F，Cl，Br，I或CF.sub.3；R.sub.5为氢，F或Cl；R.sub.6为氢，--NH.sub.2，--NHCH.sub.3，--NHC.sub.2 H.sub.5，--NHCH(CH.sub.3).sub.2，--N(CH.sub.3).sub.2，--N(C.sub.2 H.sub.5).sub.2，NH(CH.sub.2).sub.m，--OC.sub.1-C.sub.3烷基（其中m为2或3），--NHC(O)C.sub.1-C.sub.3烷基，Cl或Br；n为0或1。式(I)的化合物是钾通道阻滞剂，可用于治疗心血管疾病，如充血性心力衰竭和高血压，以及作为利尿剂。

表征谱图