5-氨基-1,3-二甲基吡唑 | 3524-32-1

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-1,3-二甲基吡唑
• 中文别名: 1,3-二甲基-1H-吡唑-5-胺；5-氨基-1,3-二甲基-1H-吡唑；1,3-二甲基-5-氨基-1H-吡唑；1,3-二甲基-1氢-吡唑-5-胺
• 英文名称: 5-Amino-1,3-dimethylpyrazole
• 英文别名: 1,3-dimethyl-1H-pyrazol-5-amine；2,5-dimethylpyrazol-3-amine
• CAS: 3524-32-1
• 化学式: C₅H₉N₃
• mdl: MFCD00051651
• 分子量: 111.147
• InChiKey: ZFDGMMZLXSFNFU-UHFFFAOYSA-N

物化性质

• 熔点：
  65-69 °C (lit.)
• 沸点：
  121-123 °C(Press: 9 Torr)
• 密度：
  1.17±0.1 g/cm3(Predicted)
• 闪点：
  88 °C
• 稳定性/保质期：
  在常温常压下，该物质是稳定的。

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36,S37/39
• 危险类别码：
  R22,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933199090
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  常温、避光、通风干燥处，密封保存。

SDS

Name:	1 3-Dimethyl-1H-pyrazol-5-amine 97% Material Safety Data Sheet
Synonym:	5-Amino-1,3-dimethylpyrazol
CAS:	3524-32-1

Section 1 - Chemical Product MSDS Name:1 3-Dimethyl-1H-pyrazol-5-amine 97% Material Safety Data Sheet
Synonym:5-Amino-1,3-dimethylpyrazol

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3524-32-1	1,3-Dimethyl-1H-pyrazol-5-amine	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 3524-32-1: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: pale yellow - yellow
Odor: characteristic odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 78 - 80 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C5H9N3
Molecular Weight: 111

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, acid chlorides.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3524-32-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,3-Dimethyl-1H-pyrazol-5-amine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 3524-32-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3524-32-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3524-32-1 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

5-氨基-1,3-二甲基吡唑是一种杂环衍生物，可用作有机合成中间体。

制备

合成5-氨基-1,3-二甲基吡唑的方法较多。一种常见的方法是使用Mannich碱与甲基肼进行缩合反应[1]。具体步骤如下：将甲基肼加入缩合锅中，加热至90-95℃，随后分30-40分钟缓慢加入3-氨基巴豆腈，反应完成后pH值为2.5-3。冷却至45℃后出料，并用清水洗涤至中性或酸性，最后干燥即可得到成品。

反应信息

• 作为反应物：
  描述：

  5-氨基-1,3-二甲基吡唑 在 sodium nitrite 、 tin(ll) chloride 作用下， 以 盐酸 为溶剂， 以50%的产率得到2,5-二甲基吡唑-3,4-二胺
  参考文献：
  名称：

  A simple method for the preparation and selective functionalization of 4,5-diaminopyrazoles

  摘要：

  A simple procedure for the synthesis and further functionalization of 4,5-diaminopyrazoles using mild conditions is reported herein. The desired products were obtained in good yield, and the structures have been confirmed by X-ray crystallography. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)00398-8
• 作为产物：
  描述：

  5 -氨基- 1,3-二甲基-4 -腈-1H -吡唑 在 sodium hydroxide 作用下， 生成 5-氨基-1,3-二甲基吡唑
  参考文献：
  名称：

  The Reaction of Malononitrile with Hydrazine^1,2

  摘要：

  DOI：

  10.1021/ja01519a044
• 作为试剂：
  描述：

  乙酸甲酯 、 一氧化碳 在 铑 5-氨基-1,3-二甲基吡唑 、 氢气 、 lithium iodide 、 碘甲烷 作用下， 以 溶剂黄146 为溶剂， 190.0 ℃ 、3.92 MPa 条件下， 生成 乙酸酐
  参考文献：
  名称：

  Process for producing carboxylic acid anhydrides

  摘要：

  本发明涉及一种生产羧酸酐的方法，其中使用羧酸酯（由醇和羧酸衍生）和含有少量氢气的一氧化碳作为原料，在液体反应介质中，在第VIII B族催化剂存在下进行羰基化反应，以生产羧酸酐。反应介质包括第VIII B族催化剂、有机卤化物、羧酸酯、碱金属盐、至少一种有机促进剂、羧酸酐和羧酸，其中有机促进剂选自以下结构形式（I）、（II）和（III）中的至少一种。根据本发明的方法，通过使用指定的有机促进剂增加了羰基化反应的反应速率。

  公开号：

  US07553991B1

文献信息

• Cascade Palladium Catalysis: A Predictable and Selectable Regiocontrolled Synthesis of<i>N</i>-Arylbenzimidazoles
  作者：Nathan T. Jui、Stephen L. Buchwald

  DOI：10.1002/anie.201306007

  日期：2013.10.25

  choice: The palladium‐catalyzed cascade reaction of 2‐chloroaryl sulfonates with arylamine and amide nucleophiles provides direct access to N‐arylbenzimidazoles. This strategy selectively produces the heterocycles based on chemoselective oxidative addition. 2‐Chloroaryl triflates (Tf) produce one regioisomer and the corresponding 2‐chloroaryl mesylates (Ms) deliver the other in a selectable manner.

  通过选择：钯催化的 2-氯芳基磺酸盐与芳胺和酰胺亲核试剂的级联反应可直接获得N-芳基苯并咪唑。该策略基于化学选择性氧化加成选择性地产生杂环。2-氯芳基三氟甲磺酸酯 (Tf) 产生一种区域异构体，相应的 2-氯芳基甲磺酸酯 (Ms) 以可选择的方式传递另一种。
• [EN] 2,4-DIAMINO-6,7-DIHYDRO-5H-PYRROLO[2,3]PYRIMIDINE DERIVATIVES AS FAK/Pyk2 INHIBITORS<br/>[FR] DÉRIVÉS DE 2,4-DIAMINO-6,7-DIHYDRO-5H-PYRROLO[2,3]PYRIMIDINE COMME INHIBITEURS DE FAK/PYK2
  申请人：CENTAURUS BIOPHARMA CO LTD

  公开号：WO2012092880A1

  公开（公告）日：2012-07-12

  The invention relates to a novel class of 2,4-diamino-6,7-dihydro-5H-pyrrolo[2,3]pyrimidine derivatives as a FAK and/or Pyk2 inhibitor, to a process for their preparation, and to a composition thereof, as well as to use of the compounds for the inhibiting FAK and/or Pyk2 and method for the treatment of a FAK and/ or Pyk2 mediated disorder or disease.

  这项发明涉及一种新型的2,4-二氨基-6,7-二氢-5H-吡咯并[2,3]嘧啶衍生物，作为FAK和/或Pyk2抑制剂，以及它们的制备方法、组合物，以及利用这些化合物抑制FAK和/或Pyk2并治疗由FAK和/或Pyk2介导的疾病或疾病的方法。
• A new general and efficient synthesis of imidazo[4,5-c]pyrazole derivatives
  作者：Chiara Beatrice Vicentini、Augusto Cesare Veronese、Paolo Giori、Bruno Lumachi、Mario Guarneri

  DOI：10.1016/s0040-4020(01)87774-7

  日期：1990.1

  A new general and efficient synthesis of imidazo[4,5-c]pyrazoles (5) is reported. The key step of this synthetic procedure is the intramolecular cyclodehydration of 5-alkylamino-4-nitrosopyrazoles (4), which affords the title compounds (5) in good yields.

  报道了咪唑并[4,5-c]吡唑的一种新的通用有效合成方法（5）。该合成方法的关键步骤是5-烷基氨基-4-亚硝基吡唑（4）的分子内环脱水，其以良好的收率提供标题化合物（5）。
• A new route to the synthesis of imidazo [4,5-c]pyrazoles
  作者：Chiara Beatrice Vicentini、Augusto Cesare Veronese、Paolo Giori、Mario Guarneri

  DOI：10.1016/s0040-4039(00)82297-2

  日期：——

  A new synthesis of imidazo [4,5-c] pyrazoles, obtained through cyclisation of 4-nitroso-5-alkylamino-pyrazoles, is described.

  描述了通过4-亚硝基-5-烷基氨基-吡唑环化获得的咪唑并[4,5-c]吡唑的新合成方法。
• The Suzuki–Miyaura Cross-Coupling Reaction of Halogenated Aminopyrazoles: Method Development, Scope, and Mechanism of Dehalogenation Side Reaction
  作者：Lukáš Jedinák、Renáta Zátopková、Hana Zemánková、Alena Šustková、Petr Cankař

  DOI：10.1021/acs.joc.6b02306

  日期：2017.1.6

  The efficient Suzuki–Miyaura cross-coupling reaction of halogenated aminopyrazoles and their amides or ureas with a range of aryl, heteroaryl, and styryl boronic acids or esters has been developed. The method allowed incorporation of problematic substrates: aminopyrazoles bearing protected or unprotected pyrazole NH, as well as the free amino or N-amide group. Direct comparison of the chloro, bromo

  卤代氨基吡唑及其酰胺或脲与一系列芳基，杂芳基和苯乙烯基硼酸或酯的有效Suzuki-Miyaura交叉偶联反应已得到开发。该方法允许掺入有问题的底物：带有保护或未保护的吡唑NH以及自由氨基或N-酰胺基的氨基吡唑。在Suzuki-Miyaura反应中对氯，溴和碘吡唑的直接比较显示，由于降低了脱卤的倾向，Br和Cl衍生物优于碘吡唑。此外，揭示了影响不希望的脱卤副反应的机理和因素。

表征谱图