1-甲基-5-氨基吡唑 | 1192-21-8

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-甲基-5-氨基吡唑
• 中文别名: 5-氨基-1-甲基-1H-吡唑；5-氨基-1-甲基吡唑
• 英文名称: 5-Amino-1-methylpyrazole
• 英文别名: 1-methyl-1H-pyrazol-5-amine；1-methyl-5-aminopyrazole；5-amino-1-methyl-1H-pyrazole；2-methylpyrazol-3-amine
• CAS: 1192-21-8
• 化学式: C₄H₇N₃
• mdl: MFCD00068156
• 分子量: 97.1197
• InChiKey: JESRNIJXVIFVOV-UHFFFAOYSA-N

物化性质

• 熔点：
  73 °C
• 沸点：
  95-96°C (0.5 mmHg)
• 密度：
  1.22±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿（少量溶解）、DMSO（少量溶解）、乙酸乙酯（少量溶解）、甲醇（少量溶解）
• pKa：
  4.16±0.10 (Predicted,Most Basic Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S36/37/39
• 海关编码：
  2933199090
• 危险品标志：
  Xn
• 危险类别码：
  R20/21/22,R36/37/38
• 危险品运输编号：
  2811
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存放于惰性气体中，避免接触空气。

SDS

Name:	1-Methyl-1H-pyrazol-5-ylamine 97% Material Safety Data Sheet
Synonym:
CAS:	1192-21-8

Section 1 - Chemical Product MSDS Name:1-Methyl-1H-pyrazol-5-ylamine 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1192-21-8	1-Methyl-1H-pyrazol-5-ylamine	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# 1192-21-8: 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: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 95 - 96 deg C @0.5mmHg
Freezing/Melting Point: 74 - 76 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: C4H7N3
Molecular Weight: 97

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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, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1192-21-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-Methyl-1H-pyrazol-5-ylamine - 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# 1192-21-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 1192-21-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1192-21-8 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

化学性质

1-甲基-5-氨基吡唑在常温常压下为暗红色固体，微溶于氯仿和二氯甲烷，在醇类溶剂和强极性的二甲基亚砜中具有一定的溶解度。其氨基基团是一种常见的反应中心，可以与酸或酰基发生反应形成相应的盐类或酰胺；此外，氨基还可以参与亲核取代反应或羰基化合物的加成反应。吡唑环中的氮原子也表现出亲电性，容易与亲核试剂反应，如可进行亲核取代反应或亲电加成反应。

用途

1-甲基-5-氨基吡唑可用作医药合成中间体。

应用

1-甲基-5-氨基吡唑广泛应用于有机合成和医药化学领域，可用于药物分子及生物活性分子的修饰与合成。在有机合成转化中，其氨基具有显著的碱性和亲核性，可参与一系列亲核取代反应，生成衍生物化的吡唑类化合物。

制备

制备1-甲基-5-氨基吡唑的方法如下：将50g（1.0mol）化合物(1-a)溶解于40mL乙醇中，并冷却至0℃。在此温度下，向溶液中滴加53g（1.0mol）化合物(1-b)，搅拌1小时。随后，加入250mL乙醇和2.5g NaHCO3，并添加31g（1.0mol）化合物(1-c)。将混合液加热至45℃并继续搅拌30分钟。冷却后，加入3g NaOEt（乙醇钠），升温至85℃搅拌3小时。最终得到含有1-甲基-5-氨基吡唑的溶液。

反应信息

• 作为反应物：
  描述：

  1-甲基-5-氨基吡唑 在 甲酸 、 乙酸酐 作用下， 以 水 、 乙酸乙酯 为溶剂， 生成 N-(1-Methyl-1H-pyrazol-5-yl)carboxamide
  参考文献：
  名称：

  Cephem compounds and processes for preparation thereof

  摘要：

  制备了7.β.-[2-5氨基-1，2，4-噻二唑-3-基)2(羧基较低烷氧基亚氨基)乙酰胺]-3-(3-氨基-2-烷基-1-吡唑啉)甲基3头孢烯4羧酸盐。它们是抗生素。

  公开号：

  US04927818A1
• 作为产物：
  描述：

  5-氨基-1-甲基-吡唑-4-甲腈 在 磷酸 作用下， 反应 20.0h， 以90%的产率得到1-甲基-5-氨基吡唑
  参考文献：
  名称：

  吡唑并[3,4-b]吡啶：合成、反应和核磁共振谱

  摘要：

  2-氯-3-甲酰基吡啶（2-氯烟醛）由雷尼镍和甲酸（3 1）还原2-氯-3-氰基吡啶得到；该中间体无法通过上述 N-氧化途径获得（3-甲酰基吡啶的过氧酸氧化产生吡啶-N-氧化物 3-羧酸）。在由 2-氯-3-甲酰基吡啶合成母体 1 时，收率受到吖嗪物质 11 的形成的影响。

  DOI：

  10.1139/v88-074
• 作为试剂：
  描述：

  1-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)-4-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2(1H)-one 、 1-甲基-5-氨基吡唑 在 1-甲基-5-氨基吡唑 作用下， 以60的产率得到1-[2-[Tert-butyl(dimethyl)silyl]oxy-1-(4-chloro-3-fluorophenyl)ethyl]-4-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]pyridin-2-one
  参考文献：
  名称：

  J. Med. Chem. 2016, 59, 5650-5660

  摘要：

  DOI：

文献信息

• [EN] THIOPHENE DERIVATIVES FOR THE TREATMENT OF DISORDERS CAUSED BY IGE<br/>[FR] DÉRIVÉS DE THIOPHÈNE POUR LE TRAITEMENT DE TROUBLES PROVOQUÉS PAR IGE
  申请人：UCB BIOPHARMA SRL

  公开号：WO2019243550A1

  公开（公告）日：2019-12-26

  Thiophene derivatives of formula (I) and a pharmaceutically acceptable salt thereof are provided. These compounds have utility for the treatment or prevention of disorders caused by IgE, such as allergy, type 1 hypersensitivity or familiar sinus inflammation.

  提供了公式（I）的噻吩衍生物及其药用可接受的盐。这些化合物对于治疗或预防由IgE引起的疾病具有用途，如过敏、1型超敏反应或家族性鼻窦炎。
• SUBSTITUTED PYRROLOPYRIMIDINE COMPOUNDS, COMPOSITIONS THEREOF, AND METHODS OF TREATMENT THEREWITH
  申请人：Signal Pharmaceutical LLC

  公开号：US20140200206A1

  公开（公告）日：2014-07-17

  Provided herein are Pyrrolopyrimidine Compounds having the following structure: wherein R 1 , R 2 , R 3 , and L are as defined herein, compositions comprising an effective amount of a Pyrrolopyrimidine Compound, and methods for treating or preventing breast cancer, more particularly triple negative breast cancer, comprising administering an effective amount of such Pyrrolopyrimidine Compounds to a subject in need thereof.

  本文提供具有以下结构的吡咯吡嘧啶化合物： 其中R1、R2、R3和L如本文所定义，包含有效量吡咯吡嘧啶化合物的组合物，以及治疗或预防乳腺癌，更具体地是三阴性乳腺癌的方法，包括向需要的受试者施用有效量的这种吡咯吡嘧啶化合物。
• [EN] 1,3 DI-SUBSTITUTED CYCLOBUTANE OR AZETIDINE DERIVATIVES AS HEMATOPOIETIC PROSTAGLANDIN D SYNTHASE INHIBITORS<br/>[FR] DÉRIVÉS D'AZÉTIDINE OU DE CYCLOBUTANE 1,3-DISUBSTITUÉS UTILISÉS COMME INHIBITEURS DE LA PROSTAGLANDINE D SYNTHASE HÉMATOPOÏÉTIQUE (H-PGDS)
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2018069863A1

  公开（公告）日：2018-04-19

  A compound of formula (I), wherein R, R1, R2, R3, Y, Y1, a, X, and Z are as defined herein. The compounds of the present invention are inhibitors of hematopoietic prostaglandin D synthase (H-PGDS) and can be useful in the treatment of Duchenne Muscular Dystrophy. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting H-PGDS activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  式（I）的化合物，其中R、R1、R2、R3、Y、Y1、a、X和Z的定义如本文所述。本发明的化合物是造血前列腺素D合成酶（H-PGDS）的抑制剂，可用于治疗杜兴氏肌肉萎缩症。因此，本发明进一步涉及包含本发明化合物的药物组合物。本发明还进一步涉及使用本发明化合物或包含本发明化合物的药物组合物来抑制H-PGDS活性和治疗相关疾病的方法。
• IRAK-4 inhibitors. Part III: A series of imidazo[1,2-a]pyridines
  作者：George M. Buckley、Richard Fosbeary、Joanne L. Fraser、Lewis Gowers、Alicia P. Higueruelo、Lynwen A. James、Kerry Jenkins、Stephen R. Mack、Trevor Morgan、David M. Parry、William R. Pitt、Oliver Rausch、Marianna D. Richard、Verity Sabin

  DOI：10.1016/j.bmcl.2008.04.042

  日期：2008.6

  Following the identification of a potent IRAK inhibitor through routine project cross screening, a novel class of IRAK-4 inhibitor was established. The SAR of imidazo[1,2-a]pyridino-pyridines and benzimidazolo-pyridines was explored.

  通过常规的项目交叉筛选鉴定出有效的IRAK抑制剂后，建立了新型的IRAK-4抑制剂。探索了咪唑并[1,2-a]吡啶基吡啶和苯并咪唑并吡啶的SAR。
• [EN] CEPHEM COMPOUNDS<br/>[FR] CEPHEMES
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2005027909A1

  公开（公告）日：2005-03-31

  The present invention relates to a compound of the formula [I]: wherein R1 is lower alkyl or hydroxy (lower) alkyl, and R2 is hydrogen or amino protecting group, or R1 and R2 are bonded together and form lower alkylene ; R3 is -A-R6 wherein A is bond, -NHCO-(CH2CO)n-, lower alkylene, -NH-CO-CO- or the like, and R6 is (a) ou (b) wherein R7, R8, R9 and R10 are independently amino, guanidino, amidino or the like ; R4 is carboxy or protected carboxy; and R5 is amino or protected amino, or a pharmaceutically acceptable salt thereof, a process for preparing a compound of the formula [I], and a pharmaceutical composition comprising a compound of the formula [I] in admixture with a pharmaceutically acceptable carrier.

  本发明涉及一种公式的化合物[I]：其中R1是低级烷基或羟基（低级）烷基，R2是氢或氨基保护基团，或者R1和R2连接并形成低级亚烷基；R3是-A-R6，其中A是键，-NHCO-(CH2CO)n-，低级亚烷基，-NH-CO-CO-或类似物质，R6是(a)或(b)其中R7，R8，R9和R10是独立的氨基，胍基，脒基或类似物质；R4是羧基或受保护的羧基；R5是氨基或受保护的氨基，或药用可接受的盐，一种制备公式化合物[I]的方法，以及一种包括与药用可接受载体混合的公式化合物[I]的药物组合物。