1-甲基-1H-吡唑-5-羧酸 | 16034-46-1

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-甲基-1H-吡唑-5-羧酸
• 中文别名: 2-甲基-2H-吡唑-3-羧酸；1-甲基-1H-吡唑-5-甲酸；1-甲基吡唑-5-羧酸；1-甲基吡唑-5-甲酸；1-甲基-吡唑-5-羧酸
• 英文名称: 1-methyl-1H-pyrazole-5-carboxylic acid
• 英文别名: 2-methylpyrazole-3-carboxylic acid；2-methyl-2H-pyrazole-3-carboxylic acid；1-methylpyrazole-5-carboxylic acid；1-methyl-5-pyrazolecarboxylic acid；1-methyl-1H-pyrazol-5-carboxylic acid；CH223191
• CAS: 16034-46-1
• 化学式: C₅H₆N₂O₂
• mdl: MFCD00464253
• 分子量: 126.115
• InChiKey: JREJQAWGQCMSIY-UHFFFAOYSA-N

物化性质

• 熔点：
  220-225 °C
• 沸点：
  306.9±15.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)
• 最大波长(λmax)：
  259nm(MeOH)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S37/39
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2933199090
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放在室温、干燥且密封的环境中。

SDS

1-Methylpyrazole-5-carboxylic Acid Revision number: 5.3
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 1-Methylpyrazole-5-carboxylic Acid

Revision number: 5.3

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 1-Methylpyrazole-5-carboxylic Acid
Percent: >97.0%(GC)(T)
CAS Number: 16034-46-1
Chemical Formula: C5H6N2O2

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
1-Methylpyrazole-5-carboxylic Acid

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: White - Almost white
No data available
Odour:
1-Methylpyrazole-5-carboxylic Acid

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:225°C (dec.)
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available
Log Pow: -0.09

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: -0.09
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
1-Methylpyrazole-5-carboxylic Acid

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用

1-甲基-1H-吡唑-5-羧酸具有良好的水溶性、去污性、稳泡性、抗菌性和易生物降解性，在香波、化妆品和工业洗涤等日用化工领域有广泛的应用。

合成方法

在氮气保护下，向干燥乙醚（600毫升）中加入1-甲基-1H-吡唑（609毫摩尔），搅拌均匀后，于-78°C下，在1小时内滴加正丁基溴（2.6 M，670毫摩尔）的己烷溶液。随后，在相同温度下继续搅拌反应混合物1小时，然后在-78°C下通入干燥的二氧化碳气体30分钟。将反应混合物升温至室温，并用水（500毫升）淬灭。分出水层，用乙醚（500毫升）洗涤并冷却至2-3℃。向搅拌的混合物中加入浓盐酸溶液，直至pH达到3。过滤收集所得沉淀物，用冰水（20毫升）洗涤，先在空气中干燥，再使用真空干燥器和P2O5进行干燥处理，最终得到白色粉末状1-甲基-1H-吡唑-5-羧酸。产物重量为35.3克，产率为45.4%。通过1H NMR（400MHz，DMSO-d6）检测，δ值分别为：13.31（1H，bs）；7.50（1H，d）；6.81（1H，d）；4.07（3H，s）。

反应信息

• 作为反应物：
  描述：

  1-甲基-1H-吡唑-5-羧酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-甲基-1H-吡唑-5-羰酰氯
  参考文献：
  名称：

  折叠碎片的平面景观：3D 环丁烷碎片库的设计和合成

  摘要：

  描述了一个包含 33 个成员的具有三维环丁烷片段的库。主成分分析、片段三规则和主惯性矩分析指导设计以生产具有三个官能团的非对映体纯顺式/反式异构体：胺、酰胺和磺酰胺。文库的计算物理化学和 3D 特性被认为对片段筛选具有吸引力。

  DOI：

  10.1002/cmdc.202200113
• 作为产物：
  描述：

  2-(1-甲基-1H-吡唑-5-基)乙醇 在 potassium permanganate 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 4.0h， 以64%的产率得到1-甲基-1H-吡唑-5-羧酸
  参考文献：
  名称：

  所有异构的2-（吡唑基）乙醇的合成和氧化

  摘要：

  描述了一种基于3-（二甲氧基甲基）-2-甲氧基四氢呋喃与肼的再循环反应制备N-取代的2-（吡唑-4-基）乙醇的有效方法。用KMnO 4氧化产生2-（吡唑-4-基）-2-氧乙酸。相反，在类似条件下的2-（吡唑-5-基）乙醇仅产生吡唑-5-羧酸，其是通过氧化然后脱羰而形成的。在该氧化反应中的2-（吡唑-3-基）乙醇得到2-氧代-2-（吡唑-3-基）乙酸和吡唑-3-羧酸的混合物。

  DOI：

  10.1007/s10593-020-02662-z
• 作为试剂：
  描述：

  3-(2-chloro-5-methoxyphenyl)pyridine-2,6-diamine 、 1-甲基-1H-吡唑-5-羧酸 在 1-甲基-1H-吡唑-5-羧酸 作用下， 生成 N-(6-氨基-5-(2-氯-5-甲氧苯基)吡啶-2-基)-1-甲基-1H-吡唑-5-甲酰胺
  参考文献：
  名称：

  Pyridine derivatives

  摘要：

  本发明涉及式(I)的化合物及其药学上可接受的盐，制备这种化合物的过程中使用的中间体，含有这种化合物的组合物以及这种化合物用于治疗疼痛的用途。

  公开号：

  US08134007B2

文献信息

• [EN] CYCLIC SULFAMIDE COMPOUNDS AND METHODS OF USING SAME<br/>[FR] COMPOSÉS DE SULFAMIDE CYCLIQUE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ASSEMBLY BIOSCIENCES INC

  公开号：WO2018160878A1

  公开（公告）日：2018-09-07

  The present disclosure provides, in part, cyclic sulfamide compounds, and pharmaceutical compositions thereof, useful as modulators of Hepatitis B (HBV) core protein, and methods of treating Hepatitis B (HBV) infection.

  本公开提供了部分环磺胺化合物及其药物组合物，可用作乙型肝炎（HBV）核心蛋白的调节剂，并用于治疗乙型肝炎（HBV）感染的方法。
• [EN] DOPAMINE D3 RECEPTOR ANTAGONISTS HAVING A BICYCLO MOIETY<br/>[FR] ANTAGONISTES DU RÉCEPTEUR D3 DE LA DOPAMINE AYANT UN FRAGMENT BICYCLO
  申请人：INDIVIOR UK LTD

  公开号：WO2017021920A1

  公开（公告）日：2017-02-09

  The disclosure provides compounds having formula (I), wherein the substituents are as defined herein. The compounds are useful for modulating the dopamine D3 receptor and for treating conditions associated therewith, such as addictions, drug dependency, and psychiatric conditions.

  该披露提供了具有化学式（I）的化合物，其中取代基如本文所定义。这些化合物可用于调节多巴胺D3受体，并用于治疗与之相关的疾病，如成瘾、药物依赖和精神疾病。
• Room Temperature Carbonylation of (Hetero) Aryl Pentafluorobenzenesulfonates and Triflates using Palladium-Cobalt Bimetallic Catalyst: Dual Role of Cobalt Carbonyl
  作者：Jayan T. Joseph、Ayyiliath M. Sajith、Revanna C. Ningegowda、Sheena Shashikanth

  DOI：10.1002/adsc.201600736

  日期：2017.2.2

  method for the carbonylation of (hetero) aryl pentafluorobenzenesulfonates and triflates under exceptionally mild conditions using palladium/dicobalt octacarbonyl [Pd/Co2(CO)8] has been developed. Besides acting as carbon monoxide (CO) source, Co2(CO)8 enhances the reaction rate by accelerating the CO insertion through an in situ generated bimetallic palladium cobalt tetracarbonyl [Pd‐Co(CO)4] complex

  已经开发了一种在异常温和的条件下使用钯/二钴八羰基[Pd / Co 2（CO）8 ]对（杂）芳基五氟苯磺酸盐和三氟甲磺酸酯进行羰基化的有效方法。除了充当一氧化碳（CO）源外，Co 2（CO）8还可以通过原位生成的双金属钯四羰基钴[Pd-Co（CO）4）加速CO的插入，从而提高反应速率。] 复杂的。在优化的反应条件下，各种活化和失活的，以及位阻和杂芳族底物的羰基化反应在室温下均能有效进行。生物学上相关的异古瓦汀和拉扎贝米中间体的高化学选择性和改进的合成方法突出了其作为有价值的合成方法的范围。该协议的通用性进一步扩展到其他亲电试剂（溴化物，氯化物和甲苯磺酸盐）。
• 吡唑并[3,4-c]吡啶类衍生物
  申请人：石药集团中奇制药技术(石家庄)有限公司

  公开号：CN105384739B

  公开（公告）日：2020-03-20

  吡唑并[3,4‑c]吡啶类衍生物。本发明涉及下式（I）的化合物，其互变异构体、其光学异构体、或其药学上可接受的盐：Z，X，RNc，RNd，RNe和RNf如权利要求1所定义。本发明还涉及包含上述化合物的药物组合物。本发明还涉及上述化合物或药用组合物在制备用于预防和/或治疗抑制Xa因子正性影响疾病的药物中的用途，特别是在制备用于在低出血风险的情况下预防和/或治疗抑制Xa因子正性影响疾病的药物中的用途。
• [EN] OXADIAZOLE INHIBITORS OF LEUKOTRIENE PRODUCTION<br/>[FR] COMPOSÉS OXADIAZOLE, INHIBITEURS DE LA PRODUCTION DE LEUCOTRIÈNES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2012027322A1

  公开（公告）日：2012-03-01

  The present invention relates to compound of formula (I) and pharmaceutically acceptable salt thereof, wherein R1-R5 are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

  本发明涉及式(I)的化合物及其药用可接受盐，其中R1-R5如本文所定义。该发明还涉及包括这些化合物的药物组合物，使用这些化合物治疗各种疾病和疾病的方法，制备这些化合物的过程以及在这些过程中有用的中间体。

表征谱图