3-氨基吡嗪-2-羧酸 | 5424-01-1

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 3-氨基吡嗪-2-羧酸
• 中文别名: 3-氨基哌嗪-2-甲酸；3-氨基哌嗪酸；3-氨基哌嗪-2-羧酸；2-氨基吡嗪-3-甲酸；3-氨基吡嗪-2-甲酸
• 英文名称: 3-aminopyrazinoic acid
• 英文别名: 3-amino-pyrazine-2-carboxylic acid；3-amino-2-pyrazinecarboxylic acid；2-aminopyrazine-3-carboxylic acid；3-Aminopyrazine-2-carboxylic acid
• CAS: 5424-01-1
• 化学式: C₅H₅N₃O₂
• mdl: MFCD00006141
• 分子量: 139.114
• InChiKey: ZAGZIOYVEIDDJA-UHFFFAOYSA-N

物化性质

• 熔点：
  205-210 °C (dec.) (lit.)
• 沸点：
  255.04°C (rough estimate)
• 密度：
  1.4551 (rough estimate)
• 溶解度：
  DMSO（微溶）、甲醇（微溶）
• LogP：
  -3.1 at 20℃ and pH7
• 表面张力：
  73.6mN/m at 1g/L and 20℃
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.1
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 安全说明：
  S26,S36
• WGK Germany：
  3
• 海关编码：
  2933599090
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 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、存放在阴凉干燥处并密封保存。

SDS

Name:	3-Aminopyrazine-2-Carboxylic Acid 99+% Material Safety Data Sheet
Synonym:	None known
CAS:	5424-01-1

Section 1 - Chemical Product MSDS Name:3-Aminopyrazine-2-Carboxylic Acid 99+% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5424-01-1	3-Aminopyrazine-2-Carboxylic Acid	99+	226-558-7

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate 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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 5424-01-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: yellow
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 205 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: > 205 deg C
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C5H5N3O2
Molecular Weight: 139.11

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5424-01-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Aminopyrazine-2-Carboxylic Acid - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 5424-01-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5424-01-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5424-01-1 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：用作有机合成中间体及利尿药氨氯吡唑的中间体。

反应信息

• 作为反应物：
  描述：

  3-氨基吡嗪-2-羧酸 在 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 potassium fluoride dihydrate 、 硫酸 、 四丁基溴化铵 、 水 、 双氧水 、 碳酸氢钠 、 potassium carbonate 、 sodium nitrite 、 三氯氧磷 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 98.25h， 生成 法匹拉韦
  参考文献：
  名称：

  实用，循序渐进的法维拉韦治疗途径

  摘要：

  开发了一种实用且循序渐进的途径开发抗病毒药物Favipiravir。从三氨基吡嗪-2-羧酸仅用六步合成法维拉韦，总收率约为22.3％。通过从优化的溶剂中重结晶，可以得到纯度很高的关键中间体3和6，这有利于大规模生产。在关键的合成反应中，将3,6-二氯吡嗪-2-腈（6）在一个锅中依次与KF和30％H 2 O 2反应，得到（从95％EtOH中结晶后）无色结晶的法维吡韦，合成的最后一步产率为60％。

  DOI：

  10.1007/s11696-017-0208-6
• 作为产物：
  描述：

  2,4-二羟基蝶啶 在 sodium hydroxide 作用下， 生成 3-氨基吡嗪-2-羧酸
  参考文献：
  名称：

  Some New Aminopyrazines and their Sulfanilamide Derivatives

  摘要：

  DOI：

  10.1021/ja01221a032

文献信息

• Indolo[2,1-biquinazoline-6,12-dione antibacterial compounds and methods
  申请人：PathoGenesis Corporation

  公开号：US05441955A1

  公开（公告）日：1995-08-15

  Methods, compounds and compositions are provided form inhibiting the growth of pathogenic mycobacteria in vitro and of treatment of pathogenic mycobacterial infections in vivo using indolo[2,1-b]quinazoline-6,12-dione compounds of the formula (I): ##STR1## wherein A, B, C, D, E, F, G and H are independently selected from carbon and nitrogen, or A and B or C and D can be taken together to be nitrogen or sulfur, and the pharmaceutically acceptable salts thereof. The methods, compounds and compositons are particularly useful for inhibiting the growth of Mycobacterium tuberculosis, and may be used alone, or in combination with other anti-Mycobacterium tuberculosis agents, such as isoniazid, rifampin, pyrazinamide, rifabutin, streptomycin and ciprofloxacin, to provide new agents for the treatment of tuberculosis, including multidrug-resistant tuberculosis (MDRTB).

  提供了一种用于体外抑制病原性分枝杆菌生长和用于体内治疗病原性分枝杆菌感染的方法、化合物和组合物，使用式(I)的吲哚并[2,1-b]喹唑啉-6,12-二酮化合物：##STR1## 其中A、B、C、D、E、F、G和H独立地选自碳和氮，或A和B或C和D可以结合在一起成为氮或硫，并且其药学上可接受的盐。这些方法、化合物和组合物特别适用于抑制结核分枝杆菌的生长，并可单独使用，或与其他抗结核分枝杆菌药物（如异烟肼、利福平、吡嗪酰胺、利福布汀、链霉素和环丙沙星）结合使用，以提供用于治疗结核病的新药物，包括多药耐药结核病（MDRTB）。
• [EN] AMINO PYRAZINE DERIVATIVES AS PHOSPHATIDYLINOSITOL 3-KINASE INHIBITORS<br/>[FR] DÉRIVÉS AMINÉS DE PYRAZINE UTILISABLES EN TANT QU'INHIBITEURS DE LA PHOSPHATIDYLINOSITOL 3-KINASE
  申请人：NOVARTIS AG

  公开号：WO2015162459A1

  公开（公告）日：2015-10-29

  The present invention provides compounds of formula (I) which inhibit the activity of PI 3-kinase gamma isoform, which are useful for the treatment of diseases mediated by the activation of PI 3-kinase gamma isoform.

  本发明提供了一种公式（I）的化合物，该化合物抑制PI 3-激酶γ同工酶的活性，对于治疗由PI 3-激酶γ同工酶激活介导的疾病是有用的。
• [EN] HETEROCYCLIC COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEURS UTILISATIONS
  申请人：INFINITY PHARMACEUTICALS INC

  公开号：WO2015051241A1

  公开（公告）日：2015-04-09

  Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.

  本发明描述了调节激酶活性的化合物和药物组合物，包括PI3激酶活性，以及用于治疗与激酶活性相关的疾病和状况的化合物、药物组合物和方法，包括PI3激酶活性。
• A Green, Facile, and One-pot Synthesis of 2,4-(1<i>H</i>,3<i>H</i>)-Quinazolinediones under Microwave Irradiations
  作者：Farzad Nikpour、Touraj Paibast

  DOI：10.1246/cl.2005.1438

  日期：2005.10

  Quinazoline-2,4-diones are of considerable interest due to their wide pharmacological properties. Here, we have described an environmentally friendly method for the one-pot synthesis of 2,4-(1H,3H)-quinazolinediones from the reaction of anthranilic acid derivatives with urea in H 2 O media under microwave irradiations. This method is simple, safe, and fast which produces high yield of products without

  由于其广泛的药理特性，喹唑啉-2,4-二酮引起了相当大的兴趣。在这里，我们描述了一种环境友好的方法，用于从邻氨基苯甲酸衍生物与尿素在 H 2 O 介质中在微波辐射下的反应中一锅合成 2,4-(1H,3H)-喹唑啉二酮。该方法简单、安全、快速，无需任何催化剂，产品收率高。
• Unsymmetrically Substituted Dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A Convenient Scaffold for Bioactive Molecule Design
  作者：Bartosz Bieszczad、Damian Garbicz、Damian Trzybiński、Damian Mielecki、Krzysztof Woźniak、Elżbieta Grzesiuk、Adam Mieczkowski

  DOI：10.3390/molecules25040906

  日期：——

  procedures allowed the synthesis of unsymmetrical dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones and three novel heterocyclic scaffolds: benzo[b]naphtho[2,3-f][1,5]diazocine-6,14(5H,13H)dione, pyrido[3,2-c][1,5]benzodiazocine-5,11(6H,12H)-dione and pyrazino[3,2-c][1,5]benzodiazocine-6,12(5H,11H)dione. For 11 of the compounds crystal structures were obtained. The preliminary cytotoxic effect against two

  一种用于合成不对称取代的二苯并 [b,f][1,5]diazocine-6,12(5H,11H)diones 的新方法已被开发出来。这种简便的三步法使用各种取代的 1H-苯并[d][1,3] 恶嗪-2,4-二酮（靛红酸酐）和 2-氨基苯甲酸作为起始材料。所得产物进一步转化为N-烷基-、N-乙酰基-和二硫代类似物。开发的程序允许合成不对称的二苯并[b,f][1,5]diazocine-6,12(5H,11H)二酮和三种新型杂环支架：苯并[b]萘并[2,3-f][1， 5]diazocine-6,14(5H,13H)dione, pyrido[3,2-c][1,5]benzodiazocine-5,11(6H,12H)-dione 和 pyrazino[3,2-c][1 ,5]benzodiazocine-6,12(5H,11H)dione。获得了 11 种化合物的晶体结构。对两种癌症（HeL

表征谱图