5-溴-2,3-二氨基吡嗪 | 89123-58-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡嗪类化合物
• 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: 5-溴-2,3-二氨基吡嗪
• 中文别名: 2,3-二氨基-5-溴吡嗪
• 英文名称: 5-bromopyrazine-2,3-diamine
• 英文别名: 5-bromo-2,3-diaminopyrazine；5-bromo-2,3-pyrazindiamine；2,3-diamino-5-bromopyrazine
• CAS: 89123-58-0
• 化学式: C₄H₅BrN₄
• mdl: MFCD06245575
• 分子量: 189.014
• InChiKey: CPYAUFLEMLTQAA-UHFFFAOYSA-N

物化性质

• 熔点：
  212-216 °C (dec.)
• 沸点：
  357.1±37.0 °C(Predicted)
• 密度：
  1.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37
• 危险类别码：
  R22,R36/37/38,R43
• WGK Germany：
  3
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H317,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
2,3-Diamino-5-bromopyrazine
Product Name:
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H315: Causes skin irritation
H317: May cause an allergic skin reaction
H319: Causes serious eye irritation
May cause respiratory irritation
H335:
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

---

Section 3. Composition/information on ingredients.
2,3-Diamino-5-bromopyrazine
Ingredient name:
CAS number: 89123-58-0

---

Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

---

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.

---

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.

---

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.
Storage: Store in closed vessels, refrigerated.

---

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.

---

Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C4H5BrN4
Molecular weight: 189

---

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, hydrogen bromide.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

5-溴-2,3-二氨基吡嗪可用作有机合成中间体和医药中间体，主要应用于实验室研发及化工生产过程。

反应信息

• 作为反应物：
  描述：

  5-溴-2,3-二氨基吡嗪 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 2,3-二氨基哌嗪
  参考文献：
  名称：

  Regioselective N-alkylation of some imidazole-containing heterocycles and their in vitro anticancer evaluation

  摘要：

  Imidazole-containing heterocycles: Imidazopyridines, imidazopyrimidines and imidazopyra-zines can exist more tautomeric forms than benzimidazoles. Their regioselectivities were determined for N-alkylations with 4-fluorobenzyl bromide under basic conditions (K2CO3) in DMF. We observed that, regioisomers were mainly formed as a mixture in this reaction and N-benzylation occurs at a higher ratio on six membered heterocycles. Their structural assignments were made with the use of two-dimensional H-1-H-1 NOE (nuclear overhauser effect spectroscopy, NOESY). Complementary structural informationwas provided by 2D-HMBC spectra of the compounds. Synthesized compounds were tested for in vitro cytotoxic activities against Human colon cancer cell line (HCT-116) and leukemia cell lines (K562 and HL-60) by MTT test. Among them, imidazopyridine analogue 10, bearing bromine atom at the C-6 position of the pyridine moiety, gave the lowest IC50 value with 6-7 mu g/mL against all three cancer cell lines. (C) 2020 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2019.127673
• 作为产物：
  描述：

  2-氨基-3,5-二溴吡嗪 在 ammonium hydroxide 作用下， 以5 g的产率得到5-溴-2,3-二氨基吡嗪
  参考文献：
  名称：

  一种咪唑并吡嗪医药中间体的制备方法

  摘要：

  本发明涉及一种咪唑并吡嗪医药中间体的制备方法，它包括以下步骤：（a）向高压釜中加入2‑氨基‑3,5‑二溴吡嗪和氨水，在氮气保护下升温至110~150℃进行反应，降温后抽滤得滤饼，干燥得化合物II；（b）将所述化合物II溶于N,N‑二甲基甲酰胺中，滴加原甲酸三乙酯和甲酸，在氮气保护下加热回流，提纯得化合物III；（c）向另一高压釜中加入所述化合物III、N‑甲基吡咯烷酮、氨水和五水硫酸铜，在氮气保护下升温至130~170℃进行反应，提纯得化合物IV；（d）将1,4‑二氧六环和所述化合物IV溶于乙酸溶液中，在冰水浴的条件下滴加NaNO2水溶液；滴加完毕后升温至40~50℃进行反应使固体析出，抽滤、洗涤即可。这样能够减少最终产品的合成步骤，从而提高其产率和纯度。

  公开号：

  CN108707150B

文献信息

• FLAP MODULATORS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：US20140221310A1

  公开（公告）日：2014-08-07

  The present invention relates to compounds of Formula (I), or a form thereof, wherein ring A, R 1 , L and R 2 are as defined herein, useful as FLAP modulators. The invention also relates to pharmaceutical compositions comprising compounds of Formula (I). Methods of making and using the compounds of Formula (I) are also within the scope of the invention.

  本发明涉及式（I）化合物，或其形式，其中环A，R1，L和R2如本文所定义，作为FLAP调节剂有用。该发明还涉及包含式（I）化合物的药物组合物。制备和使用式（I）化合物的方法也属于本发明的范围。
• [EN] FUSED IMIDAZOLE DERIVATIVES AS IL-17 MODULATORS<br/>[FR] DÉRIVÉS D'IMIDAZOLE FUSIONNÉS UTILISÉS EN TANT QU'INHIBITEURS D'IL-17
  申请人：UCB BIOPHARMA SPRL

  公开号：WO2019138017A1

  公开（公告）日：2019-07-18

  A series of substituted fused bicyclic imidazole derivatives, including benzimidazole derivatives and analogues thereof, being potent modulators of human IL-17 activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including inflammatory and autoimmune disorders.

  一系列替代的融合双环咪唑衍生物，包括苯并咪唑衍生物及其类似物，作为强效的人IL-17活性调节剂，因此在治疗和/或预防各种人类疾病，包括炎症性和自身免疫性疾病方面具有益处。
• N-Substituted Formamides as C1-Sources for the Synthesis of Benzimidazole and Benzothiazole Derivatives by Using Zinc Catalysts
  作者：Bhalchandra Bhanage、Deepak Nale

  DOI：10.1055/s-0035-1560319

  日期：——

  An efficient and convenient one-pot protocol has been developed for the synthesis of a variety of benzimidazole, benzoxazole, and benzothiazole derivatives. This novel approach uses various o-phenylenediamines and N-substituted formamides (C1 sources) in a zinc-catalyzed cyclization in the presence of poly(methylhydrosiloxane) to afford the corresponding derivatives as sole products in moderate to

  已开发出一种高效、方便的一锅法，用于合成各种苯并咪唑、苯并恶唑和苯并噻唑衍生物。这种新方法在聚（甲基氢硅氧烷）存在下在锌催化环化中使用各种邻苯二胺和 N-取代甲酰胺（C1 源），以中等至优异的产率提供相应的衍生物作为唯一产物。
• BICYCLIC AZA HETEROCYCLES, AND USE THEREOF
  申请人：Follmann Markus

  公开号：US20140148433A1

  公开（公告）日：2014-05-29

  The present application relates to novel bicyclic azaheterocycles, to processes for preparation thereof, to the use thereof, alone or in combinations, for treatment and/or prophylaxis of diseases and to the use thereof for production of medicaments for treatment and/or prophylaxis of diseases, especially for treatment and/or prophylaxis of cardiovascular disorders.

  本申请涉及新型的双环氮杂杂环化合物，其制备方法，以及单独或组合使用它们来治疗和/或预防疾病，以及使用它们来生产用于治疗和/或预防疾病的药物，特别是用于治疗和/或预防心血管疾病的药物。
• [EN] DIACYLGLYCEROL ACYLTRANSFERASE 2 INHIBITORS<br/>[FR] INHIBITEURS DE DIACYLGLYCÉROL ACYLTRANSFÉRASE 2
  申请人：PFIZER

  公开号：WO2013150416A1

  公开（公告）日：2013-10-10

  Derivatives of purine, 3H-imidazo[4,5-b]pyrimidine and 1H- imidazo[4,5-d]pyrazine of Formula I that inhibit the activity of the diacylglycerol acyltransferase 2 (DGAT2) and their uses in the treatment of diseases linked thereto in animals are described herein.

  这里描述了抑制二酰基甘油酰基转移酶2（DGAT2）活性的嘌呤衍生物，即式I的3H-咪唑并[4,5-b]嘧啶和1H-咪唑并[4,5-d]吡嗪，以及它们在治疗相关动物疾病中的用途。