2-氯-4-硝基咪唑 | 57531-37-0

• 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 - 唑类
• 中文名称: 2-氯-4-硝基咪唑
• 中文别名: 2-氯-5-硝基咪唑
• 英文名称: 2-chloro-4-nitro-1H-imidazole
• 英文别名: 2-chloro-4-nitroimidazole；2-chloro-5-nitro-1H-imidazole
• CAS: 57531-37-0
• 化学式: C₃H₂ClN₃O₂
• mdl: MFCD03419295
• 分子量: 147.521
• InChiKey: BOJZBRDIZUHTCE-UHFFFAOYSA-N

物化性质

• 熔点：
  216-217 °C
• 沸点：
  386.8±34.0 °C(Predicted)
• 密度：
  1.740±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微超声处理）、甲醇（轻微超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2933290090
• 安全说明：
  S26,S36
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-Chloro-5-nitro-1h-imidazole
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-Chloro-5-nitro-1h-imidazole
CAS number: 57531-37-0

---

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

---

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.
Store in closed vessels, refrigerated.
Storage:

---

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
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C3H2ClN3O2
Molecular weight: 147.5

---

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 chloride.

---

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

2-氯-4-硝基咪唑是一种杂环衍生物，可作为医药中间体使用。

反应信息

• 作为反应物：
  描述：

  2-氯-4-硝基咪唑 在 potassium carbonate 作用下， 生成
  参考文献：
  名称：

  Barabanov, V. P.; Tret'yakova, A. Ya.; Sharnin, G. P., Journal of general chemistry of the USSR, 1980, vol. 50, p. 1879 - 1882

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二硝基咪唑 在 盐酸 作用下， 以 水 为溶剂， 以92%的产率得到2-氯-4-硝基咪唑
  参考文献：
  名称：

  Synthesis of new generation triazolyl- and isoxazolyl-containing 6-nitro-2,3-dihydroimidazooxazoles as anti-TB agents: in vitro, structure–activity relationship, pharmacokinetics and in vivo evaluation

  摘要：

  有前途的硝基咪唑噁唑骨架提供了另一种新颖的三唑基含有的6-硝基-2,3-二氢咪唑噁唑作为抗结核病的先导化合物。

  DOI：

  10.1039/c5ob00054h
• 作为试剂：
  描述：

  (R)-1-(4-((2-methyloxiran-2-yl)-methoxy)phenyl)-4-(4-(trifluoro-methoxy)phenoxy)piperidine 、 2-氯-4-硝基咪唑 在 2-氯-4-硝基咪唑 作用下， 以73的产率得到迪拉马尼
  参考文献：
  名称：

  [EN] SYNTHETIC INTERMEDIATE OF OXAZOLE COMPOUND AND METHOD FOR PRODUCING THE SAME
  [FR] INTERMÉDIAIRE SYNTHÉTIQUE D'UN COMPOSÉ OXAZOLE ET PROCÉDÉ DE PRODUCTION ASSOCIÉ

  摘要：

  本发明的目的是提供一种高产率生产噁唑化合物的方法。该目的可以通过由式（11）表示的化合物实现：其中R1是氢原子或低烷基基团；R2是在4位被取代的1-哌啶基团，所述取代基选自（A1a）苯基上取代有一个或多个卤素取代的低烷氧基取代基的苯氧基取代基，（A1b）苯基上取代有一个或多个卤素取代的低烷基取代基的苯氧基取代基，（A1c）苯基上取代有卤素的苯基取代低烷氧基低烷基取代基，（A1d）苯基上取代有一个或多个卤素取代的低烷氧基取代基的苯基取代基，（A1e）被苯基取代且被一个或多个卤素取代的低烷氧基取代基的氨基取代基，以及低烷基取代基，和（A1f）苯基上取代有一个或多个卤素取代的低烷氧基取代基的苯基取代基；n是1至6的整数；X3是有机磺酰氧基团。

  公开号：

  WO2011093529A1

文献信息

• Highly Enantioselective, Hydrogen-Bond-Donor Catalyzed Additions to Oxetanes
  作者：Daniel A. Strassfeld、Zachary K. Wickens、Elias Picazo、Eric N. Jacobsen

  DOI：10.1021/jacs.0c03991

  日期：2020.5.20

  addition of trimethylsilyl bromide (TMSBr) to a broad variety of 3-substituted and 3,3-disubstituted oxetanes. The reaction provides direct and gen-eral access to synthetically valuable 1,3-bromohydrin building blocks from easily accessed achiral precursors. The products are readily elaborated both by nucleophilic substitution and through transition-metal-catalyzed cross-coupling reactions. The enantioselective

  精确设计的手性方酰胺衍生物可促进三甲基溴硅烷 (TMSBr) 与多种 3-取代和 3,3-二取代氧杂环丁烷的高度对映选择性加成。该反应提供了从容易获得的非手性前体中直接、普遍地获得具有合成价值的 1,3-溴醇结构单元的方法。该产物很容易通过亲核取代和过渡金属催化的交叉偶联反应来制备。对映选择性催化氧杂环丁烷开环被用作 pretomanid 的三步克级合成的一部分，pretomanid 是最近批准的用于治疗多重耐药结核病的药物。重原子动力学同位素效应（KIE）研究与溴化物从氢键供体（HBD）催化剂到活化氧杂环丁烷的对映体测定一致。虽然溴离子的亲核性预计会因与 HBD 结合而减弱，但通过阴离子抽象增强 TMSBr 试剂的路易斯酸度可实现总体速率加速。
• 雷公藤红素咪唑衍生物及其制备方法与用途
  申请人：中国药科大学

  公开号：CN109336944B

  公开（公告）日：2021-04-27

  本发明公开了一种新型雷公藤红素咪唑衍生物及其制备方法与用途，属于生物医药领域。所述雷公藤红素咪唑衍生物具有如式I所示的结构：其中R1、R2、R3分别选自H、烷基、含杂原子的烷基、卤素或硝基；X选自含3至6个碳原子的饱和或不饱和直链脂肪烃片段。该类化合物的制备方法反应条件温和，所用试剂低毒，原料易得，后处理方便，产率较高。药理实验研究表明，本发明化合物具有优良的抗肿瘤活性，可以作为制备抗肿瘤药物中的应用。
• NITROIMIDAZOOXAZINE AND NITROIMIDAZOOXAZOLE ANALOGUES AND THEIR USES
  申请人：Thompson Andrew Mark

  公开号：US20110028466A1

  公开（公告）日：2011-02-03

  The current invention pertains to nitroimidazooxazine and nitroimidazooxazole analogues, their methods of preparation, and uses of the compounds as treatment for Mycobacterium tuberculosis , for use as anti-tubercular drugs, for use as anti-protozoal agents with unexpectedly high potency against Trypanosoma cruzi or Leishmania donovani , and for the treatment of other microbial infections.

  当前的发明涉及硝基咪唑噁啉和硝基咪唑噁唑类似物，它们的制备方法，以及将这些化合物用作治疗结核分枝杆菌、用作抗结核药物、用作对克氏锥虫或唐氏利什曼原虫具有意外高效的抗原虫药剂，以及用于治疗其他微生物感染的用途。
• Repositioning Antitubercular 6-Nitro-2,3-dihydroimidazo[2,1-<i>b</i>][1,3]oxazoles for Neglected Tropical Diseases: Structure–Activity Studies on a Preclinical Candidate for Visceral Leishmaniasis
  作者：Andrew M. Thompson、Patrick D. O’Connor、Adrian Blaser、Vanessa Yardley、Louis Maes、Suman Gupta、Delphine Launay、Denis Martin、Scott G. Franzblau、Baojie Wan、Yuehong Wang、Zhenkun Ma、William A. Denny

  DOI：10.1021/acs.jmedchem.5b01699

  日期：2016.3.24

  linking oxygen for nitrogen (or piperazine), biaryl extension, and replacement of phenyl rings by pyridine. Several less lipophilic analogues displayed improved aqueous solubility, particularly at low pH, although stability toward liver microsomes was highly variable. Upon evaluation in a mouse model of acute Leishmania donovani infection, one phenylpyridine derivative (37) stood out, providing efficacy

  6-硝基-2,3-二氢咪唑[2,1- b最初在临床试验用药前驱体前药（PA-824）的备用程序中研究了[] [1,3]恶唑衍生物的结核病。表型筛选针对动素体疾病的代表性实例出乎意料地导致了DNDI-VL-2098的鉴定为潜在的内脏利什曼病（VL）的同类药物候选者。然后进行了其他工作来描述其基本结构特征，目的是在不损害针对VL的活性的情况下提高其溶解度和安全性。尽管4-硝基咪唑部分是特别需要的，但对芳氧基侧链的一些修饰是很好的耐受性，例如，将连接的氧交换成氮（或哌嗪），联芳基延伸以及用吡啶取代苯环。几种较不亲脂的类似物显示出改善的水溶性，尽管对肝微粒体的稳定性变化很大，但特别是在低pH下。在评估小鼠急性模型后利什曼原虫多诺万尼感染中，一种苯基吡啶衍生物（37）脱颖而出，其功效超过了临床前的先导药物。
• Programmed synthesis of triarylnitroimidazoles <i>via</i> sequential cross-coupling reactions
  作者：Gaurav Raina、Prakash Kannaboina、Nagaraju Mupparapu、Sushil Raina、Qazi Naveed Ahmed、Parthasarathi Das

  DOI：10.1039/c9ob00144a

  日期：——

  programmed sequential arylation reactions of 2-chloro-4-nitro-1H-imidazoles were achieved. The methods are general and were applied in a chemoselective manner for the synthesis of different multiarylated 4-nitroimidazoles bearing three different aryl groups. A salient feature is Pd-catalyzed hetero–hetero coupling at the C5 position through a NO2 directed cross-dehydrogenative coupling (CDC) approach.

  实现了2-氯-4-硝基-1 H-咪唑的过渡金属催化程序化的顺序芳基化反应。该方法是通用的，并且以化学选择性方式用于合成带有三个不同芳基的不同的多芳基化4-硝基咪唑。一个显着的特征是通过NO 2定向的交叉脱氢偶联（CDC）方法在C5位置的Pd催化的杂-杂偶联。