4-叠氮基-1-丁胺 | 88192-20-5

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 4-叠氮基-1-丁胺
• 中文别名: 4-叠氮丁-1-胺
• 英文名称: 4-azidobutan-1-amine
• 英文别名: 4-azidobutylamine
• CAS: 88192-20-5
• 化学式: C₄H₁₀N₄
• mdl: MFCD11046232
• 分子量: 114.15
• InChiKey: LFMZGBHJJNIRKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2929909090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Azidobutan-1-amine
Synonyms:

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

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Azidobutan-1-amine
CAS number: 88192-20-5

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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.

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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.

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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.

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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.

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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.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C4H10N4
Molecular weight: 114.2

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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.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

4-Azidobutylamine 是一种PROTAC连接桥，属于烷基链类。它可用于合成一系列PROTAC分子。这些分子含有两个通过连接桥相连的不同配体：一个是E3泛素连接酶配体，另一个是靶蛋白配体。PROTAC利用细胞内的泛素-蛋白酶体系统选择性地降解目标蛋白。

反应信息

• 作为反应物：
  描述：

  4-叠氮基-1-丁胺 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以90%的产率得到putrescine dihydrochloride
  参考文献：
  名称：

  Curtius Rearrangement of ω-Azido Acid Chlorides: Access to the Corresponding ω-Azido Substituted Amines and Carbamates, Useful Building Blocks for Polyamine Syntheses

  摘要：

  用三甲基硅叠氮化物处理 Ï-azido 酸氯化物，可得到 Ï-azido 异氰酸酯，这些异氰酸酯很容易以良好的产率转化成相应的 Ï-azidoamines 或 Ï-azidocarbamates。然后，通过催化氢化或有机二氯硼烷还原烷基化，可制备 1,3-和 1,4-二胺二氢氯化物。

  DOI：

  10.1055/s-1996-4438
• 作为产物：
  描述：

  四亚甲基二胺 在 triflic azide 、 potassium carbonate 、 copper(II) sulfate 作用下， 以 甲醇 、 水 为溶剂， 以61%的产率得到4-叠氮基-1-丁胺
  参考文献：
  名称：

  CONSTRUCTION AND SCREENING OF SOLUTION-PHASE DERIVED LIBRARY OF FENBUFEN AND ETHACRYNIC ACID

  摘要：

  本发明提供了一种合成和筛选溶液相衍生的芬布芬和依他克酸库的过程。本发明中具有细胞毒性的化合物对多种治疗应用是有用的。

  公开号：

  US20110306668A1
• 作为试剂：
  描述：

  4-叠氮基-1-丁胺 、 10,11-anhydro-2',4"-di-O-benzoyl-12-O-imidazolylcarbonyl-6-O-methylerythromycin A 在 4-叠氮基-1-丁胺 作用下， 生成 [(2S,3R,4S,6R)-2-[[(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-15-(4-azidobutyl)-6-[(2R,4R,5S,6S)-5-benzoyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-8-yl]oxy]-4-(dimethylamino)-6-methyloxan-3-yl] benzoate
  参考文献：
  名称：

  [EN] PROCESS FOR THE PREPARATION OF MACROLIDE ANTIBACTERIAL AGENTS
  [FR] PROCÉDÉ POUR LA PRÉPARATION D'AGENTS ANTIBACTÉRIENS MACROLIDES

  摘要：

  本文描述了制备式(I)化合物及其药学上可接受的盐、溶剂合物和水合物的过程。

  公开号：

  WO2009055557A1

文献信息

• 一类高亮度、高稳定性的活性荧光染料及其合 成和应用
  申请人：中国科学院大连化学物理研究所

  公开号：CN111334083B

  公开（公告）日：2022-03-18

  本发明提供了一类高亮度、高稳定性的活性荧光染料及其合成和应用，该染料通过萘酰亚胺4,5‑位刚性环的引入达到了荧光稳定性、亮度得到大幅度提升，其结构如图(1)所示。该类染料荧光亮度高，半峰宽窄(最高可达25nm)，对pH、黏度、温度、极性等均不敏感，在不同微环境下该类染料能够保持荧光信号的稳定性。此外，通过内酰胺位置可以简单实现多种活性基团的引入，以通过多种方式达到对目标分子的标记，这类染料能够广泛应用于生物大分子、纳米颗粒等荧光标记中。
• High-throughput synthesis of azide libraries suitable for direct “click” chemistry and in situ screening
  作者：Rajavel Srinivasan、Lay Pheng Tan、Hao Wu、Peng-Yu Yang、Karunakaran A. Kalesh、Shao Q. Yao

  DOI：10.1039/b902338k

  日期：——

  building blocks (key components in click chemistry). We report herein a highly robust and efficient strategy for high-throughput synthesis of a 325-member azide library. The method is highlighted by its simplicity and product purity. The utility of the library is demonstrated with the subsequent “click” synthesis of the corresponding bidentate inhibitors against PTP1B.

  当前药物发现中的关键挑战是开发高通量（HT）合适的化学反应，该反应可快速合成酶抑制剂的各种化学文库。叠氮化物和炔烃之间的Cu（I）催化的1,3-偶极环加成反应，称为“点击化学”，是近年来受到最广泛关注的一种方法。尽管它广受欢迎，但仍然缺乏可靠而有效的化学策略，这些策略无法访问各种包含叠氮化物的结构单元（点击化学中的关键成分）的库。我们在这里报告了一个高健壮和高效的策略，可用于325个成员的叠氮化物文库的高通量合成。该方法以其简单性和产品纯度而著称。
• Synthesis, Tumor Specificity, and Photosensitizing Efficacy of Erlotinib-Conjugated Chlorins and Bacteriochlorins: Identification of a Highly Effective Candidate for Photodynamic Therapy of Cancer
  作者：Ravindra R. Cheruku、Joseph Cacaccio、Farukh A. Durrani、Walter A. Tabaczynski、Ramona Watson、Kevin Siters、Joseph R. Missert、Erin C. Tracy、Mykhaylo Dukh、Khurshid Guru、Richard C. Koya、Pawel Kalinski、Heinz Baumann、Ravindra K. Pandey

  DOI：10.1021/acs.jmedchem.0c01735

  日期：2021.1.14

  HPPH. Furthermore, specific functional contribution of the carboxylic acid side group at position 172 and the chiral methyl group at 3(1′) to the overall activity of the chimeric compounds was assessed. Among the conjugates investigated, the PS 10 was identified as the most effective candidate for achieving tumor cell-specific accumulation and yielding improved long-term tumor control.

  厄洛替尼与 3-(1'-己氧基)乙基-3-脱乙烯基焦脱镁叶绿酸-a (HPPH) 以及结构相关的二氢卟酚和菌绿素在四吡咯环的不同位置共价连接。通过量化厄洛替尼缀合物的摄取和亚细胞沉积、组织培养物中对治疗性光处理的细胞反应以及消除 SCID 小鼠中作为异种移植物生长的相应肿瘤来确定每种修饰的功能结果。实验性人类癌症模型建立了已建立的细胞系 UMUC3（膀胱）、FaDu（下咽）以及头颈肿瘤细胞的原代培养物。将化合物的有效性与 HPPH 进行比较。此外，还评估了17 2位的羧酸侧基和3(1')位的手性甲基对嵌合化合物的总体活性的具体功能贡献。在所研究的缀合物中，PS 10被认为是实现肿瘤细胞特异性积累并改善长期肿瘤控制的最有效候选者。
• N-(Propargyl)diazenecarboxamides for ‘click’ conjugation and their 1,3-dipolar cycloadditions with azidoalkylamines in the presence of Cu(II)
  作者：Damijana Urankar、Miha Steinbücher、Jaka Kosjek、Janez Košmrlj

  DOI：10.1016/j.tet.2010.02.042

  日期：2010.4

  Propargyl functionalized diazenes 1 were prepared by two different approaches and were examined as alkyne click components in copper-catalyzed azide–alkyne cycloadditions (CuAAC) with 2-(azidomethyl)pyridine 5a and four α-azido-ω-aminoalkanes C2–C5 (5b–e). Whereas the reactions with azidoalkylamines 5b–e reached completion with copper(II) sulfate without the need of reducing agent typically in no more

  炔丙基官能化的二氮烯1通过两种不同的方法制备，并在铜催化的叠氮化物-炔烃环加成（CuAAC）中与2-（叠氮甲基）吡啶5a和四个α-叠氮基-ω-氨基链烷烃C2-C5（5b – e）。与叠氮基烷基胺5b - e的反应通常用硫酸铜（II）在不需要还原剂的情况下通常在不超过几分钟的时间内完成，而2-（叠氮甲基）吡啶5a需要添加金属铜和更长的反应时间（2 –24小时）。研究了反应性的这种差异，并根据其对CuAAC的碱效应和邻近效应进行了研究。
• Novel menadione hybrids: Synthesis, anticancer activity, and cell-based studies
  作者：Chakka Vara Prasad、Vadithe Lakshma Nayak、Sistla Ramakrishna、Uppuluri Venkata Mallavadhani

  DOI：10.1111/cbdd.13073

  日期：2018.1

  triazole hybrids were designed and synthesized by employing copper-catalyzed azide-alkyne cycloaddition (CuAAC). All the synthesized hybrids were characterized by their spectral data (1H NMR, 13C NMR, IR, and HRMS). The synthesized compounds were evaluated for their anticancer activity against five selected cancer cell lines including lung (A549), prostate (DU-145), cervical (Hela), breast (MCF-7),

  通过使用铜催化的叠氮化物-炔烃环加成反应（CuAAC）设计并合成了一系列基于甲萘醌的新型三唑杂化物。所有合成的杂种均通过其光谱数据（1 H NMR，13 C NMR，IR和HRMS）进行表征。使用MTT评估了合成的化合物对五种选定的癌细胞系的抗癌活性，这些癌细胞系包括肺癌（A549），前列腺癌（DU-145），宫颈癌（Hela），乳腺癌（MCF-7）和小鼠黑素瘤（B-16）分析。筛选结果表明，大多数合成的化合物显示出显着的抗癌活性。在测试的化合物中，三唑5和6对所有细胞系均显示出有效的活性。特别是化合物6对MCF-7细胞系显示出比标准他莫昔芬和母体甲萘醌更高的效力。流式细胞仪分析表明，化合物6在G0 / G1期停滞了细胞周期，并诱导了凋亡细胞的死亡，这通过Hoechst染色，线粒体膜电位（ΔΨm）的测定和Annexin-V-FITC分析得到了进一步证实。因此，化合物6可以被认为是作为有效的抗癌治疗剂而进一步开发的先导分子。