4-碘苄胺盐酸盐 | 59528-27-7

• 物质功能分类: 有机原料 - 氨基化合物 - 无环单胺、多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-碘苄胺盐酸盐
• 中文别名: 4-碘苄胺.盐酸盐；对碘苄胺盐酸盐
• 英文名称: p-iodobenzylamine hydrochloride
• 英文别名: 4-iodobenzylamine hydrochloride；(4-iodophenyl)methanaminium chloride；(4-iodophenyl)methanamine hydrochloride；4-iodobenzylamine*HCl；(4-iodophenyl)methanamine monohydrochloride；(4-Iodophenyl)methylazanium;chloride
• CAS: 59528-27-7
• 化学式: C₇H₈IN*ClH
• 分子量: 269.513
• InChiKey: GBJMURRFWZREHE-UHFFFAOYSA-N

物化性质

• 熔点：
  299-303 °C(lit.)
• 稳定性/保质期：
  避免接触氧化剂、酸以及强还原剂。

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  26
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2921499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  在密封的贮藏器中存放，并置于阴凉、干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Iodobenzylamine, HCl
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
4-Iodobenzylamine, HCl
Ingredient name:
CAS number: 59528-27-7

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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:

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H8IN.ClH
Molecular weight: 269.5

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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, hydrogen chloride, hydrogen Iodide.

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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

用途

4-碘苄胺盐酸盐是一种胺类衍生物，可用作有机合成中间体。

制备

将 4-碘苯甲酰胺（11 克，45 毫摩尔）悬浮于 THF（50 毫升）中，加入硼烷-THF（1M，22.5 毫升，22.5 毫摩尔）。将所得溶液加热回流过夜。冷却至冰浴后，缓慢滴加 MeOH-HCl（60 毫升），过滤沉淀并干燥，得到白色固体 4-碘苄胺盐酸盐。产率为 10.8 克，收率 88%。

反应信息

• 作为反应物：
  描述：

  4-碘苄胺盐酸盐 在 甲酸 、 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 0.17h， 生成 1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)-N-(4-iodobenzyl)-N-methylmethanamine
  参考文献：
  名称：

  CXCR3 antagonists: Quaternary ammonium salts equipped with biphenyl- and polycycloaliphatic-anchors

  摘要：

  Small-molecule ligands for the CXCR3 chemokine receptor receive considerable attention as a means to interrogate the roles of CXCR3 in vitro and in vivo and/or to potentially treat various conditions such as inflammatory diseases and cancer. We have synthesized and explored a novel class of small-molecule antagonists for CXCR3. A medium-throughput screen revealed an adamantane-guanidine as a hit. The guanidine unit was replaced by a small quaternary ammonium group, leading to ca. 5-fold increase in affinity. Substitution of the adamantane group by a myrtenyl moiety further increased affinity, while the benzyl group was decorated with an additional (substituted) aryl ring. This led to the identification of several bisaryl-based ligands with CXCR3 affinities of around 100 nM and with the ability to antagonize the functional activity of CXCL10. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.035
• 作为产物：
  描述：

  4-碘苄醇 在 盐酸 、 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 4-碘苄胺盐酸盐
  参考文献：
  名称：

  Design, synthesis, and evaluation of isoindolinone-hydroxamic acid derivatives as histone deacetylase (HDAC) inhibitors

  摘要：

  We designed and synthesized hydroxamic acid derivatives bearing a 4-(3-pyridyl)phenyl group as a cap structure, and found that they exhibit potent historic deacetylase (HDAC) inhibitory activity. A representative compound, 17a, showed more potent growth-inhibitory activity against pancreatic cancer cells and greater upregulation of p21(WAF1/CIP1) expression than the clinically used HDAC inhibitor suberoylanilide hydroxamic acid (Zolinza (TM)). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.038

文献信息

• Structure-Based Design of Potent and Orally Active Isoindolinone Inhibitors of MDM2-p53 Protein–Protein Interaction
  作者：Gianni Chessari、Ian R. Hardcastle、Jong Sook Ahn、Burcu Anil、Elizabeth Anscombe、Ruth H. Bawn、Luke D. Bevan、Timothy J. Blackburn、Ildiko Buck、Celine Cano、Benoit Carbain、Juan Castro、Ben Cons、Sarah J. Cully、Jane A. Endicott、Lynsey Fazal、Bernard T. Golding、Roger J. Griffin、Karen Haggerty、Suzannah J. Harnor、Keisha Hearn、Stephen Hobson、Rhian S. Holvey、Steven Howard、Claire E. Jennings、Christopher N. Johnson、John Lunec、Duncan C. Miller、David R. Newell、Martin E. M. Noble、Judith Reeks、Charlotte H. Revill、Christiane Riedinger、Jeffrey D. St. Denis、Emiliano Tamanini、Huw Thomas、Neil T. Thompson、Mladen Vinković、Stephen R. Wedge、Pamela A. Williams、Nicola E. Wilsher、Bian Zhang、Yan Zhao

  DOI：10.1021/acs.jmedchem.0c02188

  日期：2021.4.8

  (MDM2)-p53 protein–protein interaction with small molecules has been shown to reactivate p53 and inhibit tumor growth. Here, we describe rational, structure-guided, design of novel isoindolinone-based MDM2 inhibitors. MDM2 X-ray crystallography, quantum mechanics ligand-based design, and metabolite identification all contributed toward the discovery of potent in vitro and in vivo inhibitors of the MDM2-p53

  抑制小鼠双分钟 2 (MDM2)-p53 蛋白-蛋白与小分子的相互作用已被证明可以重新激活 p53 并抑制肿瘤生长。在这里，我们描述了基于异吲哚啉酮的新型 MDM2 抑制剂的合理的、结构指导的设计。 MDM2 X 射线晶体学、基于量子力学配体的设计和代谢物鉴定都有助于发现 MDM2-p53 与代表性化合物相互作用的有效体外和体内抑制剂，在 SJSA-1 骨肉瘤异种移植模型中诱导细胞停滞。 -每日口服给药。
• An imidazolin-2-iminato ligand organozinc complex as a catalyst for hydroboration of organic nitriles
  作者：Suman Das、Jayeeta Bhattacharjee、Tarun K. Panda

  DOI：10.1039/c9nj04076e

  日期：——

  The reaction of diethylzinc with imidazolin-2-imines (ImRNH, R = Dipp (2,6-diisopropylphenyl)), Mes (2,4,6-trimethylphenyl), and tBu (tert-butyl) afforded the corresponding dimeric zinc(II) imidazolin-2-iminato complexes [(ImRN)Zn(CH2CH3)}2] (R = Dipp, 1a; R = Mes, 1b; R = tBu, 1c). The zinc complexes were characterised using spectroscopic techniques and the molecular structure of complex 1b was established

  二乙基锌与咪唑啉-2-亚胺（Im R NH，R = Dipp（2,6-二异丙基苯基）），Mes（2,4,6-三甲基苯基）和t Bu（叔丁基）的反应得到相应的二聚体锌（II）咪唑啉-2-亚氨基配合物[（Im R N）Zn（CH 2 CH 3）} 2 ]（R = Dipp，1a ; R = Mes，1b ; R = t Bu，1c）。锌配合物用光谱技术表征，配合物1b的分子结构通过单晶X射线衍射分析确定。复杂1c将其用作在环境温度下与频哪醇硼烷（HBpin）进行有机腈化学选择性加氢硼化的催化剂，以高收率获得具有广泛底物范围的二硼胺。锌配合物1c对催化硼氢化反应具有广泛的底物范围和良好的官能团耐受性。在动力学研究的基础上提出了一个最合理的机制。
• Boron-Catalyzed Silylative Reduction of Nitriles in Accessing Primary Amines and Imines
  作者：Narasimhulu Gandhamsetty、Jinseong Jeong、Juhyeon Park、Sehoon Park、Sukbok Chang

  DOI：10.1021/acs.joc.5b00941

  日期：2015.7.17

  Silylative reduction of nitriles was studied under transition metal-free conditions by using B(C6F5)3 as a catalyst with hydrosilanes as a reductant. Alkyl and (hetero)aryl nitriles were efficiently converted to primary amines or imines under mild conditions. The choice of silanes was found to determine the selectivity: while a full reduction of nitriles was highly facile, the use of sterically bulky

  在无过渡金属的条件下，通过使用B（C 6 F 5）3作为催化剂，以氢硅烷作为还原剂，研究了腈的甲硅烷基化还原反应。在温和的条件下，烷基和（杂）芳基腈被有效地转化为伯胺或亚胺。发现硅烷的选择决定了选择性：虽然腈的完全还原非常容易，但是使用空间大体积的硅烷允许部分还原，从而生成N-甲硅烷基亚胺。
• Catalytic Staudinger Reduction at Room Temperature
  作者：Danny C. Lenstra、Joris J. Wolf、Jasmin Mecinović

  DOI：10.1021/acs.joc.9b00831

  日期：2019.5.17

  catalytic Staudinger reduction at room temperature that enables the preparation of a structurally diverse set of amines from azides in excellent yields. The reaction is based on the use of catalytic amounts of triphenylphosphine as a phosphine source and diphenyldisiloxane as a reducing agent. Our catalytic Staudinger reduction exhibits a high chemoselectivity, as exemplified by reduction of azides

  我们报道了在室温下有效的Staudinger催化还原反应，该反应能够以优异的收率从叠氮化物制备结构多样的胺。该反应基于催化量的三苯基膦作为膦源和二苯基二硅氧烷作为还原剂的使用。我们的Staudinger催化还原具有很高的化学选择性，例如叠氮化物相对于其他常见官能团（包括腈，烯烃，炔烃，酯和酮）的还原。
• Phosphine-Free Manganese Catalyst Enables Selective Transfer Hydrogenation of Nitriles to Primary and Secondary Amines Using Ammonia–Borane
  作者：Koushik Sarkar、Kuhali Das、Abhishek Kundu、Debashis Adhikari、Biplab Maji

  DOI：10.1021/acscatal.0c05406

  日期：2021.3.5

  primary and secondary amines by nitrile hydrogenation, employing a borrowing hydrogenation strategy. A class of phosphine-free manganese(I) complexes bearing sulfur side arms catalyzed the reaction under mild reaction conditions, where ammonia–borane is used as the source of hydrogen. The synthetic protocol is chemodivergent, as the final product is either primary or secondary amine, which can be controlled

  在本文中，我们报告了采用借位氢化策略通过腈加氢合成伯胺和仲胺的方法。一类带有硫侧臂的无膦锰（I）络合物在温和的反应条件下催化反应，其中氨硼烷用作氢源。合成规程是化学发散的，因为最终产物是伯胺或仲胺，可以通过改变催化剂结构和反应介质的极性来控制。该方法的显着优点是该方案无需外部添加碱或其他添加剂即可运行，并且避免了其他腈加氢反应所需的高压二氢气体的使用。利用这种方法 以高收率合成了各种各样的伯胺，对称胺和不对称仲胺。涉及动力学实验和高水平DFT计算的机理研究表明，外球面脱氢和内球面加氢在催化循环中均主要起作用。