4-氨基-N,N-二乙基苯磺酰胺 | 1709-39-3

• 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-氨基-N,N-二乙基苯磺酰胺
• 中文别名: N1-二乙基磺胺；N'-二乙基磺胺
• 英文名称: 4-(N,N-diethylaminosulfonyl)aniline
• 英文别名: 4-Amino-N,N-diethyl-benzenesulfonamide；N¹,N¹-Diethyl-sulfanilamid；NSC 15769；4-Amino-N,N-diethylbenzenesulfonamide
• CAS: 1709-39-3
• 化学式: C₁₀H₁₆N₂O₂S
• mdl: MFCD01055489
• 分子量: 228.315
• InChiKey: LTFVELCIFWEGGA-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C
• 沸点：
  375.9±44.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)
• 溶解度：
  >34.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2935009090
• 危险类别：
  IRRITANT

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N,N-Diethyl 4-aminobenzenesulfonamide
Synonyms: 4-Amino-N,N-diethylbenzenesulfonamide

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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: N,N-Diethyl 4-aminobenzenesulfonamide
CAS number: 1709-39-3

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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.
Store in closed vessels.
Storage:

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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
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H16N2O2S
Molecular weight: 228.3

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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, sulfur 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

反应信息

• 作为反应物：
  描述：

  4-氨基-N,N-二乙基苯磺酰胺 以 乙醇 为溶剂， 反应 1.33h， 生成 3-(4-N,N-diethylaminosulphonephenylamino)-1-phenylpyrazolo[3,4-d]pyrimidine-4,6-dione
  参考文献：
  名称：

  乙烯酮二硫缩醛的杂芳化：第二部分。一些新型 5-氨基吡唑-3-甲腈、3-甲酰胺和吡唑并[3,4-d]嘧啶-4-酮衍生物作为抗菌剂的合成

  摘要：

  摘要 乙烯酮二硫代缩醛 1a-d 用于合成吡唑二硫代羧酸酯 2a-d 和芳基氨基吡唑 4a、b，在芳基残基中具有两个不同的取代基（邻乙氧基和对二乙基氨基磺酰基）。描述了二硫酯 2 ate 的一些转化。之后，芳基氨基吡咯4a,b 被转化为吡唑并嘧啶衍生物8-11。

  DOI：

  10.1080/10426500108040260
• 作为产物：
  描述：

  对硝基苯磺酰氯 在 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 4-氨基-N,N-二乙基苯磺酰胺
  参考文献：
  名称：

  基于降冰片基的碳环核苷类似物作为细胞周期蛋白依赖性激酶 2 抑制剂的优化。

  摘要：

  我们报告了降冰片基部分作为细胞周期蛋白依赖性激酶 2 (CDK2) 抑制剂的新型结构基序的发现，该基序是通过筛选碳环核苷类似物文库确定的。通过使用药物化学方法将三个微摩尔命中扩展为一系列 16 种新化合物。它们对 CDK2 具有显着的微摩尔活性，并且该系列中最好的化合物达到了 IC 50190 纳米。通过建模和对接在分子细节中探索结合模式。使用基于量子力学的评分来合理化亲和力。总之，所发现的 9-羟甲基降冰片基部分通过联合实验-理论努力表明能够作为 CDK2 抑制剂的新取代基。这一发现为探索化学空间以寻找更有效的靶向这一类重要蛋白激酶的衍生物打开了大门。

  DOI：

  10.1002/jmr.2842

文献信息

• Fused heterocyclic compounds useful as kinase modulators
  申请人：Vaccaro Wayne

  公开号：US20070078136A1

  公开（公告）日：2007-04-05

  Compounds having the formula (1), and enantiomers, and diastereomers, pharmaceutically-acceptable salts, thereof, are usefuil as kinase modulators, including MK2 modulation, wherein one of E and F is a nitrogen atom and the other of E and F is a carbon atom, Z is N or CR 3 , and R 1 , R 2 , R 3 , X and Y are as defined herein.

  具有化学式（1）的化合物，以及其对映体、非对映体、药用可接受的盐，可用作激酶调节剂，包括MK2调节，其中E和F中的一个是氮原子，另一个是碳原子，Z是N或CR3，R1、R2、R3、X和Y如本文所定义。
• Optimization of a urea-containing series of nicotinamide phosphoribosyltransferase (NAMPT) activators
  作者：Anthony B. Pinkerton、E. Hampton Sessions、Paul Hershberger、Patrick R. Maloney、Satyamaheshwar Peddibhotla、Meghan Hopf、Eduard Sergienko、Chen-Ting Ma、Layton H. Smith、Michael R. Jackson、Jun Tanaka、Takashi Tsuji、Mayuko Akiu、Steven E. Cohen、Tsuyoshi Nakamura、Stephen J. Gardell

  DOI：10.1016/j.bmcl.2021.128007

  日期：2021.6

  neurodegeneration, and muscle wasting disorders. A novel strategy to boost NAD+ is to activate nicotinamide phosphoribosyltransferase (NAMPT), the putative rate-limiting step in the NAD+ salvage pathway. We previously showed that NAMPT activators increase NAD+ levels in vitro and in vivo. Herein we describe the optimization of our NAMPT activator prototype (SBI-0797812) leading to the identification of 1-(4-((4-ch

  NAD +是一种关键的细胞因子，在广泛的生物过程中发挥着多方面的作用。低水平的 NAD +与许多疾病有关，包括代谢紊乱、心血管疾病、神经变性和肌肉萎缩症。一种提高 NAD + 的新策略是激活烟酰胺磷酸核糖基转移酶 (NAMPT)，这是 NAD +补救途径中推定的限速步骤。我们之前表明 NAMPT 激活剂可在体外和体内增加 NAD +水平. 在此，我们描述了我们的 NAMPT 活化剂原型 (SBI-0797812) 的优化，导致 1-(4-((4-氯苯基)磺酰基)苯基)-3-(恶唑-5-基甲基)脲 ( 34 )的鉴定显示出更有效的 NAMPT 激活和改善的口服生物利用度。
• An Old Story in the Parallel Synthesis World: An Approach to Hydantoin Libraries
  作者：Andrey V. Bogolubsky、Yurii S. Moroz、Olena Savych、Sergey Pipko、Angelika Konovets、Maxim O. Platonov、Oleksandr V. Vasylchenko、Vasyl V. Hurmach、Oleksandr O. Grygorenko

  DOI：10.1021/acscombsci.7b00163

  日期：2018.1.8

  An approach to the parallel synthesis of hydantoin libraries by reaction of in situ generated 2,2,2-trifluoroethylcarbamates and α-amino esters was developed. To demonstrate utility of the method, a library of 1158 hydantoins designed according to the lead-likeness criteria (MW 200–350, cLogP 1–3) was prepared. The success rate of the method was analyzed as a function of physicochemical parameters

  开发了一种通过原位生成的2,2,2-三氟乙基氨基甲酸酯与α-氨基酯反应平行合成乙内酰脲文库的方法。为了证明该方法的实用性，准备了根据铅样标准（MW 200–350，cLogP 1-3）设计的1158个乙内酰脲文库。分析了该方法的成功率与产品理化参数的关系，发现该方法可以被认为是用于铅导向合成的工具。通过合理设计，使用开发的方法进行平行合成，计算机模拟和体外筛选相结合的方法，发现了一种含乙内酰脲的超微摩尔主要分子，可作为Aurora激酶A抑制剂。
• Mesoionic Carbene–Iridium Complex Catalyzed <i>Ortho</i>-Selective Hydrogen Isotope Exchange of Anilines with High Functional Group Tolerance
  作者：Wei Liu、Lei Cao、Zengyu Zhang、Gang Zhang、Shiqing Huang、Linwei Huang、Peng Zhao、Xiaoyu Yan

  DOI：10.1021/acs.orglett.0c00402

  日期：2020.3.20

  Mesoionic carbene-iridium complex 1a has been investigated in the hydrogen isotope exchange (HIE) reaction of anilines. By employing 1 mol % of 1a as catalyst, anilines were selectively deuterated at the ortho-position with high deuteration levels. High ortho-selectivity was observed for anilines with various competing directing groups, which is in contrast with catalytic results of Kerr's catalysts

  已经在苯胺的氢同位素交换（HIE）反应中研究了中性碳烯-铱配合物1a。通过使用1mol％的1a作为催化剂，以高氘化水平在邻位选择性地对苯胺进行氘化。观察到具有各种竞争性导向基团的苯胺具有较高的邻位选择性，这与Kerr催化剂的催化结果相反。
• A simple synthesis of anilines by LiAlH4/TiCl4 reduction of aromatic nitro compounds
  作者：Maria Luisa Di Gioia、Antonella Leggio、Isabella Federica Guarino、Vanessa Leotta、Emanuela Romio、Angelo Liguori

  DOI：10.1016/j.tetlet.2015.07.089

  日期：2015.9

  A rapid and efficient single-step synthesis of substituted anilines has been developed. The aromatic nitro compounds were reduced by using reducing systems generated by the action of an excess of LiAlH4 on TiCl4. Anilines substituted with different functional groups were synthesized in high yields and purity starting from the corresponding nitro compounds. The developed procedure is applicable to nitroaromatics

  已开发出快速有效的取代苯胺单步合成法。通过使用还原系统还原芳族硝基化合物，该还原系统是由过量的LiAlH 4对TiCl 4的作用所产生的。从相应的硝基化合物开始，以高收率和高纯度合成了被不同官能团取代的苯胺。所开发的方法适用于同时具有吸电子和给电子取代基的硝基芳族化合物。具有电子给体取代基的基材需要大量过量的LiAlH 4。制备的反应物体系的还原能力取决于所使用的LiAlH 4和TiCl 4的摩尔比。

表征谱图