2-碘-N-甲基苯甲酰胺 | 58084-22-3

• 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: 2-碘-N-甲基苯甲酰胺
• 英文名称: 2-iodo-N-methyl-benzamide
• 英文别名: N-methyl-2-iodobenzamide；N-methyl o-iodobenzamide；2-Iodo-N-methylbenzamide
• CAS: 58084-22-3
• 化学式: C₈H₈INO
• mdl: MFCD00099249
• 分子量: 261.062
• InChiKey: XVZYFJIGUQHFSR-UHFFFAOYSA-N

物化性质

• 沸点：
  342.3±25.0 °C(Predicted)
• 密度：
  1.719±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 储存条件：
  存储温度应为2-8°C，并请避免光照。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Iodo-N-methylbenzamide
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: 2-Iodo-N-methylbenzamide
CAS number: 58084-22-3

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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, refrigerated.
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: C8H8INO
Molecular weight: 261.1

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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 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

反应信息

• 作为反应物：
  描述：

  2-碘-N-甲基苯甲酰胺 以 二氯甲烷 、 丙酮 为溶剂， 20.0 ℃ 、140.0 kPa 条件下， 反应 5.0h， 生成 N-甲基邻苯二甲酰亚胺
  参考文献：
  名称：

  Reactivity of Ortho-Palladated Benzamides toward CO, Isocyanides, and Alkynes. Synthesis of Functionalized Isoindolin-1-ones and 4,5-Disubstituted Benzo[c]azepine-1,3-diones

  摘要：

  Aryl palladium complexes [Pd{C6H4C(O)NRR'-2}I(tmeda)] [NRR' = NH2 (1a), NHMe (1b), NMe2 (1c); tmeda = N,N,N',N'-tetramethylethylenediamine] are prepared by oxidative addition of the corresponding 2-iodophenylbenzamides to Pd(dba)(2) ([Pd-2(dba)(3)]center dot dba; dba = dibenzylideneacetone) in the presence of tmeda. Cationic cyclometalated derivatives [Pd{'2C,O-C6H4C(O)NRR'-2}(tmeda)]TfO (2ac) are obtained by iodide abstraction from the appropriate complex 1 with AgTfO, while the deprotonation of the amide function of 1a or 1b with KOtBu gives the neutral amidate complexes [Pd{'2C,N-C6H4C(O)NR-2}(tmeda)] [R = H (3a), Me (3b)]. Complexes 2a,b and 3a,b react with CO under mild conditions to yield phthalimide (4a) or N-methylphthalimide (4b), whereas the reactions of derivatives 1c and 2c with CO are very slow and give N-1,N-1,N-2,N-2-tetramethylphthalamide and phthalic anhydride. The reaction of 1b with 1 equiv of XyNC (Xy = 2,6-dimethylphenyl) or tBuNC affords Pd(0), (tmedaH)I, and 3-(2,6-dimethylphenylimino)-2-methylisoindolin-1-one (5b) or 3-(tert-butylimino)-2-methylisoindolin-1-one (5b'), respectively, while complex 1c reacts with 3 equiv of XyNC to give trans-[Pd{C('NXy)C6H4C(O)NMe2-2}I(CNXy)(2)] (6). The seven-membered palladacycles [Pd{'2C,O-C(X)'C(X')C6H4C(O)NRR'-2}(tmeda)]TfO [NRR' = NH2 and X = Ph, X' = Me (7a); NRR' = NHMe and X = Ph, X' = Me (7b), X = X' = Ph (8b), Et (9b), CO2Me (10b), X = CO2Me, X' = Ph (11b), X = CO2Et, X' = Ph (12b); NRR' = NMe2 and X = X' = Ph (8c), Et (9c)] are obtained from the reactions of 2ac with alkynes. Treatment of complexes 7a, 7b, 8b, and 9b with CO at room temperature gives the corresponding 2H-benzo[c]azepine-1,3-diones (14), resulting from the insertion of a molecule of CO into the PdC bond followed by a CN reductive coupling. In contrast, the reactions of 11b or 12b with CO in the presence of residual water or 2 equiv of ROH (R = Me, Et) lead to 2-methyl-3-phenylisoindolin-1-one derivatives (15), resulting from a CO insertion followed by an intramolecular aza-Michael addition of the NHMe moiety to the activated vinyl group and subsequent hydrolysis or alcoholysis of the acylPd bond. The neutral complex [Pd('2C,O-C14H13O5)(tmeda)] (18) was synthesized by reacting the cationic derivative 10b with NaOMe in MeOH. Depalladation of 18 gives (E)-4-[methoxy(methoxycarbonyl)methylene]-2-methylisoquinoline-1,3(2H,4H)-dione (19).

  DOI：

  10.1021/om4006406
• 作为产物：
  描述：

  N-甲基苯甲酰胺 在 N-碘代丁二酰亚胺 、 silver hexafluoroantimonate 、 三氟甲磺酸 、 nickel diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以76%的产率得到2-碘-N-甲基苯甲酰胺
  参考文献：
  名称：

  缺电子芳烃的镍催化区域选择性C–H卤化†

  摘要：

  开发了一种简单的Ni（II）催化的一般策略，用于用易获得的卤化试剂N-卤代琥珀酰亚胺（NXS; X = Br，Cl和I）对电子缺陷型芳烃进行邻卤代化。该转化是高度区域选择性的，并且观察到宽的底物范围和官能团耐受性。该发现对于酰胺，苯甲酸酯和其他具有引导基团的物质的选择性卤化可能具有重要意义。还介绍了机械研究。

  DOI：

  10.1039/c8nj06023a
• 作为试剂：
  描述：

  4-methyl-N-(prop-2-yn-1-yl)benzamide 在 pyridinium polyhydrogenfluoride 、 2-碘-N-甲基苯甲酰胺 、 Selectfluor 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以11%的产率得到5-(fluoromethyl)-2-(4-methylphenyl)oxazole
  参考文献：
  名称：

  带有配位取代基的λ3-碘烷催化剂对N-炔丙基甲酰胺的氟环化作用

  摘要：

  针对氟λ的增强的催化活性3从与的Selectfluor和HF⋅pyridineiodoarene预催化剂产生-iodane，本研究集中在λ 3个-iodanes轴承协调取代基。与4-碘苯甲醚作为我们先前方法的前催化剂相比，N-甲基-2-碘代苯甲酰胺或2-碘代苯甲酰胺在将N-炔丙基甲酰胺氟化为恶唑的过程中效果很好。对照实验表明，碘-胺络合物和环状碘化氟的平衡混合物将参与本催化反应。

  DOI：

  10.1002/adsc.202000381

文献信息

• Nematicidal Activities of Diamides with Diphenylacetylene Scaffold Against Meloidogyne Incognita
  作者：Jiling Li、Zhicheng Zhang、Xiaoyong Xu、Xusheng Shao、Zhong Li

  DOI：10.1071/ch15065

  日期：——

  With the goal of searching for new potential nematicides with high activity and low toxicity, new molecules are needed as potential prototypes for the synthesis of new nematicidal compounds. A series of novel diamides based on diphenylacetylene scaffold were designed and synthesised. The conformation of the amide was restricted through the ten-membered H-bonded ring. Their structures were characterised by 1H NMR, 13C NMR, 19F NMR, and high-resolution mass spectrometry. The preliminary bioassays evaluated against Meloidogyne Incognita indicated that most of the title compounds were endowed with moderate-to-good activities at the concentration of 25 mg L–1. In particular, compounds 9a, 9c, 9g, 9h, 9k, and 9l displayed >50 % nematicidal activity at 5 mg L–1. It is possible that the novel diamides with diphenylacetylene scaffold, which possess good nematicidal activities, provide distinct nematicidal chemotypes that can be used as leads for further optimisation.

  为了寻找高活性、低毒性的新型潜在杀线虫剂，需要新的分子作为合成新型杀线虫化合物的潜在原型。我们设计并合成了一系列基于二苯基乙炔支架的新型二酰胺。通过十元 H 键环限制了酰胺的构象。它们的结构通过 1H NMR、13C NMR、19F NMR 和高分辨率质谱进行了表征。对 Meloidogyne Incognita 的初步生物测定表明，在 25 mg L-1 的浓度下，大多数标题化合物都具有中等至良好的活性。其中，化合物 9a、9c、9g、9h、9k 和 9l 在 5 mg L-1 浓度下具有 50 % 的杀线虫活性。具有二苯基乙炔支架的新型二酰胺类化合物具有良好的杀线虫活性，可能提供了独特的杀线虫化学型，可作为进一步优化的线索。
• Palladium-Catalyzed Domino Heck/C–H Activation/Decarboxylation: A Rapid Entry to Fused Isoquinolinediones and Isoquinolinones
  作者：Xiai Luo、Liwei Zhou、Haiyan Lu、Guobo Deng、Yun Liang、Chunming Yang、Yuan Yang

  DOI：10.1021/acs.orglett.9b03883

  日期：2019.12.20

  A new palladium-catalyzed tandem cyclization of various alkene-tethered aryl iodides has been presented. In this protocol, o-bromobenzoic acids are employed as coupling parters to achieve the insertion of aromatic rings by the cleavage of C(sp2)-Br and decarboxylation, thus assembling various dibenzoisoquinolinediones and dibenzoisoquinolinones. In addition, a seven-membered ring can be constructed

  提出了一种新的钯催化串联环化各种烯烃系芳基碘化物的方法。在该协议中，邻溴苯甲酸用作偶联剂，通过C（sp2）-Br的裂解和脱羧作用实现芳香环的插入，从而组装各种二苯并异喹啉二酮和二苯并异喹啉酮。另外，可以通过使用8-溴-1-萘甲酸来构建七元环。值得注意的是，这种方法能够形成区域选择性的产物并具有广泛的底物范围。
• Carbonylative Synthesis of Phthalimides and Benzoxazinones by Using Phenyl Formate as a Carbon Monoxide Source
  作者：Sujit P. Chavan、Bhalchandra M. Bhanage

  DOI：10.1002/ejoc.201500109

  日期：2015.4

  efficient palladium-catalyzed carbonylative cyclization of N-substituted 2-iodobenzamides and 2-iodoanilides was investigated for the synthesis of phthalimides and benzoxazinones, respectively, by using phenyl formate as a CO source. The present catalytic protocol circumvents the use of an expensive phosphine ligand as well as solvent in the case of the phthalimide synthesis. Moreover, mild reaction conditions

  通过使用甲酸苯酯作为 CO 源，研究了一种简单有效的钯催化的 N-取代 2-碘苯甲酰胺和 2-碘苯胺的羰基化环化反应，分别用于合成邻苯二甲酰亚胺和苯并嗪酮。本催化协议在邻苯二甲酰亚胺合成的情况下避免使用昂贵的膦配体以及溶剂。此外，温和的反应条件和对各种官能团的耐受性增强了该方法的普遍适用性。
• Benzo[b]furane and benzo[b]thiophene derivatives
  申请人：Kehler Jan

  公开号：US20060287386A1

  公开（公告）日：2006-12-21

  The present invention relates to benzo[b]furane and benzo[b]thiophene derivatives of the general formula IV as the free base or salts thereof and their use.

  本发明涉及通用公式IV的苯并[b]呋喃和苯并[b]噻吩衍生物作为自由碱或其盐，及其用途。
• Ultrasound assisted Cu-catalyzed decarbonylative Sonogashira coupling-cyclization strategy: Synthesis and evaluation of 3-heteroarylmethylene isoindolin-1-ones against SIRT1
  作者：P. Ganapathisivaraja、G. Venkata Nageswara Rao、Abburi Ramarao、Mandava Bhuvan Tej、Muthineni Sai Praneeth、Ravikumar Kapavarapu、Mandava V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.molstruc.2021.131788

  日期：2022.2

  as potential inhibitors of SIRT1. A sonochemical approach based on the Cu(I)-catalyzed decarbonylative Sonogashira coupling-cyclization strategy was developed for accessing this class of compounds. The approach involved a faster and milder synthesis of 3-heteroarylmethylene isoindolin-1-ones with high regioselectivity via cross-coupling of 2-iodobenzamides with heteroaryl alkynyl acids followed by 5-exo-dig

  在报道的 3-亚甲基异吲哚啉-1-one 衍生物的 HDAC1 抑制/抗癌特性的推动下，探索了一系列 3-杂芳基亚甲基取代的异吲哚啉-1-酮作为 SIRT1 的潜在抑制剂。开发了一种基于 Cu(I) 催化脱羰 Sonogashira 偶联环化策略的声化学方法，用于获取此类化合物。该方法涉及通过2-碘苯甲酰胺与杂芳基炔酸的交叉偶联，然后进行 5 -exo-dig，以更快、更温和的方式合成具有高区域选择性的 3-heteroarylmethylene isoindolin-1-ones。在同一个锅中进行异环化。当所需产物以可接受的产率获得时，该方法后来扩展到合成 3-芳基亚甲基异吲哚啉-1-酮。当在体外测试 SIRT1 抑制潜力时，一些 3-杂芳基亚甲基异吲哚啉-1-酮显示出良好的活性，其中化合物3e表现最好，而 3-芳基类似物的活性较低。根据SAR分析，杂芳基部分的有效性顺序表现为咪唑-5-