2-碘-4,5-二甲氧基苯甲酸甲酯 | 173043-61-3

• 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-4,5-二甲氧基苯甲酸甲酯
• 英文名称: methyl 2-iodo-4,5-dimethoxybenzoate
• 英文别名: methyl 4,5-dimethoxy-2-iodo-benzoate
• CAS: 173043-61-3
• 化学式: C₁₀H₁₁IO₄
• mdl: MFCD09800786
• 分子量: 322.099
• InChiKey: HFQDMAXTSBDKRB-UHFFFAOYSA-N

物化性质

• 熔点：
  105-107 °C(Solv: methanol (67-56-1))
• 沸点：
  352.8±42.0 °C(Predicted)
• 密度：
  1.631±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8℃，请避光、干燥密封保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 2-iodo-4,5-dimethoxybenzoate
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: Methyl 2-iodo-4,5-dimethoxybenzoate
CAS number: 173043-61-3

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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: C10H11IO4
Molecular weight: 322.1

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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, 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-4,5-二甲氧基苯甲酸甲酯 在 platinum(IV) oxide 、 甲基溴化镁 、 水 、 氢气 、 palladium diacetate 、 乙酸酐 、 三(邻甲基苯基)磷 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， -30.0~100.0 ℃ 、101.33 kPa 条件下， 反应 91.08h， 生成 多萘哌齐碱
  参考文献：
  名称：

  苯甲酸的直接碳环化：环酮的催化剂控制合成和串联式aHH（酰基-Heck-Heck）反应的发展

  摘要：

  已经开发了由简单的邻烯丙基苯甲酸衍生物形成外亚甲基茚满酮和茚满的现象。在这些反应中茚满酮或茚满酮产物的选择性形成是通过选择辅助配体来控制的。这种新工艺具有较低的环境足迹，因为使用低催化剂负载量可以高收率形成产物，而转化中反应物产生的唯一化学计量的化学废物是乙酸。活性环化催化剂向Hermman-Beller palladacycle的转化被用于一锅串联的酰基Heck-Heck（aHH）反应中，并用于多奈哌齐的合成。

  DOI：

  10.1002/chem.201403561
• 作为产物：
  描述：

  2-碘-4,5-二甲氧基苯甲醛 在 草酰氯 、 双氧水 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 2-碘-4,5-二甲氧基苯甲酸甲酯
  参考文献：
  名称：

  钯催化的串联反应来构建苯并[ C ^ ]菲啶：应用到苯并的全合成[ C ^ ]菲啶生物碱†

  摘要：

  通过钯催化氮杂双环烯烃与邻碘苯甲酸酯的开环偶联，然后串联环化，可实现苯并[ c ]菲啶的简洁高效合成。该策略已成功应用于苯并[ c ]菲啶生物碱的全合成，如血红碱，白屈菜红碱，尼替丁 和阿维辛。

  DOI：

  10.1039/c0ob01208d
• 作为试剂：
  描述：

  乙烯基二甲基乙氧基硅烷 、 5-(2,2-Dimethoxyethyl)-6-iodo-1,3-benzodioxole 在 bis-triphenylphosphine-palladium(II) chloride 、 bis(η3-allyl-μ-chloropalladium(II)) 、 2-碘-4,5-二甲氧基苯甲酸甲酯 、 四丁基氟化铵 、 三乙胺 、 亚磷酸三乙酯 作用下， 生成 5-(2,2-Dimethoxy-ethyl)-6-vinyl-benzo[1,3]dioxole 、 methyl 2-[(E)-2-[6-(2,2-dimethoxyethyl)-1,3-benzodioxol-5-yl]ethenyl]-4,5-dimethoxybenzoate
  参考文献：
  名称：

  通过钯催化的异香豆素的合成正式合成亚硝胺

  摘要：

  的异喹诺酮中间体9为两面针的合成通过的异香豆素钯催化形成来合成7从ø -styrylbenzoic酸衍生物5，将其从芳基的钯催化偶联反应来制备碘化物1和2与乙烯基硅烷。

  DOI：

  10.1016/0040-4039(95)02059-4

文献信息

• Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols
  作者：Yuvraj Satkar、Luisa F. Yera-Ledesma、Narendra Mali、Dipak Patil、Pedro Navarro-Santos、Luis A. Segura-Quezada、Perla I. Ramírez-Morales、César R. Solorio-Alvarado

  DOI：10.1021/acs.joc.9b00161

  日期：2019.4.5

  An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a nontoxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled monoiodination was achieved by buffering the reaction medium with K3PO4. This protocol proceeds with short reaction times, at mild temperatures, in an open flask, and generally with high

  通过使用碘基苯作为无毒的碘（III）基氧化剂和碘化铵作为廉价的碘原子源，开发了一种用于亲电子碘化苯酚的氧化方法。通过用K 3 PO 4缓冲反应介质来实现完全受控的单碘化。在温和的温度下，在开放的烧瓶中，该方案以较短的反应时间进行，并且通常收率很高。用富电子和贫电子的酚以及杂环探索了革兰氏反应以及该方案的范围。量子化学计算显示，PhII（OH）·NH 3是最可能的碘化活性物质，呈反应性“ I +synthon。鉴于碘代芳烃部分的相关性，我们在本文中提出了实用，有效和简单的方法，其具有允许进入碘代芳烃核心单元的宽泛的官能团范围。
• From C ₁ to C ₂ : TMSCF ₃ as a Precursor for Pentafluoroethylation
  作者：Qiqiang Xie、Lingchun Li、Ziyue Zhu、Rongyi Zhang、Chuanfa Ni、Jinbo Hu

  DOI：10.1002/anie.201807873

  日期：2018.10

  A highly efficient copper‐mediated aromatic pentafluoroethylation method using TMSCF3 as the sole fluoroalkyl source is described. The reaction proceeds by a key C1 to C2 process, that is, the generation of CuCF3 from TMSCF3, followed by a subsequent spontaneous transformation into CuC2F5. Various aryl iodides were pentafluoroethylated with the TMSCF3‐derived CuC2F5. This method represents the first

  描述了一种高效的铜介导的芳香族五氟乙基化方法，该方法使用TMSCF 3作为唯一的氟代烷基来源。反应的进行通过密钥C 1至C 2的处理，即，CuCF的产生3从TMSCF 3，之后进行随后的自发转变为CUC 2 ˚F 5。各种芳基碘化物都用TMSCF 3衍生的CuC 2 F 5进行了五氟乙基化。该方法代表了使用市售的TMSCF 3作为五氟乙基前体对芳基碘进行五氟乙基化的第一种实用而有效的方法。
• Synthesis of Isocoumarins and α-Pyrones via Palladium-Catalyzed Annulation of Internal Alkynes
  作者：Richard C. Larock、Mark J. Doty、Xiaojun Han

  DOI：10.1021/jo9821628

  日期：1999.11.1

  factors. A number of 3,4-disubstituted isocoumarins and polysubstituted alpha-pyrones have been prepared in good yields by treating halogen- or triflate-containing aromatic and alpha,beta-unsaturated esters, respectively, with internal alkynes in the presence of a palladium catalyst. Synthetically, the methodology provides an especially simple and convenient regioselective route to isocoumarins and alpha-pyrones

  通过在钯催化剂的存在下用内部炔烃分别处理含卤素或三氟甲磺酸酯的芳族和α，β-不饱和酯，已经以良好的产率制备了许多3，4-二取代的异香豆素和多取代的α-吡喃酮。合成地，该方法提供了一种特别简单和方便的区域选择性途径，用于对含有芳基，甲硅烷基，酯，叔烷基和其他受阻基团的异香豆素和α-吡喃酮。据信该反应通过七元的Paladacyclic环复合物进行，其中反应的区域化学由空间因素控制。通过分别处理含卤素或三氟甲磺酸酯的芳族和α，β-不饱和酯，已经以高收率制备了许多3,4-二取代的异香豆素和多取代的α-吡喃酮，在钯催化剂存在下与内部炔烃反应。综上，该方法为包含芳基，甲硅烷基，酯，叔烷基和其他受阻基团的异香豆素和α-吡喃酮提供了特别简单和方便的区域选择性途径。据信该反应通过七元的Paladacyclic环复合物进行，其中反应的区域化学由空间因素控制。
• [EN] SUBSTITUTED ISOINDOLONYL 2,2'-BIPYRIMIDINYL COMPOUNDS, ANALOGUES THEREOF, AND METHODS USING SAME<br/>[FR] COMPOSÉS D'ISOINDOLONYLE 2,2'-BIPYRIMIDINYLE SUBSTITUÉS, ANALOGUES DE CEUX-CI, ET PROCÉDÉS LES UTILISANT
  申请人：ARBUTUS BIOPHARMA INC

  公开号：WO2021097075A1

  公开（公告）日：2021-05-20

  The present disclosure includes substituted isoindolinyl 2,2'-bipyrimidinyl compounds, analogues thereof, and compositions comprising the same, which can be used to treat and/or prevent hepatitis B virus (HBV) and/or hepatitis B virus (HBV)-hepatitis D virus (HDV) infection in a patient.

  本公开涵盖了替代的异吲哚基2,2'-联吡啶基化合物，其类似物，以及包含它们的组合物，可用于治疗和/或预防患者体内的乙型肝炎病毒（HBV）和/或乙型肝炎病毒（HBV）-丙型肝炎病毒（HDV）感染。
• Controllable double CF₂-insertion into sp² C–Cu bond using TMSCF₃: a facile access to tetrafluoroethylene-bridged structures
  作者：Qiqiang Xie、Ziyue Zhu、Lingchun Li、Chuanfa Ni、Jinbo Hu

  DOI：10.1039/c9sc05018c

  日期：——

  controllable double CF2-insertion into pentafluorophenylcopper species using TMSCF3 as difluoromethylene source has been developed. The newly generated fluoroalkylcopper(I) species, C6F5CF2CF2Cu, shows good reactivity towards a myriad of structurally diverse aryl, heteroaryl and alkenyl iodides. This protocol is easy to handle, ready to scale up and applicable for the synthesis of relative complex molecules

  已开发出一种使用 TMSCF 3作为二氟亚甲基源的可控双 CF 2插入五氟苯基铜物质的高效方法。新生成的氟烷基铜 ( I ) 物质 C 6 F 5 CF 2 CF 2 Cu 对大量结构多样的芳基、杂芳基和烯基碘化物表现出良好的反应性。该协议易于处理，可扩大规模并适用于相对复杂分子的合成，从而为轻松获取四氟乙烯桥接结构提供了一种便捷的方法。