呋喃-2,5-二甲酸二甲酯 | 4282-32-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 呋喃-2,5-二甲酸二甲酯
• 中文别名: 呋喃-2,5-二羧酸二甲酯；2,5-呋喃二甲酸二甲酯；呋喃-2,5-二甲酸甲酯
• 英文名称: furan-2,5-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 2,5-furandicarboxylate；dimethyl furan-2,5-dicarboxylate；2,5-furandicarboxylic acid dimethyl ester；FDMC；furan-2,5-dimethylcarboxylate；Furan-2,5-dicarbonsaeure-dimethylester；2,5-Furan-dicarbonsaeuredimethylester；2,5-dimethyl furan-2,5-dicarboxylate；DMFD；FDME；2,5-furandicarboxylic acid methyl ester；2,5-dimethylfuran dicarboxylate；DMFDC
• CAS: 4282-32-0
• 化学式: C₈H₈O₅
• mdl: MFCD00092317
• 分子量: 184.149
• InChiKey: UWQOPFRNDNVUOA-UHFFFAOYSA-N

物化性质

• 熔点：
  112°C
• 沸点：
  278.08°C (rough estimate)
• 密度：
  1.3840 (rough estimate)
• 保留指数：
  1346;1346

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2932190090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存放于惰性气体中，避免与空气接触。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Dimethyl furan-2,5-dicarboxylate
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: Dimethyl furan-2,5-dicarboxylate
CAS number: 4282-32-0

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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: C8H8O5
Molecular weight: 184.1

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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.

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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

应用

呋喃-2,5-二甲酸二甲酯可用作有机合成中间体和医药中间体，主要应用于实验室研发和化工医药合成过程。

反应信息

• 作为反应物：
  描述：

  呋喃-2,5-二甲酸二甲酯 在 C₁₅H₂₉MnNO₃P₂⁽¹⁺⁾*Br^(1-) 、 potassium tert-butylate 、 氢气 作用下， 以 1,4-二氧六环 为溶剂， 120.0 ℃ 、3.0 MPa 条件下， 反应 48.0h， 以58%的产率得到2,5-呋喃二甲醇
  参考文献：
  名称：

  定义的锰钳配合物催化酯加氢制醇

  摘要：

  已经开发出了第一个锰催化的酯加氢成醇的方法。Mn（CO）5 Br与[HN（CH 2 CH 2 P（Et）2）2 ]的组合产生阳离子和中性Mn PNP钳形配合物的混合物，这使得能够还原各种酯底物，包括芳族化合物和脂族酯以及二酯和内酯。值得注意的是，具有异丙基或环己基取代基的相关钳形配合物显示出非常低的活性。

  DOI：

  10.1002/anie.201607233
• 作为产物：
  描述：

  葡糖二酸 在 五氯化磷 、 对甲苯磺酸 作用下， 反应 6.0h， 生成 呋喃-2,5-二甲酸二甲酯
  参考文献：
  名称：

  Lewkowski, Polish Journal of Chemistry, 2001, vol. 75, # 12, p. 1943 - 1946

  摘要：

  DOI：

文献信息

• 一种从糠醛生产呋喃二甲酸及其衍生物的方法
  申请人：华东师范大学

  公开号：CN111153876B

  公开（公告）日：2023-07-28

  本申请公开了一种从糠醛生产呋喃二甲酸及其衍生物的方法，包括如下步骤：糠醛在氢气条件下还原至2‑甲基呋喃，2‑甲基呋喃发生乙酰化反应得到5‑甲基‑2‑乙酰基呋喃，5‑甲基‑2‑乙酰基呋喃与酯反应得到5‑甲基‑2‑呋喃甲酸甲酯，5‑甲基‑2‑呋喃甲酸甲酯在氧气条件下被氧化为2,5‑呋喃二甲酸单甲酯，将2,5‑呋喃二甲酸单甲酯水解为2,5‑呋喃二甲酸或与进一步与甲醇酯化生成2,5‑呋喃二甲酸二甲酯。本发明使用廉价的五碳呋喃化合物糠醛作为原料，以增长碳链的策略制备2,5‑呋喃二甲酸及其衍生物，使得原料成本极大地降低。本发明产品纯度高，可直接用作PET聚酯的聚合单体。
• Aerobic oxidative esterification of 5-hydroxymethylfurfural to dimethyl furan-2,5-dicarboxylate by using homogeneous and heterogeneous PdCoBi/C catalysts under atmospheric oxygen
  作者：Feng Li、Xing-Long Li、Chuang Li、Jing Shi、Yao Fu

  DOI：10.1039/c8gc01393d

  日期：——

  pharmaceutical intermediates. In this paper, oxidative esterification of 5-HMF has been carried out by using homogeneous and heterogeneous PdCoBi/C catalysts under atmospheric oxygen. The effect of reaction conditions on product distribution has been studied under both homogeneous and heterogeneous catalytic conditions. The highest yields of oxidative esterification products are obtained at 93% and 96% by

  平台分子5-羟甲基糠醛（HMF）转化为许多增值衍生物引起了人们的极大兴趣。FDCA及其酯是HMF的重要衍生物，可用作聚酯单体和医药中间体。在本文中，通过在大气氧下使用均相和非均相的PdCoBi / C催化剂进行了5-HMF的氧化酯化反应。在均相和非均相催化条件下都研究了反应条件对产物分布的影响。通过使用均相和非均相的PdCoBi / C催化剂，氧化酯化产物的最高收率分别为93％和96％。所述催化剂通过X射线光电子能谱（XPS）和粉末X射线衍射（XRD）来表征。根据底物的膨胀，催化体系具有更好的相容性。提出了一种反应机理，并进行了循环实验。
• Poly(alkylene 2,5-furandicarboxylate)s (PEF and PBF) by ring opening polymerization
  作者：Juan Carlos Morales-Huerta、Antxon Martínez de Ilarduya、Sebastián Muñoz-Guerra

  DOI：10.1016/j.polymer.2016.02.003

  日期：2016.3

  The preparation of cyclic ethylene and butylene 2,5-furandicarboxylate oligoesters and their conversion to furan-based polyesters poly(ethylene furanoate) (PEF) and poly(butylene furanoate) (PBF) by ring-opening polymerization (ROP) are described. The cyclic oligoesters were obtained in high yields by both high dilution condensation and thermal cyclodepolymerization methods, and they consisted of mixtures

  描述了环状乙烯和丁烯2,5-呋喃二甲酸低聚酯的制备及其通过开环聚合（ROP）转化为呋喃基聚酯的聚呋喃乙烯酸酯（PEF）和聚呋喃丁烯酸酯（PBF）。通过高稀释缩合法和热环解聚法均能以高收率获得环状低聚酯，它们由小尺寸的混合物组成。通过半制备色谱分离出环状二聚体，三聚体和四聚体低聚酯，发现它们是熔点在140-200°C范围内的结晶化合物。混合物和单个物种的Sn（Oct）2催化的ROP得到的PEF和PBF的重均分子量为50,000至60,000 g mol -1。发现丁烯的聚合速率高于亚乙基环状低呋喃酸酯的聚合速率，并且随着循环尺寸的减小聚合速率也略有增加。通过ROP制备的PEF和PBF的热性能与通过熔融缩聚获得的这些聚酯的热性能完全一致。
• [EN] FLOW CHEMISTRY SYNTHESIS OF ISOCYANATES<br/>[FR] SYNTHÈSE CHIMIQUE EN FLUX D'ISOCYANATES
  申请人：UNIV CALIFORNIA

  公开号：WO2021119606A1

  公开（公告）日：2021-06-17

  The disclosure provides, inter alia, safe and environmentally-friendly methods, such as flow chemistry, to synthesize isocyanates, such as methylene diphenyl diisocyanate, toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and tetramethylxylene diisocyanate.

  该披露提供了诸如流动化学等安全环保的方法，用于合成异氰酸酯，例如亚甲基二苯基二异氰酸酯、甲苯二异氰酸酯、己二胺二异氰酸酯、异佛尔酮二异氰酸酯和四甲基二异氰酸酯。
• [EN] FUNCTIONALIZED BIFURAN AND SYNTHESIS THEREOF<br/>[FR] BIFURANNE FONCTIONNALISÉ ET SYNTHÈSE DE CE DERNIER
  申请人：EXXONMOBIL CHEMICAL PATENTS INC

  公开号：WO2019182693A1

  公开（公告）日：2019-09-26

  A 5,5'-Di-(protected)-2,2' -bifuran: wherein each R1 is independently an unsubstituted or substituted 5- or 6-member 1,3-dioxo-2-y1 ring radical. Processes for making the bifuran include coupling 2-(protected)-furfural. Processes for using the bifuran include deprotection, functionalization, and/or polymerization to form a polyester. The polyester can be a renewable, high-performing polyester offering a combination of low cost of production, high sustainability, and excellent performance.

  一种5,5'-二-(保护基)-2,2'-联吡喃：其中每个R1独立地是未取代或取代的5-或6-成员1,3-二氧杂-2-基环辅基。制备该联吡喃的方法包括偶联2-(保护基)-呋喃。使用该联吡喃的方法包括去保护、官能化和/或聚合以形成聚酯。该聚酯可以是一种可再生、高性能的聚酯，提供了低生产成本、高可持续性和优异性能的组合。

表征谱图