2,5-呋喃二甲醇 | 1883-75-6

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 2,5-呋喃二甲醇
• 中文别名: 2,5-二羟甲基呋喃；呋喃-2,5-二基二甲醇；2,5呋喃二甲醇；5(羟甲基)糠醇；5-(羟甲基)呋喃醇；呋喃-2,5-二甲醇；2,5-呋喃二甲酸二甲醇；FDM
• 英文名称: 2,5-bis-(hydroxymethyl)furan
• 英文别名: furan-2,5-dimethanol；2,5-furandimethanol；BHMF；2,5-dihydroxymethylfuran；furan-2,5-diyldimethanol；DHMF；[5-(hydroxymethyl)furan-2-yl]methanol
• CAS: 1883-75-6
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: DSLRVRBSNLHVBH-UHFFFAOYSA-N

物化性质

• 熔点：
  74-77 °C
• 沸点：
  275 °C
• 密度：
  1.283
• 闪点：
  120 °C
• 溶解度：
  可溶于乙腈（少许）、DMSO（少许）
• LogP：
  -1.326 (est)
• 保留指数：
  1229

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 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：
  2～8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,5-Furandimethanol
Synonyms: 2,5-Dihydromethylfuran

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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: 2,5-Furandimethanol
CAS number: 1883-75-6

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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: C6H8O3
Molecular weight: 128.1

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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

外观：白色至类淡黄色粉末。

主要用途：2,5-呋喃二甲醇（BHMF）是化工中间体，在生物质基呋喃类衍生化合物中具有广泛的应用潜力，近年来受到了学术界和工业界的高度重视。作为原料，它可合成药物中间体、核苷衍生物、冠醚和呋喃等；也可用作溶剂、软化剂、湿润剂、粘结剂、表面活性剂及合成增塑剂等。此外，2,5-呋喃二甲醇还可以作为单体用于合成聚酯、聚氨酯等聚合材料，降低衣料涂层挥发性有机物的含量，有望完全或部分替代涂料中的丙二醇；同时，它也可在分子识别研究中用作人造受体。

合成方法：2,5-呋喃二甲醇可以通过5-羟甲基糠醛（HMF）的甲酰基还原得到。HMF是酸催化果糖脱水的产物。还原过程可由镍、铜铬铁矿、氧化铂、氧化钴或氧化钼和汞齐钠在高温高压下进行催化，在水中，铜或铂催化剂的存在下加氢可以主要得到2,5-呋喃二甲醇；而在更强烈的条件下，还会进一步将呋喃环还原生成2,5-二(羟甲基)四氢呋喃。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  糠醇	(2-furyl)methyl alcohol	98-00-0	C5H6O2	98.1014
  5-羟甲基糠醛	5-hydroxymethyl-2-furfuraldehyde	67-47-0	C6H6O3	126.112
  2,5-呋喃二甲酸	furan-2,5-dicarboxylic acid	3238-40-2	C6H4O5	156.095
  2,5-二甲基呋喃	2,5-dimethylfuran	625-86-5	C6H8O	96.1289
  ——	2,5-bis(acetoxymethyl)furan	5076-10-8	C10H12O5	212.202
  ——	(5-(hydroxymethyl)furan-2-yl)methyl acetate	89630-82-0	C8H10O4	170.165

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5-甲基-2-呋喃甲醇	2-hydroxymethyl-5-methylfuran	3857-25-8	C6H8O2	112.128
  2,5-呋喃二甲醇二甲基醚	2,5-bis(methoxymethyl)furan	18801-76-8	C8H12O3	156.181
  ——	5-(methoxymethyl)-2-furanmethanol	934-93-0	C7H10O3	142.155
  糠醇	(2-furyl)methyl alcohol	98-00-0	C5H6O2	98.1014
  5-羟甲基糠醛	5-hydroxymethyl-2-furfuraldehyde	67-47-0	C6H6O3	126.112
  [5-(氨基甲基)呋喃-2-基]甲醇	5-hydroxymethylfurfurylamine	88910-22-9	C6H9NO2	127.143
  ——	2-(formyloxy)methyl-5-(hydroxymethyl)furan	1253934-87-0	C7H8O4	156.138
  ——	2,5-bis[(formyloxy)methyl]furan	1008130-34-4	C8H8O5	184.149
  ——	2,5-bis(ethoxymethyl)furan	99181-63-2	C10H16O3	184.235
  2-呋喃甲醇,5-(乙氧基甲基)-	5-(ethoxymethyl)furfuryl alcohol	113983-97-4	C8H12O3	156.181

反应信息

• 作为反应物：
  描述：

  2,5-呋喃二甲醇 在 Rh-Re/SiO₂ 三氟甲磺酸 、 氢气 作用下， 以 环丁砜 、 水 为溶剂， 120.0~125.0 ℃ 、8.0 MPa 条件下， 反应 5.5h， 生成 四氢吡喃-2-甲醇
  参考文献：
  名称：

  Preparation of caprolactone, caprolactam, 2,5-tetrahydrofuran dimethanol, 1,6-hexanediol or 1,2,6-hexanetriol from 5-hydroxymethyl-2-furfuraldehyde

  摘要：

  本发明涉及一种制备己内酯的方法，包括将5-羟甲基-2-呋喃醛经过加氢转化为选自2,5-四氢呋喃二甲醇、1,6-己二醇和1,2,6-己三醇中至少一种中间化合物，然后从该中间化合物制备己内酯。此外，该发明还涉及一种制备1,2,6-己三醇的方法，包括从可再生来源制备5-羟甲基-2-呋喃醛，将5-羟甲基-2-呋喃醛转化为2,5-四氢呋喃二甲醇，再将2,5-四氢呋喃二甲醇转化为1,2,6-己三醇。此外，该发明还涉及一种从1,2,6-己三醇制备1,6-己二醇的方法，其中将1,2,6-己三醇进行环闭合反应，从而形成2-羟基吡喃基甲醇，然后对2-羟基吡喃基甲醇进行加氢，形成1,6-己二醇。

  公开号：

  EP2390247A1
• 作为产物：
  描述：

  (5-(1,3-dioxan-2-yl)furan-2-yl)methanol 在 NiRe_0.5/TiO₂ 、 氢气 、 sodium carbonate 作用下， 以 水 为溶剂， 40.0 ℃ 、5.0 MPa 条件下， 反应 4.0h， 以89%的产率得到2,5-呋喃二甲醇
  参考文献：
  名称：

  Selective hydrogenation of 5-hydroxymethylfurfural and its acetal with 1,3-propanediol to 2,5-bis(hydroxymethyl)furan using supported rhenium-promoted nickel catalysts in water

  摘要：

  高BHMF产率是通过保护5-HMF的甲酰基团，然后在氢化反应过程中平衡其脱保护速率来实现的。

  DOI：

  10.1039/c9gc03856f
• 作为试剂：
  描述：

  2,5-呋喃二甲醇 、 氢气 在 2,5-呋喃二甲醇 作用下， 以the first reactor zone effluent stream, in the presence of a second heterogeneous reduction catalyst to form the 1,2,6-hexanetriol (HTO)的产率得到1,2,6-己三醇
  参考文献：
  名称：

  PROCESS FOR PRODUCTION OF HEXANETRIOL FROM 5-HYDROXYMETHYLFURFURAL

  摘要：

  提供使用氢气和异质还原催化剂进行化学催化转化的5-羟甲基糠醛的工业规模转化，以生产1,2,6-己三醇和1,6-己二醇等商品化学品。这些反应适用于连续流反应器。提供了进行转化的方法，以及产物和催化剂的组成。

  公开号：

  US20160194298A1

文献信息

• Hydrogenation of Esters to Alcohols Catalyzed by Defined Manganese Pincer Complexes
  作者：Saravanakumar Elangovan、Marcel Garbe、Haijun Jiao、Anke Spannenberg、Kathrin Junge、Matthias Beller

  DOI：10.1002/anie.201607233

  日期：2016.12.5

  The first manganese‐catalyzed hydrogenation of esters to alcohols has been developed. The combination of Mn(CO)5Br with [HN(CH2CH2P(Et)2)2] leads to a mixture of cationic and neutral Mn PNP pincer complexes, which enable the reduction of various ester substrates, including aromatic and aliphatic esters as well as diesters and lactones. Notably, related pincer complexes with isopropyl or cyclohexyl

  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。
• Zirconium and hafnium polyhedral oligosilsesquioxane complexes – green homogeneous catalysts in the formation of bio-derived ethers <i>via</i> a MPV/etherification reaction cascade
  作者：Shipra Garg、Daniel K. Unruh、Clemens Krempner

  DOI：10.1039/d0cy01864c

  日期：——

  i·(HOPri)}2 (I), [(cyclohexyl)7Si7O12]ZrOPri·(HOPri)}2 (II), [(isobutyl)7Si7O12]HfOPri·(HOPri)}2 (III) and [(cyclohexyl)7Si7O12]HfOPri·(HOPri)}2 (IV), were synthesized in good yields from the reactions of M(OPri)4 (M = Zr, Hf) with R-POSS(OH)3 (R = isobutyl, cyclohexyl), resp. I–IV were characterized by 1H, 13C and 29Si NMR spectroscopy and their dimeric solid-state structures were confirmed by

  多面体低聚倍半硅氧烷络合物[（（异丁基）7 Si 7 O 12 ] ZrOPr i ·（HOPr i）}} 2（I），[（环己基）7 Si 7 O 12 ] ZrOPr i ·（HOPr i）} 2（II），[（（异丁基）7 Si 7 O 12 ] HfOPr i ·（HOPr i）}} 2（III）和[（环己基）7 Si 7 O 12 ] HfOPr i·（HOPr i）} 2（IV），是由M（OPr i）4（M = Zr，Hf）与R-POSS（OH）3（R =异丁基，环己基）反应合成的，收率很高。I – IV用1 H，13 C和29 Si NMR光谱表征，其二聚体固态结构通过X射线分析证实。I – IV在异丙醇中催化2-羟基和4-羟基，2-甲氧基和4-甲氧基苯甲醛和香兰素还原成醚化成各自的异丙醚，作为“绿色”溶剂和试剂。一世– IV是耐用且坚固的均相催化剂，可在100–160°
• PROCESS FOR PREPARING DI-, TRI- AND POLYAMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION
  申请人：SCHAUB Thomas

  公开号：US20120232293A1

  公开（公告）日：2012-09-13

  Process for preparing primary amines which have at least one functional group of the formula (—CH 2 —NH 2 ) and at least one further primary amino group by alcohol amination of starting materials having at least one functional group of the formula (—CH 2 —OH) and at least one further functional group (—X), where (—X) is selected from among hydroxyl groups and primary amino groups, by means of ammonia with elimination of water, wherein the reaction is carried out homogeneously catalyzed in the presence of at least one complex catalyst comprising at least one element selected from groups 8, 9 and 10 of the Periodic Table and also at least one donor ligand.

  通过醇胺化起始物质制备至少具有一个功能基团（—CH2—NH2）和至少一个进一步的初级氨基基团的初级胺的过程，其中起始物质至少具有一个功能基团（—CH2—OH）和至少一个进一步的功能基团（—X），其中（—X）从羟基和初级氨基中选择，通过氨与水的消除，反应在至少包含来自周期表8、9和10族中选择的至少一个元素以及至少一个给体配体的至少一个复合催化剂的存在下均匀催化进行。
• Ammonia borane enabled upgrading of biomass derivatives at room temperature
  作者：Wenfeng Zhao、Sebastian Meier、Song Yang、Anders Riisager

  DOI：10.1039/d0gc02372h

  日期：——

  Simplifying biomass conversion to valuable products with high efficiency is pivotal for the sustainable development of society. Herein, an efficient catalyst-free system using ammonia borane (AB) as the hydrogen donor is described, which enables controllable reaction selectivity towards four value-added products in excellent yield (82–100%) under very mild conditions. In particular, the system is uniquely

  高效地将生物质转化为有价值的产品对于社会的可持续发展至关重要。本文描述了一种有效的无催化剂系统，该系统使用氨硼烷（AB）作为氢供体，在非常温和的条件下，该系统能够以优异的收率（82-100％）对四种增值产品进行可控的反应选择性。特别是，该系统在室温下生产γ-戊内酯（GVL）具有独特的效率。原位结合NMR和计算研究阐明了AB在甲醇中的氢转移机理，从水中的乙酰丙酸酯形成GVL的新途径，以及在同一系统中还原和还原胺化之间的竞争机理。此外，采用一锅，两步策略将碳水化合物以高收率直接转化为GVL。通过在室温下在甲醇中使用这种无催化剂的策略，可以在30分钟的短时间内制备出范围相当广的产品。
• Noble metal-free upgrading of multi-unsaturated biomass derivatives at room temperature: silyl species enable reactivity
  作者：Hu Li、Wenfeng Zhao、Wenshuai Dai、Jingxuan Long、Masaru Watanabe、Sebastian Meier、Shunmugavel Saravanamurugan、Song Yang、Anders Riisager

  DOI：10.1039/c8gc02934b

  日期：——

  A simple and robust catalytic system is described for the controllable conversion of biomass-derived chemicals.

  描述了一个简单而坚固的催化系统，用于可控地转化生物质衍生化学品。

表征谱图