2-溴呋喃 | 584-12-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 2-溴呋喃
• 英文名称: 2-bromofuran
• 英文别名: 2-bromofurane
• CAS: 584-12-3
• 化学式: C₄H₃BrO
• 分子量: 146.971
• InChiKey: OYMCMWPHMPODNK-UHFFFAOYSA-N

物化性质

• 熔点：
  116 °C
• 沸点：
  52 °C
• 密度：
  1.662
• 闪点：
  3°C
• 最大波长(λmax)：
  216nm(EtOH)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  3
• 安全说明：
  S26,S37/39
• 危险品运输编号：
  UN 1993
• 海关编码：
  2932190090
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 储存条件：
  温度低于0°C；存放于惰性气体中；避免与空气接触并防止加热。

SDS

Name:	2-Bromofuran 97% Material Safety Data Sheet
Synonym:
CAS:	584-12-3

Section 1 - Chemical Product MSDS Name:2-Bromofuran 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
584-12-3	2-Bromofuran	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.Air sensitive.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4C/39F.) Store under nitrogen.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 584-12-3: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 52 - 54 deg C @180mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C4H3BrO
Molecular Weight: 147

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to air.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, hydrogen bromide, acrid smoke and fumes, bromine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 584-12-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Bromofuran - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 584-12-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 584-12-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 584-12-3 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-溴呋喃 在 hexabromocyclopenta-1,3-diene 作用下， 以 乙腈 为溶剂， 以20%的产率得到2,5-二溴呋喃
  参考文献：
  名称：

  新型溴化试剂。六溴环戊二烯的亲电子溴化

  摘要：

  六溴环戊二烯有效和区域选择性地溴化活化的芳族化合物，该过程被解释为涉及通过溴离子的释放容易形成五溴环戊二烯阴离子。

  DOI：

  10.1039/c39820000778
• 作为产物：
  描述：

  呋喃 在 hexabromocyclopenta-1,3-diene 作用下， 以 乙腈 为溶剂， 以75%的产率得到2-溴呋喃
  参考文献：
  名称：

  新型溴化试剂。六溴环戊二烯的亲电子溴化

  摘要：

  六溴环戊二烯有效和区域选择性地溴化活化的芳族化合物，该过程被解释为涉及通过溴离子的释放容易形成五溴环戊二烯阴离子。

  DOI：

  10.1039/c39820000778

文献信息

• Pd(0)-Catalyzed Direct Inter- and Intramolecular C–H Functionalization of 4-Carboxyimidazoles
  作者：Steven Frippiat、Christine Baudequin、Christophe Hoarau、Antoine Peresson、Thibaut Perse、Yvan Ramondenc、Cédric Schneider、Olivier Querolle、Patrick Angibaud、Virginie Poncelet、Lieven Meerpoel、Vincent Levacher、Laurent Bischoff

  DOI：10.1055/s-0040-1708003

  日期：2020.6

  The palladium-catalyzed arylation and alkenylation of N-substituted methyl imidazole-4-carboxylates are described through inter- and intramolecular pathways. Both direct C2–H and C5–H arylation and alkenylation proceed under Pd(0)/Cu(I) cooperative catalysis and Pd(0) catalysis, respectively, in low-polarity 1,4-dioxane solvent. The methodology gives access to C2 (hetero)aryl or alkenyl imidazoles

  通过分子间和分子内途径描述了钯催化的 N-取代甲基咪唑-4-羧酸酯的芳基化和烯基化。在低极性 1,4-二恶烷溶剂中，直接 C2-H 和 C5-H 芳基化和烯基化分别在 Pd(0)/Cu(I) 协同催化和 Pd(0) 催化下进行。该方法可以获得 C2（杂）芳基或烯基咪唑以及具有五至七元中间环的创新 C2-和 C5-芳基化的稠合咪唑三环。
• N-Heterocyclic carbene palladium (II)-pyridine (NHC-Pd (II)-Py) complex catalyzed heck reactions
  作者：Dan Li、Qingqiang Tian、Xuetong Wang、Qiang Wang、Yin Wang、Siwei Liao、Ping Xu、Xin Huang、Jianyong Yuan

  DOI：10.1080/00397911.2021.1919711

  日期：——

  Abstract A mild, efficient, and practical catalytic system for the synthesis of highly privileged stilbene pharmacophores is reported. This system uses N-heterocyclic carbene palladium (II) Pyridine (NHC-Pd (II)-Py) complex to catalyze the formation of carbon-carbon bonds between olefin derivatives and various bromide. This simple, gentle and user-friendly method can offer a variety of stilbene products

  摘要 报道了一种温和、高效且实用的催化系统，用于合成高度特权的二苯乙烯药效团。该系统使用N-杂环卡宾钯(II)吡啶(NHC-Pd(II)-Py)配合物催化烯烃衍生物与各种溴化物之间形成碳-碳键。这种简单、温和且用户友好的方法可以在无溶剂条件下以优异的收率提供各种二苯乙烯产品。且其放大反应收率优良，可应用于工业领域。该方法的实用性突出表现在其可合成一系列生物活性分子或重要的医药中间体的通用性和模块化合成。
• Rh-Catalyzed Conjugate Addition of Arylzinc Chlorides to Thiochromones: A Highly Enantioselective Pathway for Accessing Chiral Thioflavanones
  作者：Ling Meng、Ming Yu Jin、Jun Wang

  DOI：10.1021/acs.orglett.6b02453

  日期：2016.10.7

  A highly efficient asymmetric synthesis of chiral thioflavanones is developed via conjugate addition of arylzinc reagents to thiochromones using Rh(COD)Cl2/(R)-3,4,5-MeO-MeOBIPHEP catalyst. This method overcomes catalyst poisoning and substrate inertness and affords a series of chiral thioflavanones (2-arylthiochroman-4-ones) in good yields (up to 91% yield) with excellent ee values (up to 97% ee)

  通过使用Rh（COD）Cl 2 /（R）-3,4,5-MeO-MeOBIPHEP催化剂将芳基锌试剂共轭添加到硫代色酮中，开发了一种高效的手性硫代黄酮酮的不对称合成方法。此方法克服了催化剂中毒和底物惰性的问题，并以良好的收率（最高91％的收率）和优异的ee值（最高ee的97％）提供了一系列手性硫代黄烷酮（2-芳基硫代色烷-4-酮）。既定的不对称合成为进一步的药物研究铺平了道路。
• HFO-1234yf as a CF3-building block: Synthesis of trifluoromethyl-benzophenone derivatives by deoxygenative aromatisation
  作者：Ben J. Murray、Lee T. Boulton、Graham Sandford

  DOI：10.1016/j.jfluchem.2021.109774

  日期：2021.5

  Trifluoromethyl ynones derived from the 4th generation refrigerant 2,3,3,3-tetrafluoropropene (HFO-1234yf) undergo rapid Diels-Alder cycloaddition reactions with furans in near quantitative yields. Subsequent deoxygenation of the resulting oxabicyclic adducts leads to formation of ortho-trifluoromethylbenzophenones in generally good yields without the need for purification by column chromatography

  衍生自第四代制冷剂2,3,3,3-四氟丙烯（HFO-1234yf）的三氟甲基乙炔与呋喃的快速Diels-Alder环加成反应以接近定量的产率进行。所得的氧双环加合物的随后脱氧导致通常以高收率形成邻-三氟甲基二苯甲酮，而无需通过柱色谱法纯化。在所有情况下均观察到对单一区域异构体的完全选择性。该方法提供了从廉价的原料到高度取代的CF 3-芳族体系的新途径，这可能难以通过既定方法选择性地获得。
• Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides
  作者：Jiandong Liu、Qinghua Ren、Xinghua Zhang、Hegui Gong

  DOI：10.1002/anie.201607959

  日期：2016.12.12

  This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy‐to‐operate nickel‐catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional‐group tolerance. The nickel‐catalytic system displays

  这项工作强调了在温和且易于操作的镍催化反应条件下，通过芳基卤化物与乙烯基溴的还原偶联来合成取代的乙烯基芳烃。广泛使用的芳基卤化物，包括杂芳族化合物和乙烯基溴化物，以中等至优异的收率生产了具有高官能团耐受性的产品。镍催化系统在两个C（sp 2）-卤化物偶合体之间显示出良好的化学选择性，从而证明了不同于其他逐步方案的机理途径。

表征谱图