二苯并[b,d]呋喃-2-甲醛 | 5397-82-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 二苯并[b,d]呋喃-2-甲醛
• 中文别名: 二苯并呋喃-2-甲醛
• 英文名称: dibenzofuran-2-carbaldehyde
• 英文别名: dibenzo[b,d]furan-2-carbaldehyde；(2-dibenzofuranyl)-carboxaldehyde；Dibenzofuran-2-carboxaldehyde
• CAS: 5397-82-0
• 化学式: C₁₃H₈O₂
• mdl: MFCD00136272
• 分子量: 196.205
• InChiKey: OVJMIWIVPWPZMN-UHFFFAOYSA-N

物化性质

• 熔点：
  74 °C
• 沸点：
  360.5±15.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2932999099
• 危险性防范说明：
  P264,P280,P302+P352+P332+P313+P362+P364,P305+P351+P338+P337+P313
• 危险性描述：
  H315,H319
• 储存条件：
  存放于惰性气体中以避免与空气接触。

SDS

Name:	Dibenzo[b d]furan-2-carbaldehyde Material Safety Data Sheet
Synonym:	none know
CAS:	5397-82-0

Section 1 - Chemical Product MSDS Name:Dibenzo[b d]furan-2-carbaldehyde Material Safety Data Sheet
Synonym:none know

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5397-82-0	Dibenzo[b,d]furan-2-carbaldehyde	97+%	unlisted

Hazard Symbols: XN
Risk Phrases: 22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Causes respiratory tract irritation.
Chronic:
No information found.

---

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. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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:

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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:
Vacuum or sweep up material and place into a suitable disposal container. Avoid generating dusty conditions.

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Section 7 - HANDLING and STORAGE
Handling:
Use with adequate ventilation. Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

---

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# 5397-82-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Solid
Color: Pale orange
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 73 - 74 deg C
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: C13H8O2
Molecular Weight: 196.21

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5397-82-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Dibenzo[b,d]furan-2-carbaldehyde - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 5397-82-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5397-82-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5397-82-0 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

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
  ——	2-hydroxymethyl-dibenzo[b,d]furan	86607-82-1	C13H10O2	198.221
  二苯并呋喃	dibenzofuran	132-64-9	C12H8O	168.195
  2-溴二苯并呋喃	2-bromodibenzo[b,d]furan	86-76-0	C12H7BrO	247.091

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  2-甲基二苯并呋喃	2-methyldibenzofuran	7320-51-6	C13H10O	182.222
  二苯并呋喃-2-甲酸	dibenzofuran-2-carboxylic acid	22439-48-1	C13H8O3	212.205
  ——	2-methylnaphtho[2,3-b]benzofuran	117043-97-7	C17H12O	232.282
  ——	2-hydroxymethyl-dibenzo[b,d]furan	86607-82-1	C13H10O2	198.221
  ——	methyl dibenzo[b,d]furan-2-carboxylate	58841-72-8	C14H10O3	226.232
  ——	2-(bromomethyl)dibenzo[b,d]furan	193013-87-5	C13H9BrO	261.118
  2-(氯甲基)二苯并[b,d]呋喃	2-chloromethyldibenzofuran	77358-96-4	C13H9ClO	216.667
  ——	2-vinyldibenzo[b,d]furan	13629-85-1	C14H10O	194.233
  ——	2-ethynyldibenzo[b,d]furan	1378260-35-5	C14H8O	192.217
  ——	2-(2,2-diethoxyethyliminomethyl)-dibenzofuran	23985-76-4	C19H21NO3	311.381

反应信息

• 作为反应物：
  描述：

  二苯并[b,d]呋喃-2-甲醛 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.66h， 生成 2-(氯甲基)二苯并[b,d]呋喃
  参考文献：
  名称：

  SUBSTITUTED 6,7-DIALKOXY-3-ISOQUINOLINOL DERIVATIVES AS INHIBITORS OF PHOSPHODIESTERASE 10 (PDE10A)

  摘要：

  本发明涉及具有以下公式的化合物 其中R'，R1，到R7和Ar如本文所述定义。这些化合物作为磷酸二酯酶10（PDE10A）的抑制剂，可用于治疗中枢神经系统疾病，如精神疾病，也可用于治疗例如肥胖、2型糖尿病、代谢综合征、葡萄糖不耐受、疼痛和眼科疾病。

  公开号：

  US20120214837A1
• 作为产物：
  描述：

  6-羟基-3-联苯甲醛 在 caesium carbonate 、 copper(I) bromide 、 三甲基乙酸 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以44%的产率得到二苯并[b,d]呋喃-2-甲醛
  参考文献：
  名称：

  Cu-Catalyzed Oxidative C(sp²)–H Cycloetherification of o-Arylphenols for the Preparation of Dibenzofurans

  摘要：

  A new process involving copper-catalyzed aerobic C(sp(2))-H activation, followed by cycloetherification, has been developed. This reaction serves as a direct method for the preparation of multisubstituted dibenzofurans starting with o-arylphenols. The presence of a strong para-electron-withdrawing group (e.g., NO2) on the phenol is essential for the success of the reaction.

  DOI：

  10.1021/ol203442a

文献信息

• Efficient Dimerization Disruption of <i>Leishmania infantum</i> Trypanothione Reductase by Triazole-phenyl-thiazoles
  作者：Alejandro Revuelto、Héctor de Lucio、Juan Carlos García-Soriano、Pedro A. Sánchez-Murcia、Federico Gago、Antonio Jiménez-Ruiz、María-José Camarasa、Sonsoles Velázquez

  DOI：10.1021/acs.jmedchem.1c00206

  日期：2021.5.13

  chemotype that yields noncompetitive, slow-binding inhibitors of LiTryR. Several compounds bearing (poly)aromatic substituents dramatically improve the ability to disrupt LiTryR dimerization relative to reference imidazoles. Molecular modeling studies identified an almost unexplored hydrophobic region at the interfacial domain as the putative binding site for these compounds. A subsequent structure-based

  通过破坏其同二聚体界面来抑制婴儿利什曼原虫锥硫酮二硫化物还原酶（Li TryR）已被证明是寻找新型抗利什曼原虫药物的替代且尚未开发的策略。概念证明首先是通过肽和肽模拟物获得的。基于之前报道的含有咪唑-苯基-噻唑支架的二聚化干扰剂，我们现在报道了一种新的基于 1,2,3-三唑的化学型，该化学型产生非竞争性、缓慢结合的Li TryR 抑制剂。相对于参考咪唑，几种带有（多）芳香族取代基的化合物显着提高了破坏Li TryR 二聚化的能力。分子建模研究确定了界面域中几乎未被探索的疏水区域作为这些化合物的假定结合位点。随后基于结构的设计产生了一种对称的三唑类似物，它表现出比Li TryR 更有效的抑制活性，并增强了杀利什曼病的活性。值得注意的是，其中几种新型含三唑化合物能够杀死细胞培养物中的细胞外和细胞内寄生虫。
• Simple and Efficient Ruthenium-Catalyzed Oxidation of Primary Alcohols with Molecular Oxygen
  作者：Ritwika Ray、Shubhadeep Chandra、Debabrata Maiti、Goutam Kumar Lahiri

  DOI：10.1002/chem.201601800

  日期：2016.6.20

  oxidation of a wide variety of primary, as well as secondary benzylic, allylic, heterocyclic, and aliphatic, alcohols with molecular oxygen as the primary oxidant and without any base or hydrogen‐ or electron‐transfer agents. Most importantly, a high degree of selectivity during alcohol oxidation has been predicted for complex settings. Preliminary mechanistic studies including 18O labeling established

  从生态和经济的角度来看，利用分子氧（O 2）作为化学计量的氧化剂的氧化转化在有机合成中至关重要。采用O 2的醇氧化反应在均相催化中是稀缺的，并且此类系统的功效受到受限的底物范围（最涉及仲醇氧化）或实际因素（例如，需要过量的碱或添加剂）的限制。使用O 2的催化系统在没有任何添加剂的情况下，作为“主要”氧化剂的情况很少见。通过开发有效的钌催化氧化方案，可以解决这一长期存在的问题，该方案可以平滑氧化多种分子氧为分子的伯醇和仲醇，仲醇，烯丙基，杂环和脂肪族醇。主要氧化剂，无任何碱或氢或电子转移剂。最重要的是，对于复杂的环境，已经预测了醇氧化过程中的高度选择性。包括18 O标记在内的初步机理研究确定了原位形成氧-钌中间体作为循环中的活性催化物质，并在限速步骤中涉及了两个电子氢化物的转移。
• Metal-Free Direct Deoxygenative Borylation of Aldehydes and Ketones
  作者：Jianbin Li、Haining Wang、Zihang Qiu、Chia-Yu Huang、Chao-Jun Li

  DOI：10.1021/jacs.0c03813

  日期：2020.7.29

  Direct conversion of aldehydes and ketones into alkylboronic esters via deoxygenative borylation represents an unknown yet highly desirable transformation. Herein, we present a one-step and metal-free method for carbonyl deoxy-borylation under mild conditions. A wide range of aromatic aldehydes and ketones are tolerated and successfully converted into the corresponding benzylboronates. By the same

  通过脱氧硼酸化将醛和酮直接转化为烷基硼酸酯是一种未知但非常理想的转化。在此，我们提出了一种在温和条件下进行羰基脱氧硼酰化的一步法和无金属方法。可以耐受多种芳香醛和酮，并成功转化为相应的苄基硼酸酯。通过与脂肪醛和酮相同的脱氧歧管，它还可以简明合成 1,1,2-三（硼酸酯），这是目前缺乏有效合成方法的化合物家族。鉴于其简单性和多功能性，我们预计这种新颖的硼酸化方法可以在有机硼合成中显示出巨大的前景，并在学术和工业环境中激发更多的羰基脱氧转化。
• SUBSTITUTED 6, 7-DIALKOXY-3-ISOQUINOLINE DERIVATIVES AS INHIBITORS OF PHOSPHODIESTERASE 10 (PDE 10A)
  申请人：Allergan, Inc.

  公开号：US20150158895A1

  公开（公告）日：2015-06-11

  The invention relates to compounds of the formula or a pharmaceutically acceptable salt thereof, wherein R′, R 1 through R 7 and Ar are as defined herein. These compounds are useful as inhibitors of phosphodiesterase 10 (PDE10A) which are useful in treating central nervous system diseases such as psychosis and also in treating, for example, obesity, type II diabetes, metabolic syndrome, glucose intolerance, pain and ophthalmic diseases.

  本发明涉及具有以下公式的化合物，或其药用可接受盐，其中R'，R1至R7和Ar如本文所述定义。这些化合物作为磷酸二酯酶10（PDE10A）的抑制剂，可用于治疗中枢神经系统疾病，如精神疾病，也可用于治疗例如肥胖、II型糖尿病、代谢综合征、葡萄糖不耐症、疼痛和眼科疾病。
• Synthesis of Dibenzofurans via C–H Activation of <i>o</i>-Iodo Diaryl Ethers
  作者：Niranjan Panda、Irshad Mattan、Dinesh Kumar Nayak

  DOI：10.1021/acs.joc.5b00634

  日期：2015.7.2

  An efficient method for the synthesis of dibenzofuran from o-iododiaryl ether using reusable Pd/C under ligand-free conditions has been developed. Synthesis of o-iododiaryl ether was achieved in one pot through sequential iodination and O-arylation of phenol under mild reaction conditions.

  已经开发了一种在无配体条件下使用可重复使用的Pd / C由邻碘二芳基醚合成二苯并呋喃的有效方法。在温和的反应条件下，通过顺序碘化和苯酚的邻芳基化，可以在一锅中完成邻碘二芳基醚的合成。