1-(4-氟苯基)-1,3-二氢异苯并呋喃-5-腈 | 64169-67-1

• 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 - 有机杂环化合物 - 异香豆素
• 中文名称: 1-(4-氟苯基)-1,3-二氢异苯并呋喃-5-腈
• 中文别名: 1-(4-氟苯基)-1,3-二氢异苯并呋喃-5-甲腈；5-氰基-1-(4-氟苯基)-1,3-二氢异苯并呋喃；1-(4-氟苯基)-1,3-二氢-5-氰基苯酞(简称:5-氰基-4-氟苯酞)；5-氰基-1-(4-氟苯基)-1,3-二氢化-异苯并呋喃；西酞普兰氢溴酸盐中间体
• 英文名称: 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
• 英文别名: 1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
• CAS: 64169-67-1
• 化学式: C₁₅H₁₀FNO
• mdl: MFCD06200812
• 分子量: 239.249
• InChiKey: YXCRMKYHFFMNPT-UHFFFAOYSA-N

物化性质

• 熔点：
  95-97°C
• 沸点：
  375°C
• 密度：
  1.29
• 溶解度：
  可溶于氯仿（轻微）、二氯甲烷、甲醇（轻微，超声处理）
• 稳定性/保质期：
  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• RTECS号：
  YT5250000
• 海关编码：
  2932999099
• 安全说明：
  S22,S36/37
• 危险类别码：
  R22
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H315,H319
• 储存条件：
  请将存放在密封容器内，并置于阴凉、干燥处。

SDS

1-(4-Fluorophenyl)-1,3-dihydroisobenzofuran-5- Revision number: 5
carbonitrile
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 1-(4-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Acute toxicity (Oral) Category 4
Category 4
Acute toxicity (Dermal)
Acute toxicity (Inhalation) Category 4
Skin corrosion/irritation Category 2
Serious eye damage/eye irritation Category 2A
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Harmful if swallowed, in contact with skin or if inhaled
Hazard statements
Causes skin irritation
Causes serious eye irritation
Precautionary statements:
[Prevention] Avoid breathing dust/fume/gas/mist/vapours/spray.
Use only outdoors or in a well-ventilated area.
Do not eat, drink or smoke when using this product.
Wash hands thoroughly after handling.
Wear protective gloves and eye/face protection.
[Response] IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for
breathing. Call a POISON CENTER or doctor/physician if you feel unwell.
IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
Rinse mouth.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Wash contaminated clothing before reuse.
Call a POISON CENTER or doctor/physician if you feel unwell.
carbonitrile

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Section 2. HAZARDS IDENTIFICATION
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 1-(4-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
>98.0%(GC)
Percent:
CAS Number: 64169-67-1
Chemical Formula: C15H10FNO

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Call a POISON CENTER or doctor/physician if you feel unwell.
Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
Skin contact:
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Rinse cautiously with water for several minutes. Remove contact lenses, if present
Eye contact:
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Keep container tightly closed. Store in a freezer.
Storage conditions:
Store locked up.
Store away from incompatible materials such as oxidizing agents.
Heat-sensitive
Comply with laws.
Packaging material:
carbonitrile

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator, self-contained breathing apparatus(SCBA), supplied air respirator,
etc. Use respirators approved under appropriate government standards and follow
local and national regulations.
Hand protection: Impervious gloves.
Safety goggles. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Impervious protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: Very pale yellow - Pale yellow
Odour: No data available
pH: No data available
Melting point/freezing point:100°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Chemical stability:
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Hydrogen fluoride
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
No data available
Crustacea:
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
carbonitrile

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Section 12. ECOLOGICAL INFORMATION
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：用于制备药物西普酞兰的中间体

反应信息

• 作为反应物：
  描述：

  1-(4-氟苯基)-1,3-二氢异苯并呋喃-5-腈 在 氨 、 氢气 作用下， 以 甲苯 为溶剂， 120.0 ℃ 、3.0 MPa 条件下， 反应 16.0h， 以88%的产率得到5-Aminomethyl-1-(4-Fluoro-phenyl)-1,3-dihydro-isobenzofuran
  参考文献：
  名称：

  由MOF-碳模板制备的钴基纳米颗粒作为有效的氢化催化剂†

  摘要：

  用于工业相关氢化反应的高效和选择性纳米结构催化剂的开发继续是化学研究的实际目标。尤其是腈和硝基芳烃的氢化对于伯胺的生产非常重要，伯胺构成了高级化学品，生命科学分子和材料的重要原料和关键中间体。在这里，我们报道了石墨烯壳包封的Co 3 O 4的制备-和钴-纳米颗粒通过碳上对苯二甲酸钴对苯二甲酸MOF的模板合成和随后的热解而负载在碳上。所得的纳米颗粒产生稳定且可重复使用的催化剂，用于官能化和结构多样的芳族，杂环和脂肪族腈以及硝基化合物选择性氢化为伯胺（> 65实例）。这种新型的基于非贵金属的氢化方案的合成和实用性通过将数种反应的规模扩大到数克规模并回收催化剂得到了证明。

  DOI：

  10.1039/c8sc02807a
• 作为产物：
  描述：

  5-溴苯酞 在 lithium aluminium tetrahydride 、 磷酸 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 1-(4-氟苯基)-1,3-二氢异苯并呋喃-5-腈
  参考文献：
  名称：

  Reddy, M. Pulla; Bhujanga Rao; Usharani, Asian Journal of Chemistry, 2011, vol. 23, # 4, p. 1829 - 1832

  摘要：

  DOI：
• 作为试剂：
  描述：

  1-(4'-氟苯基)-1,3-二氢异苯并呋喃-5-甲醛 、 盐酸羟胺 、 三乙胺 在 三乙胺盐酸盐 、 乙酸酐 、 sodium hydroxide 、 甲苯 、 水 、 Brine 、 magnesium sulfate 、 Silica gel 、 1-(4-氟苯基)-1,3-二氢异苯并呋喃-5-腈 、 Ethanol hexane 作用下， 以 甲苯 为溶剂， 反应 7.0h， 以to give crude 1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (14.2 g)的产率得到1-(4-氟苯基)-1,3-二氢异苯并呋喃-5-腈
  参考文献：
  名称：

  Production method of 5-phthalancarbonitrile compound, intermediate therefor and production method of the intermediate

  摘要：

  本发明提供了一种5-苯并三氰基化合物的生产方法，其中包括使用式（I）的新化合物作为关键中间体，其中X是氯原子、溴原子或碘原子。本发明的方法对环境的负担较小（不使用对环境造成巨大负担的试剂，如重金属、金属氰化物、亚硫酰氯等），并且是安全的。本发明的方法基于一种完全不同于传统5-苯并三氰基化合物生产方法的全新策略。

  公开号：

  US20020045770A1

文献信息

• [EN] PERMANENTLY POSITIVELY CHARGED ANTIDEPRESSANTS<br/>[FR] ANTIDÉPRESSEURS CHARGÉS POSITIVEMENT EN PERMANENCE
  申请人：UNIV AARHUS

  公开号：WO2013026455A1

  公开（公告）日：2013-02-28

  The present invention provides compounds comprising a substructure of below formula 3: or a salt or prodrug thereof and the use of such compounds in treatment of e.g. CNS disorders.

  本发明提供了包含如下式3的亚结构的化合物：或其盐或前药，以及这些化合物在治疗例如中枢神经系统疾病中的用途。
• [EN] ANTI-HIV COMPOUNDS<br/>[FR] COMPOSÉS ANTI-VIH
  申请人：PANACOS PHARMACEUTICALS INC

  公开号：WO2009085256A1

  公开（公告）日：2009-07-09

  Thiazole derivatives represented by Formula (I) are disclosed, where R1, R2, R3, A, X, Y, Z, R6 and R7 are disclosed herein. These thiazole derivatives and pharmaceutical compositions comprising these derivatives are useful in the treatment of HIV mediated diseases and conditions.

  公式（I）代表的噻唑衍生物已被披露，其中在此披露了R1、R2、R3、A、X、Y、Z、R6和R7。这些噻唑衍生物和包含这些衍生物的药物组合物在治疗HIV介导的疾病和症状方面是有用的。
• Chemoselective α,β‐Dehydrogenation of Saturated Amides
  作者：Christopher J. Teskey、Pauline Adler、Carlos R. Gonçalves、Nuno Maulide

  DOI：10.1002/anie.201808794

  日期：2019.1.8

  We report a method for the selective α,β‐dehydrogenation of amides in the presence of other carbonyl moieties under mild conditions. Our strategy relies on electrophilic activation coupled to in situ selective selenium‐mediated dehydrogenation. The α,β‐unsaturated products were obtained in moderate to excellent yields, and their synthetic versatility was demonstrated by a range of transformations.

  我们报告了一种在温和条件下在其他羰基存在下选择性 α,β-脱氢酰胺的方法。我们的策略依赖于亲电激活与原位选择性硒介导的脱氢作用相结合。α,β-不饱和产物以中等至优异的收率获得，并且它们的合成多功能性通过一系列转化得到证明。机理实验表明亲电子 Se IV物质的形成。
• α-Fluorination of carbonyls with nucleophilic fluorine
  作者：Pauline Adler、Christopher J. Teskey、Daniel Kaiser、Marion Holy、Harald H. Sitte、Nuno Maulide

  DOI：10.1038/s41557-019-0215-z

  日期：2019.4

  unique properties of fluorine, and the ability of fluorination to change the properties of organic molecules, there is significant interest from medicinal chemists in innovative methodologies that enable the synthesis of new fluorinated motifs. State-of-the-art syntheses of α-fluorinated carbonyl compounds invariably rely on electrophilic fluorinating agents, which can be strongly oxidizing and difficult

  鉴于氟的独特性质以及氟化改变有机分子性质的能力，药物化学家对能够合成新的氟化基序的创新方法产生了浓厚的兴趣。最先进的 α-氟化羰基化合物的合成总是依赖于亲电子氟化剂，其具有强氧化性且难以处理。在这里，我们表明，将烯醇伴侣的极性反转为烯醇鎓的极性使得亲核氟化剂能够用于酰胺的直接化学选择性α-C-H-氟化。减少这些产品可以很容易地获得 β-氟化胺，这种方法的价值体现在易于制备许多药物和农用化学品的氟化类似物。
• Process for the preparation of 1-(3-dimethylaminopropyl)-1-(4-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
  申请人：ORION CORPORATION FERMION

  公开号：US20020115872A1

  公开（公告）日：2002-08-22

  Method for the preparation of 1-(3-dimethylaminopropyl)-1-(4-fluoro-phenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (citalopram) comprising the reaction of a compound of formula 1 wherein X is a halogen, with organometallic dimethylaminopropyl halide. Other aspects of the invention are new compounds of formula II and formula III and their preparation.

  制备1-(3-二甲基氨基丙基)-1-(4-氟苯基)-1,3-二氢异苯并呋喃-5-羧腈（西酞普兰）的方法包括将式1的化合物与有机金属二甲基氨基丙基卤化物反应。该发明的其他方面是式II和式III的新化合物及其制备。

表征谱图