3-(4-氟苯氧基)丙腈 | 85169-02-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(4-氟苯氧基)丙腈
• 英文名称: 3-(4-fluorophenoxy)propanenitrile
• 英文别名: 3-(4-fluoro-phenoxy)propionitrile
• CAS: 85169-02-4
• 化学式: C₉H₈FNO
• mdl: MFCD01569391
• 分子量: 165.167
• InChiKey: MSQBUHCLFYFIGC-UHFFFAOYSA-N

物化性质

• 沸点：
  274 °C(lit.)
• 密度：
  1.165 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 3-(4-Fluorophenoxy)propionitrile
CAS-No. : 85169-02-4
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C9H8FNO
Molecular Weight : 165,16 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Hydrogen fluoride
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Normal measures for preventive fire protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection not required. For nuisance exposures use type OV/AG (US) or type ABEK
(EU EN 14387) respirator cartridges. Use respirators and components tested and approved under
appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: liquid
Colour: colourless
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and 274 °C
boiling range
g) Flash point > 110,00 °C - closed cup
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density 1,165 g/mL at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-(4-氟苯氧基)丙腈 在 盐酸 作用下， 以 水 为溶剂， 以95%的产率得到3-(4-氟苯氧基)丙酸
  参考文献：
  名称：

  酸活化蒙脱石K-10介导的分子内酰化：简单方便地合成4-色满酮

  摘要：

  3-芳氧基丙酸在 AA.Mont.K-10 的存在下在甲苯中回流 30-45 分钟，以良好到极好的产率进行分子内环化。在邻位、间位、对位带有各种取代基的苯基环会发生这种环化反应。该方法涉及简单的后处理，适用于大规模制备。经多相酸处理的催化剂可以再生并最多使用三个循环，而活性损失最小。

  DOI：

  10.1016/j.tetlet.2021.153372
• 作为产物：
  描述：

  4-氟苯酚 、 丙烯腈 在 sodium 作用下， 生成 3-(4-氟苯氧基)丙腈
  参考文献：
  名称：

  酸活化蒙脱石K-10介导的分子内酰化：简单方便地合成4-色满酮

  摘要：

  3-芳氧基丙酸在 AA.Mont.K-10 的存在下在甲苯中回流 30-45 分钟，以良好到极好的产率进行分子内环化。在邻位、间位、对位带有各种取代基的苯基环会发生这种环化反应。该方法涉及简单的后处理，适用于大规模制备。经多相酸处理的催化剂可以再生并最多使用三个循环，而活性损失最小。

  DOI：

  10.1016/j.tetlet.2021.153372

文献信息

• Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids
  作者：Hyung-Seok Yoo、Seung Hwan Son、Yang Yil Cho、Soo Jin Lee、Hyu Jeong Jang、Young Min Kim、Dong Hwan Kim、Nam Yong Kim、Boyoung Y. Park、Yong Sup Lee、Nam-Jung Kim

  DOI：10.1021/acs.joc.9b01162

  日期：2019.8.16

  total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92%.

  合宜地通过一锅二价的苯并二氢吡喃酮与芳基硼酸通过串联钯（II）催化合成了苯并二氢吡喃酮（一类具有化学未活化β位点的简单酮），合成了47种黄烷酮。该反应提供了一种以高达92％的收率获得各种黄烷酮（包括天然产物，如柚皮苷三甲醚）的新颖途径。
• CHROMENE DERIVATIVES AS INHIBITORS OF TCR-NCK INTERACTION
  申请人：Artax Biopharma Inc.

  公开号：US20190263792A1

  公开（公告）日：2019-08-29

  The present invention provides compounds that modulate the interaction of TCR with Nck, compositions thereof, and methods of treatment using the same.

  本发明提供了调节TCR与Nck相互作用的化合物，以及这些化合物的组合物和使用它们的治疗方法。
• Design and synthesis of highly potent and selective human peroxisome proliferator-activated receptor α agonists
  作者：Yukiyoshi Yamazaki、Kazutoyo Abe、Tsutomu Toma、Masahiro Nishikawa、Hidefumi Ozawa、Ayumu Okuda、Takaaki Araki、Soichi Oda、Keisuke Inoue、Kimiyuki Shibuya、Bart Staels、Jean-Charles Fruchart

  DOI：10.1016/j.bmcl.2007.05.066

  日期：2007.8

  A combination of benzoxazole, phenoxyalkyl side chain, and phenoxybutyric acids was identified as a highly potent and selective human peroxisome proliferator-activated receptor alpha (PPARalpha) agonist. The synthesis, structure-activity relationship (SAR) studies, and in vivo activities of the representative compounds are described.

  苯并恶唑，苯氧基烷基侧链和苯氧基丁酸的组合被确定为高度有效和选择性的人类过氧化物酶体增殖物激活受体α（PPARalpha）激动剂。描述了代表性化合物的合成，结构-活性关系（SAR）研究和体内活性。
• Synthesis, absolute configuration and conformation of the aldose reductase inhibitor sorbinil
  作者：Reinhard Sarges、Jon Bordner、Beryl W. Dominy、Michael J. Peterson、Earl B. Whipple

  DOI：10.1021/jm00149a030

  日期：1985.11

  The aldose reductase inhibitor 2,3-dihydro-6-fluorospiro[4H-1-benzopyran-4,4'-imidazolidine]-2',5 '-dione was resolved into its enantiomers. Sorbinil, the S isomer, was found to be a better inhibitor of the enzyme in vitro and in vivo than the corresponding R isomer. X-ray data on sorbinil, which were used to determine its absolute configuration, are presented. NMR studies of sorbinil in solution indicate

  醛糖还原酶抑制剂2,3-二氢-6-氟螺[4H-1-苯并吡喃-4,4'-咪唑烷] -2'，5'-二酮被拆分为其对映体。Sorbinil，S异构体，在体内外比相应的R异构体是更好的酶抑制剂。介绍了用于确定其绝对构型的山梨醇X射线数据。溶液中山梨醇的NMR研究表明，存在两个构象异构体，它们具有较低的能量转换障碍。
• Process for preparing 6-fluoro-4-chromanone using
  申请人：Kanegafuchi Kagaku Kogyo Kabushiki Kaisha

  公开号：US04625042A1

  公开（公告）日：1986-11-25

  The present invention relates to 3-(4-fluorophenoxy)propionitrile having the formula (I): ##STR1## a process for preparing 3-(4-fluorophenoxy)propionitrile having the formula (I) which comprises reacting 4-fluorophenol and acrylonitrile in the presence of a tertiary amine, a process for preparing 6-fluoro-4-chromanone having the formula (II): ##STR2## which comprises reacting 3-(4-fluorophenoxy)propionitrile having the formula (I) with an acid, and a process for preparing 6-fluoro-4-chromanone having the formula (II) which comprises reacting 4-fluorophenol with acrylonitrile in the presence of a catalyst to give 3-(4-fluorophenoxy)propionitrile having the formula (I), which is then reacted with an acid. 6-Fluoro-4-chromanone is an important intermediate for the synthesis of (S)-2,3-dihydro-6-fluoro-spiro[4H-1-benzopyran-4,4'-imidazolidine]-2',5'di one (USAN: sorbinil).

  本发明涉及具有化学式(I)的3-(4-氟苯氧基)丙腈：##STR1##一种制备具有化学式(I)的3-(4-氟苯氧基)丙腈的方法，包括在三级胺的存在下，将4-氟苯酚和丙烯腈反应的步骤，一种制备具有化学式(II)的6-氟-4-色酮的方法：##STR2##包括将具有化学式(I)的3-(4-氟苯氧基)丙腈与酸反应的步骤，以及一种制备具有化学式(II)的6-氟-4-色酮的方法，包括在催化剂的存在下，将4-氟苯酚与丙烯腈反应以得到具有化学式(I)的3-(4-氟苯氧基)丙腈，然后将其与酸反应。6-氟-4-色酮是合成(S)-2,3-二氢-6-氟-螺[4H-1-苯并吡喃-4,4'-咪唑啉]-2',5'二酮（USAN：索比尼尔）的重要中间体。