(E)-1-fluoro-4-(2-nitroprop-1-en-1-yl)benzene | 775-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-fluoro-4-(2-nitroprop-1-en-1-yl)benzene
• 英文别名: (E)-1-fluoro-4-(2-nitroprop-1-enyl)benzene；Benzene, 1-fluoro-4-(2-nitropropenyl)-；1-fluoro-4-[(E)-2-nitroprop-1-enyl]benzene
• CAS: 775-31-5
• 化学式: C₉H₈FNO₂
• 分子量: 181.166
• InChiKey: VOAXWARMFBBINZ-VOTSOKGWSA-N

物化性质

• 熔点：
  64-66 °C
• 沸点：
  262.2±15.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 4-Fluoro-Beta-Nitropropenylbenzene
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 3), H301
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
T Toxic R25
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
Toxic if swallowed.
Precautionary statement(s)
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
Supplemental Hazard none
Statements
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 181,17 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
4-Fluoro-Beta-Nitropropenylbenzene
Acute Tox. 3; H301 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
4-Fluoro-Beta-Nitropropenylbenzene
T, R25 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Take victim immediately to hospital. Consult a physician.
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. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting if necessary.
Further information
No data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Wear respiratory protection. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. 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
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous
materials causing chronic effects
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling
the product.
Personal protective equipment
Eye/face protection
Face shield and safety glasses 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
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N99 (US) or type P2 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use
respirators and components tested and approved under appropriate government standards such
as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
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 No data available
boiling range
g) Flash point No data available
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 No data available
n) Water solubility No data available
o) Partition coefficient: n- No data available
octanol/water
p) Auto-ignition 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
Stable under recommended storage conditions.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
In the event of fire: see section 5

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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 sensitisation
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
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
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. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: 2811 IMDG: 2811 IATA: 2811
UN proper shipping name
ADR/RID: TOXIC SOLID, ORGANIC, N.O.S. (4-Fluoro-Beta-Nitropropenylbenzene)
IMDG: TOXIC SOLID, ORGANIC, N.O.S. (4-Fluoro-Beta-Nitropropenylbenzene)
IATA: Toxic solid, organic, n.o.s. (4-Fluoro-Beta-Nitropropenylbenzene)
Transport hazard class(es)
ADR/RID: 6.1 IMDG: 6.1 IATA: 6.1
Packaging group
ADR/RID: III IMDG: III IATA: III
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
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
No data available
Chemical Safety Assessment

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (E)-1-fluoro-4-(2-nitroprop-1-en-1-yl)benzene 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.17h， 以78%的产率得到3-(4-fluorophenyl)-2-methyl-2-nitrooxirane
  参考文献：
  名称：

  Nitroepoxides as Versatile Precursors to 1,4-Diamino Heterocycles

  摘要：

  Nitroepoxides are easily transformed into 1,4-diamino heterocycles such as quinoxalines and pyrazines by treatment with 1,2-benzenediamines and ammonia, respectively. Additionally, related saturated heterocycles, such as piperazines and tetrahydroquinoxalines, can be accessed by treatment with 1,2-diamines and a reducing agent. These transformations are efficient, provide access privileged, bioactive structures, and produce minimal waste.

  DOI：

  10.1021/ol500444z
• 作为产物：
  描述：

  硝基乙烷 、 对氟苯甲醛 在 ammonium acetate 作用下， 反应 2.0h， 生成 (E)-1-fluoro-4-(2-nitroprop-1-en-1-yl)benzene
  参考文献：
  名称：

  具有深手性口袋的磷配体的设计：通过不对称氢化实际合成手性β-芳胺

  摘要：

  WingPhos是一种C 2对称的双磷配体，具有较深且定义明确的手性口袋。在（E）-β-芳基-N-乙酰基酰胺，环状β-芳基酰胺和杂环β-芳基酰胺的铑催化不对称氢化反应中显示出很高的效率。可以合成一系列具有良好ee值（nbd = 3,5-降冰片二烯； TON =周转数）的手性β-芳基异丙胺，2-氨基四氢呋喃和3-氨基苯并二氢吡喃。

  DOI：

  10.1002/anie.201300646

文献信息

• [EN] FLUOROMETHYL-SUBSTITUTED PYRROLE CARBOXAMIDES<br/>[FR] PYRROLE CARBOXAMIDES SUBSTITUÉS PAR UN FLUOROMÉTHYLE
  申请人：GRUENENTHAL GMBH

  公开号：WO2014032801A1

  公开（公告）日：2014-03-06

  The invention relates to pyrrole carboxamides bearing a fluoromethyl- moiety as voltage gated calcium channel blockers, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

  这项发明涉及带有氟甲基基团的吡咯羧酰胺作为电压门控钙通道阻滞剂，以及含有这些化合物的药物组合物，还涉及这些化合物用于治疗和/或预防疼痛以及其他疾病和/或紊乱。
• FLUOROMETHYL-SUBSTITUTED PYRROLE CARBOXAMIDES
  申请人：GRUNENTHAL GMBH

  公开号：US20140066426A1

  公开（公告）日：2014-03-06

  The invention relates to pyrrole carboxamides bearing a fluoromethyl-moiety as voltage gated calcium channel blockers, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

  这项发明涉及带有氟甲基基团的吡咯酮羧酰胺作为电压门控钙通道阻滞剂，以及含有这些化合物的药物组合物，还涉及这些化合物用于治疗和/或预防疼痛以及其他疾病和/或紊乱。
• A Novel Entry to 3,4,5-Trisubstituted 2-Pyrrolidones from Isoxazoline-N-oxides
  作者：Alexey Sukhorukov、Petr Zhmurov、Pavel Ushakov、Roman Novikov、Sema Ioffe

  DOI：10.1055/s-0037-1610213

  日期：2018.9

  A novel strategy for the synthesis of stereochemically defined 3,4,5-trisubstituted 2-pyrrolidones was developed. The suggested approach involves reductive domino-type recyclization of 3-aminomethyl-substituted isoxazolines as a key stage. The latter are prepared via α-C–H functionalization of readily available isoxazoline-N-oxides.

  开发了一种合成立体化学定义的 3,4,5-三取代 2-吡咯烷酮的新策略。建议的方法包括将 3-氨基甲基取代的异恶唑啉还原多米诺型再循环作为关键阶段。后者是通过容易获得的异恶唑啉-N-氧化物的 α-C-H 官能化制备的。
• Synthesis, Antiproliferative and Pro-Apoptotic Effects of Nitrostyrenes and Related Compounds in Burkitt's Lymphoma
  作者：Andrew J. Byrne、Sandra A. Bright、Darren Fayne、James P. McKeown、Thomas McCabe、Brendan Twamley、Clive Williams、Mary J. Meegan

  DOI：10.2174/1573406413666171002123907

  日期：2018.2.6

  identified as a lead target structure for the development of particularly effective compounds targeting Burkitt's lymphoma (BL). OBJECTIVES The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt's lymphoma (BL). METHODS A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions.

  背景技术淋巴细胞癌（淋巴瘤）约占全世界恶性疾病的12％。硝基苯乙烯支架被认为是开发针对Burkitt淋巴瘤（BL）的特别有效的化合物的主要靶标结构。目的目前的研究目的是合成一组硝基苯乙烯化合物并评估其在伯基特氏淋巴瘤（BL）中的活性。方法使用Henry Knoevenagel缩合反应设计和合成一组结构变化的化合物。单晶X射线分析证实了这些新颖结构的六个实例的E构型。还研究了许多与硝基苯乙烯有关的化合物，包括1，3-双（芳基）-2-硝基丙烯与含有硝基乙烯基药效团的杂环支架，例如3-硝基-2-苯基-2H-色烯。使用BL细胞系EBV-MUTU-1和EBV + DG-75（耐化学性）评估化合物的抗增殖活性，以建立初步的结构活性关系。结果成功建立了具有优化的硝基苯乙烯骨架和3-硝基-2-苯基-2Hchromne结构的铅化合物，在MUTU-1细胞中的典型IC50值分别为0.45 µM和0.47 µM，
• Highly regio- and diastereoselective [3 + 2]-cycloadditions involving indolediones and α,β-disubstituted nitroethylenes
  作者：Madhuri P. Rao、Shubha S. Gunaga、Johannes Zuegg、Rambabu Pamarthi、Madhu Ganesh

  DOI：10.1039/c9ob01429b

  日期：——

  A highly diastereoselective [3 + 2]-cycloaddition strategy involving multiple oxindoles and several α,β-disubstituted nitroethylenes is developed to access tetra-substituted α-spiropyrrolidine frameworks. A variety of α-amino acids were employed for the first time in order to generate azomethine ylides under thermal conditions, affording regioisomers 13 and 14 merely by changing the α-substituents

  一种高度非对映选择性的[3 + 2]-环加成策略涉及多个羟吲哚和几个α，β-二取代的硝基乙烯被开发来访问四取代的α-螺并吡咯烷骨架。为了在热条件下生成甲亚胺基团，首次使用了多种α-氨基酸，仅通过改变α-氨基酸的α-取代基（R = H和取代的碳）即可提供区域异构体13和14。该反应可耐受甘氨酸，羟吲哚和硝基乙烯上的各种空间需求，富电子和缺电子的芳基和氮取代基。遵循绿色化学原理，操作简单，例如使用无金属，非惰性的环境，使用非卤代溶剂和易于分离，使此过程对扩大机会具有吸引力。该反应具有良好的产率（80-94％）和非对映选择性（高达98：2），有利于（顺式，顺式）-螺氧并吲哚，在相同条件下与β-硝基苯乙烯相比，区域选择性相反。两种带有未保护酰胺的螺吡咯烷环加合物对革兰氏阳性MRSA表现出显着活性。

表征谱图