4-氟代-N-(4-甲氧基亚苄基)苯胺 | 3381-48-4

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯胺系列
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-氟代-N-(4-甲氧基亚苄基)苯胺
• 中文别名: N-(4-甲氧基亚苄基)-4-氟苯胺；N-(4-甲氧苯亚甲基)-4-氟苯胺
• 英文名称: N-(4-methoxybenzylidene)-4-fluoroaniline
• 英文别名: N-(4-fluorophenyl)-1-(4-methoxyphenyl)methanimine
• CAS: 3381-48-4
• 化学式: C₁₄H₁₂FNO
• 分子量: 229.254
• InChiKey: ZICFPEHQRZAFBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  65-69 °C (lit.)
• 沸点：
  349.7±27.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi,N
• 安全说明：
  S26,S39,S61
• 危险类别码：
  R41,R51/53
• WGK Germany：
  3
• 海关编码：
  2925290090
• 危险品运输编号：
  UN 3077 9/PG 3

SDS

---

Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : N-(4-Methoxybenzylidene)-4-fluoroaniline
CAS-No. : 3381-48-4
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Serious eye damage (Category 1)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Risk of serious damage to eyes. Toxic to aquatic organisms, may cause long-term adverse effects in the
aquatic environment.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
H318 Causes serious eye damage.
Precautionary statement(s)
P280 Wear protective gloves/ eye protection/ face protection.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R41 Risk of serious damage to eyes.
R51/53 Toxic to aquatic organisms, may cause long-term adverse effects in the
aquatic environment.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S39 Wear eye/face protection.
S61 Avoid release to the environment. Refer to special instructions/ Safety
data sheets.
Other hazards - none

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 4-Fluoro-N-(4-methoxybenzylidene)aniline
Formula : C14H12FNO
Molecular Weight : 229,25 g/mol
Component Concentration
N-(4-Methoxybenzylidene)-4-fluoroaniline
CAS-No. 3381-48-4 -

---

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. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

---

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

---

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
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.

---

Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.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.
Specific end uses
no data available

---

Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
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 N100 (US) or type P3 (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).

---

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 Melting point/range: 65 - 69 °C - lit.
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- log Pow: 3,732
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

---

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

---

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 Causes eye burns.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

---

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
Toxic to aquatic life.

---

Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. 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.

---

Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: 3077 IMDG: 3077 IATA: 3077
UN proper shipping name
ADR/RID: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (N-(4-
Methoxybenzylidene)-4-fluoroaniline)
IMDG: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (N-(4-
Methoxybenzylidene)-4-fluoroaniline)
IATA: Environmentally hazardous substance, solid, n.o.s. (N-(4-Methoxybenzylidene)-4-
fluoroaniline)
Transport hazard class(es)
ADR/RID: 9 IMDG: 9 IATA: 9
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: yes IMDG Marine pollutant: yes IATA: yes
Special precautions for user
Further information
EHS-Mark required (ADR 2.2.9.1.10, IMDG code 2.10.3) for single packagings and combination
packagings containing inner packagings with Dangerous Goods > 5L for liquids or > 5kg for solids.

---

---

SECTION 15 - REGULATORY INFORMATION
N/A

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-氟代-N-(4-甲氧基亚苄基)苯胺 在 C₄₄H₅₃N₅OPRu⁽¹⁺⁾*Cl^(1-) 、 potassium tert-butylate 、 氢气 作用下， 以 2-甲基四氢呋喃 为溶剂， 70.0 ℃ 、500.01 kPa 条件下， 反应 6.0h， 生成 4-氟-N-(4-甲氧基苄基)苯胺
  参考文献：
  名称：

  含卢替丁衍生的钳式CNC配体的钌（II）配合物：CN键的合成，结构和催化加氢

  摘要：

  通过与相应的银卡宾衍生物进行重金属化制备了一系列含卢剔啶衍生的钳式CNC配体的Ru络合物。这些衍生物的表征显示了CN配体的mer和fac配位，这取决于N-杂环卡宾片段的翼尖。在存在t BuOK的情况下，Ru-CNC络合物在一系列亚胺的氢化中具有活性。另外，这些络合物催化菲啶啶的可逆氢化。详细的NMR光谱研究表明，CNC配体具有去质子化能力，并参与了配体辅助的二氢活化。更有趣的是，Ru-CNC络合物5 e（BF4）能够向金属-配体骨架中添加醛亚胺以产生酰胺基络合物。最后，通过DFT计算对亚胺的氢化机理进行了研究。计算的机理包括在钳形配体或第二个配位的H 2分子的协助下，外球面逐步将氢转移至CN键。

  DOI：

  10.1002/chem.201406040
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 异氰酸对氟苯基酯 在 tetrabutoxytitanium 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 55.0h， 以61%的产率得到4-氟代-N-(4-甲氧基亚苄基)苯胺
  参考文献：
  名称：

  Ⅳ族金属醇盐催化的芳基异氰酸酯和芳族醛的室温复分解：实验和计算研究

  摘要：

  芳香醛和芳基异氰酸酯在室温下不反应。然而，我们首次表明，在催化量的正丁氧基（IV）基团的存在下，它们在室温下易位，随着二氧化碳的挤出而生成亚胺。作用机理已经通过化学计量反应的研究进行了研究。异氰酸芳基酯向正丁醇金属中的插入非常迅速。插入产物与醛的反应负责复分解。在第（IV）组金属的正丁醇盐中，发现Ti（O n Bu）4（8aTi）比Zr（O n Bu）4更有效（8aZr）和Hf（O n Bu）4（8aHf）进行复分解。使用模型配合物Ti（OMe）4（8bTi），Zr（OMe）4（8bZr）和Hf（OMe）4（8bHf）在B3LYP / LANL2DZ水平上以计算方式探究了这些醇盐的复分解活性中出乎意料的巨大差异理论。这些研究表明，由Zr和Hf形成的插入产物与由Ti形成的插入产物非常稳定。这使得Zr和Hf络合物的后续反应是不利的。

  DOI：

  10.1016/j.jorganchem.2009.10.044

文献信息

• Visible-Light Photocatalytic Synthesis of Amines from Imines via Transfer Hydrogenation Using Quantum Dots as Catalysts
  作者：Zi-Wei Xi、Lei Yang、Dan-Yan Wang、Chao-Dan Pu、Yong-Miao Shen、Chuan-De Wu、Xiao-Gang Peng

  DOI：10.1021/acs.joc.8b01651

  日期：2018.10.5

  core/shell quantum dots (QDs) can be used as stable and highly active photoredox catalysts for efficient transfer hydrogenation of imines to amines with thiophenol as a hydrogen atom donor. This reaction proceeds via a proton-coupled electron transfer (PCET) from the QDs conduction band to the protonated imine followed by hydrogen atom transfer from the thiophenol to the α-aminoalkyl radical. This precious

  CdSe / CdS核/壳量子点（QDs）可以用作稳定和高活性的光氧化还原催化剂，用于以硫酚为氢原子供体的亚胺有效转移加氢成胺。该反应通过从QDs导带到质子化的亚胺的质子偶联电子转移（PCET）进行，然后氢原子从苯硫酚转移到α-氨基烷基。这种无贵金属的转化很容易扩大规模，可以通过一锅法直接从醛，胺和苯硫酚中进行。该方案的其他优势包括：广泛的底物范围，胺产物的高收率，极低的催化剂负载量（0.001 mol％），高周转率（10 5），以及在室温下在中性介质中使用可见光或阳光的温和反应条件。
• Correlation between molecular dipole moment and centrosymmetry in some crystalline diphenyl ethers
  作者：Archan Dey、Gautam R. Desiraju

  DOI：10.1039/b502516h

  日期：——

  The presence of a large molecular dipole moment in diphenyl ethers leads unequivocally to a centrosymmetric crystal structure.

  二苯醚中大分子偶极矩的存在无疑导致了中心对称的晶体结构。
• N-Alkylation of amines through hydrogen borrowing over a heterogeneous Cu catalyst
  作者：Federica Santoro、Rinaldo Psaro、Nicoletta Ravasio、Federica Zaccheria

  DOI：10.1039/c3ra44364g

  日期：——

  Substitution of alkylhalides for the synthesis of amines is a relevant target for synthetic chemists. Secondary amines can be obtained in a one pot-one step reaction from secondary and benzylic alcohols and aniline over a heterogeneous copper catalyst. The process does not require any additive, is intrinsically safe and produces no waste.

  烷基卤代物在合成胺方面的替代，是合成化学家关注的重点。通过采用多相铜催化剂，可在一次反应中从二级醇、苄醇以及苯胺一步合成二级胺，且整个过程无需添加额外物质，本质上安全，且不会产生废物。
• Asymmetric Petasis Borono‐Mannich Allylation Reactions Catalyzed by Chiral Biphenols
  作者：Yao Jiang、Scott E. Schaus

  DOI：10.1002/anie.201611332

  日期：2017.2

  Chiral biphenols catalyze the asymmetric Petasis borono‐Mannich allylation of aldehydes and amines through the use of a bench‐stable allyldioxaborolane. The reaction proceeds via a two‐step, one‐pot process and requires 2–8 mole % of 3,3′‐Ph2‐BINOL as the optimal catalyst. Under microwave heating the reaction affords chiral homoallylic amines in excellent yields (up to 99 %) and high enantioselectivies

  手性联苯酚通过使用工作台稳定的烯丙基二氧硼杂硼烷催化醛和胺的不对称 Petasis 硼-曼尼希烯丙基化。该反应通过两步一锅法进行，需要 2-8 摩尔%的 3,3'-Ph 2 -BINOL 作为最佳催化剂。在微波加热下，该反应以优异的产率（高达 99%）和高对映选择性（高达 99:1）提供手性高烯丙胺。催化反应是真正的多组分缩合反应，而醛和胺都可以具有广泛的结构和电子特性。在反应中使用巴豆基二氧硼杂硼烷会产生具有反式和顺式非对映异构体的立体发散产物，其与相应的 E-和 Z-硼杂硼烷立体异构体均具有良好的非对映选择性和对映选择性。
• Allylic C(sp³)–H alkylation <i>via</i> synergistic organo- and photoredox catalyzed radical addition to imines
  作者：Jiaqi Jia、Rajesh Kancherla、Magnus Rueping、Long Huang

  DOI：10.1039/d0sc00819b

  日期：——

  A new catalytic method for the direct alkylation of allylic C(sp3)–H bonds from unactivated alkenes via synergistic organo- and photoredox catalysis is described. The transformation achieves an efficient, redox-neutral synthesis of homoallylamines with broad functional group tolerance, under very mild reaction conditions. Mechanistic investigations indicate that the reaction proceeds through the N-centered

  描述了一种新的催化方法，用于通过协同的有机和光氧化还原催化作用，使未活化烯烃中的烯丙基C（sp 3）-H键直接烷基化。该转化在非常温和的反应条件下实现了具有宽泛的官能团耐受性的高烯丙基胺的高效，氧化还原中性合成。机理研究表明该反应通过以N为中心的自由基中间体进行，该中间体是通过将烯丙基自由基加成至亚胺而产生的。