3-溴-4,6-二硝基氟苯 | 400-91-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-溴-4,6-二硝基氟苯
• 英文名称: 1-bromo-3-fluoro-4,6-dinitrobenzene
• 英文别名: 1-bromo-5-fluoro-2,4-dinitrobenzene；5-bromo-2,4-dinitrofluorobenzene；5-Bromo-2,4-dinitrofluorbenzene；1-bromo-5-fluoro-2,4-dinitro-benzene；1-Brom-5-fluor-2,4-dinitro-benzol；3-Brom-1-fluor-4,6-dinitro-benzol
• CAS: 400-91-9
• 化学式: C₆H₂BrFN₂O₄
• mdl: MFCD00024181
• 分子量: 264.995
• InChiKey: DLNYTDLCDYDPLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2904909090

SDS

---

Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 3-Bromo-4,6-dinitrofluorobenzene
CAS-No. : 400-91-9
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]
Acute toxicity, Oral (Category 4)
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
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)
R22 Harmful if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
Other hazards - none

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C6H2BrFN2O4
Molecular Weight : 264,99 g/mol
Component Concentration
3-Bromo-4,6-dinitrofluorobenzene
CAS-No. 400-91-9 -

---

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 bromide gas, 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
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.

---

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.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
Safety glasses with side-shields conforming to EN166 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
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
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 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- log Pow: 1,491
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
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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
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
no data available

---

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: - 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

---

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
no data available

---

Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  3-溴-4,6-二硝基氟苯 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (2R,3S,4E,6E)-8-<(3-bromo-4,6-dinitrophenyl)amino>-3-methoxy-2,4-dimethyl-4,6-octadienal dimethyl acetal
  参考文献：
  名称：

  The chemistry of aurodox and related antibiotics

  摘要：

  这些研究导致了抗生素奥罗多克斯的完整结构阐明，包括所有十一个手性中心的手性以及所有七个外环双键的顺式-反式异构体。奥罗多克斯在立体化学上与莫西霉素相关。因此，奥罗多克斯可以描述为N-[7-[5(R)-[7-[1,2-二氢-4-羟基-1-甲基-2-酮-3-吡啶基]-6-甲基-7-酮-1(E),3(E),5(E)-庚三烯基]四氢-3(S),4(R)-二羟基呋喃-2(S)-基]-6(S)-甲氧基-5,7(R)-二甲基-2(E),4(E)-庚二烯基]-α(S)-乙基-5,5-二甲基四氢-2(R),3(R),4(R)-三羟基-6(S)-[1(E),3(Z)-戊二烯基]-2H-吡喃-2-乙酰胺。莫西霉素，可能与基罗霉素相同，是相应的N-去甲基同系物。

  DOI：

  10.1139/v80-080
• 作为产物：
  描述：

  2-溴-4-氟-1-硝基苯 在 硫酸 、 硝酸 作用下， 以 水 为溶剂， 反应 0.5h， 以50%的产率得到3-溴-4,6-二硝基氟苯
  参考文献：
  名称：

  新型吡咯硝酮类似物的设计，合成和杀真菌活性

  摘要：

  通过简便的方法设计和合成了一系列含有噻吩部分的吡咯硝酮新类似物，并通过1 H核磁共振（NMR）和高分辨率质谱对它们的结构进行了表征。分离了异构体IV-h和Vh，并通过2D NMR鉴定了其结构，包括异核多量子相干（HMQC），异核多键相关（HMBC）和核Overhauser效应光谱（NOESY）光谱。评估了它们对5种真菌的杀真菌活性，结果表明，某些标题化合物在体外对solternaria solani表现出优异的杀真菌活性，玉蜀黍赤霉，轮纹轮纹病菌，镰孢属omysporum，和尾孢花生在50微克毫升的剂量-1。一些化合物在低剂量下显示中等活性。化合物Vh可被认为是进一步设计农业杀菌剂的主要结构。

  DOI：

  10.1021/jf902320e

文献信息

• Transition-Metal-Free Formal Sonogashira Coupling and α-Carbonyl Arylation Reactions
  作者：Birgit Prüger、Gretchen E. Hofmeister、Christian Borch Jacobsen、David G. Alberg、Martin Nielsen、Karl Anker Jørgensen

  DOI：10.1002/chem.200902911

  日期：2010.3.22

  Sonogashira coupling and α‐carbonyl arylation reactions have been developed. These transformations are based on the nucleophilic aromatic substitution (SNAr) of β‐carbonyl sulfones to electron‐deficient aryl fluorides, producing a key intermediate that, depending on the reaction conditions, gives the aromatic alkynes or α‐aryl carbonyl compounds. The development of these reactions is presented and, based

  已经开发出无过渡金属的形式化Sonogashira偶联和α-羰基芳基化反应。这些转化基于亲核芳族取代（S Nβ-羰基砜的Ar）变成电子不足的芳基氟化物，产生了一种关键中间体，根据反应条件，该中间体会生成芳族炔烃或α-芳基羰基化合物。介绍了这些反应的进展，并基于在碱性和酸性条件下的研究提出了机理。为了进一步开发正式的Sonogashira偶联，还公开了一种温和的两步操作规程，扩展了反应概念。已证明这些反应的范围可用于从一系列具有各种官能团的缺电子的芳基氟化物和芳基，杂芳基，烷基和烷氧基取代的砜亲核试剂合成Sonogashira和α-羰基芳基化产物。这些无过渡金属的反应在取代方式方面对金属催化的反应形式起到了补充作用，
• Catalytic Asymmetric Synthesis of 3,3′-Diaryloxindoles as Triarylmethanes with a Chiral All-Carbon Quaternary Center: Phase-Transfer-Catalyzed S_NAr Reaction
  作者：Seiji Shirakawa、Kenta Koga、Takashi Tokuda、Kenichiro Yamamoto、Keiji Maruoka

  DOI：10.1002/anie.201403046

  日期：2014.6.10

  Catalytic asymmetric synthesis of unsymmetrical triarylmethanes with a chiral all‐carbon quaternary center was achieved by using a chiral bifunctional quaternary phosphonium bromide catalyst in the SNAr reaction of 3‐aryloxindoles under phase‐transfer conditions. The presence of a urea moiety in the chiral phase‐transfer catalyst was important for obtaining high enantioselectivity in this reaction

  在相转移条件下，通过手性双官能季铵溴化甲烷催化剂在3-芳基氧吲哚的S N Ar反应中使用手性双碳四级溴化catalyst催化剂，实现了具有手性全碳季中心的不对称三芳基甲烷的催化不对称合成。手性相转移催化剂中尿素部分的存在对于在该反应中获得高对映选择性很重要。
• Discovery of new potent molecular entities able to inhibit mPGES-1
  作者：Simone Di Micco、Stefania Terracciano、Vincenza Cantone、Katrin Fischer、Andreas Koeberle、Antonio Foglia、Raffaele Riccio、Oliver Werz、Ines Bruno、Giuseppe Bifulco

  DOI：10.1016/j.ejmech.2017.10.039

  日期：2018.1

  disclosed molecules, except for LY3023705, which recently entered clinical trials, are available for clinical use, therefore the discovery of new effective mPGES-1 inhibitors with increased drug–like properties are urgently needed. Continuing our work aimed at identifying new chemical platforms able to interact with this enzyme, here we describe the discovery of potent mPGES-1 modulators, featuring a 1-fluoro-2

  谷胱甘肽依赖性膜蛋白mPGES-1参与PGE 2的生产，已被公认为开发抗炎和抗癌药物的战略目标。已证明选择性控制炎症刺激诱导的PGE 2水平，既不影响组成性产生的PGE 2，也不影响稳态前列腺素，因此其调节可代表控制PGE 2的更好策略。与使用传统抗炎药相比，这种药物具有严重的副作用。尽管进行了深入的研究以鉴定有效的mPGES-1抑制剂作为药物开发的有吸引力的候选药物，但除LY3023705（最近进入临床试验）外，所公开的分子均无法用于临床，因此发现了新的有效mPGES-迫切需要1种具有类似药物特性的抑制剂。继续我们旨在鉴定能够与该酶相互作用的新化学平台的工作，在此我们描述了通过加工和对接一种有效的mPGES-1调节剂的发现，该调节剂具有基于1-氟-2,4-二硝基联苯的支架。少量可合成的分子集合，围绕两个主要片段构建，在我们的计算机筛选中披露。已合成并测试了得分最高的命中数据，其中五个预测
• Reagent-Based DOS: Developing a Diastereoselective Methodology to Access Spirocyclic- and Fused Heterocyclic Ring Systems
  作者：V. Surendra Babu Damerla、Chiranjeevi Tulluri、Rambabu Gundla、Lava Naviri、Uma Adepally、Pravin S. Iyer、Y. L. N. Murthy、Nampally Prabhakar、Subhabrata Sen

  DOI：10.1002/asia.201200385

  日期：2012.10

  Herein, we report a diversity‐oriented‐synthesis (DOS) approach for the synthesis of biologically relevant molecular scaffolds. Our methodology enables the facile synthesis of fused N‐heterocycles, spirooxoindolones, tetrahydroquinolines, and fused N‐heterocycles. The two‐step sequence starts with a chiral‐bicyclic‐lactam‐directed enolate‐addition/substitution step. This step is followed by a ring‐closure

  在这里，我们报告了生物相关的分子支架合成的面向多样性的合成（DOS）方法。我们的方法能够轻松合成稠合的N-杂环，螺氧基吲哚酮，四氢喹啉和稠合的N-杂环。两步序列从手性双环内酰胺指导的烯醇酸酯加成/取代步骤开始。此步骤之后，将环固定在内置支架亲电体上，从而导致立体选择性碳环和螺环形成。我们使用了计算机分析工具，根据化学多样性和选定的类药物特性来校准我们的化合物。我们通过在两种癌细胞系中筛选支架来评估其生物学意义。综上所述，我们的DOS方法提供了多种多样的新型支架，
• Improved Asymmetric S_NAr Reaction of β-Dicarbonyl Compounds Catalyzed by Quaternary Ammonium Salts Derived from Cinchona Alkaloids
  作者：Sara Kobbelgaard、Marco Bella、Karl Anker Jørgensen

  DOI：10.1021/jo060627l

  日期：2006.6.1

  limitation of the asymmetric nucleophilic aromatic substitution reaction of α-substituted 1,3-dicarbonyl compounds and activated aromatic systems catalyzed by N-benzyl-O-benzoylcinchoninium or cinchonidinium salts are presented. Several novel O-benzoylcinchona alkaloid derived salts have been prepared and evaluated as catalysts in this reaction, which can proceed with enantioselectivites up to 96% ee. Various

  提出了α-取代的1,3-二羰基化合物与N-苄基-O-苯甲酰基金鸡鎓盐或金鸡啶鎓盐催化的活化芳族体系的不对称亲核芳族取代反应的范围和局限性。几本新颖的O已经制备了-苯甲酰金鸡纳生物碱衍生的盐，并在该反应中作为催化剂进行了评估，该盐可以进行对映体选择性高达ee达96％的反应。评价了各种1，3-二羰基化合物和活化的芳族体系用于芳族亲核取代反应，并且发现产率和对映选择性非常依赖于底物和试剂。产物官能化为例如螺-氧代吲哚，1,3α，α-二取代的二羰基化合物与几种亲核试剂的开环反应以及旋光性S N中非对映选择性降低酮官能度的范围报告了Ar产品。