2,3,5,6-四氟吡啶-4-腈 | 16297-07-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2,3,5,6-四氟吡啶-4-腈
• 中文别名: 2,3,5,6-四氟-4-吡啶甲腈
• 英文名称: 2,3,5,6-tetrafluoro-4-pyridinecarbonitrile
• 英文别名: 2,3,5,6-tetrafluoropyridine-4-carbonitrile；4-cyanotetrafluoropyridine；4-cyano-2,3,5,6-tetrafluoropyridine；2,3,5,6-tetrafluoroisonicotinonitrile；2,3,5,6-tetrafluoro-4-cyanopyridine
• CAS: 16297-07-7
• 化学式: C₆F₄N₂
• mdl: MFCD00075302
• 分子量: 176.073
• InChiKey: JXISJBVJNUKKBK-UHFFFAOYSA-N

物化性质

• 熔点：
  66-68 °C (lit.)
• 沸点：
  166.1±35.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  按规定使用这些物质不会分解，并且它们能避免与氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 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：
  36.7
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xn,Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R20/21/22
• WGK Germany：
  3
• 危险标志：
  GHS07
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 危险性防范说明：
  P261,P280,P305 + P351 + P338
• 储存条件：
  请将药品存放在密闭、阴凉、干燥的地方。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 2,3,5,6-Tetrafluoro-4-pyridinecarbonitrile
CAS-No. : 16297-07-7
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
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Inhalation (Category 4)
Acute toxicity, Dermal (Category 4)
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 by inhalation, in contact with skin and 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.
H312 Harmful in contact with skin.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H332 Harmful if inhaled.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P280 Wear protective gloves/ protective clothing.
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)
R20/21/22 Harmful by inhalation, in contact with skin and 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.
S37/39 Wear suitable gloves and eye/face protection.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C6F4N2
Molecular Weight : 176,07 g/mol
Component Concentration
2,3,5,6-Tetrafluoro-4-pyridinecarbonitrile
CAS-No. 16297-07-7 -

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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. 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

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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, Hydrogen cyanide (hydrocyanic acid)
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
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.

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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.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 use(s)
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
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).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: crystalline
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 66 - 68 °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- 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
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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation Harmful if inhaled. Causes respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin 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

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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. 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.

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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

制备方法与用途

2,3,5,6-四氟-4-吡啶甲腈是一种全氟化芳杂环化合物，通常被称为四氟-4-氰基吡啶。它能与1,3-二羰基体系反应生成相应的5,6环稠合呋喃衍生物。此外，2,3,5,6-四氟-4-吡啶甲腈还能与脒反应，在吡啶环的C-3位进行亲核取代，并在分子内环化到侧链氰基上，从而形成6,6稠合的嘧啶并吡啶体系。据报道，这种化合物还能够与以硫为中心的亲核试剂发生反应。

反应信息

• 作为反应物：
  描述：

  2,3,5,6-四氟吡啶-4-腈 在 sodium tetrahydroborate 、 二异丁基氢化铝 作用下， 以 甲醇 、 乙醚 、 正己烷 为溶剂， 生成 2,3,5,6-tetrafluoro-4-(1-hydroxymethyl)pyridine
  参考文献：
  名称：

  合成四（多氟-4-吡啶基）卟啉衍生物作为乙酰胆碱酯酶抑制剂。

  摘要：

  合成了新的四（多氟-4-吡啶基）卟啉衍生物（2-4）和水溶性卟啉（5），以研究它们与鳗鱼中乙酰胆碱酯酶的相互作用。已经发现这些化合物是Ki值为microM范围的有效的可逆酶抑制剂。此外，卟啉（5）显示出广泛的抗癌活性。

  DOI：

  10.1016/s0960-894x(00)00254-7
• 作为产物：
  描述：

  4-氰基吡啶 在 potassium fluoride 、 五氯化磷 作用下， 反应 20.0h， 生成 2,3,5,6-四氟吡啶-4-腈
  参考文献：
  名称：

  Synthesis of some fluorine-containing pyridinealdoximes of potential use for the treatment of organophosphorus nerve-agent poisoning

  摘要：

  Fluoroheterocyclic aldoximes were screened as therapeutic agents for the treatment of anticholinesterase poisoning. 2-Fluoropyridine-3- and -6-aldoxime, and 3-fluoropyridine-2- and -4-aldoxime, were synthesised. Attempts to obtain 3,5,6-trifluoropyridine-2,4-bis(aldoxime) and -2-aldoxime, however, proved unsuccessful. Pentafluorobenzaldoxime was prepared by oximation of pentafluorobenzaldehyde. Acid dissociation constants (pK(a)) and second-order rate constants (k(ox)-) of the fluorinated pyridinealdoximes towards satin were measured. 2,3,5,6-Tetrafluoropyridine-4-aldoxime had the best profile: its k(ox)- approached that of the therapeutic oxime P2S (310 vs. 120 l mol(-1) min(-1)), but its higher pK(a) (9.1 vs. 7.8) fell short of the target figure of 8 required for reactivation of inhibited acetylcholinesterase in vivo. N-alkylation of the fluorinated pyridine-aldoximes may reduce their pK(a) nearer to 8 and enhance their therapeutic potential. Crown Copyright (c) 2011 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.05.028

文献信息

• Highly Chemoselective CarbonCarbon σ-Bond Activation: Nickel/Lewis Acid Catalyzed Polyfluoroarylcyanation of Alkynes
  作者：Yasunori Minami、Hirofumi Yoshiyasu、Yoshiaki Nakao、Tamejiro Hiyama

  DOI：10.1002/anie.201207880

  日期：2013.1.14

  Selective CC bond cleavage: A catalyst consisting of nickel(0)/DPEphos and BPh3 is highly effective for the addition of polyfluorobenzonitriles to alkynes through selective activation of the CCN bond over the CH or CF bonds. The addition reaction is applicable to the sequential insertion of two different alkynes into CCN and CH bonds (see scheme).

  选择性CC键裂解：由镍（0）/ DPEphos和BPh 3组成的催化剂通过在CH或CF键上选择性激活CCN键，对于将多氟苄腈加成炔烃非常有效。加成反应适用于将两个不同的炔烃依次插入CCN和CH键（参见方案）。
• Pyrido[3,2-b][1,4]oxazine and pyrido[2,3-b][1,4]benzoxazine systems from tetrafluoropyridine derivatives
  作者：Graham Sandford、Rachel Slater、Dmitrii S. Yufit、Judith A.K. Howard、Antonio Vong

  DOI：10.1016/j.jfluchem.2014.05.003

  日期：2014.11

  Pyrido[3,2-b][1,4]oxazine and pyrido[2,3-b][1,4]benzoxazine systems were synthesised by annelation reactions involving highly fluorinated pyridine derivatives and nitrogen and oxygen centred difunctional nucleophiles by sequential regioselective nucleophilic aromatic substitution processes.

  吡啶并[3,2-B] [1,4]恶嗪和吡啶并[2,3-B] [1,4]苯并恶嗪系统是通过涉及通过顺序区域选择性高度氟化的吡啶衍生物和氮和氧为中心的双官能亲核成环反应合成亲核芳香取代过程。
• Fluorinated Aromatic Monomers as Building Blocks To Control α-Peptoid Conformation and Structure
  作者：Diana Gimenez、Guangfeng Zhou、Matthew F. D. Hurley、Juan A. Aguilar、Vincent A. Voelz、Steven L. Cobb

  DOI：10.1021/jacs.8b13498

  日期：2019.2.27

  biomaterials. However, obtaining stable secondary structures is challenging, and designing these requires effective control of the peptoid tertiary amide cis/trans equilibrium. Herein, we report new fluorine-containing aromatic monomers that can control peptoid conformation. Specifically, we demonstrate that a fluoro-pyridine group can be used to circumvent the need for monomer chirality to control the cis/trans

  Peptoids 是药物开发和生物材料领域感兴趣的肽模拟物。然而，获得稳定的二级结构具有挑战性，设计这些需要有效控制拟肽叔酰胺顺/反平衡。在此，我们报告了可以控制拟肽构象的新型含氟芳香单体。具体来说，我们证明了氟-吡啶基团可用于规避单体手性来控制顺式/反式平衡的需要。我们还表明，在单体的 α-碳上掺入三氟甲基（NCF3Rpe）而不是甲基（NRpe）会使顺式异构体偏好增加 5 倍。
• Imidazopyridine and pyrimidinopyridine systems from perfluorinated pyridine derivatives
  作者：Matthew W. Cartwright、Graham Sandford、Jamaal Bousbaa、Dmitrii S. Yufit、Judith A.K. Howard、John A. Christopher、David D. Miller

  DOI：10.1016/j.tet.2007.05.016

  日期：2007.7

  gave a [6,6]-fused pyrimidinopyridine system arising from initial nucleophilic substitution at the C-3 position of the pyridine ring followed by intramolecular cyclization onto the pendant cyano group. The systems prepared by this annelation methodology further demonstrate the utility of perfluorinated heterocyclic substrates for the synthesis of heterocyclic scaffolds that possess multiple functionality

  通过分子内亲核芳族取代过程与苯甲idine胺进行五氟吡啶退火，可分两步以高收率得到咪唑并吡啶体系，而烷基am通过竞争性消除反应得到4-氨基四氟吡啶。4-苯基磺酰基四氟吡啶与am反应生成相应的咪唑并[4,5- b]吡啶体系。相反，4-氰基四氟吡啶产生[6,6]-融合的嘧啶二吡啶体系，这是由于在吡啶环的C-3位置发生了最初的亲核取代，随后分子内环化到了氰基侧基上。通过这种脱核方法制备的系统进一步证明了全氟化杂环底物在合成具有多种功能并在药物发现领域具有潜在应用的杂环支架上的实用性。
• 一种热激活延迟荧光材料的合成方法及其应 用
  申请人：南京工业大学

  公开号：CN104387369B

  公开（公告）日：2017-09-08

  本发明开发了一种原料廉价易得，无需加入贵金属催化剂，操作简便，反应条件温和，生产成本低，产率高，便于商业化的一步法合成氰基吡啶和咔唑类化合物的方法，涉及有机电致发光材料领域，具体涉及一步法合成一种热激活延迟荧光材料及将其作为OLED器件的发光层。