2-肼基-4-三氟甲基嘧啶 | 197305-97-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-肼基-4-三氟甲基嘧啶
• 英文名称: 2-hydrazino-4-(trifluoromethyl)pyrimidine
• 英文别名: 2-hydrazinyl-4-(trifluoromethyl)pyrimidine；[4-(trifluoromethyl)pyrimidin-2-yl]hydrazine
• CAS: 197305-97-8
• 化学式: C₅H₅F₃N₄
• 分子量: 178.117
• InChiKey: XQCAINVUBSAUBJ-UHFFFAOYSA-N

物化性质

• 熔点：
  99-101 °C(lit.)
• 沸点：
  187.4±50.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)
• 溶解度：
  溶于酸水溶液。
• 稳定性/保质期：
  常温常压下稳定，避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.8
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 危险等级：
  IRRITANT, IRRITANT-HARMFUL
• 危险等级：
  6.1
• 危险品标志：
  T
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R23/24/25,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933990090
• 危险品运输编号：
  UN 2811
• 危险标志：
  GHS06
• 危险性描述：
  H301,H311,H315,H319,H331,H335
• 危险性防范说明：
  P261,P280,P301 + P310,P305 + P351 + P338,P311
• 包装等级：
  III
• 危险类别：
  6.1
• 储存条件：
  密封储存，应存放在阴凉干燥的库房中。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 2-Hydrazino-4-(trifluoromethyl)pyrimidine
CAS-No. : 197305-97-8
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 3)
Acute toxicity, Dermal (Category 3)
Acute toxicity, Oral (Category 3)
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
Toxic 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 Danger
Hazard statement(s)
H301 Toxic if swallowed.
H311 Toxic in contact with skin.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H331 Toxic 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.
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
P311 Call a POISON CENTER or doctor/ physician.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R23/24/25 Toxic 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.
S36/37/39 Wear suitable protective clothing, gloves and eye/face protection.
S45 In case of accident or if you feel unwell, seek medical advice immediately
(show the label where possible).
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C5H5F3N4
Molecular Weight : 178,12 g/mol
Component Concentration
2-Hydrazino-4-(trifluoromethyl)pyrimidine
CAS-No. 197305-97-8 -

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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
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
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
Wear respiratory protection. 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.
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 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
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.
Immersion protection
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: > 480 min
Material tested:Dermatril® ( Z677272, Size M)
Splash protection
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: > 30 min
Material tested:Dermatril® ( Z677272, Size M)
data source: KCL GmbH, D-36124 Eichenzell, phone [phone], test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an Industrial Hygienist familiar with the specific situation of anticipated use by our
customers. It should not be construed as offering an approval for any specific use scenario.
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).

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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 Melting point/range: 99 - 101 °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) 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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation Toxic if inhaled. Causes respiratory tract irritation.
Ingestion Toxic if swallowed.
Skin
Toxic 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: 2811 IMDG: 2811 IATA: 2811
UN proper shipping name
ADR/RID: TOXIC SOLID, ORGANIC, N.O.S. (2-Hydrazino-4-(trifluoromethyl)pyrimidine)
IMDG: TOXIC SOLID, ORGANIC, N.O.S. (2-Hydrazino-4-(trifluoromethyl)pyrimidine)
IATA: Toxic solid, organic, n.o.s. (2-Hydrazino-4-(trifluoromethyl)pyrimidine)
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
no data available

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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：

  2-肼基-4-三氟甲基嘧啶 在 水 、 氧气 、 copper(II) sulfate 作用下， 反应 6.0h， 以82%的产率得到4-三氟甲基嘧啶
  参考文献：
  名称：

  Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO₄in water

  摘要：

  首次在催化量的CuSO4存在下实现了一步简单的脱氢反应。以CuSO4 (2 mol%)为催化剂，水为溶剂，脱氢产物获得了良好的产率（66-95%）。此外，成功合成了药物 nebularine 和 Vidarabine，并且 Vidarabine 可在0.923公斤规模生产，显示出良好的工业应用潜力。

  DOI：

  10.1039/c3gc41658e
• 作为产物：
  描述：

  2-氯-4-三氟甲基嘧啶 在 一水合肼 作用下， 以 乙醇 为溶剂， 以80%的产率得到2-肼基-4-三氟甲基嘧啶
  参考文献：
  名称：

  通过分子内 Diels-Alder 反应从 2-腙基嘧啶合成 7-氮杂-吲唑的预变形活化嘧啶

  摘要：

  在与烯烃和炔烃的 Diels-Alder 环加成反应中，嘧啶几乎是非反应性的伙伴，之前仅报道过在剧烈条件下的反应。我们描述了 2-腙基嘧啶，很容易从市售的 2-卤代嘧啶中分两步获得，如何通过三氟乙酰化异常活化。这允许在非常温和的反应条件下进行狄尔斯-阿尔德环加成反应，从而产生大量多样化的氮杂吲唑，这是药物化学中普遍存在的支架。该反应是通用的、可扩展的并且具有优异的官能团耐受性。拜耳 Vericiguat 关键中间体的直接合成说明了这种环加成策略的潜力。

  DOI：

  10.1021/jacs.9b07037

文献信息

• Metal-free One-pot Synthesis of 1,2,4-Triazolo[4,3-<i>a</i>]pyridines from 2-Hydrazinylpyridines
  作者：L. Madhava Reddy、V. Veerabadra Reddy、P. Sai Prathima、Ch. Krishna Reddy、B. V. Subba Reddy

  DOI：10.1002/adsc.201800512

  日期：2018.8.17

  A metal‐free one‐pot strategy has been developed for the synthesis of 3‐aryl[1,2,4]triazolo[4,3‐a]pyridines through an oxidative cyclization of 2‐(2‐arylidenehydrazinyl)pyridines by utilizing molecular iodine in DMSO. This is the first report on the synthesis of 3‐aroyl[1,2,4]triazolo[4,3‐a]pyridines directly from α‐aryl methyl ketones or ethyl benzoylacetate or styrenes or phenylacetylenes and 2‐hydrazinylpyridines

  已开发出一种无金属的单锅策略，该方法通过利用分子间的2-（2-亚芳基肼基嗪）吡啶的氧化环化反应来合成3-芳基[1,2,4]三唑并[4,3- a ]吡啶DMSO中的碘。这是第一个关于直接由α-芳基甲基酮或苯甲酰乙酸乙酯或苯乙烯或苯乙炔和2-羟基苯并吡啶经碘促进的氧化法合成3-芳基[1,2,4]三唑并[4,3- a ]吡啶的报告。环化。碘的催化使用使该方法相当简单，更加方便和经济。而且，该方案在温和的反应条件下显示了较宽的底物范围，可以取代危险金属试剂的使用。
• <i>o</i>-Iodoxybenzoic Acid (IBX) as a Viable Reagent in the Manipulation of Nitrogen- and Sulfur-Containing Substrates:  Scope, Generality, and Mechanism of IBX-Mediated Amine Oxidations and Dithiane Deprotections
  作者：K. C. Nicolaou、Casey J. N. Mathison、Tamsyn Montagnon

  DOI：10.1021/ja0400382

  日期：2004.4.28

  o-Iodoxybenzoic acid (IBX), a highly versatile hypervalent iodine(V) reagent, was found to efficiently mediate the dehydrogenation of amines in addition to facilitating the oxidative cleavage of dithioacetals and dithioketals. Through the development of relevant IBX-based protocols, a plethora of useful synthetic intermediates, including imines, oximes, ketones, and aromatic N-heterocycles, were found

  发现邻碘苯甲酸 (IBX) 是一种用途广泛的高价碘 (V) 试剂，除了促进二硫缩醛和二硫缩酮的氧化裂解外，还可以有效介导胺的脱氢。通过开发相关的基于 IBX 的协议，发现大量有用的合成中间体，包括亚胺、肟、酮和芳香族 N-杂环，在特别温和的条件下很容易获得。对这些转化的进一步研究导致了对有价值的机械细节的阐明，从而得出结论，它们是通过离子而不是单电子转移 (SET) 途径进行的。
• Thrombopoietin mimetics
  申请人：——

  公开号：US20040019190A1

  公开（公告）日：2004-01-29

  Invented are non-peptide TPO mimetics. Also invented are novel processes and intermediates used in the preparation of the presently invented compounds. Also invented is a method of treating thrombocytopenia, in a mammal, including a human, in need thereof which comprises administering to such mammal an effective amount of a selected hydroxy- 1 -azobenzene derivative.

  发明了非肽类TPO类似物。还发明了用于制备目前发明的化合物的新工艺和中间体。还发明了一种治疗血小板减少症的方法，包括给予需要的哺乳动物，包括人类，有效量的选择性羟基-1-偶氮苯衍生物。
• Synthesis of <i>ortho</i> -Azophenols by Formal Dehydrogenative Coupling of Phenols and Hydrazines or Hydrazides
  作者：Kenneth Virgel N. Esguerra、Jean-Philip Lumb

  DOI：10.1002/chem.201701226

  日期：2017.6.27

  synthesis, with applications as pigments and molecular switches. Herein, we describe a catalytic aerobic process that couples phenols and hydrazines or hydrazides for their synthesis. The key aromatic C-N bond is formed via condensation between the hydrazine or hydrazide and an ortho-quinone, which triggers a redox-isomerization to install the azo functionality. Notable features include rapid access to

  摘要：偶氮酚是有机合成中重要的生色团和试剂，具有颜料和分子开关的作用。在本文中，我们描述了一种催化好氧过程，该过程将苯酚和肼或酰肼偶联以进行合成。关键的芳族CN键是通过肼或酰肼与邻醌之间的缩合形成的，这会触发氧化还原异构化以安装偶氮官能团。显着的功能包括在使用简单的未活化底物的条件下，在室温下使用地球上存在的大量铜催化剂，可快速获得具有多种电子构型的高度官能化的偶氮酚，包括“推挽式”系统。 ，并产生水作为唯一的化学计量副产物。
• Layered Zirconium Sulfophenyl Phosphonate as Heterogeneous Catalyst in the Synthesis of Pyrazoles and 4,5,6,7-Tetrahydro-1(2)<i>H</i>-indazoles
  作者：Massimo Curini、Ornelio Rosati、Valerio Campagna、Francesca Montanari、Giancarlo Cravotto、Mauro Boccalini

  DOI：10.1055/s-2005-921904

  日期：——

  Pyrazoles and tetrahydroindazoles may be prepared by condensation of 1,3-diones and hydrazines under layered zirconium sulfophenyl phosphonate catalysis, in solvent-free conditions.

  吡唑和四氢吲哒唑可以通过在无溶剂条件下，层状锆磺苯膦酸盐催化剂的作用下，由1,3-二酮和肼缩合制备得到。