5-三氟甲基-1H-吡唑-4-羧酸 | 543739-84-0

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-三氟甲基-1H-吡唑-4-羧酸
• 中文别名: 3-三氟甲基-1H-吡唑-4-羧酸；5-三氟甲基-1H-吡唑-4-羧酸(CASNo.1259932-11-0)；3-三氟甲基吡唑-4-羧酸
• 英文名称: 5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid
• CAS: 543739-84-0
• 化学式: C₅H₃F₃N₂O₂
• 分子量: 180.086
• InChiKey: VHKMTORCXXPIFI-UHFFFAOYSA-N

物化性质

• 熔点：
  248-253°C
• 沸点：
  349.9±42.0 °C(Predicted)
• 密度：
  1.682±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

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：
  66
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P264,P270,P301+P310,P321,P330,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 3-(Trifluoromethyl)pyrazole-4-carboxylic acid
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.
CAS-No. : 543739-84-0
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
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)
H301 Toxic if swallowed.
Precautionary statement(s)
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C5H3F3N2O2
Molecular Weight : 180,01 g/mol
CAS-No. : 543739-84-0
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
3-(Trifluoromethyl)pyrazole-4-carboxylic acid
CAS-No. 543739-84-0 Acute Tox. 3; H301 <= 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
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 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.
Specific end use(s)
A part 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 Melting point/range: 248 - 253 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration 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
Other decomposition products - no data available
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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with
an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company.
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. (3-(Trifluoromethyl)pyrazole-4-carboxylic acid)
IMDG: TOXIC SOLID, ORGANIC, N.O.S. (3-(Trifluoromethyl)pyrazole-4-carboxylic acid)
IATA: Toxic solid, organic, n.o.s. (3-(Trifluoromethyl)pyrazole-4-carboxylic acid)
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
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
H301 Toxic if swallowed.
Full text of R-phrases referred to under sections 2 and 3
R25 Toxic if swallowed.
Further information
Copyright 2013 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.

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  3-三氟甲基吡唑-4-羧酸乙酯	ethyl 3-trifluoromethyl-1H-pyrazole-4-carboxylate	155377-19-8	C7H7F3N2O2	208.14

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3,4-bis(trifluoromethyl)-pyrazole	19968-19-5	C5H2F6N2	204.075

反应信息

• 作为反应物：
  描述：

  5-三氟甲基-1H-吡唑-4-羧酸 在 sulfur tetrafluoride 、 氢氟酸 作用下， 反应 12.0h， 以69%的产率得到3,4-bis(trifluoromethyl)-pyrazole
  参考文献：
  名称：

  “Reported, but Still Unknown.” A Closer Look into 3,4-Bis- and 3,4,5-Tris(trifluoromethyl)pyrazoles

  摘要：

  Straightforward practical synthetic approaches to 3,4-bis- and 3,4,5-tris(trifluoromethyl)pyrazoles have been developed. The key step of the both syntheses is a transformation of the carboxylic group in a pyrazole core into the trifluoromethyl group by sulfur tetrafluoride. The elaborated synthetic protocols allow gram-scale preparation of the target products. The obtained compounds are comprehensively characterized by means of crystallographic analysis, determination of pK(a) values and fluorescence measurements.

  DOI：

  10.1021/jo202305c
• 作为产物：
  描述：

  乙氧基-2-亚甲基三氟乙酰乙酸乙酯 在 lithium hydroxide 、 肼 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 5-三氟甲基-1H-吡唑-4-羧酸
  参考文献：
  名称：

  新型针对琥珀酸脱氢酶的抗真菌药物的权宜之计：带有二苯醚片段的吡唑-4-甲酰肼衍生物

  摘要：

  含有柔性酰胺链的吡唑-4-羧酰胺支架已经成为靶向琥珀酸脱氢酶（SDH）的高效农业杀菌剂的分子骨架。基于上述琥珀酸脱氢酶抑制剂（SDHI）的重要结构特征，在生物活性分子与SDH之间的虚拟对接比较的指导下，合理构思了三种新型的带有联苯醚部分的吡唑-4-甲酰肼衍生物。与分子对接比较的虚拟验证结果一致，体外抗真菌生物测定表明，标题化合物的骨架结构应优化为N '-（4-苯氧基苯基）-1 H-吡唑-4-碳酰肼支架。惊人地N '-（4-苯氧基苯基）-1 H-吡唑-4-碳酰肼衍生物对solani solani的影响11o，对禾谷镰刀菌（Fusarium graminearum）的11m和对灰葡萄孢的11g表现出优异的抗真菌作用，相应的EC 50值为0.14、0.27和0.52 μg/ mL，明显优于多菌灵（针对多菌灵（0.34μg / mL）和禾本科镰刀菌（0.57μg/ mL））和戊硫吡拉（对灰霉病）（0

  DOI：

  10.1021/acs.jafc.0c03736

文献信息

• Discovery of Pyrido[2,3-<i>b</i>]indole Derivatives with Gram-Negative Activity Targeting Both DNA Gyrase and Topoisomerase IV
  作者：Yimin Hu、Houguang Shi、Mingwei Zhou、Qingcheng Ren、Wei Zhu、Weixing Zhang、Zhiwei Zhang、Chengang Zhou、Yongqiang Liu、Xiao Ding、Hong C. Shen、S. Frank Yan、Fabian Dey、Waikwong Wu、Guanglei Zhai、Zheng Zhou、Zhiheng Xu、Ying Ji、Hua Lv、Tianyi Jiang、Wen Wang、Yunhua Xu、Maarten Vercruysse、Xiangyu Yao、Yi Mao、Xiaomin Yu、Kenneth Bradley、Xuefei Tan

  DOI：10.1021/acs.jmedchem.0c00768

  日期：2020.9.10

  2-carboxamide substituted azaindole chemical scaffold with only Gram-positive (GP) activity into a novel series with also potent activity against a range of MDR GN pathogens. By systematically fine-tuning the many physicochemical properties, we identified lead compounds such as 17r with a balanced profile showing potent GN activity, high aqueous solubility, and desirable PK features. Moreover, we showed the bactericidal

  耐多药（MDR）革兰氏阴性（GN）病原体的出现和可以有效治疗这些严重感染的可用抗生素的减少，是现代医学的主要威胁。开发针对MDR GN病原体的新型抗生素特别困难，因为化合物必须渗透到具有非常不同的理化特性的GN双膜中，并且必须规避过多的耐药机制，例如多重外排泵和靶标修饰。细菌II型拓扑异构酶DNA促旋酶（GyrA 2 B 2）和拓扑异构酶IV（ParC 2 E 2）是所有细菌物种中高度保守的靶标，在临床上已通过氟喹诺酮类药物验证。靶向II型拓扑异构酶ATPase域（GyrB / ParE）的双重抑制剂可以克服基于靶标的氟喹诺酮耐药性。但是，很少有ATPase抑制剂对GN病原体具有活性。在这项研究中，我们展示了一种成功的策略，可以将仅具有革兰氏阳性（GP）活性的2-羧酰胺取代的氮杂吲哚化学支架转变成对一系列MDR GN病原体也具有有效活性的新型系列。通过系统地微调许多理化性质，我们鉴定出了具
• Novel acyl coenzyme A (CoA): Diacylglycerol acyltransferase-1 inhibitors: Synthesis and biological activities of diacylethylenediamine derivatives
  作者：Yoshihisa Nakada、Thomas D. Aicher、Yvan Le Huerou、Timothy Turner、Scott A. Pratt、Stephen S. Gonzales、Steve A. Boyd、Hiroshi Miki、Toshihiro Yamamoto、Hiroshi Yamaguchi、Koki Kato、Shuji Kitamura

  DOI：10.1016/j.bmc.2010.01.067

  日期：2010.4

  A series of diacylethylenediamine derivatives were synthesized and evaluated for their inhibitory activity against DGAT-1 and pharmacokinetic profile to discover new small molecule DGAT-1 inhibitors. Among the compounds, N-[2-([1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]carbonyl}amino)ethyl]-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide 3x showed potent inhibitory activity and excellent PK profile

  合成了一系列二酰基乙二胺衍生物，并评估了其对DGAT-1的抑制活性和药代动力学，以发现新的小分子DGAT-1抑制剂。在化合物中，N- [2-（[1-苯基-3-（三氟甲基）-1 H-吡唑-4-基]羰基}氨基）乙基] -6-（2,2,2-三氟乙氧基）吡啶-3-羧酰胺3x显示出强大的抑制活性和出色的PK曲线。饮食引起的肥胖症小鼠口服3倍导致体重增加减少和白色脂肪组织重量减少。
• Inhibitors of 15-hydroxyprostaglandin dehydrogenase for stimulating pigmentation of the skin or skin appendages
  申请人：Michelet Jean-Francois

  公开号：US20060034786A1

  公开（公告）日：2006-02-16

  Inhibitors of 15-hydroxyprostaglandin dehydrogenase (15-PGDH), for example tetrazole, styrylpyrazole, phenylfuran, phenylthiophene, phenylpyrrazole, pyrazolecarboxamide, 2-thioacetamide and azo compounds, are useful for promoting or stimulating pigmentation of the skin and/or skin appendages and/or for preventing and/or for limiting depigmentation and/or whitening of the skin and/or skin appendages, notably for preventing and/or limiting canities.

  15-羟基前列腺素脱氢酶（15-PGDH）的抑制剂，例如四唑、苯基吡唑、苯基呋喃、苯基噻吩、苯基吡唑、吡唑羧酰胺、2-硫代乙酰胺和偶氮化合物，可用于促进或刺激皮肤和/或皮肤附属物的色素沉淀和/或预防和/或限制皮肤和/或皮肤附属物的脱色和/或变白，特别是用于预防和/或限制白发。
• A Dipolar Cycloaddition Reaction To Access 6-Methyl-4,5,6,7-tetrahydro-1<i>H</i>-[1,2,3]triazolo[4,5-<i>c</i>]pyridines Enables the Discovery Synthesis and Preclinical Profiling of a P2X7 Antagonist Clinical Candidate
  作者：Christa C. Chrovian、Akinola Soyode-Johnson、Alexander A. Peterson、Christine F. Gelin、Xiaohu Deng、Curt A. Dvorak、Nicholas I. Carruthers、Brian Lord、Ian Fraser、Leah Aluisio、Kevin J. Coe、Brian Scott、Tatiana Koudriakova、Freddy Schoetens、Kia Sepassi、David J. Gallacher、Anindya Bhattacharya、Michael A. Letavic

  DOI：10.1021/acs.jmedchem.7b01279

  日期：2018.1.11

  7-tetrahydro-5H-[1,2,3]triazolo[4,5-c]pyridine P2X7 antagonists that contain a synthetically challenging chiral center. The structure–activity relationships of the new compounds are described. Two of these compounds, (S)-(2-fluoro-3-(trifluoromethyl)phenyl)(1-(5-fluoropyrimidin-2-yl)-6-methyl-1,4,6,7-tetrahydro-5H-[1,2,3]triazolo[4,5-c]pyridin-5-yl)methanone (compound 29) and (S)-(3-fluoro-2-(trifluoromet

  开发了一个单锅偶极环加成反应/ Cope消除序列，以访问新颖的1,4,6,7-四氢-5 H- [1,2,3]三唑[4,5- c ]吡啶P2X7拮抗剂，该拮抗剂包含合成的具有挑战性的手性中心。描述了新化合物的结构-活性关系。这些化合物中的两种，（S）-（2-氟-3-（三氟甲基）苯基）（1-（5-氟嘧啶-2-基）-6-甲基-1,4,6,7-四氢-5 H -[1,2,3]三唑并[4,5 - c ]吡啶-5-基）甲酮（化合物29）和（S）-（3-氟-2-（三氟甲基）吡啶-4-基）（1 -（5-氟嘧啶-2-基）-6-甲基-1,4,6,7-四氢-5 H- [1,2,3]三唑[4,5- c在低剂量下，发现大鼠吡啶[5-吡啶基]甲酮（化合物35）具有很强的P2X7受体占有率，ED 50值分别为0.06和0.07 mg / kg。与29相比，化合物35的溶解度显着，并且对临床前物种显示出良好的耐受性。选择化
• Ccr5 antagonists as therapeutic agents
  申请人：Kazmierski Mieczyslaw Wieslaw

  公开号：US20060229336A1

  公开（公告）日：2006-10-12

  The present invention relates to compounds of formula (I) or a pharmaceutically acceptable derivatives thereof, useful in the treatment of prophylazis of CCR5-related diseases and disorders, for example, in the inhibition of HIV replication, the prevention or treatment of HIV infection, and in the treatment of the resulting acquired immune deficiency syndrome (AIDS).

  本发明涉及式(I)化合物或其药学上可接受的衍生物，用于预防CCR5相关疾病和障碍的治疗，例如，抑制HIV复制，预防或治疗HIV感染，以及治疗由此产生的获得性免疫缺陷综合症（AIDS）。