2-羟基-6-(2-噻吩)-4-三氟甲基烟腈 | 3335-45-3

• 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-羟基-6-(2-噻吩)-4-三氟甲基烟腈
• 英文名称: 2-oxo-6-(thiophen-2-yl)-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 2-hydroxy-6-thiophen-2-yl-4-(trifluoromethyl)pyridine-3-carbonitrile
• CAS: 3335-45-3
• 化学式: C₁₁H₅F₃N₂OS
• mdl: MFCD00741364
• 分子量: 270.235
• InChiKey: UBBGOCKMIMCHLZ-UHFFFAOYSA-N

物化性质

• 熔点：
  278°C
• 沸点：
  390.2±42.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 危险品运输编号：
  UN 3439

SDS

Name:	2-Hydroxy-6-(2-thienyl)-4-(trifluoromethyl)nicotinonitrile 97% Material Safety Data Sheet
Synonym:
CAS:	3335-45-3

Section 1 - Chemical Product MSDS Name:2-Hydroxy-6-(2-thienyl)-4-(trifluoromethyl)nicotinonitrile 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3335-45-3	2-Hydroxy-6-(2-thienyl)-4-(trifluorome	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. May cause respiratory tract irritation.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 3335-45-3: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 293 - 295 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C11H5F3N2OS
Molecular Weight: 270

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids, bases, oxidizing agents, acid chlorides.
Hazardous Decomposition Products:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide, fluorine, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3335-45-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Hydroxy-6-(2-thienyl)-4-(trifluoromethyl)nicotinonitrile - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: NITRILES, SOLID, TOXIC, N.O.S.*
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
IMO
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
RID/ADR
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 3335-45-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3335-45-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3335-45-3 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-羟基-6-(2-噻吩)-4-三氟甲基烟腈 在 potassium carbonate 、 potassium iodide 、 氯乙酰胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到2-amino-6-(thiophen-2-yl)-4-(trifluoromethyl)nicotinonitrile
  参考文献：
  名称：

  简单的一锅合成新型三环喹唑啉酮

  摘要：

  从蒽醌和由TsOH·H 2 O促进的1,3-环二酮开始，已经完成了一系列三环喹唑啉酮的合成。本文提出的方案基于Retro-Dieckmann型反应，导致将二酮作为无环单元掺入产品。简单的反应条件，广泛的范围，优异的收率是该方案的优点。此外，该方法学扩展至吡啶并嘧啶酮和苯并咪唑并吡啶的合成。

  DOI：

  10.1016/j.tetlet.2017.01.106
• 作为产物：
  描述：

  2-乙酰基噻吩 在 三乙烯二胺 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 生成 2-羟基-6-(2-噻吩)-4-三氟甲基烟腈
  参考文献：
  名称：

  Discovery and structure–activity relationships study of novel thieno[2,3-b]pyridine analogues as hepatitis C virus inhibitors

  摘要：

  Current treatment for hepatitis C is barely satisfactory, there is an urgent need to develop novel agents for combating hepatitis C virus infection. This study discovered a new class of thieno[ 2,3-b] pyridine derivatives as HCV inhibitors. First, a hit compound characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. And then, structure activity relationship study of the hit compound led to the discovery of several potent compounds without obvious cytotoxicity in vitro (12c, EC50 = 3.3 mu M, SI > 30.3, 12b, EC50 = 3.5 mu M, SI > 28.6, 10l, EC50 = 3.9 mu M, SI > 25.6, 12o, EC50 = 4.5 mu M, SI > 22.2, respectively). Although the mechanism of them had not been clearly elucidated, our preliminary optimization of this class of compounds had provided us a start point to develop new anti-HCV agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.075

文献信息

• Synthesis of novel isoxazole functionalized pyrazolo[3,4‐ <i>b</i> ]pyridine derivatives; their anticancer activity
  作者：Sampath Ravula、Ramana Reddy Bobbala、Balakrishna Kolli

  DOI：10.1002/jhet.3968

  日期：2020.6

  A series of novel isoxazole functionalized pyrazolo[3,4‐b]pyridine derivatives 5a‐n were prepared, respectively, initiated from 6‐thiophenyl‐4‐(trifluoromethyl)‐1H ‐pyrazolo[3,4‐b ]pyridin‐3‐amine 3 through selective N ‐propargylation, and these N ‐propargylated compounds 4 were cyclized with aryloximes by using of sodium hypochlorite, and obtained the title products 5a‐n . All the final products 5a‐n

  一系列新颖的异恶唑官能吡唑并[3,4-b]吡啶衍生物的图5a-n的制备，分别从6-噻吩基-4-（三氟甲基）-1发起ħ -吡唑并[3,4- b ]吡啶-3-胺3通过选择性N炔丙基化，而这些N炔丙基化的化合物4通过使用次氯酸钠与芳基肟环合，获得标题产物5a-n。所有最终产品5a‐n已提交针对四种癌细胞系（例如“ HeLa-宫颈癌（CCL-2）”）的抗癌活性；COLO 205-结肠癌（CCL‐222）；HepG2-肝癌（HB-8065）；MCF7-乳腺癌（HTB-22）”；发现化合物5c，5d和5h在微摩尔浓度下具有更突出的抗癌活性。
• Green Synthetic Approach and Antimicrobial Evaluation for Some Novel Pyridyl Benzoate Derivatives
  作者：H. A. Eldeab

  DOI：10.1134/s1070428019070200

  日期：2019.7

  4-chlorobenzoates have been synthesized by microwave-assisted condensation of the corresponding 2-oxo-1,2-dihydropyridine-3-carbonitriles with 4-chlorobenzoyl chloride under solvent-free conditions. Alternatively, some compounds have also been prepared by conventional heating in methylene chloride in the presence of triethylamine. The structure of the synthesized compounds has been confirmed by spectral data (FTIR

  在无溶剂的条件下，通过微波辅助缩合相应的2-oxo-1,2-二氢吡啶-3-腈与4-氯苯甲酰氯，合成了两个系列的4-氯苯甲酸吡啶基酯。或者，还通过在三乙胺存在下在二氯甲烷中常规加热来制备一些化合物。合成化合物的结构已通过光谱数据（FTIR，1D和2D NMR）证实。评价了新的苯甲酸吡啶基酯对革兰氏阴性和革兰氏阳性细菌的抗菌活性。3-氰基-5-[（4-羟基苯基）二氮烯基] -4-甲基-6-苯基吡啶-2-基4-氯苯甲酸酯对革兰氏阳性细菌（枯草芽孢杆菌和金黄色葡萄球菌）的活性）与用作标准抗生素的丁胺卡那霉素相当。
• Synthesis and reactions of 4-trifluoromethyl-3-cyano pyridine-2(<i>1H</i>)-thione/one derivatives
  作者：Nora M. Rateb

  DOI：10.1080/17415993.2011.628994

  日期：2011.12.1

  cyanothioacetamide and cyanoacetamide under solvent-free conditions at 25 °C to give pyridine-2(1H)thione/one derivatives in excellent yields. These compounds were further reacted by grinding with different halogenated reagents to give 2-S/O-alkyl pyridine derivatives. The latter compounds were utilized for the synthesis of thieno[2,3-b]pyridine, pyrazolopyridine, pyridothienopyrimidine and pyridothienooxazinone

  4,4,4-Trifluoro-1-(thiophen-2-yl)butane-1,3-dione 通过与氰硫代乙酰胺和氰基乙酰胺在 25 °C 无溶剂条件下研磨反应得到吡啶-2(1H) 硫酮/one 衍生物以优异的产量。这些化合物通过与不同的卤化试剂研磨进一步反应，得到 2-S/O-烷基吡啶衍生物。后一种化合物用于合成噻吩并[2,3-b]吡啶、吡唑并吡啶、吡啶并噻吩并嘧啶和吡啶并噻吩并恶嗪酮衍生物。
• Synthesis and antimicrobial activity of 4-trifluoromethylpyridine nucleosides
  作者：Shaikha S. Alneyadi、Anas A. Abdulqader、Alaa A. Salem、Ibrahim M. Abdou

  DOI：10.1515/hc-2017-0019

  日期：2017.6.27

  discovery of new antibacterial agents. Fluorinated pyridine nucleosides 4–7 and non-nucleoside analogues 8a,b were synthesized and evaluated for their antibacterial activities against Staphylococcus aureus, Bacillus infantis, Escherichia coli and Stenotrophomonas maltophilia. The minimum inhibitory concentrations (MICs) of the new nucleosides 4–7 range from 1.3 to 4.9 μg/mL and MICs of fluoroaryl derivatives

  摘要 4-三氟甲基吡啶衍生物 4-8 是发现新抗菌剂的良好候选物。合成了氟化吡啶核苷 4-7 和非核苷类似物 8a、b，并评估了它们对金黄色葡萄球菌、婴儿芽孢杆菌、大肠杆菌和嗜麦芽窄食单胞菌的抗菌活性。新核苷 4-7 的最低抑菌浓度 (MIC) 范围为 1.3 至 4.9 μg/mL，氟芳基衍生物 8a、b 的最低抑菌浓度 (MIC) 范围为 1.8-5.5 μg/mL。在类似条件下，参考药物阿莫西林的活性为 1.0–2.0 μg/mL。
• Synthesis of novel hetero ring fused pyridine derivatives; Their anticancer activity, CoMFA and CoMSIA studies
  作者：G. Santhosh Kumar、Y. Poornachandra、Shravan Kumar Gunda、K. Ratnakar Reddy、Jaheer Mohmed、Kamal Shaik、C. Ganesh Kumar、B. Narsaiah

  DOI：10.1016/j.bmcl.2018.04.031

  日期：2018.7

  and 8a-h were screened against four human cancer cell lines (HeLa, COLO205, Hep G2 and MCF 7) and one normal cell line (HEK 293). Compounds 4e, 4f, 4g, 5h, 7c, 7d, 7e and 7f showed significant anticancer activity against all the cell lines at micro molar concentration and found to be non-toxic to normal cell line. Studies for HeLa, COLO205 and MCF-7 using CoMFA and CoMSIA. Models from 3D-QSAR provided

  一系列新颖的呋喃并[2,3-b]吡啶-2-甲酰胺4a-h /吡啶并[3'，2'：4,5]呋喃并[3,2-d]嘧啶-4（3H）-衍生物由吡啶2（1H）1通过与α-溴乙基酯的选择性O-烷基化，然后环化，然后与不同的脂族伯胺反应获得4，再与原乙酸三乙酯/原甲酸三乙酯反应，制得5a-p。还制备了新颖的呋喃[2,3-b]吡啶-2-碳酰肼席夫碱7a-h和吡啶基[3'，2'：4,5]呋喃[3,2-d]嘧啶-4（3H）-衍生物8a-h由呋喃[2,3-b]吡啶羧酸酯衍生物3开始，与水合肼反应形成6，并与各种取代的醛反应并环化。针对4种人类癌细胞系（HeLa，COLO205，Hep G2和MCF 7）和一种正常细胞系（HEK 293）。化合物4e，4f，4g，5h，7c，7d，7e和7f在微摩尔浓度下对所有细胞系均表现出显着的抗癌活性，并且对正常细胞系无毒。使用CoMFA和CoMSIA研究HeLa，COLO2