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4-Fluorophenyl isothiocyanate is an organic compound that serves as a valuable intermediate in the synthesis of various chemical compounds, particularly thiourea derivatives and -(4-phenylsulfonyl)-benzoic acid hydrazide. It is characterized by its clear yellow appearance in its liquid state after melting.

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  • 1544-68-9 Structure
  • Basic information

    1. Product Name: 4-FLUOROPHENYL ISOTHIOCYANATE
    2. Synonyms: 1-fluoro-4-isothiocyanato-benzen;Isothiocyanic acid, p-fluorophenyl ester;isothiocyanicacid,p-fluorophenylester;p-Fluorophenyl isothiocyanate;4-FLUOROPHENYL ISOTHIOCYANATE 98%;Isothiocyanic Acid 4-Fluorophenyl Ester;Isothiocyanic acid p-fluorophenyl;4-Fluorophenyl isothiocyanate,98%
    3. CAS NO:1544-68-9
    4. Molecular Formula: C7H4FNS
    5. Molecular Weight: 153.18
    6. EINECS: 216-280-4
    7. Product Categories: Phenyls & Phenyl-Het;Phenyl isocyanate&Phenyl isothiocyanate;Phenyls & Phenyl-Het;Organic Building Blocks;Sulfur Compounds;Thiocyanates/Isothiocyanates;Fluorine series
    8. Mol File: 1544-68-9.mol
  • Chemical Properties

    1. Melting Point: 24-26 °C(lit.)
    2. Boiling Point: 228 °C(lit.)
    3. Flash Point: 193 °F
    4. Appearance: White crystalline power
    5. Density: 1.25
    6. Vapor Pressure: 0.134mmHg at 25°C
    7. Refractive Index: 1.6195-1.6215
    8. Storage Temp.: 0-6°C
    9. Solubility: N/A
    10. Sensitive: Moisture Sensitive
    11. BRN: 636596
    12. CAS DataBase Reference: 4-FLUOROPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
    13. NIST Chemistry Reference: 4-FLUOROPHENYL ISOTHIOCYANATE(1544-68-9)
    14. EPA Substance Registry System: 4-FLUOROPHENYL ISOTHIOCYANATE(1544-68-9)
  • Safety Data

    1. Hazard Codes: C,T,Xi
    2. Statements: 34-42
    3. Safety Statements: 23-26-36/37-39-45
    4. RIDADR: UN 1759 8/PG 2
    5. WGK Germany: 3
    6. RTECS: NX8760000
    7. F: 10-21-19
    8. TSCA: T
    9. HazardClass: 8
    10. PackingGroup: III
    11. Hazardous Substances Data: 1544-68-9(Hazardous Substances Data)

1544-68-9 Usage

Uses

Used in Chemical Synthesis:
4-Fluorophenyl isothiocyanate is used as a key intermediate in the synthesis of thiourea derivatives, which are important compounds in the pharmaceutical and chemical industries. These derivatives exhibit a wide range of applications, including their use as agrochemicals, pharmaceuticals, and dyes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Fluorophenyl isothiocyanate is used as a starting material for the preparation of -(4-phenylsulfonyl)-benzoic acid hydrazide. 4-FLUOROPHENYL ISOTHIOCYANATE has potential applications in the development of new drugs, particularly those targeting various diseases and conditions.
Used in Research and Development:
4-Fluorophenyl isothiocyanate is also utilized in research and development settings, where it is employed to explore new chemical reactions and synthesize novel compounds with potential applications in various industries, such as agriculture, pharmaceuticals, and materials science.

Check Digit Verification of cas no

The CAS Registry Mumber 1544-68-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,4 and 4 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1544-68:
(6*1)+(5*5)+(4*4)+(3*4)+(2*6)+(1*8)=79
79 % 10 = 9
So 1544-68-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H5F2NO2/c8-7(9)11-5-2-1-4(10)3-6(5)12-7/h1-3H,10H2

1544-68-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (A15561)  4-Fluorophenyl isothiocyanate, 98%   

  • 1544-68-9

  • 5g

  • 257.0CNY

  • Detail
  • Alfa Aesar

  • (A15561)  4-Fluorophenyl isothiocyanate, 98%   

  • 1544-68-9

  • 25g

  • 1258.0CNY

  • Detail
  • Aldrich

  • (128406)  4-Fluorophenylisothiocyanate  98%

  • 1544-68-9

  • 128406-5G

  • 409.50CNY

  • Detail

1544-68-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Fluorophenyl Isothiocyanate

1.2 Other means of identification

Product number -
Other names Isothiocyanic Acid 4-Fluorophenyl Ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1544-68-9 SDS

1544-68-9Relevant articles and documents

Synthesis and biological activities of hydroxyl-protected fluorine-containing 4,4-dihydroxylmethyl-2-aryl-iminothiazolidines

Liu, Chuanxiang,Xu, Xiaoyong,Li, Zhong,Chen, Weidong,Huang, Qingchun,Qian, Xuhong

, p. 53 - 58 (2005)

Eight novel compounds were synthesized by a facile and mild method with high yields, and the structures of all the compounds were characterized by 1H NMR IR mass and high resolution mass spectroscopy. Their inhibitory activity against insect-flight and trehalase in vitro were screened. Some target compounds have moderate inhibitory activity against trehalase, and show inhibition action to insect-flight.

Synthesis of isothiocyanates using DMT/NMM/TsO? as a new desulfurization reagent

Janczewski, ?ukasz,Kolesińska, Beata,Kr?giel, Dorota

, (2021/05/29)

Thirty-three alkyl and aryl isothiocyanates, as well as isothiocyanate derivatives from esters of coded amino acids and from esters of unnatural amino acids (6-aminocaproic, 4-(aminomethyl)benzoic, and tranexamic acids), were synthesized with satisfactory or very good yields (25–97%). Synthesis was performed in a “one-pot”, two-step procedure, in the presence of organic base (Et3 N, DBU or NMM), and carbon disulfide via dithiocarbamates, with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO? ) as a desulfurization reagent. For the synthesis of aliphatic and aromatic isothiocyanates, reactions were carried out in a microwave reactor, and selected alkyl isothiocyanates were also synthesized in aqueous medium with high yields (72–96%). Isothiocyanate derivatives of L-and D-amino acid methyl esters were synthesized, under conditions without microwave radiation assistance, with low racemization (er 99 > 1), and their absolute configuration was confirmed by circular dichroism. Isothiocyanate derivatives of natural and unnatural amino acids were evaluated for antibacterial activity on E. coli and S. aureus bacterial strains, where the most active was ITC 9e.

A catalyst-free method for the synthesis of 1,4,2-dithiazoles from isothiocyanates and hydroxylamine triflic acid salts

An, Zhenyu,Liu, Yafeng,Ren, Yi,Wang, Ting,Yan, Rulong

supporting information, p. 6206 - 6209 (2021/07/28)

A catalyst-free method for the preparation of 1,4,2-dithiazoles is developed by reactions of isothiocyanates with hydroxylamine triflic acid salts. This reaction achieves C-S, C-N, and S-N bond formation, and a range of products are obtained in moderate to good yields. The obvious feature is using shelf-stable hydroxylamine triflic acid salts as a N source to synthesize heterocycles under mild conditions.

NaOH-promoted one-pot aryl isothiocyanate synthesis under mild benchtop conditions

Li, Hang,Liu, Xinyun,Yin, Xiaogang

supporting information, p. 839 - 844 (2021/05/27)

In this work, we have established a green synthesis of aryl isothiocyanates promoted by the low-cost and readily available NaOH from aryl amines and carbon disulfide in a one-pot procedure. The developed protocol features no extra desulfurating reagents and mild benchtop conditions, in which NaOH serves as both the base and the desulfurating reagent to decompose the dithiocarbamate intermediate. Fourteen examples of aryl amines bearing electronic neutral, rich and poor substituents, as well as benzylamine, have proved to be compatible substrates in the developed method to furnish the corresponding isothiocyanates. The reaction has been performed on a gram scale to further demonstrate its synthetic utility. Compared to the reported base-promoted synthesis of aryl isothiocyanates that requires the use of special equipment, such as the ball mill or the microwave reactor, the simplicity in operation and scalability enables this method to efficiently access a variety of aryl isothiocyanates.

Discovery of boronic acid-based potent activators of tumor pyruvate kinase M2 and development of gastroretentive nanoformulation for oral dosing

Patle, Rajkumar,Shinde, Shital,Patel, Sagarkumar,Maheshwari, Rahul,Jariyal, Heena,Srivastava, Akshay,Chauhan, Neelam,Globisch, Christoph,Jain, Alok,Tekade, Rakesh K.,Shard, Amit

, (2021/05/19)

Several studies have established that cancer cells explicitly over-express the less active isoform of pyruvate kinase M2 (PKM2) is critical for tumorigenesis. The activation of PKM2 towards tetramer formation may increase affinity towards phosphoenolpyruvate (PEP) and avoidance of the Warburg effect. Herein, we describe the design, synthesis, and development of boronic acid-based molecules as activators of PKM2. The designed molecules were inspired by existing anticancer scaffolds and several fragments were assembled in the derivatives. 6a-6d were synthesized using a multi-step synthetic strategy in 55–70% yields, starting from cheap and readily available materials. The compounds were selectively cytotoxic to kill the cancerous cells at 80 nM, while they were non-toxic to the normal cells. The kinetic studies established the compounds as novel activators of PKM2 and (E/Z)-(4-(3-(2-((4-chlorophenyl)amino)-4-(dimethylamino)thiazol-5-yl)-2-(ethoxycarbonyl)-3-oxoprop-1-en-1-yl) phenyl)boronic acid (6c) emerged as the most potent derivative. 6c was further evaluated using various in silico tools to understand the molecular mechanism of tetramer formation. Docking studies revealed that 6c binds to the PKM2 dimer at the dimeric interface. Further to ascertain the binding site and mechanism of action, rigorous MD (molecular dynamics) simulations were undertaken, which led to the conclusion that 6c stabilizes the center of the dimeric interface that possibly promotes tetramer formation. We further planned to make a tablet of the developed molecule for oral delivery, but it was seriously impeded owing to poor aqueous solubility of 6c. To improve aqueous solubility and retain 6c at the lower gastrointestinal tract, thiolated chitosan-based nanoparticles (TCNPs) were prepared and further developed as tablet dosage form to retain anticancer potency in the excised goat colon. Our findings may provide a valuable pharmacological mechanism for understanding metabolic underpinnings that may aid in the clinical development of new anticancer agents targeting PKM2.

Design, synthesis and biological evaluation of novel 2,4-disubstituted quinazoline derivatives targeting H1975 cells via EGFR-PI3K signaling pathway

Chao, Gao,Dai, Honglin,Ke, Yu,Li, Erdong,Lihong, Shan,Liu, Hongmin,Liu, Limin,Si, Xiaojie,Wang, Zhengjie,Yang, Zhang,Zhang, Luye,Zhang, Qiurong,Zheng, Jiaxin

, (2021/07/28)

In order to find new and highly effective anti-tumor drugs with targeted therapeutic effects, a series of novel 4-aminoquinazoline derivatives containing N-phenylacetamide structure were designed, synthesized and evaluated for antitumor activity against four human cancer cell lines (H1975, PC-3, MDA-MB-231 and MGC-803) using MTT assay. The results showed that the compound 19e had the most potent antiproliferative activity against H1975, PC-3, MDA-MB-231 and MGC-803 cell lines. At the same time, compound 19e could significantly inhibit the colony formation and migration of H1975 cells. Compound 19e also arrested the H1975 cell cycle in the G1 phase and mediated cell apoptosis, promoted the accumulation of ROS in H1975 cells. Furthermore, compound 19e exerted antitumor effect in vitro by reducing the expression of anti-apoptotic protein Bcl-2 and increasing the pro-apoptotic protein Bax and p53. Mechanistically, compound 19e could significantly decreased the phosphorylation of EGFR and its downstream protein PI3K in H1975 cells. Which indicated that compound 19e targeted H1975 cell via interfering with EGFR-PI3K signaling pathway. Molecular docking showed that compound 19e could bind into the active pocket of EGFR. Those work suggested that compound 19e would have remarkable implications for further design of anti-tumor agents.

Iron-promoted one-pot approach: Synthesis of isothiocyanates

Pendem, Venkata Bhavanarushi,Nannapaneni, Madhavi

, p. 485 - 490 (2020/02/18)

We have established a facile and versatile synthesis for the construction of isothiocyanates from their respective amines in the presence of an eco-friendly, inexpensive, easily available Iron catalyst under mild conditions. This reaction provides the target products through the formation of thiocarbamate salt as an intermediate. Both aromatic amines and aliphatic amines provided the respective target products in moderate to high yield under optimized reaction conditions. However, electron withdrawing substituents were difficult to give target product at room temperature, whereas, they obtained final products in good yield at moderate temperature. In addition, mechanistic studies were revealed that the synthetic route involved iron based subsequent reactions of addition and removal of sulfur.

Synthesis of thiocarbamoyl fluorides and isothiocyanates using amines with CF3SO2Cl

Jiang, Lvqi,Yi, Wenbin,Wei, Jingjing,Liang, Shuaishuai

, p. 12374 - 12381 (2020/11/10)

A practical and efficient method to synthesize thiocarbamyl fluorides and isothiocyanates from amines with trifluoromethanesulfonyl chloride was developed. In the presence of the reducing agent triphenylphosphine and sodium iodide, thiocarbamyl fluorides and isothiocyanates were synthesized from secondary/primary amine in moderate to excellent yields, respectively. A broad scope of substrates and good functional group compatibility were observed.

Integrated Synthesis Using Isothiocyanate-Substituted Aryllithiums by Flow Chemistry

Lee, Hyune-Jea,Torii, Daiki,Jeon, Yongju,Yoshida, Jun-Ichi,Kim, Heejin

supporting information, p. 1899 - 1902 (2020/09/11)

The isothiocyanate (NCS) group is an attractive functional group in the field of organic and pharmaceutical chemistry. It can be transformed into other heteroatomic functional groups. It usually acts as the inductive group of biological activity and has also been traditionally used as the fluorescent-labeling reagent. However, it is not compatible with strong bases. When the NCS group is at para position in halobenzenes, it generally undergoes nucleophilic additions upon reaction with strong bases. To the best of our knowledge, there is currently no general methodology for the formation and reactions of NCS-functionalized aryllithiums for meta and para substituents. Herein, we report the continuous-flow generation of NCS-substituted aryllithiums from the corresponding haloarenes via a selective halogen-lithium exchange reaction and its reaction with various electrophiles to yield NCS-containing products. We also achieved an integrated synthesis through sequential reactions of the NCS-containing compounds with additional nucleophiles using the continuous-flow reactors.

Synthesis and biological evaluation of innovative thiourea derivatives as PHGDH inhibitors

Xiang, Jiawei,Tao, Lei,Zhou, Yue,Tan, Yuping,Li, Zicheng,Zhao, Yinglan,Sun, Qingxiang,Luo, Youfu

, p. 3873 - 3886 (2020/05/29)

In order to discover novel compounds with inhibitory activity against 3-phosphoglycerate dehydrogenase (PHGDH), a series of thiourea derivatives were designed and synthesized based on the structural modification of compound 5d. Compound 5d emerged from the visual database of ChemDiv of 200,000 small molecules by docking score ranking. Inhibition experiments on PHGDH activity of newly synthesized compounds were performed in vitro. Compounds with more than 30percent inhibitory rate at 25?μM on PHGDH were screened for IC50 measurement. Anti-proliferative activity of 4a, 5a, 6e, 6n against A2780, MDA-MB-468, MDA-MB-231 and HEK293T in vitro was evaluated. The results showed that the compound 4a displayed the best inhibitory activity on PHGDH among the newly synthesized compounds, and the compounds 4a, 5a, 6n had a better proliferation inhibition effect on human A2780 cell line than NCT-503 reported previously. In addition, 2D interaction diagrams revealed potential action modes of active compounds with PHGDH.

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