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3-Chlorophenyl isothiocyanate is an organic compound characterized as a clear yellow liquid. It is a derivative of isothiocyanates, which are known for their reactivity and use in various chemical syntheses.

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  • 2392-68-9 Structure
  • Basic information

    1. Product Name: 3-CHLOROPHENYL ISOTHIOCYANATE
    2. Synonyms: 3-Chlorophenylisothiocyanate,98%;3-Chlorophenyl isothiocyanate 98%;1-Chloro-3-isothiocyanatobenzene;Benzene, 1-chloro-3-isothiocyanato-;Isothiocyanic acid, 3-chlorophenyl ester;Isothiocyanic acid, m-chlorophenyl ester;isothiocyanicacid,3-chlorophenylester;isothiocyanicacid,m-chlorophenylester
    3. CAS NO:2392-68-9
    4. Molecular Formula: C7H4ClNS
    5. Molecular Weight: 169.63
    6. EINECS: -0
    7. Product Categories: Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Organic Building Blocks;Sulfur Compounds;Thiocyanates/Isothiocyanates
    8. Mol File: 2392-68-9.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 249-250 °C
    3. Flash Point: >110°C
    4. Appearance: clear yellow liquid
    5. Density: 1.292
    6. Vapor Pressure: 0.0361mmHg at 25°C
    7. Refractive Index: 1.658-1.66
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. Water Solubility: 33.93mg/L(25 oC)
    11. Sensitive: Moisture Sensitive
    12. BRN: 636856
    13. CAS DataBase Reference: 3-CHLOROPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
    14. NIST Chemistry Reference: 3-CHLOROPHENYL ISOTHIOCYANATE(2392-68-9)
    15. EPA Substance Registry System: 3-CHLOROPHENYL ISOTHIOCYANATE(2392-68-9)
  • Safety Data

    1. Hazard Codes: T,Xn
    2. Statements: 42-36/37/38-23/24/25-20/21/22
    3. Safety Statements: 45-36/37/39-26-37/39
    4. RIDADR: 2810
    5. WGK Germany: 3
    6. RTECS: NX8474500
    7. HazardClass: 8
    8. PackingGroup: III
    9. Hazardous Substances Data: 2392-68-9(Hazardous Substances Data)

2392-68-9 Usage

Uses

Used in Pharmaceutical Synthesis:
3-Chlorophenyl isothiocyanate is used as a synthetic intermediate for the creation of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
As a reactive compound, 3-chlorophenyl isothiocyanate is also utilized in chemical research to explore its properties and potential reactions with other molecules. This can lead to the discovery of new chemical entities and advancements in the field of chemistry.
Used in the Synthesis of Specific Compounds:
3-Chlorophenyl isothiocyanate has been specifically used in the synthesis of complex organic molecules such as 2-[(3-chlorophenyl)amino]naphtho[2,1-b]furo-5H-[3,2-d][1,3,4]thiadiazolo[3,2-i]pyrimidin-5-one and (S)-N-[3-N-(3-chlorophenyl)-4-(3-fluorophenyl)piperazine]-1-carbothioamido-2-oxooxazolidin-5-yl)methyl]acetamide. These compounds may have potential applications in various fields, including pharmaceuticals and materials science.

Check Digit Verification of cas no

The CAS Registry Mumber 2392-68-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,3,9 and 2 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 2392-68:
(6*2)+(5*3)+(4*9)+(3*2)+(2*6)+(1*8)=89
89 % 10 = 9
So 2392-68-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H4ClNS/c8-6-2-1-3-7(4-6)9-5-10/h1-4H

2392-68-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A11999)  3-Chlorophenyl isothiocyanate, 97%   

  • 2392-68-9

  • 5g

  • 372.0CNY

  • Detail
  • Alfa Aesar

  • (A11999)  3-Chlorophenyl isothiocyanate, 97%   

  • 2392-68-9

  • 25g

  • 1339.0CNY

  • Detail
  • Alfa Aesar

  • (A11999)  3-Chlorophenyl isothiocyanate, 97%   

  • 2392-68-9

  • 100g

  • 4962.0CNY

  • Detail
  • Aldrich

  • (253766)  3-Chlorophenylisothiocyanate  98%

  • 2392-68-9

  • 253766-5G

  • 506.61CNY

  • Detail

2392-68-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-chloro-3-isothiocyanatobenzene

1.2 Other means of identification

Product number -
Other names Isothiocyanic acid,m-chlorophenyl 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:2392-68-9 SDS

2392-68-9Relevant articles and documents

Microwave mediated synthesis of 2-aminooxazoles

Klug, Trevan,Cronin, Adam,O'Brien, Eli,Schioldager, Ryan,Johnson, Hunter,Gleason, Cameron,Schmid, Connor,Soderberg, Nathan,Manjunath, Aashrita,Liyanage, Duminda,Lazaro, Horacio,Kimball, Joshua J.,Eagon, Scott

supporting information, (2021/12/14)

A microwave mediated synthesis of 2-aminooxazoles at 150 °C was developed, providing products with a variety of functional groups. The reaction takes 5 min and provides product with a simple precipitation at moderate to good yields without the need for recrystallization or flash chromatography.

COMPOUNDS WITH COPPER- OR ZINC-ACTIVATED TOXICITY AGAINST MICROBIAL INFECTION

-

, (2022/02/05)

Heterocyclic compounds with a novel pyrazole thioamide-based NNSN structural motif, having highly effective zinc- or copper-activated toxicity against microbial infections at micromolar or nanomolar minimum inhibitory concentrations (MIC), and methods of making and using same.

4-PHENYL-N-(PHENYL)THIAZOL-2-AMINE DERIVATIVES AND RELATED COMPOUNDS AS ARYL HYDROCARBON RECEPTOR (AHR) AGONISTS FOR THE TREATMENT OF E.G. ANGIOGENESIS IMPLICATED OR INFLAMMATORY DISORDERS

-

Paragraph 00221; 00314, (2021/06/26)

4-phenyl-N-(phenyl)thiazol-2-amine and 4-(pyridin-3-yl)-N-( phenyl) thiazol-2-amine derivatives and the corresponding thiadiazole, thiophene, oxazole, oxadiazole, imidazole and triazole derivatives and related compounds as aryl hydrocarbon receptor (AHR) agonists for the treatment of angiogenesis implicated disorders, such as e.g. retinopathy, psoriasis, rheumatoid arthritis, obesity and cancer, or inflammatory disorders.

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.

Design, synthesis, and biological evaluation of novel substituted thiourea derivatives as potential anticancer agents for NSCLC by blocking K-Ras protein-effectors interactions

Cheng, Minghui,Meng, Xin,Tang, Haikang,Xu, Wenqing,Yang, Fujun,Zhang, Yuan

, p. 344 - 353 (2019/12/30)

Mutation of the proto-oncogene K-Ras is one of the most common molecular mechanisms in non-small cell lung cancer. Many drugs for treating lung cancer have been developed, however, due to clinical observed K-Ras mutations, corresponding chemotherapy and targeted therapy for such mutation are not efficient enough. In this study, on the basis of the crystal structure of K-Ras, 21 analogues (TKR01–TKR21) containing urea or thiourea were rationally designed, which can effectively inhibit the lung cancer cell A549 growth. The designing of these compounds was based on the structure of K-Ras protein, and the related groups were replaced by bioisosteres to improve the affinity and selectivity. Biological testing revealed that compound TKR15 could significantly inhibit the proliferation of A549 cell with IC50 of 0.21 μM. Docking analysis showed that the TKR15 can effectively bind to the hydrophobic cavity and form a hydrogen bond with the Glu37. In addition, through flow apoptosis assay and immunofluorescence staining assay, it confirmed that this compound can inhibit A549 cell proliferation with the mechanism of blocking K-RasG12V protein and effector proteins interactions through the apoptotic pathway. In conclusion, our studies in finding novel potent compound (TKR15) with confirmed mechanism showed great potential for further optimisation and other medicinal chemistry relevant studies.

Synthesis and antitumor activity of novel pyridazinone derivatives containing 1,3,4-thiadiazole moiety

Qin, Junhu,Zhu, Mei,Zhu, Hongmei,Zhang, Liqiong,Fu, Yihong,Liu, Jiamin,Wang, Zhenchao,OuYang, Guiping

, p. 592 - 599 (2020/03/16)

A series of novel pyridazinone derivatives containing the 1,3,4-thiadiazole moiety were synthesized and characterized by 1H NMR, 13C NMR, spectroscopies HRMS and IR. Among them, the structure of compound 5c (2-(Tert-butyl)?4-chloro-5-((5-((2-ethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was unambiguously confirmed via single crystal X-ray diffraction analysis. The inhibitory activity of all the target compounds against MGC-803 and Bcap-37 was determined by MTT assay, with doxorubicin (the inhibition rates were 95.5 ± 0.4% and 95.7 ± 1.0% respectively) as a control. The preliminary results showed that the inhibitory activity of compound 5n (2-(Tert-butyl)?4-chloro-5-((5-((3-fluorophenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was superior to the others. The inhibition rates of MGC-803 and Bcap-37 cells were 86.3 ± 2.2% and 92.3 ± 0.6% at a concentration of 10 μmol/L, respectively. The preliminary structure-activity relationship showed that when the 2-position of the benzene ring was substituted by a methyl group, such as compound 5j (2-(Tert-butyl)?4-chloro-5-((5-((2,3-dimethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), it exhibited good anticancer activity on MGC-803 cells. Besides, introducing fluorine, chlorine, or trifluoromethyl group onto the benzene ring, such as compound 5 m (2-(Tert-butyl)?4-chloro-5-((5-((4-(trifluoromethoxy)phenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), displayed good anticancer activity on MGC-803 and Bcap-37 cells.

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.

Synthesis methods for isothiocyanate derivative

-

Paragraph 0033; 0034; 0035; 0036; 0085; 0086; 0087; 0088, (2019/05/22)

The invention discloses synthesis methods for an isothiocyanate derivative. The first synthesis method includes reacting raw materials, including primary amine, trifluoromethyltrimethylsilane, potassium fluoride and sulfur, with an organic solvent at the room temperature to obtain the isothiocyanate derivative. The synthetic isothiocyanate derivative has the advantages of simple operation, safety,high efficiency, non-toxicity, low raw material price, mild condition, high yield, wide application range of substrates, high compatibility of functional groups and the like. The second synthesis method includes reacting raw materials, including the primary amine, silver trifluoromethane and potassium bromide, with the organic solvent at the room temperature to obtain the isothiocyanate derivative. The isothiocyanate derivative has the advantages of simple operation, safety, high efficiency, easy availability of the raw materials, nearly quantitative yield, wide application range of the substrates, applicability to selective post-modification of drugs or complex compounds, and the like.

Design, synthesis, antiproliferative and antibacterial evaluation of quinazolinone derivatives

Wang, Hai-Xin,Liu, Hai-Ying,Li, Wei,Zhang, Shuai,Wu, Zheng,Li, Xin,Li, Cai-Wen,Liu, Yu-Ming,Chen, Bao-Quan

, p. 203 - 214 (2019/01/04)

A series of novel quinazolinone derivatives bearing a disulfide bond were designed and synthesized. Their in vitro antiproliferative activities were evaluated using CCK-8 assay against SMMC-7721, Hela, A549 and MCF-7 human cancer cell lines and normal cell lines L929. The preliminary bioassay results demonstrated that all compounds 7a–7h, 8a–8h and 9a–9h exhibited antiproliferation with various degrees, and some compounds showed better effects than positive control 5-fluorouracil against different cancer cell lines. Among these compounds, 8c and 9f showed significant antiproliferative activity against SMMC-7721 cells with IC50 values of 2.88 and 2.56 μM, respectively. In Hela cells, compounds 9c and 9d showed highly effective biological activity with IC50 values of 3.16 and 2.68 μM, respectively. Compounds 7a and 9a exhibited good inhibitory effect against A549 cells with IC50 values of 3.53 and 3.54 μM, respectively. In MCF-7 cells, compounds 7e, 8e and 9e displayed excellent activity with IC50 values of 1.26, 1.12 and 1.85 μM, respectively. Besides, most of the tested compounds showed low cytotoxic effect against the normal cell lines L929. Biological evaluation indicated that all the tested compounds possessed antibacterial activity with certain degrees.

Design, computational studies, synthesis and biological evaluation of thiazole-based molecules as anticancer agents

Anuradha,Patel, Sagarkumar,Patle, Rajkumar,Parameswaran, Preethi,Jain, Alok,Shard, Amit

, p. 20 - 30 (2019/04/25)

Background: Abolition of cancer warrants effective treatment modalities directed towards specific pathways dysregulated in tumor proliferation and survival. The antiapoptotic Bcl-2 proteins are significantly altered in several tumor types which position them as striking targets for therapeutic intervention. Here we designed, computationally evaluated, synthesized, and biologically tested structurally optimized thiazole-based small molecules as anticancer agents. Methods: The virtually designed 200 molecules were subjected to rigorous docking and in silico ADME-Toxicity studies. Out of this, 23 skeletally diverse thiazole-based molecules which passed pan assay interference compounds (PAINS) filter and were synthetically feasible were synthesized in 3 steps using cheap and readily available reagents. The molecules were in vitro evaluated against Bcl-2-Jurkat, A-431 cancerous cell lines and ARPE-19 cell lines. Molecular Dynamics (MD) simulation studies were performed to analyse conformational changes induced by ligand 32 in Bcl-2. Flow cytometry analysis of compound 32 treated Bcl-2 cells was done to check apoptosis. Results: The molecules exhibited appreciable interactions with Bcl-2 and were having acceptable drug like properties as tested in silico. The multi step synthesis yielded 23 skeletally diverse thiazole-based molecules in up to 80% yield. The molecules simultaneously inhibited Bcl-2 Jurkat cells in vitro without causing detectable toxicity to normal cells (ARPE-19 cells). Among them molecules 32, 50, 53, 57 and 59 showed considerable activities against Bcl-2 Jurkat and A-431cell lines at concentrations ranging from 32–46 μM and 34–52 μM, respectively. The standard doxorubicin exhibited IC50 in Bcl-2 Jurkat and A-431cell lines at 45.87 μM and 42.37 μM, respectively. The molecule 32, almost equipotent in both the cell lines was subjected to molecular dynamics (MD) simulation with Bcl-2 protein (4IEH). It was shown that 32 interacted with protein majorly via hydrophobic interactions and few H-bonding interactions. Fluorescence-activated cell sorting (FACS) analysis established that molecule is dragging cancerous cells towards apoptosis. Discussion and conclusion: The chemical intuition was checked by computation coupled with biological results confirmed that thiazole-based hits have the potential to be developed downstream into potent and safer leads against antiapoptotic Bcl-2 cells.

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