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FMOC ISOTHIOCYANATE, also known as 9-fluorenylmethoxycarbonyl isothiocyanate, is a light yellow solid that serves as a valuable reagent in the field of organic chemistry and pharmaceutical synthesis. It is widely recognized for its ability to form stable carbamates with amines, which makes it a versatile building block in the creation of various biologically active compounds.

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  • 199915-38-3 Structure
  • Basic information

    1. Product Name: FMOC ISOTHIOCYANATE
    2. Synonyms: 9-fluorenylmethoxycarbonyl isothiocyanate;9-Fluorenylmethoxycarbonyl isothiocyanate, 9-Fluorenylmethyl isothiocyanatoformate;O-(9H-fluoren-9-yl)methyl carbonisothiocyanatidate;9H-Fluoren-9-ylmethoxycarbonyl isothiocyanate;Carbon(isothiocyanatidic) acid 9H-fluoren-9-ylmethyl ester;Fmoc isothiocyanate >=98.0% (CHN);9H-fluoren-9-ylmethyl N-(sulfanylidenemethylidene)carbamate;Fmoc-isothiocyanate≥ 95% (NMR)
    3. CAS NO:199915-38-3
    4. Molecular Formula: C16H11NO2S
    5. Molecular Weight: 281.33
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 199915-38-3.mol
  • Chemical Properties

    1. Melting Point: 42-46 °C
    2. Boiling Point: 433.1°C at 760 mmHg
    3. Flash Point: 215.7°C
    4. Appearance: Clear yellow to brown/Liquid
    5. Density: 1.26
    6. Vapor Pressure: 1.05E-07mmHg at 25°C
    7. Refractive Index: 1.653
    8. Storage Temp.: −20°C
    9. Solubility: ethanol: soluble
    10. BRN: 7930648
    11. CAS DataBase Reference: FMOC ISOTHIOCYANATE(CAS DataBase Reference)
    12. NIST Chemistry Reference: FMOC ISOTHIOCYANATE(199915-38-3)
    13. EPA Substance Registry System: FMOC ISOTHIOCYANATE(199915-38-3)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 37/38-41
    3. Safety Statements: 36/39
    4. WGK Germany: 3
    5. RTECS:
    6. F: 10
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 199915-38-3(Hazardous Substances Data)

199915-38-3 Usage

Uses

Used in Pharmaceutical Synthesis:
FMOC ISOTHIOCYANATE is used as a starting material for the preparation of biologically relevant pharmacophores named N-aryl-N′-carboalkoxy guanidines. These compounds exhibit a range of pharmacological activities, making them essential in the development of new drugs.
Used in Organic Chemistry:
In the synthesis of N-aryl-N-thiazolyl derivatives, FMOC ISOTHIOCYANATE serves as an intermediate step. These derivatives are known for their diverse applications in the pharmaceutical and chemical industries, including their use as precursors for the development of novel therapeutic agents.
Used in Neuropeptide Y Receptor Antagonists:
FMOC ISOTHIOCYANATE is utilized to synthesize cyclic isothiourea derivatives, which have been identified as potent neuropeptide Y (NPY) Y1 receptor antagonists. These antagonists play a crucial role in the treatment of various neurological disorders and conditions related to the NPY system.
Used in the Synthesis of Heterocyclic Compounds:
FMOC ISOTHIOCYANATE is employed in the preparation of 2-aminothiazoles, aminobenz-imidazole conjugated thiazoles, and thiazole-derived cyclopeptides. These heterocyclic compounds are known for their diverse biological activities and potential applications in the pharmaceutical industry, including their use as antimicrobial, anticancer, and antiviral agents.

Check Digit Verification of cas no

The CAS Registry Mumber 199915-38-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,9,9,1 and 5 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 199915-38:
(8*1)+(7*9)+(6*9)+(5*9)+(4*1)+(3*5)+(2*3)+(1*8)=203
203 % 10 = 3
So 199915-38-3 is a valid CAS Registry Number.
InChI:InChI=1/C16H11NO2S/c18-16(17-10-20)19-9-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15H,9H2

199915-38-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Aldrich

  • (10919)  Fmocisothiocyanate  ≥98.0% (CHN)

  • 199915-38-3

  • 10919-1G

  • 1,692.99CNY

  • Detail
  • Aldrich

  • (10919)  Fmocisothiocyanate  ≥98.0% (CHN)

  • 199915-38-3

  • 10919-5G

  • 6,154.20CNY

  • Detail

199915-38-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 9H-fluoren-9-ylmethyl N-(sulfanylidenemethylidene)carbamate

1.2 Other means of identification

Product number -
Other names FMOC isothiocyanate

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:199915-38-3 SDS

199915-38-3Relevant articles and documents

Convenient Synthesis of Thiohydantoins, Imidazole-2-thiones and Imidazo[2,1-b]thiazol-4-iums from Polymer-Supported α-Acylamino Ketones

Králová, Petra,Maloň, Michal,Koshino, Hiroyuki,Soural, Miroslav

, (2018)

The preparation of 5-methylene-thiohydantoins using solid-phase synthesis is reported in this paper. After sulfonylation of immobilized Ser (t-Bu)-OH with 4-nitrobenzenesulfonyl chloride followed by alkylation with various bromoketones, the 4-Nos group was removed and the resulting polymer-supported α-acylamino ketones reacted with Fmoc-isothiocyanate. Cleavage of the Fmoc protecting group was followed by the spontaneous cyclative cleavage releasing the 5-methylene-thiohydantoin derivatives from the polymer support. Reduction with triethylsilane (TES) yielded the corresponding 5-methyl-thiohydantoins. When Fmoc-isothiocyanate was replaced with alkyl isothiocyanates, the trifluoroacetic acid (TFA) mediated cleavage from the polymer support, which was followed by the cyclization reaction and the imidazo[2,1-b]thiazol-4-iums were obtained. Their conversion in deuterated dimethylsulfoxide led to imidazole-2-thiones.

A convenient synthesis of 2-(9H-fluoren-9-ylmethoxycarbonylamino)-thiazole-4-carboxylic acid via N-Fmoc-thiourea

Le, Kang,Goodnow Jr., Robert A.

, p. 1891 - 1895 (2004)

2-(9H-Fluoren-9-ylmethoxycarbonylamino)-thiazole-4-carboxylic acid has been prepared in high yield from 3-bromopyruvic acid and (aminothioxomethyl)carbamic acid 9H-fluoren-9-ylmethyl ester (N-Fmoc-thiourea) that was obtained from potassium thiocyanate.

HETEROARYL COMPOUNDS FOR TREATING HUNTINGTON'S DISEASE

-

Page/Page column 216, (2020/01/24)

The present description relates to compounds, forms, and pharmaceutical compositions thereof and methods of using such compounds, forms, or compositions thereof for treating or ameliorating Huntington's disease. In particular, the present description relates to substituted benzothiazole compounds of Formula (I) or (II), forms and pharmaceutical compositions thereof and methods of using such compounds, forms, or compositions thereof for treating or ameliorating Huntington's disease.

BET BROMODOMAIN PROTEIN DEGRADERS WITH CLEAVABLE LINKERS

-

Paragraph 0337-0338, (2019/04/11)

The present disclosure provides compounds represented by Formula (I): Formula (I) and the pharmaceutically acceptable salts and solvates thereof, wherein R1, R2a, R2b, R3a, R3b, R4, Y, =, Ar, W, L, and B are as defined as set forth in the specification. The present disclosure also provides compounds of Formula (I)I for use to treat a condition or disorder responsive to inhibition and/or degradation of BET bromodomains such as cancer.

FUSED 1,4-OXAZEPINES AS BET PROTEIN DEGRADERS

-

Paragraph 0534-0536, (2018/04/13)

The present disclosure provides compounds represented by Formula I and the pharmaceutically acceptable salts, hydrates, and solvates thereof, wherein R1, R2a, R2b, R3a, R3b, R4, Ar, L, X, Y, and B are as defined as set forth in the specification. The present disclosure also provids compounds of Formula I for use to treat a condition or disorder responsive to degradation of BET bromodomains such as cancer.

Discovery of QCA570 as an Exceptionally Potent and Efficacious Proteolysis Targeting Chimera (PROTAC) Degrader of the Bromodomain and Extra-Terminal (BET) Proteins Capable of Inducing Complete and Durable Tumor Regression

Qin, Chong,Hu, Yang,Zhou, Bing,Fernandez-Salas, Ester,Yang, Chao-Yie,Liu, Liu,McEachern, Donna,Przybranowski, Sally,Wang, Mi,Stuckey, Jeanne,Meagher, Jennifer,Bai, Longchuan,Chen, Zhuo,Lin, Mei,Yang, Jiuling,Ziazadeh, Danya N.,Xu, Fuming,Hu, Jiantao,Xiang, Weiguo,Huang, Liyue,Li, Siwei,Wen, Bo,Sun, Duxin,Wang, Shaomeng

, p. 6685 - 6704 (2018/08/17)

Proteins of the bromodomain and extra-terminal (BET) family are epigenetics "readers" and promising therapeutic targets for cancer and other human diseases. We describe herein a structure-guided design of [1,4]oxazepines as a new class of BET inhibitors and our subsequent design, synthesis, and evaluation of proteolysis-targeting chimeric (PROTAC) small-molecule BET degraders. Our efforts have led to the discovery of extremely potent BET degraders, exemplified by QCA570, which effectively induces degradation of BET proteins and inhibits cell growth in human acute leukemia cell lines even at low picomolar concentrations. QCA570 achieves complete and durable tumor regression in leukemia xenograft models in mice at well-tolerated dose-schedules. QCA570 is the most potent and efficacious BET degrader reported to date.

SUBSTITUTED AMINOTHIAZOLES AS INHIBITORS OF CANCERS, INCLUDING HEPATOCELLULAR CARCINOMA, AND AS INHIBITORS OF HEPATITIS VIRUS REPLICATION

-

Paragraph 0123; 0138; 0139, (2013/04/24)

Pharmaceutical compositions of the invention are presented which comprise substiuted aminothiazoles derivatives. The substiuted aminothiazoles derivatives have a disease-modifying action in the treatment of diseases associated with unregulated cell growth. Such diseases include cancers such as hepatocellular carcinoma, and viral infections from a hepatitis virus.

THIAZOLE COMPOUNDS AS ACTIVATORS OF SOLUBLE GUANYLATE CYCLASE

-

Page/Page column 33-34, (2010/04/03)

Disclosed are compounds of formula (I) wherein R1 and R2 are independently selected from hydrogen, halo, C1-4alkyl, C1-4alkoxy, CF3 and OCF3; -Y- represents formula (IA) R3 represents hydrogen, fluoro, chloro or C1-4alkyl; R4a and R4b each independently represent hydrogen, C1-4alkyl, C1-4alkoxy, CF3 or halo; and R5 represents a group Z-X; wherein Z is absent or represents (CH2)2 or O; and X represents formula (IB) wherein: J and L both represent CH, or one of J and L represents CH and the other represents N; when both J and L represent CH, R6 represents hydrogen, halo, CF3, C1-4alkyl or C1-4alkoxy in a meta or ortho position relative to the R7 substituent and R7 represents hydrogen, halo, CF3, OCF3, C1-4alkyl, C1-4alkoxy, CH2OH, CN, CONR8R9 or CO2H; or when one of J or L represents N, R6 represents hydrogen or halo in a meta or ortho position relative to the R7 substituent and R7 represents hydrogen, halo, CF3, C1-4alkyl, C1-4alkoxy, CH2OH, CN, CONR8R9 or CO2H; and R8 and R9 are independently selected from hydrogen and C1-4alkyl; or salts thereof which activate soluble guanylate cyclase (sGC), pharmaceutical compositions containing them, their use in medicine, and processes for their preparation.

Substituted hydantoins

-

Page/Page column 11; 15-16, (2008/06/13)

The present invention relates to compounds of the formula which are useful in treating diseases characterized by the hyperactivity of MEK. Accordingly the compounds are useful in the treatment of diseases, such as, cancer, cognative and CNS disorders and inflammatory/autoimmune diseases.

Methods for the solid phase synthesis of 2-amino-4(H)-quinazolinone derivatives

-

, (2008/06/13)

The present invention relates to solid phase synthesis of substituted 2-amino-4(H)-quinazolinone compounds of formula (I): having pharmacological activity, to processes for their preparation, to a combinatorial library and solid phase methods for preparing libraries of the compounds, to utilizing libraries of the compounds for drug discovery, and to pharmaceutical compositions thereof.

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