132740-43-3

Basic information

• Product Name: 4-FLUOROBENZYL ISOCYANATE
• Synonyms: 4-Fluorobenzyl isocyanate, 98% 1GR;487309_ALDRICH;ZINC02568124;4-Fluorophenylmethyl isocyanate;p-Fluorobenzyl isocyanate;4-FLUOROBENZYL ISOCYANATE;4-Fluorobenzyl isocyanate, GC 98%;4-FLUOROBENZYL ISOCYANATE 98%
• CAS NO: 132740-43-3
• Molecular Formula: C₈H₆FNO
• Molecular Weight: 151.14
• Product Categories: Aryl Fluorinated Building Blocks;Building Blocks;C7-C8;Chemical Synthesis;Fluorinated Building Blocks;Nitrogen Compounds;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 132740-43-3.mol

Chemical Properties

• Boiling Point: 211 °C(lit.)
• Flash Point: 199 °F
• Appearance: Colorless/Liquid
• Density: 1.186 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.256mmHg at 25°C
• Refractive Index: n20/D 1.505(lit.)
• Storage Temp.: Store under Argon
• Sensitive: Lachrymatory
• CAS DataBase Reference: 4-FLUOROBENZYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-FLUOROBENZYL ISOCYANATE(132740-43-3)
• EPA Substance Registry System: 4-FLUOROBENZYL ISOCYANATE(132740-43-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN 2206 6.1/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 132740-43-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Fluorobenzyl isocyanate is used as a reagent in the synthesis of complex organic molecules, particularly in the pharmaceutical industry. Its unique structure allows for the creation of new compounds with potential therapeutic applications.
Used in the Synthesis of 3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide:
In this application, 4-Fluorobenzyl isocyanate serves as a key intermediate in the synthesis of a specific oxazolo[3,4-a]pyrazine derivative. 4-FLUOROBENZYL ISOCYANATE may have potential uses in the development of new drugs targeting various medical conditions.
Used in the Synthesis of (S)-2-(4-fluorobenzyl)-7-hydroxy-10,10a-dihydroimidazo[1,5-b]isoquinoline-1,3(2H,5H)-dione:
4-Fluorobenzyl isocyanate is also utilized in the synthesis of another complex organic molecule, an imidazo[1,5-b]isoquinoline derivative. 4-FLUOROBENZYL ISOCYANATE may exhibit biological activities that could be harnessed for therapeutic purposes.

InChI:InChI=1/C8H6FNO/c9-8-3-1-7(2-4-8)5-10-6-11/h1-4H,5H2

Upstream product

• 459-04-1 4-Fluorophenylacetyl chloride 
• 405-50-5 p-Fluorophenylacetic acid 
• 140-75-0 para-fluorobenzylamine 
• 75-44-5 phosgene 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 503-38-8 trichloromethyl chloroformate 

Downstream Products

• 910114-63-5 methyl N-({[(4-fluorobenzen-1-yl)methyl]amino}carbonyl)carbamimidothioate 
• 851315-91-8 C₂₆H₂₇FN₈O₃ 
• 1438000-14-6 N-(4-fluorobenzyl)benzisothiazol-3-one-2-amide 
• 847555-75-3 (S)-SHA 68 
• 847555-74-2 (R)-SHA 68 
• 1261167-91-2 C₂₂H₁₇FN₆O₂ 
• 1261168-06-2 1-(4-fluorobenzyl)-4-(1-(4-methoxybenzyl)-5-amino-1H-imidazol-4-yl)-5-imino-1H-imidazol-2(5H)-one 
• 1259908-92-3 C₂₁H₃₀FN₃O₃ 
• 1226709-97-2 C₂₂H₂₈FN₃O₂ 
• 1226709-95-0 C₂₁H₂₅F₂N₃O 
• 1226709-94-9 C₂₀H₂₄ClFN₄O 
• 1226709-93-8 C₂₁H₂₅ClFN₃O 
• 1226709-91-6 C₂₄H₂₉BrFN₃O 
• 1104026-53-0 5-(quinolin-3-ylamino)-3,4-dihydro-1H-[2,6]naphthyridine-2-carboxylic acid 4-fluoro-benzylamide 

Relevant articles and documents

Design and Synthesis of 4-Alkylidene-β-lactams: Benzyl- and Phenethyl-carbamates as Key Fragments to Switch on Antibacterial Activity

The emergence of multidrug-resistant bacterial strains is particularly important in chronic pathologies such as cystic fibrosis (CF), in which persistent colonization and selection of resistant strains is favored by the frequent and repeated use of antibacterial agents. Staphylococcus aureus is a common pathogen in CF patients that has an associated increased multidrug resistance. In previous studies we demonstrated that the presence of a 4-alkylidene side chain directly linked to a β-lactam appeared to strengthen the potency against S. aureus, especially against methicillin-resistant S. aureus (MRSA) strains. In the present study, 21 new 4-alkylidene-β-lactams were synthesized and evaluated for antibacterial activity. We designed the new compounds to have aryl, benzyl, or phenethyl-carbamate groups on the C3 hydroxyethyl side chain. We found a correlation between biological activity and the nitrogen substituent of the carbamate group, and two phenethyl-carbamate β-lactams were shown to be valuable antibacterial agents against selected linezolid-resistant strains, with a minimum inhibitory concentrations of 2–4 mg L?1.

NOVEL CYCLICSULFONIMIDOYLPURINONE COMPOUNDS AND DERIVATIVES FOR THE TREATMENT AND PROPHYLAXIS OF VIRUS INFECTION

The present invention relates to compounds of formula (I), wherein R1, R2 and R3 and n are as described herein, or pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.

Amide compound, pharmaceutical composition, preparation method and application thereof

The invention provides an amide compound, a pharmaceutical composition, a preparation method and application thereof and belongs to the field of medicine. Structure of the amide compound is shown as aformula I. The preparation method includes: in an alkaline condition and in an organic solvent, allowing a compound I and a compound II to be in condensation reaction. The amide compound or pharmaceutically acceptable salt thereof have long-acting sensory and/or motion blocking activity, can be used for preparing long-acting local anesthetic or analgesic and is long in efficacy lasting time, little side effect and high in medication safety.

Enantioselective synthesis of 3,5-disubstituted thiohydantoins and hydantoins

A mild method to convert optically pure amino acid thiourea and urea derivatives to thiohydantoins and hydantoins, respectively, is described. It provides an efficient way to realize enantioselective synthesis of thiohydantoins and hydantoins with good to high isolated yields and enantiomeric purities. We found that the enantiomeric purities were highly dependent on the reaction conditions including bases, solvents, and temperature.

Structure-based drug design and potent anti-cancer activity of tricyclic 5:7:5-fused diimidazo[4,5-d:4′,5′-f][1,3]diazepines

Judicial structural modifications of 5:7-fused ring-expanded nucleosides (RENs), based on molecular modeling studies with one of its known targets, human RNA helicase (hDDX3), led to the lead, novel, 5:7-5-fused tricyclic heterocycle (1). The latter exhibited promising broad-spectrum in vitro anti-cancer activity against a number of cancer cell lines screened. This paper describes our systematic, albeit limited, structure-activity relationship (SAR) studies on this lead compound, which produced a number of analogs with broad-spectrum in vitro anti-cancer activities against lung, breast, prostate, and ovarian cancer cell lines, in particular compounds 15i, 15j, 15m and 15n which showed IC 50 values in submicromolar to micromolar range, and are worthy of further explorations. The SAR data also enabled us to propose a tentative SAR model for future SAR efforts for ultimate realization of optimally active and minimally toxic anti-cancer compounds based on the diimidazo[4,5-d:4′, 5′-f][1,3]diazepine structural skeleton of the lead compound 1.

Design, synthesis and evaluation of 1,2-benzisothiazol-3-one derivatives as potent caspase-3 inhibitors

A number of 1,2-benzisothiazol-3-one derivatives were prepared through structural modification of the original compound from high-throughput screening. Some analogues (e.g., 6b, 6r, 6s and 6w) were identified as novel and potent caspase inhibitors with IC50 of nanomolar. Structure-activity relationship (SAR) studies for caspase-3 inhibition were evaluated in vitro. Molecular modeling studies provided further insight into the interaction of this class of compounds with activated caspase-3. The present small molecule caspase-3 inhibitor with novel structures different from structures of known caspase inhibitors revealed a new direction for therapeutic strategies directed against diseases involving abnormally up-regulated apoptosis.

Development of synthetic aminopeptidase N/CD13 inhibitors to overcome cancer metastasis and angiogenesis

Cancer metastasis is a major barrier to its treatment and an important cause of patient death. Antimetastatic agents hold promise for patients with advanced metastatic tumors. Aminopeptidase N/CD13 (APN) is being pursued by many as an important target against cancer metastasis and angiogenesis, but there are few reports on the in vivo evaluation of synthetic APN inhibitors. Herein, a series of compounds targeting APN were synthesized and evaluated for their antimetastasis and antiangiogenesis potency both in vitro and in vivo. Excitingly, compounds 4m, 4t, and 4cc, with the most potent APN inhibitory activities, displayed significant antimetastasis and antiangiogenesis effects in vitro and in vivo, suggesting that those synthetic APN inhibitors have the potential to overcome cancer metastasis and angiogenesis.

Synthesis and biological evaluation of glycogen synthase kinase 3 (GSK-3) inhibitors: An fast and atom efficient access to 1-aryl-3-benzylureas

The glycogen synthase kinase 3 (GSK-3) is implicated in multiple cellular processes and has been linked to the pathogenesis of Alzheimer's disease (AD). In the course of our research topic we synthesized a library of potent GSK-3 inhibitors. We utilized the urea scaffold present in the potent and highly selective GSK-3 inhibitor AR-A014418 (AstraZeneca). This moiety suits both (a) a convergent approach utilizing readily accessible building blocks and (b) a divergent approach based on a microwave heating assisted Suzuki coupling. We established a chromatography-free purification method to generate products with sufficient purity for the biological assays. The structure-activity relationship of the library provided the rationale for the synthesis of the benzothiazolylurea 66 (IC50 = 140 nM) and the pyridylurea 62 (IC 50 = 98 nM), which displayed two to threefold enhanced activity versus the reference compound 18 (AR-A014418: IC50 = 330 nM) in our assays.

"TRPV1 VANILLOID RECEPTOR ANTAGONISTS WITH A BICYCLIC PORTION"

The invention discloses compounds of formula I wherein Y is a group of formula A, B, C, D, or E: and W, Q, n, R1, R2, R3, U1-U5, J and K have the meanings given in the description. The compounds of formula I are TRPV1 antagonists and are useful as active

TRPV1 vanilloid receptor antagonists with a bicyclic portion

The invention discloses compounds of formula I wherein Y s selected from a group of formula and W, Q, n, R1, R2, R3, U1-U5 have the meanings given in the description. The compounds of formula I are TRPV1 antagonists and are useful as active ingredients of pharmaceutical compositions for the treatment of pain and other conditions ameliorated by the inhibition of the vanilloid receptor TRPV1. 1.