TETRAFLUOROSUCCINIMIDE

Base Information

• Chemical Name: TETRAFLUOROSUCCINIMIDE
• CAS No.: 377-33-3
• Molecular Formula: C4HF4NO2
• Molecular Weight: 171.05
• Hs Code.: 2925190090
• Mol file: 377-33-3.mol

Synonyms:Succinimide,a,a,b,b-tetrafluoro- (8CI);3,3,4,4-Tetrafluorosuccinimide;NSC 146773;Perfluorosuccinimide;Tetrafluorosuccinimide;

Chemical Property of TETRAFLUOROSUCCINIMIDE

Chemical Property:

• Vapor Pressure: 0.577mmHg at 25°C
• Melting Point: 66-67 °C
• Refractive Index: 1.373
• Boiling Point: 189.2 °C at 760 mmHg
• PKA: 0.82±0.70(Predicted)
• Flash Point: 68.2 °C
• PSA: 46.17000
• Density: 1.7 g/cm³
• LogP: 0.24220

Purity/Quality:

97% ^*data from raw suppliers

Tetrafluorosuccinimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi,F

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of TETRAFLUOROSUCCINIMIDE

There total 3 articles about TETRAFLUOROSUCCINIMIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2,2,3,3-tetrafluorosuccinamide (377-37-7) → 3,3,4,4-tetrafluorosuccinimide (377-33-3)

Guidance literature:

With sulfuric acid; at 190 ℃; under 20 Torr;

DOI:10.1021/ja01147a064

Reference yield:

Perfluor-bernsteinsaeure-monoamid (425-08-1) → 3,3,4,4-tetrafluorosuccinimide (377-33-3)

Guidance literature:

With phosphorus pentoxide;

DOI:10.1021/jo00239a041

Reference yield:

→ 3,3,4,4-tetrafluorosuccinimide (377-33-3)

Guidance literature:

Perfluorbernsteinsaeure-monoamid, P2O5, Δ;

upstream raw materials:

2,2,3,3-tetrafluorosuccinamide

Perfluor-bernsteinsaeure-monoamid

Downstream raw materials:

(+/-)-3,3,4,4-tetrafluoropyrrolidine hydrochloride

trans-carbonyl(tetrafluorosuccinimidato-N)bis(triphenylphosphine)iridium

Pd(C₆H₅)(NCOC₂F₄CO)(P(C₆H₅)3)2

Rh(CO)(NCOC₂F₄CO)(P(C₆H₅)3)2

Refernces

Discovery of the dual orexin receptor antagonist [(7 R)-4-(5-chloro-1,3- benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl][5-methyl-2-(2 H -1,2,3-triazol-2-yl)phenyl]methanone (MK-4305) for the treatment of insomnia

10.1021/jm100541c

The research focuses on the development of a dual orexin receptor antagonist for treating insomnia. The study began with compound 4, a diazepane-based orexin receptor antagonist, which had excellent brain penetration and potency but suffered from high clearance and low bioavailability. Efforts to improve its pharmacokinetics led to the identification of compound 10 with a 7-methyl substitution on the diazepane core, which displayed good potency, improved pharmacokinetics, and excellent in vivo efficacy. However, compound 10 formed reactive metabolites in microsomal incubations. A mechanistic hypothesis and an in vitro assay to assess bioactivation led to the replacement of the fluoroquinazoline ring of 10 with a chlorobenzoxazole to provide 3 (MK-4305), a potent dual orexin receptor antagonist that is currently being tested in phase III clinical trials for the treatment of primary insomnia. Chemicals such as 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid, 2,5-dichloro-1,3-benzoxazole, and various diazepane cores played crucial roles in the synthesis and optimization of these compounds.