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(2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran is a complex organic compound with a specific stereochemistry and functional groups. It is characterized by its fluorine atom at the 6th position, a 3,4-dihydro ring, and an oxirane (epoxide) group attached to the 2nd position of the benzopyran structure. (2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran is likely to have unique chemical and biological properties due to its specific structural features.

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  • 793669-26-8 Structure
  • Basic information

    1. Product Name: (2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran
    2. Synonyms: (2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran;(2S*,2'R*)-Nebivolol Impurity C;(2R)-6-fluoro-2-[(2S)-oxiran-2-yl]-3,4-dihydro-2H-chromene
    3. CAS NO:793669-26-8
    4. Molecular Formula: C11H11FO2
    5. Molecular Weight: 194.2
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 793669-26-8.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 292℃
    3. Flash Point: 138℃
    4. Appearance: /
    5. Density: 1.299
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: (2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran(CAS DataBase Reference)
    10. NIST Chemistry Reference: (2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran(793669-26-8)
    11. EPA Substance Registry System: (2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran(793669-26-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 793669-26-8(Hazardous Substances Data)

793669-26-8 Usage

Uses

Used in Pharmaceutical Industry:
(2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran is used as an intermediate in the synthesis of Nebivolol (N387933), which is a cardioselective beta-1 receptor blocking agent. This application is significant because Nebivolol is utilized in the treatment of hypertension and other cardiovascular conditions, making this compound an essential part of the pharmaceutical development process.

Check Digit Verification of cas no

The CAS Registry Mumber 793669-26-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 7,9,3,6,6 and 9 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 793669-26:
(8*7)+(7*9)+(6*3)+(5*6)+(4*6)+(3*9)+(2*2)+(1*6)=228
228 % 10 = 8
So 793669-26-8 is a valid CAS Registry Number.

793669-26-8Relevant articles and documents

Preparation method and application of Smo inhibitor based on Nebivolol

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Paragraph 0042; 0044; 0057-0062, (2019/10/17)

The invention discloses a preparation method and an application of a Smo inhibitor based on Nebivolol. The structural formula of the Smo inhibitor is as shown in a formula (I). The invention further discloses a synthetic method and an application of the Smo inhibitor. According to the Smo inhibitor, a beta-receptor retardant Nebivolol with inhibitory activity for Smo proteins serves as a lead compound, and optimization reconstruction is implemented based on the beta-receptor retardant Nebivolol to obtain the Smo inhibitor with good inhibitory activity.

PROCESS FOR THE SYNTHESIS OF INTERMEDIATES OF NEBIVOLOL

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Page/Page column 29-32, (2017/08/20)

The present invention relates to a novel process for the synthesis of the intermediate compounds constituted by chromanyl haloketones of formula III and 6-fluoro-2-(oxiran-2-yl) chromans of formula I. The intermediates thus obtained can be used for the sy

Studies directed toward the exploitation of vicinal diols in the synthesis of (+)-nebivolol intermediates

Devi, Runjun,Das, Sajal Kumar

, p. 571 - 578 (2017/03/29)

While the exploitation of the Sharpless asymmetric dihydroxylation as the source of chirality in the synthesis of acyclic molecules and saturated heterocycles has been tremendous, its synthetic utility toward chiral benzo-annulated heterocycles is relatively limited. Thus, in the search for wider applications of Sharpless asymmetric dihydroxylation-derived diols for the synthesis of benzo-annulated heterocycles, we report herein our studies in the asymmetric synthesis of (R)-1-((R)-6-fluorochroman-2-yl)ethane-1,2-diol, (R)-1-((S)-6-fluorochroman-2-yl)ethane-1,2-diol and (S)-6-fluoro-2-((R)-oxiran-2-yl)chroman, which have been used as late-stage intermediates for the asymmetric synthesis of the antihypertensive drug (S,R,R,R)-nebivolol. Noteworthy is that a large number of racemic and asymmetric syntheses of nebivolol and their intermediates have been described in the literature, however, the Sharpless asymmetric dihydroxylation has never been employed as the sole source of chirality for this purpose.

A process for the preparation of nebivolol and wherein the intermediate compound

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Paragraph 0097-0098, (2016/11/17)

The invention discloses a preparation method of nebivolol used for preparing medicines for treating hypertension of slight or medium degrees, and an intermediate compound. The preparation method comprises the following steps: taking 6-fluoro-2-(1-hydroxy-2-paratoluensulfonyl oxygroup-ethyl)-3,4-dihydrobenzopyrans as an initial raw material, introducing amino, then coupling with 6- fluoro-3,4-dihydro-2-epoxy ethyl-2H-1-benzopyran, and preparing (S,R,R,R) and (R,S,S,S)-nebivolol. Compared with a prior art, the preparation method has the advantages of novel design, simple operation and high yield, the usage of hazardous reagent such as ssodium azide and sodium hydride can be avoided, a column chromatography purifying method is avoided, so that the preparation method conforms to industrial production.

Preparation of 6-fluoro -3,4-dihydro -2H-1-benzopyran-2-oxirane improved method

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, (2016/10/07)

The invention relates to an improvement method for preparing a nebivolol key intermediate, namely 6-fluorin-3,4-dihydro-2H-1-benzopyranyl-2-epoxy ethane. The method comprises the following steps of: (a) condensing a compound (IV) and dihalogenated methane in the presence of an organic metal lithium compound to obtain a compound (II); (b) reducing the compound (II) to obtain a compound (III); and (c) performing cyclization on the compound (III) under alkaline condition to obtain a compound (I). The scheme of the invention has the advantages of readily available raw materials, easiness in operating, greatly increased reaction yield and purity and high contribution to industrial mass production.

PROCESS FOR PREPARATION OF NEBIVOLOL AND IT'S SALTS

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Page/Page column 14; 15, (2016/12/07)

The present invention discloses a new process for preparation of Nebivolol or it's pharmaceutically acceptable salt. More particularly, the invention discloses an improved economical process for the preparation of intermediate, 6-fluoro-3,4- dihydro-2H-1-benzopyran-2-carboxaldehyde of Formula – II, converting the 6- fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde of Formula – II into mixture of [R*(S*)]-6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran and [R*(R*)]-6-fluoro-3,4-dihydro-2-oxiranyl-2H-1-benzopyran of Formula-V and separation of diastereomers of (R*)-6-Fluoro-3,4-dihydro-2-((S*)-oxiran-2-yl)- 2H-benzopran by forming azeotrope.

Method for preparing nebivolol hydrochloride epoxy intermediate 6-fluoro-2-epoxy ethyl chroman

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Paragraph 0045, (2016/12/22)

The invention discloses a method for preparing a nebivolol hydrochloride epoxy intermediate 6-fluoro-2-epoxy ethyl chroman. The method includes the following steps that firstly, under the conditions that water, phosphate, inorganic alkali B1, zinc chloride, a hydrogen source, aldose reductase and NADPH exist, the temperature is 30-70 DEG C and the pH value is 6.0-8.0, a reduction reaction happens to 2-chloro-1-(6-fluorochromane-2-yl)-ethanon, and 2-chloro-1-(6-fluorochromane-2-yl)-alcohol is obtained; secondly, 2-chloro-1-(6-fluorochromane-2-yl)-alcohol is heated in a C1-C6 alkanol solvent and inorganic alkali B2 for a reflux reaction, an organic ester solvent is added dropwise for crystallization after the reaction ends, and 6-fluoro-2-epoxy ethyl chroman is obtained. The preparation method is mild in reaction condition, raw materials and solvents are easy to obtain, and the method is suitable for industrial production.

A kind of nebivolol hydrochloride synthetic method

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, (2017/03/28)

The invention discloses a synthetic method of nebivolol. The synthetic method comprises the following steps: by taking a 2-amino-1-(-6-fluoro-2-chromanyl) ethanol diastereomer mixture as an initial raw material, firstly, recrystallizing and separating the 2-amino-1-(-6-fluoro-2-chromanyl) ethanol diastereomer mixture to respectively obtain corresponding diastereomers A and B; carrying out reactions such as diazotization, halogenation and cyclization on the diastereomer B to synthesize an epoxy compound; and then, carrying out a reaction on the obtained epoxy compound and the diastereomer A to obtain nebivolol. The method disclosed by the invention is mild in reaction condition, simple and convenient to operate and short in synthetic line, and is suitable for industrialized batch production of nebivolol.

A PROCESS FOR THE PREPARATION OF 6-FLUORO-3,4-DIHYDRO-2H-CHROMENE- 2-CARBALDEHYDE

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, (2014/08/06)

The present invention relates to a process for ihe preparation of 6-f!uoro-3,4-dihydro- 2H-chromene-2-carbaidehyde which is useful as an Intermediate in the synthesis of Nebivolol or its pharmaceutical acceptable salts.

PROCESS FOR THE PREPARATION OF EPOXIDES AS INTERMEDIATES FOR THE SYNTHESIS OF NEBIVOLOL

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Page/Page column 24, (2013/03/26)

The present invention relates to a novel process of synthesis of epoxides, 6-fluoro-2- (oxiran-2-yl) chroman (Figure 1), intermediates for the synthesis of nebivolol, depicted in Scheme (1), enabling to obtain the above- mentioned epoxides in a racemic or semichiral form.

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