(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran

Description Physical Form synthesis

Product Name: (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran
CAS No.: 915095-89-5
Chemical Name: (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran
Synonyms: (S)-3-(4-(5-broMo-2-chlorobenzyl)phenoxy)tetrahydrofuran;915085-89-5;EMpagliflozin InterMediate;(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan;(3S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydro-furan;(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)-benzene;Furan, 3-[4-[(5-broMo-2-chlorophenyl)Methyl]phenoxy]tetrahydro-, (3S)-;EG4-Br;Empagliflozin-7;EMpagliflozin int3
CBNumber: CB82652160
Molecular Formula: C17H16BrClO2
Formula Weight: 367.66
MOL File: 915095-89-5.mol

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(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran Property

Melting point:: 49-51°C
Boiling point:: 459.1±45.0 °C(Predicted)
Density: 1.431±0.06 g/cm3 (20 ºC 760 Torr)
storage temp.: Sealed in dry,Room Temperature
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
color: White to Off-White
optical activity: Consistent with structure
InChI: InChI=1S/C17H16BrClO2/c18-14-3-6-17(19)13(10-14)9-12-1-4-15(5-2-12)21-16-7-8-20-11-16/h1-6,10,16H,7-9,11H2/t16-/m0/s1
InChIKey: HUNLNKBDQXGMAP-INIZCTEOSA-N
SMILES: O1CC[C@H](OC2=CC=C(CC3=CC(Br)=CC=C3Cl)C=C2)C1

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Safety

HS Code: 2932190090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TRC

Product number: B680755
Product name: (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran
Packaging: 10g
Price: $105
Updated: 2021/12/16

Ark Pharm

Product number: P000537154
Product name: (S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran
Purity: 97%
Packaging: 1g
Price: $22
Updated: 2021/12/16

Ark Pharm

Product number: P000537154
Product name: (S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran
Purity: 97%
Packaging: 5g
Price: $60
Updated: 2021/12/16

Biosynth Carbosynth

Product number: IB75174
Product name: (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan
Packaging: 2g
Price: $60
Updated: 2021/12/16

Ark Pharm

Product number: P000537154
Product name: (S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran
Purity: 97%
Packaging: 10g
Price: $89
Updated: 2021/12/16

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(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran Chemical Properties,Usage,Production

Description

(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran is used as a reactant to efficiently synthesize SGLT- 2 Epagliflozin inhibitors.

Physical Form

Solid

synthesis

To a mixture of AlCl3 (61.7 g, 0.463 mol) and (S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (100 g, 0.231 mol) in toluene (450 mL) was added 1,1,3,3-tetramethyldisiloxane (40.4 g, 0.301 mol) over 1 hour at<20 °C. The mixture was held at 20-23 °C for an additional 1.5 hours and cooled to 0-5 °C. The cooled solution was slowly added to ice-water (400 mL) over 15 min and the layers separated. The organic was treated with 3N NaOH (400 mL) at room temperature for 16-24 hours and the layers were separated. The organic was concentrated to a low volume (~130 mL). After diluted with acetonitrile (450 mL), the solution was again concentrated to a low volume (~130 mL). To the residue was added acetonitrile (400 mL) followed by a slow addition of water (200 mL). The resulting mixture was cooled to 0-3 °C and held for 2 hours. The solids were collected by filtration and dried in oven to give product. (S)-3-(4-(2-chloro-5- bromobenzyl)phenoxy)tetrahydrofuran (2a). 92% as white crystals.

Uses

(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran is used as a reactant in the efficient synthesis of empagliflozin inhibitor of SGLT-2 utilizing AlCl3-promoted silane reduction of β-glycopyranoside.

References

[1] Organic Letters, 2014, vol. 16, # 16, p. 4090 - 4093
[2] Patent: CN106905305, 2017, A. Location in patent: Paragraph 0056; 00057; 0058; 0059
[3] Patent: US2006/258749, 2006, A1. Location in patent: Page/Page column 24-25
[4] Patent: US2006/258749, 2006, A1. Location in patent: Page/Page column 25
[5] Patent: US2006/258749, 2006, A1. Location in patent: Page/Page column 25

(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran Preparation Products And Raw materials

Raw materials

Preparation Products

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(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran Suppliers

Canada 1 China 358 India 25 United Kingdom 2 United States 7 Global 393

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View Lastest Price from (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran manufacturers

Handan City Zechi trading Co., LTD

Product: (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran 915095-89-5
Price: US $1.00/g
Min. Order: 100g
Purity: 99
Supply Ability: 1000
Release date: 2025-08-11

WUHAN FORTUNA CHEMICAL CO., LTD

Product: (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan 915095-89-5
Price: US $0.00-0.00/Kg/Drum
Min. Order: 1KG
Purity: 99%min
Supply Ability: 1000kg
Release date: 2021-11-19

Shaanxi Dideu New Materials Co. Ltd

Product: (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran 915095-89-5
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10000KGS
Release date: 2025-02-19

915095-89-5, (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuranRelated Search:

2,3-Butanediol Empagliflozin (R)-Isomer Empagliflozin Impurity 23 Acetoxy Empagliflozin ((2R,3S,4R,5R,6S)-6-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)Methyl acetate N/A Butanoic acid, 4-chloro-3-hydroxy-, (3S)- (S)-3-(4-benzylphenoxy)tetrahydrofuran (R)-3-(p-toluenesulfonyl) oxytetrahydrofuran Empagliflozin (S)-(+)-3-Hydroxytetrahydrofuran 4-(5-broMo-2-chlorobenzyl)phenol Benzo[b]thiophene, 2-[(5-broMo-2-fluorophenyl)Methyl]- (2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone (2S,3R,4S,5S,6R)-2-(3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)-4-chlorophenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylbromide (S)-3-(4-(2-Chloro-5-iodobenzyl)phenoxy)tetrahydrofuran (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone

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