(5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE

Product Name: (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE
CAS No.: 444335-16-4
Chemical Name: (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE
Synonyms: (R)-3-(4-BroMo-3-fluorophenyl)-5-(hydroxyMethyl)oxazolidin-2-one;(5R)-3-(4-broMo-3-fluorophenyl)-5-(hydroxyMethyl)-1,3-oxazolidin-2-one;zolidin-2-one;Torezolid Intermediate3;Thiophene,2-(4-bromoethyl)-;3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)-2-oxazolidinone;(5R)-3-(4-Bromo-Fluorophenyl)-5-Hydroxy methyloxazolidin-2-One;(5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE;(5R)-3-(4-Bromo-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-...;(5R)-3-(4-bromo-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-onea
CBNumber: CB7289019
Molecular Formula: C10H9BrFNO3
Formula Weight: 290.09
MOL File: 444335-16-4.mol

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(5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE Property

Boiling point:: 401.6±35.0 °C(Predicted)
Density: 1.701±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
pka: 14.05±0.10(Predicted)
Appearance: White to light yellow Solid
optical activity: -36° (C=0.01 g/ml, DMSO)
InChI: InChI=1S/C10H9BrFNO3/c11-8-2-1-6(3-9(8)12)13-4-7(5-14)16-10(13)15/h1-3,7,14H,4-5H2/t7-/m1/s1
InChIKey: UGBKYDASQNOIHP-SSDOTTSWSA-N
SMILES: O1[C@@H](CO)CN(C2=CC=C(Br)C(F)=C2)C1=O

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: B700175
Product name: (5R)-3-(4-Bromo-3-fluorophenyl)-5-(hydroxymethyl)-2-oxazolidinone
Packaging: 1g
Price: $70
Updated: 2021/12/16

Matrix Scientific

Product number: 094329
Product name: (R)-3-(4-Bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one
Purity: 95+%
Packaging: 250mg
Price: $115
Updated: 2021/12/16

ChemScene

Product number: CS-M3231
Product name: 2-Oxazolidinone,3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)-,(5R)-
Purity: 99.43%
Packaging: 10g
Price: $141
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CCH0031212
Product name: (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE
Purity: 95.00%
Packaging: 5G
Price: $253.05
Updated: 2021/12/16

ChemScene

Product number: CS-M3231
Product name: 2-Oxazolidinone,3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)-,(5R)-
Purity: 99.43%
Packaging: 25g
Price: $283
Updated: 2021/12/16

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(5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE Chemical Properties,Usage,Production

Uses

(5R)-3-(4-Bromo-3-fluorophenyl)-5-(hydroxymethyl)-2-oxazolidinone is an oxazolidinone derivative and often used for chiral synthesis. Oxazolidinone are also used as antimicrobial agents.

Synthesis

510729-01-8

60456-26-0

444335-16-4

General procedure for the synthesis of (5R)-3-(4-bromo-3-fluorophenyl)-5-hydroxymethoxazolidin-2-one from phenylmethyl N-(4-bromo-3-fluorophenyl)formate and glycidyl butyrate: 119 g (367 mmol) of phenylmethyl N-(4-bromo-3-fluorophenyl)formate was dissolved in 300 mL of tetrahydrofuran and 150 mL of dimethylformamide mixed solvent and 38.19 g (477 mmol) of lithium tert-butoxide was added slowly dropwise at 0 °C. The reaction solution was stirred for 10 min, then 63 mL (440 mmol) of (R)-glycidyl butyrate and 21 mL (550 mmol) of methanol were added, and the resulting solution continued to be stirred for 3 h at room temperature. Upon completion of the reaction, the pH of the reaction mixture was adjusted to about 6 with aqueous ammonium chloride, followed by concentration under reduced pressure. The concentrate was dissolved in 1000 mL of 80% ethyl acetate/hexane mixed solvent, washed sequentially with water and saturated aqueous sodium chloride solution (brine), and the organic phase was dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, purification by column chromatography afforded 93 g (320 mmol) of (5R)-3-(4-bromo-3-fluorophenyl)-5-hydroxymethoxazolidin-2-one as a white solid (yield: 87%).1H NMR (600 MHz, CDCl3) δ 7.53 (m, 2H), 7.15 (dd, J1 = 9.0 Hz, J2 = 2.4 Hz, 1H), 4.77 (m, 1H), 4.00 (m, 3H), 3.77 (m, 1H), 2.10 (t, J = 6.0 Hz, 1H).

References

[1] Patent: EP2692727, 2014, A2. Location in patent: Paragraph 0161-0162
[2] Patent: US2014/179691, 2014, A1. Location in patent: Paragraph 0172-0174
[3] Patent: US9133213, 2015, B2. Location in patent: Page/Page column 28; 29
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 23, p. 5310 - 5321
[5] Patent: WO2015/66413, 2015, A1. Location in patent: Page/Page column 141; 142

(5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE Preparation Products And Raw materials

Raw materials

Preparation Products

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(5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE Suppliers

China 207 India 2 United Kingdom 1 United States 10 Global 220

BOC Sciences

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View Lastest Price from (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE manufacturers

Henan Aochuang Chemical Co.,Ltd.

Product: (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one 444335-16-4
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1Ton
Release date: 2022-09-30

Shaanxi Dideu Medichem Co. Ltd

Product: (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE 444335-16-4
Price: US $0.10/KG
Min. Order: 1KG
Purity: 99.0%
Supply Ability: 1000Tons
Release date: 2024-08-04

ZHUHAI HRD PHARMACEUTICAL CO., LTD.

Product: (5R)-3-(4-Bromo-3-fluorophenyl)-5-hydroxymethyloxazoliding-2-one 444335-16-4
Price: US $0.00/kg Ton
Min. Order: 1kg Ton
Purity: 99%+
Supply Ability: 2 tons/month
Release date: 2022-10-09

444335-16-4, (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONERelated Search:

5-Bromo-2-pyridinecarbonitrile 2-(1-methyltetrazol-5-yl)pyridine 3-(DIMETHYLAMINO)-1-(NAPHTHALEN-1-YL)PROPAN-1-ONE HYDROCHLORIDE 3-benzyl-6-bromo-2-methoxyquinoline 4-Bromo-2-nitroaniline 4-Pyrimidinamine, 2,5-dichloro-N-[2-[(1-methylethyl)sulfonyl]phenyl]- 2,5-Dichloro-N-[2-[(1-methylethyl)thio]phenyl]-4-pyrimidinamine 3-benzyl-6-bromo-2-chloroquinoline 3-(dimethylamino)-1-(naphthalen-5-yl)propan-1-one 5-Methyl-2-(1-Methylethoxy)-4- (4-piperidinyl)- BenzenaMine hydrochloride (1:2) Tedizolid Phosphate CarbaMic acid, N-[3-fluoro-4-[6-(2-Methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-, phenylMethyl ester 5-BROMO-2-(2-METHYL-2H-TETRAZOL-5-YL)-PYRIDINE 2-(2-Methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine Torezolid 5-BROMO-2-(1H-TETRAZOL-5-YL)PYRIDINE Benzyl (4-broMo-3-fluorophenyl)carbaMate (5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE

2-Oxazolidinone,3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)-, (5R)-

(5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE

Torezolid Intermediate3

3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)-2-oxazolidinone

(R)-3-(4-BroMo-3-fluorophenyl)-5-(hydroxyMethyl)oxazolidin-2-one

(R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one444335-16-4

(5R)-3-(4-broMo-3-fluorophenyl)-5-(hydroxyMethyl)-1,3-oxazolidin-2-one

(5R)-3-(4-bromo-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-onea

zolidin-2-one

(5R)-3-(4-BROMO-3-FLUOROPHENYL)-5-HYDROXYMETHYLOXAZOLIDIN-2-ONE ISO 9001：2015 REACH

(5R)-3-(4-Bromo-Fluorophenyl)-5-Hydroxy methyloxazolidin-2-One

(5R)-3-(4-Bromo-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-...

(R)-3-(4-BroMo-3-fluorophenyl)Chemicalbook-5-(hydroxyMethyl)oxazolidin-2-one

Thiophene,2-(4-bromoethyl)-

(5R)-3-(4-Bromo-3-fluorophenyl)-5-hydroxymethyloxazoliding-2-one

444335-16-4

Tedizolid intermediates

444335-16-4