[ CAS No. 576-86-3 ] {[proInfo.proName]}

Name: 576-86-3|2,4-Dibromo-6-fluorophenol|98%
Brand: Ambeed
SKU: A632322
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2D 3D

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Quality Control of [ 576-86-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 576-86-3 ]

SDS Specification

Alternatived Products of [ 576-86-3 ]

Product Details of [ 576-86-3 ]

CAS No. :	576-86-3	MDL No. :	MFCD00042233
Formula :	C₆H₃Br₂FO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XJDJZAUITWTZAS-UHFFFAOYSA-N
M.W :	269.89	Pubchem ID :	2773980
Synonyms :

Calculated chemistry of [ 576-86-3 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.82
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.12
Log Po/w (XLOGP3) :	3.54
Log Po/w (WLOGP) :	3.48
Log Po/w (MLOGP) :	3.41
Log Po/w (SILICOS-IT) :	3.15
Consensus Log Po/w :	3.14

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.19
Solubility :	0.0175 mg/ml ; 0.0000649 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.65
Solubility :	0.0605 mg/ml ; 0.000224 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.81
Solubility :	0.0422 mg/ml ; 0.000156 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.48

Safety of [ 576-86-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 576-86-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 576-86-3 ]
Downstream synthetic route of [ 576-86-3 ]

[ 576-86-3 ] Synthesis Path-Upstream 1~4

1
[ 367-12-4 ]
[ 2105-94-4 ]
[ 576-86-3 ]

Reference： [1] Tetrahedron, 2012, vol. 68, # 46, p. 9456 - 9463

2
[ 367-12-4 ]
[ 2105-94-4 ]
[ 576-86-3 ]
[ 2040-89-3 ]

Reference： [1] Dalton Transactions, 2013, vol. 42, # 33, p. 11926 - 11940

3
[ 367-12-4 ]
[ 2105-94-4 ]
[ 576-86-3 ]
[ 2040-89-3 ]

Reference： [1] Dalton Transactions, 2013, vol. 42, # 33, p. 11926 - 11940

4
[ 576-86-3 ]
[ 320-76-3 ]
[ 329-49-7 ]

Reference： [1] Journal of the American Chemical Society, 1944, vol. 66, p. 1872

[ 576-86-3 ] Synthesis Path-Downstream 1~15

1
[ 576-86-3 ]
[ 320-76-3 ]
[ 329-49-7 ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 1872

2
[ 367-12-4 ]
[ 576-86-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-chloro-N-fluoro-benzenesulfonamide; potassium bromide In acetonitrile at 20℃; for 0.333333h;
76%	With ammonium peroxodisulfate; sodium bromide In water at 20℃; for 6h; Irradiation;	11 Example 1: 2,4,6-tribromophenol: General procedure: 1 mmol of phenol was added to a photocatalytic reactor,5.0 mmol sodium bromide, 0.2 mmol amine persulfate, 3 mL water, at room temperature,The reaction was performed in a photocatalytic reactor at 5W for 6 hours.After the reaction was completed, it was extracted with a small amount of ethyl acetate, and the organic phase was recrystallized.A white solid was obtained with a yield of 83%.
	With bromine; acetic acid

With water; bromine

Reference： [1]Jiang, Pan-Pan; Yang, Xian-Jin [RSC Advances, 2016, vol. 6, # 93, p. 90031 - 90034]
[2]Current Patent Assignee: FUJIAN MEDICAL UNIVERSITY - CN110143852, 2019, A Location in patent: Paragraph 0012; 0022
[3]Raiford; Le Rosen [Journal of the American Chemical Society, 1944, vol. 66, p. 2080]
[4]Finger et al. [Journal of the American Chemical Society, 1959, vol. 81, p. 94,95, 97]

3
[ 576-86-3 ]
[ 79-11-8 ]
[ 319-51-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide

Reference： [1]Finger et al. [Journal of the American Chemical Society, 1959, vol. 81, p. 94,95, 97]

4
[ 576-86-3 ]
[ 64-19-7 ]
NaNO₂ [ No CAS ]
[ 320-76-3 ]
[ 329-49-7 ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 1872

5
[ 367-12-4 ]
[ 7726-95-6 ]
[ 64-19-7 ]
[ 576-86-3 ]

Reference： [1]Raiford; Le Rosen [Journal of the American Chemical Society, 1944, vol. 66, p. 2080]

6
[ 367-12-4 ]
[ 2105-94-4 ]
[ 576-86-3 ]

Yield	Reaction Conditions	Operation in experiment
	With vanadate(V)-dependent bromoperoxidase I from Ascophyllum nodosum; dihydrogen peroxide; sodium bromide In water; <i>tert</i>-butyl alcohol at 23℃; for 72h; Enzymatic reaction; Overall yield = 106 mg;	General procedure: A solution of H2O2 (1.0 mL, 0.825 M) and NaBr (77.2 mg, 0.75 mmol) in MES-buffer (500 mM, pH 6.2) was added with a syringe pump (8 h, 2.08 mL/min) to a solution of substrate 1, or 8 (0.75 mmol) and VBrPO(AnI) [55.2 mL (0.5626 mg/mL; 558 UT/mg), 17.3 UT, 0.036 mmol% for 1a, 1c, and 8; 62.8 mL (0.4505 mg/mL; 611 UT/mg), 17.3 UT, 0.031 mmol% for 1b and 1d-f] in MES-buffer (500 mM, pH 6.2, 10.0 mL) and tBuOH (3.3 mL). The reaction mixturewas stirred at 23 °C for 3 d. The aqueous layer was extracted with Et2O (4*10 mL). Combined organic extracts were dried (MgSO4). The solvent was removed under reduced pressure (14 mbar, 40 °C) to afford a product mixture, whichwas analyzed by 1H NMR or GC, using pentachlorobenzene (1H NMR, 1aed and), 1- bromodecane (1H NMR, for 1e), or n-decane (GC, for 8) as an internal standard in comparison to spectroscopic data from authentic references. pH and bromoperoxidase activity (triiodide assay35)were determined from the aqueous layer.
	Stage #1: 2-fluorophenol In acetonitrile at 20℃; for 0.0833333h; Stage #2: With N-Bromosuccinimide In acetonitrile at 20℃; for 24h;	Representative procedure for the preparation of compound 11a General procedure: To a solution of phenol (470.6 mg, 5 mmol) in MeCN (10 mL) was added con. H2SO4 (285 μL, 1.05 equiv.) at room temperature, the mixture was stirred for 5 min. Then, NBS (934.4 mg, 1.05 equiv.) was added to the mixture. The reaction was monitored using TLC analysis. The mixture was evaporated to dryness. H2O (15 mL) was added to the residue and extracted with CH2Cl2 (3 x 15 mL). The combined organic layers were washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to afford the crude product. The major product was isolated using silica gel chromatography to obtain the product as light yellow liquid; yield: 79% (0.69 g).

Reference： [1]Wischang, Diana; Hartung, Jens [Tetrahedron, 2012, vol. 68, # 46, p. 9456 - 9463]
[2]Wu, Yong-Qi; Lu, Hai-Jia; Zhao, Wen-Ting; Zhao, Hong-Yi; Lin, Zi-Yun; Zhang, Dong-Feng; Huang, Hai-Hong [Synthetic Communications, 2020, vol. 50, # 6, p. 813 - 822]

7
[ 367-12-4 ]
[ 2105-94-4 ]
[ 576-86-3 ]
[ 2040-89-3 ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 11926 - 11940

8
[ 576-86-3 ]
2-fluoro-4,6-dimethylphenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 50 °C 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate / 1,2-dimethoxyethane; water / 90 °C / Inert atmosphere 3: hydrogen; palladium 10% on activated carbon / ethanol / 1 h / 10 - 35 °C