Home Cart Sign in  
Chemical Structure| 496-69-5 Chemical Structure| 496-69-5

Structure of 2-Bromo-4-fluorophenol
CAS No.: 496-69-5

Chemical Structure| 496-69-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 496-69-5 ]

CAS No. :496-69-5
Formula : C6H4BrFO
M.W : 191.00
SMILES Code : OC1=CC=C(F)C=C1Br
MDL No. :MFCD00010614
InChI Key :MEYRABVEYCFHHB-UHFFFAOYSA-N
Pubchem ID :605472

Safety of [ 496-69-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 496-69-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
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 36.12
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.8
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.63
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.71
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.67
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.48
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.46

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.17
Solubility 0.128 mg/ml ; 0.000669 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.71
Solubility 0.377 mg/ml ; 0.00197 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.96
Solubility 0.211 mg/ml ; 0.00111 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.6 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.22

Application In Synthesis of [ 496-69-5 ]

* 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.

  • Downstream synthetic route of [ 496-69-5 ]

[ 496-69-5 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 13195-50-1 ]
  • [ 496-69-5 ]
  • [ 190966-87-1 ]
  • 2
  • [ 100-97-0 ]
  • [ 496-69-5 ]
  • [ 178546-34-4 ]
YieldReaction ConditionsOperation in experiment
83% Hexamethylenetetramine (14.7 g, 105 mmol) was slowly added to a solution of 2-bromo-4-fluoro-phenol (10 g, 52.4 mmol) in trifluoroacetic acid (40 ml) at rt and heated to reflux for 18 h. The reaction mixture was cooled to rt and then water (60 ml) and sulfuric acid (30 ml, 50%) were added. The mixture was stirred for 3 h at rt and then extracted twice with ethyl acetate. The combined organic extracts were washed with 1N HCl, water, dried (Na2SO4), filtered and concentrated under reduced pressure to give 9.5 g (83%) of 3-bromo-5-fluoro-2-hydroxy-benzaldehyde.1H NMR (400 MHz, chloroform-d) delta ppm 9.82 (s, 1H), 7.55-7.62 (m, 1H), 7.21-7.32 (M, 1H).
73% With trifluoroacetic acid; for 10h;Reflux; Weigh compound 30-1 (1.02 g, 5.33 mmol) in trifluoroacetic acid (7 mL), Ulotropine (1.5 g, 10.66 mmol) was added in portions. The system was reacted at reflux for 10 h. After the reaction is over, The system was adjusted to pH = 1 with a 1N hydrochloric acid solution, and the aqueous phase was extracted with ethyl acetate (15 mL x 3). Combined organic phases, Wash with saturated saline (10mL x 1), Dried over anhydrous sodium sulfate, The solvent was distilled off under reduced pressure, The residue was purified by column chromatography (eluent: petroleum ether / ethyl acetate = 100: 1-80: 1), Compound 30-2 was obtained (yellow solid, 739 mg).
With trifluoroacetic acid; at 80℃; a) 3-Bromo-5-fluoro-2-hydroxybenzaldehyde A mixture of 2-bromo-4-fluorophenol (5 g, 26.18 mmol), trifluoroacetic acid (60 mL), and hexamethylemetetramine (3.68 g, 26.29 mmol) was stirred overnight at 80 C. The resulting solution was extracted with ethyl acetate (2*20 mL) and the organic layers combined. The resulting mixture was washed with H2O. The resulting mixture was washed with sodium bicarbonate (aq). The resulting residue was dried over anhydrous sodium sulfate and concentrated under vacuum to yield 3-bromo-5-fluoro-2-hydroxybenzaldehyde as a yellow solid.
To a solution of 2-bromo-4-fluorophenol (2g) in trifluoroacetic acid (10mL) was added hexamethylenetetramine (2.94g) at room temperature, and the resulting mixture was stirred under reflux for 20 hours. A 50% aqueous solution of sulfuric acid was added to the reaction mixture, and the mixture was stirred for further 4 hours at room temperature. The reaction mixture was extracted with ethyl acetate, and washed with water, 1mol/L hydrochloric acid and brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give the title compound (1.93g). 1H-NMR (CDCl3) delta ppm: 7.25-7.30 (1H, m), 7.56-7.61 (1H, m), 9.83 (1H, s), 11.35 (1H, s)

  • 3
  • [ 50-00-0 ]
  • [ 496-69-5 ]
  • [ 178546-34-4 ]
YieldReaction ConditionsOperation in experiment
93% With triethylamine; magnesium chloride; In tetrahydrofuran; at 160℃; for 0.25h;Microwave irradiation; To a solution of MgCl2 (powder 325 mesh, 5.0 g, 52 mmol, 2 eq), paraformaldehyde (3.0 g, 79 mmol, 3 eq) and Et3N (7.0 mL, 52 mmol, 2 eq) in THF (60 mL) was added 220 (5.0 g, 26 mmol, 1 eq), heated in the microwave at 160 C for 15 min. TLC (3:2 Hexane:DCM) showed complete consumption of 220. THF was evaporated and the reaction mixture was taken up in EtOAc, washed with brine, dried, filtered and concentrated in vacuo to afford 5.2 g of 221 which was used without purification. Yield 93%.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 496-69-5 ]

Fluorinated Building Blocks

Chemical Structure| 147460-41-1

A568552 [147460-41-1]

2-Bromo-5-fluorophenol

Similarity: 0.95

Chemical Structure| 452-08-4

A111871 [452-08-4]

2-Bromo-4-fluoro-1-methoxybenzene

Similarity: 0.91

Chemical Structure| 2040-89-3

A115265 [2040-89-3]

2-Bromo-6-fluorophenol

Similarity: 0.89

Chemical Structure| 27407-11-0

A148536 [27407-11-0]

3-Bromo-4-fluorophenol

Similarity: 0.89

Chemical Structure| 433939-27-6

A400666 [433939-27-6]

3-Bromo-5-fluorophenol

Similarity: 0.89

Aryls

Chemical Structure| 147460-41-1

A568552 [147460-41-1]

2-Bromo-5-fluorophenol

Similarity: 0.95

Chemical Structure| 452-08-4

A111871 [452-08-4]

2-Bromo-4-fluoro-1-methoxybenzene

Similarity: 0.91

Chemical Structure| 2040-89-3

A115265 [2040-89-3]

2-Bromo-6-fluorophenol

Similarity: 0.89

Chemical Structure| 27407-11-0

A148536 [27407-11-0]

3-Bromo-4-fluorophenol

Similarity: 0.89

Chemical Structure| 433939-27-6

A400666 [433939-27-6]

3-Bromo-5-fluorophenol

Similarity: 0.89

Bromides

Chemical Structure| 147460-41-1

A568552 [147460-41-1]

2-Bromo-5-fluorophenol

Similarity: 0.95

Chemical Structure| 452-08-4

A111871 [452-08-4]

2-Bromo-4-fluoro-1-methoxybenzene

Similarity: 0.91

Chemical Structure| 2040-89-3

A115265 [2040-89-3]

2-Bromo-6-fluorophenol

Similarity: 0.89

Chemical Structure| 27407-11-0

A148536 [27407-11-0]

3-Bromo-4-fluorophenol

Similarity: 0.89

Chemical Structure| 433939-27-6

A400666 [433939-27-6]

3-Bromo-5-fluorophenol

Similarity: 0.89