Home Cart Sign in  
Chemical Structure| 185345-46-4 Chemical Structure| 185345-46-4

Structure of 185345-46-4

Chemical Structure| 185345-46-4

3-Bromo-5-fluoro-4-hydroxybenzaldehyde

CAS No.: 185345-46-4

4.5 *For Research Use Only !

Cat. No.: A177980 Purity: 95%

Change View

Size Price

US Stock

Global Stock

In Stock
100mg łÇʶÊÊ Inquiry Inquiry
250mg łÇ˶ÊÊ Inquiry Inquiry
1g łÇÿ¶ÊÊ Inquiry Inquiry
5g łÍó¶ÊÊ Inquiry Inquiry
10g łîÿ¶ÊÊ Inquiry Inquiry
25g łÇîÿ¶ÊÊ Inquiry Inquiry

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 100mg

    łÇʶÊÊ

  • 250mg

    łÇ˶ÊÊ

  • 1g

    łÇÿ¶ÊÊ

  • 5g

    łÍó¶ÊÊ

  • 10g

    łîÿ¶ÊÊ

  • 25g

    łÇîÿ¶ÊÊ

In Stock

- +

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

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

Alternative Products

Product Details of [ 185345-46-4 ]

CAS No. :185345-46-4
Formula : C7H4BrFO2
M.W : 219.01
SMILES Code : O=CC1=CC(F)=C(O)C(Br)=C1
MDL No. :MFCD21606586
InChI Key :FSLFKQZWBRMALB-UHFFFAOYSA-N
Pubchem ID :18701750

Safety of [ 185345-46-4 ]

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

Computational Chemistry of [ 185345-46-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 41.51
TPSA ?

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

37.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.39
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

1.82
Log Po/w (WLOGP)?

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

2.53
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.

1.97
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

2.6
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.06

Water Solubility

Log S (ESOL):?

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

-2.68
Solubility 0.455 mg/ml ; 0.00208 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.

-2.22
Solubility 1.31 mg/ml ; 0.00598 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

-2.91
Solubility 0.269 mg/ml ; 0.00123 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.

-6.34 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

0.0
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

1.0 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)

1.38

Application In Synthesis of [ 185345-46-4 ]

* 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 [ 185345-46-4 ]

[ 185345-46-4 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 405-05-0 ]
  • [ 185345-46-4 ]
YieldReaction ConditionsOperation in experiment
48% With bromine; acetic acid; at 45.0℃; for 26.0h; Intermediate 26. 3-bromo-5-fluoro-4-hydroxybenzaldehyde (26)26; [0198] To a solution of 3-fluoro-4-hydroxybenzaldehyde (2 g, 14.3 mmol, 1 eq, Oakwood Products, Inc., West Columbia, SC, USA) in acetic acid (60 mL), was added a solution of bromine(2.7 g, 17.0 mmol, 1.2 eq) in acetic acid(10 mL), and the mixture was stirred at 45 C for 26 h. After concentration in vacuo, brine (50 mL) was added to the residue and the mixture was extracted with EtOAc(3 X 80 mL). The combined organic layers were dried (Na2SO4), concentrated in vacuo, and purified by reversed phase semi-preparative .HPLC to afford 1.5 g (48%) of_3-bromo-5-fluoro-4- hydroxybenzaldehyde (26).
48% With bromine; In acetic acid; at 45.0℃; for 26.0h; Intermediate 12: 3-bromo-5-fluoro-4-hydroxybenzaldehyde (12)12[0157] To a solution of 3-fluoro-4-hydroxybenzaldehyde (2 g, 14.3 mmol, 1 eq) in acetic acid (60 mL), was added a solution of bromine(2.7 g, 17.0 mmol, 1.2 eq) in acetic acid(10 mL), and the mixture was stirred at 45 C for 26h. After concentration in vacuo, brine (50 mL) was added to the residue and the mixture was extracted with EtOAc(3 X 80 mL). The combined organic layers were dried (Na2SO4), concentrated in vacuo, and purified by reversed phase semi-preparative .HPLC to afford 1.5 g (48 %) of_3-bromo-5-fluoro-4-hydroxybenzaldehyde (12).
  • 2
  • [ 451-40-1 ]
  • [ 185345-46-4 ]
  • [ 57-13-6 ]
  • [ 1283119-08-3 ]
YieldReaction ConditionsOperation in experiment
33% With hydrogenchloride; In ethanol; water; at 95.0℃; for 50.0h;Inert atmosphere; [00305] Step 1: Synthesis of 4-(3-bromo-5-fluoro-4-hydroxyphenyl)-5,6-diphenyl- 3,4-dihydropyrimidin-2(lH)-one: To a mixture of 3-bromo-5-fluoro-4- hydroxybenzaldehyde (Intermediate 77) (600 mg, 2.7 mmol), 1,2-diphenylethanone (538 mg, 2.7 mmol), urea (493 mg, 8.2 mmol) and cone HC1 (1 mL) in ethanol (4 mL) was heated at 95C for 50 hours. The mixture was evaporated under reduced pressure and was purified by silica gel column chromatography (petroleum ether/ethyl acetate =2: 1) to give product (400 mg, yield 33%) as yellow solid. 1H NMR (DMSO 300MHz) : deltaIotaOmicronLambdaIota (brs, 1H), 8.66 (s, 1H), 7.45 (s, 1H), 7.24-6.95 (m, 10H), 6.75 (d, J = 7.8 Hz, 2H), 5.07 (s, 1H). [00306]
  • 3
  • [ 185345-46-4 ]
  • [ 1283119-07-2 ]
  • 4
  • [ 185345-46-4 ]
  • [ 1283119-09-4 ]
  • 5
  • [ 1394291-51-0 ]
  • [ 185345-46-4 ]
YieldReaction ConditionsOperation in experiment
88% With oxygen; cobalt(II) diacetate tetrahydrate; sodium hydroxide; In ethylene glycol; at 80.0℃; under 760.051 Torr; for 8.0h; General procedure: a mixture of substrate 1a(1 mmol), cobalt salt (n1mol%) and NaOH (n2 equiv)in EG (5 mL) was stirred with O2 (1 atm) being bubbled, under 80 oCfor 8 h. Hydrochloric acid (10 mL, 2%) and methyl tert-butyl ether (MTBE, 10 mL) were successively added to the reactionmixture. The organic layer was separated, and the aqueous phase was furtherextracted with MTBE(10 mL × 2). The combined organic phase was dried over anhydrous sodium sulfateand concentrated to give a residue, which was purified by column chromatographyon silica gel (eluents: petroleum ether/ethyl acetate, 10/1) to provide thedesired products 2a.
  • 6
  • [ 185345-46-4 ]
  • 5-(furan-2-carbonyl)indolin-2-one [ No CAS ]
  • 3-(3-bromo-5-fluoro-4-methoxybenzylidene)-5-(furan-2-carbonyl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With piperidine; In ethanol; at 80.0℃; for 16.0h;Inert atmosphere; General procedure: Piperidine (8.7 muL, 0.088 mmol), 3,5-difluoro-4-hydroxybenzaldehyde (69.5 mg, 0.44 mmol) and S3 (100.0 mg, 0.44 mmol) were dissolved in EtOH (2.0 mL). The mixture was heated to 80 oC for 16 h. The orange solid was filtered and washed with 1N HCl and Et2O to afford 3 (114.0 mg, 70%, mixture of E/Z isomers).
 

Historical Records

Technical Information

• Acidity of Phenols • Alkyl Halide Occurrence • Arndt-Eistert Homologation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Halogenation of Phenols • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hunsdiecker-Borodin Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Oxidation of Phenols • Passerini Reaction • Paternò-Büchi Reaction • Pechmann Coumarin Synthesis • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Carboxylic Acids • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Reactions of Dihalides • Reformatsky Reaction • Reimer-Tiemann Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

Related Functional Groups of
[ 185345-46-4 ]

Fluorinated Building Blocks

Chemical Structure| 178546-34-4

A643499 [178546-34-4]

3-Bromo-5-fluoro-2-hydroxybenzaldehyde

Similarity: 0.86

Chemical Structure| 399-00-8

A152062 [399-00-8]

5-Bromo-4-fluoro-2-hydroxybenzaldehyde

Similarity: 0.81

Chemical Structure| 1427438-90-1

A142114 [1427438-90-1]

4-Bromo-2-fluoro-6-hydroxybenzaldehyde

Similarity: 0.80

Chemical Structure| 1009093-60-0

A358321 [1009093-60-0]

3-Bromo-5-fluoro-2-methoxybenzaldehyde

Similarity: 0.78

Chemical Structure| 2040-89-3

A115265 [2040-89-3]

2-Bromo-6-fluorophenol

Similarity: 0.78

Aryls

Chemical Structure| 178546-34-4

A643499 [178546-34-4]

3-Bromo-5-fluoro-2-hydroxybenzaldehyde

Similarity: 0.86

Chemical Structure| 399-00-8

A152062 [399-00-8]

5-Bromo-4-fluoro-2-hydroxybenzaldehyde

Similarity: 0.81

Chemical Structure| 1427438-90-1

A142114 [1427438-90-1]

4-Bromo-2-fluoro-6-hydroxybenzaldehyde

Similarity: 0.80

Chemical Structure| 1009093-60-0

A358321 [1009093-60-0]

3-Bromo-5-fluoro-2-methoxybenzaldehyde

Similarity: 0.78

Chemical Structure| 2040-89-3

A115265 [2040-89-3]

2-Bromo-6-fluorophenol

Similarity: 0.78

Bromides

Chemical Structure| 178546-34-4

A643499 [178546-34-4]

3-Bromo-5-fluoro-2-hydroxybenzaldehyde

Similarity: 0.86

Chemical Structure| 399-00-8

A152062 [399-00-8]

5-Bromo-4-fluoro-2-hydroxybenzaldehyde

Similarity: 0.81

Chemical Structure| 1427438-90-1

A142114 [1427438-90-1]

4-Bromo-2-fluoro-6-hydroxybenzaldehyde

Similarity: 0.80

Chemical Structure| 1009093-60-0

A358321 [1009093-60-0]

3-Bromo-5-fluoro-2-methoxybenzaldehyde

Similarity: 0.78

Chemical Structure| 2040-89-3

A115265 [2040-89-3]

2-Bromo-6-fluorophenol

Similarity: 0.78

Aldehydes

Chemical Structure| 178546-34-4

A643499 [178546-34-4]

3-Bromo-5-fluoro-2-hydroxybenzaldehyde

Similarity: 0.86

Chemical Structure| 399-00-8

A152062 [399-00-8]

5-Bromo-4-fluoro-2-hydroxybenzaldehyde

Similarity: 0.81

Chemical Structure| 1427438-90-1

A142114 [1427438-90-1]

4-Bromo-2-fluoro-6-hydroxybenzaldehyde

Similarity: 0.80

Chemical Structure| 1009093-60-0

A358321 [1009093-60-0]

3-Bromo-5-fluoro-2-methoxybenzaldehyde

Similarity: 0.78

Chemical Structure| 188813-02-7

A136746 [188813-02-7]

3-Bromo-5-fluorobenzaldehyde

Similarity: 0.76