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Structure of 7500-37-0

Chemical Structure| 7500-37-0

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Product Details of [ 7500-37-0 ]

CAS No. :7500-37-0
Formula : C10H9BrO3
M.W : 257.08
SMILES Code : CC(OCC(C1=CC=C(Br)C=C1)=O)=O
MDL No. :MFCD00174274
Boiling Point : No data available
InChI Key :DYDDLQHJYMWTMU-UHFFFAOYSA-N
Pubchem ID :343879

Safety of [ 7500-37-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 7500-37-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.2
Num. rotatable bonds 4
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 55.24
TPSA ?

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

43.37 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.23
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

2.22
Log Po/w (WLOGP)?

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

2.19
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.

2.02
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

2.62
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.26

Water Solubility

Log S (ESOL):?

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

-2.89
Solubility 0.335 mg/ml ; 0.0013 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.

-2.77
Solubility 0.441 mg/ml ; 0.00172 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

-3.68
Solubility 0.0533 mg/ml ; 0.000207 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

Yes
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

Yes
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.

-6.29 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

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<0.0
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)

1.62

Application In Synthesis of [ 7500-37-0 ]

* 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 [ 7500-37-0 ]

[ 7500-37-0 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 25128-35-2 ]
  • [ 7500-37-0 ]
  • 2-(4-bromo-phenyl)-3-hydroxy-quinoline-4,8-dicarboxylic acid [ No CAS ]
  • 3
  • [ 127-09-3 ]
  • [ 99-73-0 ]
  • [ 7500-37-0 ]
YieldReaction ConditionsOperation in experiment
82% With PEG2(at)SiO2(at)Fe3O4; In water; for 1.25h;Reflux; General procedure: A magnetically stirred solution of alpha-bromo ketone (1.0 mmol) andNaX (2.0 mmol) in water (5.0 mL), PEGSiO2Fe3O4 (50 mg) was added. The resulting suspension was stirred under reflux conditions for the time shown in Table 1. After completion of the reaction that confirmed by TLC, the MNPs were removed magnetically and solid was filtered off, washed with water and subjected to flash chromatography.The desired phenacyl derivatives obtained in 82% to 94% isolated yields.
74% With 1,4-bis(imidazol-1-yl)butane-based poly(ionic liquid); In water; at 60℃; for 0.25h;Green chemistry; General procedure: A magnetically stirred mixture of alpha-bromo ketone (1.0 mmol) with NaY (1.5 mmol) and the catalyst 3(0.01 g) in water (5 mL) was heated to 60C for the time specified in the table. Progress of the reaction was monitored by TLC. After completion of the reaction,diethyl ether (3×5 mL) was added and the obtained organic phase was separated and dried with CaCl2. The solvent was removed in vacuo. The residue formed was purified by column chromatography on silica gel to give the corresponding phenacyl derivatives.
  • 4
  • [ 628-52-4 ]
  • [ 99-73-0 ]
  • [ 7500-37-0 ]
  • 5
  • [ 99-73-0 ]
  • Acetic acid (R)-4-((R)-2,3-dimethyl-cyclopent-2-enyl)-4-hydroxy-pentyl ester [ No CAS ]
  • [ 7500-37-0 ]
  • 6
  • [ 109-83-1 ]
  • [ 7500-37-0 ]
  • 6-(4-Bromo-phenyl)-4-methyl-3,4-dihydro-2H-[1,4]oxazine [ No CAS ]
  • 7
  • [ 109-83-1 ]
  • [ 7500-37-0 ]
  • [ 83081-06-5 ]
  • 8
  • [ 111-75-1 ]
  • [ 7500-37-0 ]
  • [ 83081-11-2 ]
  • 10
  • [ 7500-37-0 ]
  • [ 92093-23-7 ]
  • [ 160332-70-7 ]
  • 11
  • [ 7500-37-0 ]
  • Acetic acid (S)-2-(4-bromo-phenyl)-2-hydroxy-ethyl ester [ No CAS ]
  • [ 306763-43-9 ]
  • 12
  • [ 64-19-7 ]
  • [ 99-73-0 ]
  • [ 7500-37-0 ]
YieldReaction ConditionsOperation in experiment
90.2% With triethylamine; In acetonitrile; at 80℃; for 2h; 4-(Bromoacetyl)bromobenzene (6.00 g, 21.6 mmol, 1 equiv),Acetonitrile (50 mL), triethylamine (6.0 mL, 43.2 mmol, 2 equiv),Acetic acid (2.5 mL, 43.2 mmol, 2 equiv) was placed in a 100 mL eggplant bottle in turn.The temperature was raised to 80 C for 2 hours. After the reaction was completed, the solvent was evaporated, and the residue was dissolved in dichloromethane (100 mL).Wash the organic layer with 2N hydrochloric acid (100 mL), and wash several layers with saturated aqueous sodium carbonate (100 mL).The organic layer was washed with distilled water, dried over anhydrous sodium sulfate, evaporated and evaporated5.01 g of a yellow solid was obtained in a yield of 90.2%.
  • 13
  • [ 60488-44-0 ]
  • [ 99-73-0 ]
  • [ 7500-37-0 ]
  • [ 102444-12-2 ]
  • 15
  • [ 10534-59-5 ]
  • [ 99-73-0 ]
  • [ 7500-37-0 ]
  • 16
  • [ 7500-37-0 ]
  • [ 110-73-6 ]
  • [ 83081-09-8 ]
  • 17
  • [ 99-73-0 ]
  • [ 56-36-0 ]
  • [ 7500-37-0 ]
  • 21
  • [ 108-22-5 ]
  • [ 7500-37-0 ]
  • [ 306763-43-9 ]
  • [ 306282-43-9 ]
  • (R)-2-methylcarbonyloxy-1-(4-bromophenyl)ethyl acetate [ No CAS ]
  • 22
  • [ 4209-02-3 ]
  • [ 64-19-7 ]
  • [ 7500-37-0 ]
  • 23
  • [ 7500-37-0 ]
  • [ 92093-23-7 ]
  • 24
  • [ 4209-02-3 ]
  • [ 127-08-2 ]
  • [ 7500-37-0 ]
  • 25
  • [ 99-90-1 ]
  • [ 64-19-7 ]
  • [ 7500-37-0 ]
  • 26
  • [ 127-09-3 ]
  • 4-Br-C6H4-COCH2-Br(Cl) [ No CAS ]
  • [ 7500-37-0 ]
  • 27
  • [ 20205-43-0 ]
  • [ 7500-37-0 ]
  • [ 924899-55-8 ]
  • 28
  • [ 108-24-7 ]
  • [ 99-90-1 ]
  • [ 7500-37-0 ]
  • 29
  • C12H15NO2Br(1+)*C7H7SO3(1-) [ No CAS ]
  • [ 7500-37-0 ]
  • 32
  • [ 7500-37-0 ]
  • [ 306763-43-9 ]
  • 33
  • [ 7500-37-0 ]
  • [ 306282-43-9 ]
  • 34
  • [ 108-86-1 ]
  • ς-[2,4,6-(CH3)3C6H2]Ni(2,2'-bipyridyl)Br [ No CAS ]
  • [ 7500-37-0 ]
  • 35
  • [ 7500-37-0 ]
  • [ 83081-06-5 ]
 

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bouveault-Blanc Reduction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Ester Cleavage • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • 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 Dihalides • Reactions with Organometallic Reagents • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • 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

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[ 7500-37-0 ]

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