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Chemical Structure| 25834-16-6 Chemical Structure| 25834-16-6

Structure of 25834-16-6

Chemical Structure| 25834-16-6

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CAS No.: 25834-16-6

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Product Details of [ 25834-16-6 ]

CAS No. :25834-16-6
Formula : C8H2Br2O3
M.W : 305.91
SMILES Code : O=C(O1)C2=C(Br)C=CC(Br)=C2C1=O
MDL No. :MFCD01117424
InChI Key :OUAOHMOFJGFOSR-UHFFFAOYSA-N
Pubchem ID :54169537

Safety of [ 25834-16-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Computational Chemistry of [ 25834-16-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 51.59
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.

1.51
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

2.67
Log Po/w (WLOGP)?

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

2.52
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.

3.1
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

3.17
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.6

Water Solubility

Log S (ESOL):?

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

-3.76
Solubility 0.0531 mg/ml ; 0.000174 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.

-3.23
Solubility 0.179 mg/ml ; 0.000585 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

-4.16
Solubility 0.0213 mg/ml ; 0.0000697 mol/l
Class?

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

Moderately 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

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.

-6.27 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

2.0 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)

2.06

Application In Synthesis of [ 25834-16-6 ]

* 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 [ 25834-16-6 ]

[ 25834-16-6 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 85-44-9 ]
  • [ 25834-16-6 ]
YieldReaction ConditionsOperation in experiment
15% With sulfuric acid; dibromohydantoin,; for 4.0h; 592 g of phthalic anhydride was added to 1 L of concentrated sulfuric acid (70% by mass), and the mixture was dissolved and dissolved. After the solution was dissolved, 572 g of dibromohydantoin was added in three portions.The temperature was controlled by a water bath. After mechanical stirring for 4 hours, the reaction system was poured into 2.5 L of ice water, and 5 L of dichloromethane was added thereto, stirred well, and suction filtered.The filter cake was washed with dichloromethane, and 1.25 L of a saturated aqueous sodium thiosulfate solution was added to the filtrate to remove brown.The organic layer was dried over anhydrous sodium sulfate and evaporatedThe mixture was heated to reflux with ethyl acetate, and then filtered, and then filtered, and ethyl acetate was evaporated to give a white solid (I) (3,6-dibromophthalic anhydride) in a yield of 15%.
  • 2
  • [ 25834-16-6 ]
  • [ 123-31-9 ]
  • [ 42985-19-3 ]
  • 3
  • 3,6-dibromophthalic acid [ No CAS ]
  • [ 25834-16-6 ]
YieldReaction ConditionsOperation in experiment
69% With acetic anhydride; for 1.0h;Reflux; 3,6-dibromophthalic acid (34c) (2.5 g, 7.71 mmol) was refluxed for 1 hour with acetic anhydride (8.33 ml, 81.5 mmol). The reaction mixture was cooled in an ice bath and the resulting precipitate was filtered, washed with cold ether and dried under reduced pressure to afford 4,7-dibromoisobenzofuran- l ,3-dione (34d) (1.6 g , 69 %) as a solid. MS (EI) m/z: 306.9 (M+ l). ? NMR (400 MHz, DMSO): 8 8.05 (s, 2H).
  • 5
  • [ 25834-16-6 ]
  • <i>N</i>-methylene-glycine nitrile [ No CAS ]
  • [ 857802-04-1 ]
  • 6
  • [ 25834-16-6 ]
  • [ 56073-96-2 ]
  • 3,6-dibromo-<i>N</i>-[4-(2-methoxycarbonylamino-1<i>H</i>-benzoimidazol-5-ylsulfanyl)-phenyl]-phthalamic acid [ No CAS ]
  • 7
  • [ 25834-16-6 ]
  • [ 56073-96-2 ]
  • sodium; 3,6-dibromo-2-[4-(2-methoxycarbonylamino-1<i>H</i>-benzoimidazol-5-ylsulfanyl)-phenylcarbamoyl]-benzoate [ No CAS ]
  • 8
  • [ 25834-16-6 ]
  • <i>N</i>,<i>N</i>-(3,6-dibromo-phthaloyl)-glycine [ No CAS ]
  • 9
  • [ 25834-16-6 ]
  • <i>N</i>,<i>N</i>-(3,6-dibromo-phthaloyl)-glycin-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Typical halogen-containing anhydrides include: 3-chlorophthalic anhydride, 4-bromophthalic anhydride, 3,6-dibromophthalic anhydride, tetrabromophthalic anhydride, tetrachlorophthalic anhydride, 1,4,5,6,7,7-hexachlorobicyclo(2.2.1)-5-heptene-2,3-dicarboxylic anhydride. 1,4,5,6,7,7-hexachloro-2-methylbicyclo(2.2.1)-5-heptene-2,3-dicarboxylic anhydride, 1,4,5,6,7,7-hexachlorobicyclo(2.2.1)-5-heptene-2-acetic-2-carboxylic anhydride 5,6,7,8,9,9-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-5,8-methano-2,3-naphthalene dicarboxylic anhydride, ...
  • 12
  • [ 104-75-6 ]
  • [ 25834-16-6 ]
  • [ 863027-98-9 ]
YieldReaction ConditionsOperation in experiment
In acetic acid; Example 1 N-(2-ethylhexyl)-3,6-dibromophthalimide: <strong>[25834-16-6]3,6-Dibromo phthalic anhydride</strong> (1.53 g, 5 mmol), 2-ethylhexyl amine (0.84 g, 6.5 mmol) and glacial acetic acid (30 ml) were combined and refluxed under argon for two hours. After most of the acetic acid was removed under reduced pressure, N-(2-ethylhexyl)-3,6-dibromophthalimide was separated via column chromatography (silica gel, dichloromethane:hexanes 1:3). Colorless crystals were obtained after recrystallization from hexanes (1.88 g, 90%). 1H NMR (CDCl3, 400 MHz, ppm): delta 7.63 (s, 2H), 3.56 (d, 2H), 1.80 (m, 1H), 1.29 (m, 8H), 0.88 (m, 6H). 13C NMR (CDCl3, 100 MHz, ppm): delta 165.34, 139.71, 131.42, 117.71, 42.66, 38.46, 30.77, 28.76, 24.09, 23.16, 14.26, 10.59. mp: 65 C. GC-MS: m/z: 415 (C16H19Br2NO2+), 319 (100%). Anal. Calcd for C16H19Br2NO2(%): C, 46.07; H, 4.59; N, 3.36.
  • 14
  • [ 25834-16-6 ]
  • [ 1219795-55-7 ]
  • 15
  • [ 62281-06-5 ]
  • [ 25834-16-6 ]
  • [ 1391835-88-3 ]
  • 16
  • [ 25834-16-6 ]
  • [ 1387566-56-4 ]
  • 17
  • [ 25834-16-6 ]
  • [ 1387566-54-2 ]
  • 18
  • [ 25834-16-6 ]
  • [ 108-91-8 ]
  • [ 1387566-55-3 ]
  • 19
  • [ 25834-16-6 ]
  • [ 866767-16-0 ]
YieldReaction ConditionsOperation in experiment
62.5% With urea; In 5,5-dimethyl-1,3-cyclohexadiene; at 150℃; for 0.5h;Microwave irradiation; 4.7- dibromoisobenzofuran- l ,3-dione (34d) (1.6 g, 5.23 mmol), urea (0.47 g, 7.86 mmol) and xylene (15 ml) were mixed together and heated in a microwave for 30 min at 150C. The resulting reaction mixture was cooled at room temperature and the precipitate so obtained was filtered, washed with water and dried under reduced pressure to afford 4,7-dibromoisoindoline- l ,3-dione (34e) ( 1 g, 62.5%) as a solid. MS (EI) m/z: 305.9 (M+ l). ? NMR (400 MHz, DMSO): 8 1 1.69 (s, 1H), 7.86 (d, J = 8.4 Hz, 2H)..
  • 20
  • [ 25834-16-6 ]
  • [ 1417569-16-4 ]
  • 21
  • [ 25834-16-6 ]
  • [ 1417569-18-6 ]
  • 22
  • [ 25834-16-6 ]
  • [ 1610046-78-0 ]
  • 23
  • [ 25834-16-6 ]
  • [ 1610046-79-1 ]
  • 24
  • [ 25834-16-6 ]
  • [Cu(4,7-bis(4-pyridyl)-1,1,3,3-tetramethylisoindolin-2-yloxyl)2(SiF6)] [ No CAS ]
  • 26
  • [ 25834-16-6 ]
  • [ 100-46-9 ]
  • [ 1610046-75-7 ]
YieldReaction ConditionsOperation in experiment
96% With acetic acid; at 130℃; for 20.0h; 153 g of <strong>[25834-16-6]3,6-dibromophthalic anhydride</strong> was added to 1 L of acetic acid, and 65 g of benzylamine was added thereto with stirring, and the reaction was stirred at 130 C for 20 hours.After cooling, the resulting mixture was suction filtered, washed with 0.1 L of acetic acid.A white solid (2-benzyl-4,7-dibromoisoindoline-1,3-dione) was obtained in a yield of 96%. .
  • 27
  • [ 25834-16-6 ]
  • [ 100-46-9 ]
  • [ 1610046-76-8 ]
  • 28
  • [ 143-27-1 ]
  • [ 25834-16-6 ]
  • [ 1613460-24-4 ]
  • 29
  • [ 25834-16-6 ]
  • [ 3241-20-1 ]
  • [ 890705-11-0 ]
  • 30
  • [ 25834-16-6 ]
  • [ 24552-04-3 ]
  • N-(2-ethylhexyl)-3,6-dibromophthalimide [ No CAS ]
 

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • 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 • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • 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 Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • 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 • Wittig Reaction • Wolff-Kishner Reduction

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