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Chemical Structure| 1122-12-9 Chemical Structure| 1122-12-9

Structure of 3,4-Dibromofuran-2,5-dione
CAS No.: 1122-12-9

Chemical Structure| 1122-12-9

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Product Details of [ 1122-12-9 ]

CAS No. :1122-12-9
Formula : C4Br2O3
M.W : 255.85
SMILES Code : O=C(C(Br)=C1Br)OC1=O
MDL No. :MFCD00030673
InChI Key :GEKJEMDSKURVLI-UHFFFAOYSA-N
Pubchem ID :70727

Safety of [ 1122-12-9 ]

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

Computational Chemistry of [ 1122-12-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 0
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 35.98
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.

1.08
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

1.68
Log Po/w (WLOGP)?

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

1.07
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.

0.96
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

2.0
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.36

Water Solubility

Log S (ESOL):?

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

-2.48
Solubility 0.838 mg/ml ; 0.00328 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.

-2.21
Solubility 1.59 mg/ml ; 0.00623 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

-2.19
Solubility 1.67 mg/ml ; 0.00652 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.

-6.67 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

1.0
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)

2.44

Application In Synthesis of [ 1122-12-9 ]

* 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 [ 1122-12-9 ]

[ 1122-12-9 ] Synthesis Path-Downstream   1~35

  • 3
  • [ 67-56-1 ]
  • [ 1122-12-9 ]
  • [ 55052-05-6 ]
  • 4
  • [ 67-56-1 ]
  • [ 1122-12-9 ]
  • [ 1114-20-1 ]
  • 5
  • [ 917-64-6 ]
  • [ 1122-12-9 ]
  • 3,4-dibromo-5,5-dimethyl-5<i>H</i>-furan-2-one [ No CAS ]
  • 6
  • [ 1122-12-9 ]
  • [ 571-60-8 ]
  • [ 99562-95-5 ]
  • 7
  • [ 1122-12-9 ]
  • [ 64-17-5 ]
  • [ 55052-06-7 ]
  • [ 13677-32-2 ]
  • 8
  • [ 1122-12-9 ]
  • [ 120-12-7 ]
  • 11,12-dibromo-9,10-dihydro-9,10-ethano-anthracene-11,12-dicarboxylic acid-anhydride [ No CAS ]
  • 10
  • [ 1122-12-9 ]
  • [ 1165952-91-9 ]
  • 2<i>exo</i>,3<i>exo</i>-dibromo-bicyclo[2.2.2]oct-5-ene-2<i>endo</i>,3<i>endo</i>-dicarboxylic acid-anhydride [ No CAS ]
  • 11
  • [ 1122-12-9 ]
  • [ 62-53-3 ]
  • 3-anilino-4-bromo-1-phenyl-pyrrole-2,5-dione [ No CAS ]
  • 12
  • [ 1122-12-9 ]
  • [ 62-53-3 ]
  • dianilino-maleic acid-anhydride [ No CAS ]
  • 13
  • [ 1122-12-9 ]
  • [ 123-31-9 ]
  • [ 51847-26-8 ]
  • 16
  • [ 1122-12-9 ]
  • [ 108-67-8 ]
  • 2,3-dibromo-4-oxo-4-(2.4.6-trimethyl-phenyl)-<i>cis</i>-crotonic acid [ No CAS ]
  • 17
  • [ 1122-12-9 ]
  • [ 71-43-2 ]
  • [ 85653-69-6 ]
  • 18
  • [ 1122-12-9 ]
  • [ 15111-21-4 ]
  • 20
  • [ 55052-06-7 ]
  • [ 1122-12-9 ]
  • 21
  • [ 55052-06-7 ]
  • [ 1122-12-9 ]
  • [ 64-17-5 ]
  • 23
  • [ 543-20-4 ]
  • [ 1122-12-9 ]
  • 24
  • [ 1122-12-9 ]
  • [ 874-14-6 ]
  • [ 52695-25-7 ]
  • 25
  • [ 1122-12-9 ]
  • [ 64-17-5 ]
  • [ 55052-06-7 ]
  • 26
  • [ 1122-12-9 ]
  • [ 100-51-6 ]
  • [ 55052-04-5 ]
  • 27
  • [ 108-31-6 ]
  • [ 1122-12-9 ]
YieldReaction ConditionsOperation in experiment
87% With aluminum (III) chloride; bromine; at 120℃; for 16h;Sealed tube; Synthesis of 3,4-Dibromomaleic anhydride: A mixture of maleic anhydride (2.0 g, 20.39 mmol), aluminum chloride (40.8 mg, 0.3 mmol), and bromine (2.1 ml, 40.78 mmol), was heated at 120 °C for 16 h in sealed tube. After that, it was allowed to coolroom temperature and the reaction mixture was added to ethyl acetate. The ethylacetate solution was filtered and the filtrate was evaporated. To the resulting reddishsolid, 100 nil CHC13 was added and filtered. The filtrate was evaporated to get off-white (yellow) solid in 87percent yield. 13C NMR(CDC13) oe(ppm): 131.8, 159.0.
83% With aluminum (III) chloride; bromine; at 160℃; for 20h;Sealed tube; Under an inert atmosphere, a mixture of maleic anhydride (1.50 g, 15.3 mmol), A1C13 (0.30 g, 0.21 mmol) and Br2 (1.57 mL, 30.6 mmol) was heated at 160 °C in a sealed ampule for 20 h. Upon cooling to room temperature the reaction mixture was carefully opened to air, EtOAc was added the solid filtered off and repeatedly washed with further EtOAc. The filtrate was finally concentrated in vacuo to give the title compound (1) as a yellow solid (3.25 g, 12.8 mmol, 83percent). m.p. 107-110°C; vmax (cm"1) 1769, 1706, 1590; 6C (CDC13, 125 MHz) 164.4 (s), 125.9 (s); HRMS (CI) calculated for C403Br2 [M]+ 253.82087, observed: 253.82082.
78% With aluminum (III) chloride; bromine; at 160℃; for 16h;Inert atmosphere; Sealed tube; Under an inert atmosphere, a solution of maleic anhydride(1.50 g, 15.3 mmol, 1 eq), aluminium trichloride (300 mg,0.21 mmol, cat.) and bromine (4.95 g, 30.6 mmol, 2 eq) was heated at 160° C. in a sealed ampule (note?blast shield) for 16 h. Upon cooling to 21° C. the reaction mixture was stirred for a further 24 h and careffilly opened to ait EtOAc was added and the solid filtered off and repeatedly washed with thrther EtOAc. The filtrate was finally concentrated in vacuo to give the title compound was a yellow solid which was used without thrther purification (3.05 g, 11.9 mmol, 78percent yield).m.p 107-110° C.; ?3CNMR(15OMHz, CD3OD) oe 163.33 (s),125.28 (s); IR (MeOH) 1769, 1706, 1590 cm?; HRMS (CI) calcd for C40313r2 [M]253.82087, 253.82082 observed.
With aluminum (III) chloride; bromine; at 120℃; for 16h;Sealed tube; Maleic anhydride (2.0 g, 20 mmol), aluminum(III) chloride (68 mg, 0.51 mmol) and bromine (2.1 mL, 41 mmol) were placed in a sealed reaction vessel and heated to 120 °C for 16 h. After cooling to RT, the reaction was diluted with EtOAc (30 mL) and filtered. The filtrate was then concentrated in vacuo to yield the crude product, 3,4-dibromofuran-2,5-dione, as an orange solid which was used in the next step without further purification. The 3,4-dibromofuran-2,5- dione (1.0 g, 3.9 mmol) was placed in a round-bottomed flask and dissolved in glacial acetic acid (10 mL) at RT. 3.4-Dichloroaniline (0.70 g, 4.3 mmol) was added at RT and then the reaction was heated at reflux for 3 h (120 - 130 °C). The reaction was then cooled to RT and volatiles were removed in vacuo. The crude product was recrystallized from MeOH to yield the title compound as a reddish-brown solid (1.3 g, 80percent). 1H-NMR (400 MHz, DMSO-d6): delta 7.80 (d, J = 8.6 Hz, 1H), 7.69 (d, J = 1.6 Hz, 1H), 7.42 (dd, J = 1.8 Hz, 6.8 Hz, 1H). 13C- NMR (100 MHz, DMSO-d6): delta 162.9, 131.3, 131.2, 131.1 , 129.9, 128.7, 127.3.

  • 29
  • [ 67-56-1 ]
  • [ 1122-12-9 ]
  • [ 2207-27-4 ]
  • (1R,2R,3S,6S,7S)-2,3-Dibromo-1,7,8,9-tetrachloro-6-methoxy-4-oxo-5-oxa-tricyclo[4.3.0.03,7]non-8-ene-2-carboxylic acid methyl ester [ No CAS ]
  • 30
  • [ 1122-12-9 ]
  • [ 2207-27-4 ]
  • 2,6-Dibromo-1,7,8,9-tetrachloro-10,10-dimethoxy-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione [ No CAS ]
  • 31
  • [ 1122-12-9 ]
  • [ 80027-18-5 ]
  • 32
  • [ 1122-12-9 ]
  • [ 123-01-3 ]
  • (Z)-2,3-Dibromo-4-(4-dodecyl-phenyl)-4-oxo-but-2-enoic acid [ No CAS ]
  • 33
  • [ 1122-12-9 ]
  • [ 1459-09-2 ]
  • (Z)-2,3-Dibromo-4-(4-hexadecyl-phenyl)-4-oxo-but-2-enoic acid [ No CAS ]
  • 34
  • [ 1122-12-9 ]
  • [ 1459-10-5 ]
  • 3,4-Dibromo-5-hydroxy-5-(4-tetradecyl-phenyl)-5H-furan-2-one [ No CAS ]
  • 35
  • [ 1122-12-9 ]
  • [ 4445-07-2 ]
  • (Z)-2,3-Dibromo-4-(4-octadecyl-phenyl)-4-oxo-but-2-enoic acid [ 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

Categories

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[ 1122-12-9 ]

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