54335-33-0|Methyl 2,4-dibromobenzoate| Ambeed

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Quality Control of [ 54335-33-0 ] Purity: 97% SDS Specification

COA

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NMR

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Product Details of [ 54335-33-0 ]

CAS No. :	54335-33-0
Formula :	C₈H₆Br₂O₂
M.W :	293.94
SMILES Code :	COC(=O)C1=C(Br)C=C(Br)C=C1
MDL No. :	MFCD09954350
InChI Key :	SBKBVWPHNYFFCV-UHFFFAOYSA-N
Pubchem ID :	22572357

Safety of [ 54335-33-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 54335-33-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	53.12
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.57
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.56
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.0
Log P_o/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.	3.38
Log P_o/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	3.05
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.11

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.14
Solubility	0.0211 mg/ml ; 0.0000719 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.8
Solubility	0.0468 mg/ml ; 0.000159 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	-4.17
Solubility	0.0199 mg/ml ; 0.0000676 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	Yes
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.	-5.57 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<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)	1.57

Application In Synthesis of [ 54335-33-0 ]

* 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 [ 54335-33-0 ]

[ 54335-33-0 ] Synthesis Path-Downstream 1~25

1
[ 67-56-1 ]
[ 59615-16-6 ]
[ 54335-33-0 ]

References: [1]Journal of the Chemical Society,1895,vol. 67,p. 602.

2
[ 611-00-7 ]
[ 54335-33-0 ]

References: [1]Journal of the Chemical Society,1895,vol. 67,p. 602.

3
[ 78222-69-2 ]
[ 54335-33-0 ]

References: [1]Journal of the Chemical Society,1895,vol. 67,p. 602.

4
[ 67-56-1 ]
[ 611-00-7 ]
[ 54335-33-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With thionyl chloride; at 0℃; for 3.0h;Reflux;	At 0 °C, thionyl chloride (3.57 g, 30 mmol) was added dropwise into a solution of 2,4-dibromobenzoicacid (5.60 g, 20 mmol) in methanol (100 mL) slowly. The ice-salt bath used was removed after that dropping and then the reaction mixture was heated to reflux for 3 hours. TLC and LCMS indicated that starting materials reacted completely. The solvent and excess thionyl chloride were removed by rotary evaporation to give a crude product. Then the crude product was dissolved in dichloromethane (100 mL), washed successively with saturated sodium bicarbonate solution (100 mLx2) and saturated brine (100 mL), dried with anhydrous sodium sulfate and filtered. A yellow solid product (5.92 g, 100percent yield) was obtained by rotary evaporation. The molecular ion peak shown by liquid chromatography-mass spectrometry was: MS (ESI): m/z 292.8/294.7/269.9 [M+H]+.
96%	With sulfuric acid; at 0℃;Reflux;	General procedure: The corresponding acid (5 mmol) was dissolved in CH3OH (20 mL), and then H2SO4 (8 equiv) was added at 0 °C, the reaction mixture was then refluxed for 24?48 h. After cooling, the solvent was evaporated. To the resulting mixture was slowly added a solution of 10percent Na2CO3 (200 mL), and then the aqueous solution was extracted with ethyl acetate. The organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography to obtain compound 3 or compound 4a and 4b.
213.6 g	With sulfuric acid;Reflux;	Step 1: To a 2 L round-bottom flask, 2,4-dibromobenzoicacid (250 g, 0.90 mol) in MeOH (2 L) and concentrated H2SO4 (18.4 g, 0.19 mol) were added. The mixture was refluxed overnight before cooled to room temperature. The resulting precipitate was then filtered, washed with cold methanol and dried under vacuum. It yielded 213.6 g methyl 2,4-dibromobenzoate as a yellow solid. To a 2 L round-bottom flask was added 2,4-dibromobenzoate (200.7 g, 0.69 mol) in 1 L dry DMF. CuCN (123.8 g, 1.38 mol) and NaI (22.8 g, 0.15 mol) were introduced next. The mixture was stirred overnight at 160 °C under nitrogen atmosphere. After the reaction was complete, it was extracted with ethyl acetate (500 mL × 3),washed with water (500 mL) and purified over silica gel (PE/EtOAc = 5/1) to give 93.5 g methyl 2,4-dicyanobenzoate as a brown solid (yield: 72.8 percent).

References: [1]Patent: EP3048103,2016,A1 .Location in patent: Paragraph 0077; 0078.
[2]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 2490 - 2494.
[3]Chemistry - A European Journal,2010,vol. 16,p. 1780 - 1784.
[4]Asian Journal of Chemistry,2014,vol. 26,p. 6655 - 6657.

5
[ 54335-33-0 ]
[ 619-42-1 ]

References: [1]Chemistry - A European Journal,2010,vol. 16,p. 1780 - 1784.

6
[ 54335-33-0 ]
[ 666747-06-4 ]

Yield	Reaction Conditions	Operation in experiment
43%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 1.0h;	At 0 °C, lithium aluminum hydride (1.14 g, 30 mmol) was dropped into a solution of <strong>[54335-33-0]methyl 2,4-dibromobenzoate</strong> (5.90 g, 20 mmol) in tetrahydrofuran (120 mL) slowly. The ice-salt bath used was removed after that dropping. The reaction was complete (detected with LCMS and TLC) after stirred for 1 hour at room temperature. The mixture was cooled to 0 °C again and the reaction was quenched with water (1.14 mL) and 10percent NaOH solution (11.4 mL) respectively. After stirred for 15 min at room temperature, the mixture was filtered and then the filter cake was washed with tetrahydrofuran (60 mL2) and ethyl acetate EA (60 mL2). The filtrate was dried with anhydrous sodium sulfate, filtered, concentrated, and then purified by column chromatography (elution system: petroleum ether: ethyl acetate = 10/1-4/1) to obtain a colorless oil product (2.3 g, 43percent yield). The molecular ion peak shown by liquid chromatography-mass spectrometry was: MS (ESI): m/z 246.9/248.9/250.9 [M-OH]+.

References: [1]Patent: EP3048103,2016,A1 .Location in patent: Paragraph 0079; 0080.

7
[ 54335-33-0 ]
[ 90110-98-8 ]

References: [1]Patent: EP3048103,2016,A1 .

8
[ 54335-33-0 ]
(Z)-3-bromo-N'-hydroxy-4-hydroxymethyl benzamidine [ No CAS ]

References: [1]Patent: EP3048103,2016,A1 .

9
[ 54335-33-0 ]
2-bromo-4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzyl alcohol [ No CAS ]

References: [1]Patent: EP3048103,2016,A1 .

10
[ 54335-33-0 ]
2-bromo-4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde [ No CAS ]

References: [1]Patent: EP3048103,2016,A1 .

11
[ 54335-33-0 ]
1-{2-bromo-4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzyl}-3-azetidine carboxylic acid [ No CAS ]

References: [1]Patent: EP3048103,2016,A1 .

12
[ 54335-33-0 ]
[ 104-94-9 ]
C₂₂H₂₂N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 100℃;Inert atmosphere;	General procedure: To a solution of benzoic acid methyl ester (3, 4a,b) (500 mg), the respective arylamine compounds (2.4 equiv for 3, 1.2 equiv for 4a,b), Cs2CO3 (2.8 equiv for 3, 1.4 equiv for 4a,b), BINAP (0.08 equiv) in 1,4-dioxane (5 mL) was added Pd(OAc)2 (5 mol percent) under nitrogen. And the reaction mixture was stirred at 100 °C for 10?24 h. The reaction mixture was cooled to room temperature, and then H2O was added. The mixture was extracted with ethyl acetate, and then the organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography.