7194-78-7|2-(3-Bromophenyl)-2-oxoacetic acid| Ambeed

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Quality Control of [ 7194-78-7 ] Purity: 98% SDS Specification

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Product Details of [ 7194-78-7 ]

CAS No. :	7194-78-7
Formula :	C₈H₅BrO₃
M.W :	229.03
SMILES Code :	O=C(O)C(C1=CC=CC(Br)=C1)=O
MDL No. :	MFCD07698694
Boiling Point :	No data available
InChI Key :	NOKUFSBJFYUWLW-UHFFFAOYSA-N
Pubchem ID :	12252914

Safety of [ 7194-78-7 ]

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

Computational Chemistry of [ 7194-78-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	46.11
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	54.37 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.22
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	2.75
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.72
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.	1.44
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	1.76
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.78

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.23
Solubility	0.135 mg/ml ; 0.000588 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.	-3.55
Solubility	0.065 mg/ml ; 0.000284 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	-2.58
Solubility	0.604 mg/ml ; 0.00264 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	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.	-5.74 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.	0.56

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)	1.61

Application In Synthesis of [ 7194-78-7 ]

* 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 [ 7194-78-7 ]

[ 7194-78-7 ] Synthesis Path-Downstream 1~35

1
[ 7194-78-7 ]
[ 1187-42-4 ]
[ 75669-48-6 ]

References: [1]Agricultural and Biological Chemistry,1983,vol. 47,p. 1561 - 1568.

4
[ 49839-81-8 ]
[ 7194-78-7 ]

References: [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2000,vol. 39,p. 734 - 739.
[2]Bulletin of the Chemical Society of Japan,2003,vol. 76,p. 2335 - 2340.
[3]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2007,vol. 46,p. 445 - 448.

5
[ 7194-78-7 ]
[ 17220-38-1 ]
6-(3-bromo-phenyl)-[1,2,5]oxadiazolo[3,4-<i>b</i>]pyrazin-5-ol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3133 - 3136.

6
[ 7194-78-7 ]
[ 72111-73-0 ]

References: [1]Agricultural and Biological Chemistry,1983,vol. 47,p. 1561 - 1568.

7
[ 7194-78-7 ]
[ 72113-61-2 ]

References: [1]Agricultural and Biological Chemistry,1983,vol. 47,p. 1561 - 1568.

8
[ 7194-78-7 ]
[ 72113-60-1 ]

References: [1]Agricultural and Biological Chemistry,1983,vol. 47,p. 1561 - 1568.

9
[ 7194-78-7 ]
[ 74-88-4 ]
[ 81316-36-1 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In DMF (N,N-dimethyl-formamide); at 40℃; for 1h;	A 100-ml round-bottom flask fitted with a stirbar, condenser, and septum was flushed with N2 and charged with 3-bromoacetophenone (2.50 g) and anhydrous pyridine (20 mL), followed by selenium dioxide (2.8 g). The reaction mixture was heated to 100 C. After one hour, the reaction was cooled to room temperature and pyridine was distilled off under reduced pressure. The resulting thick oil was partitioned between 50 ml 1N HCl and 50 ml EtOAc. The aqueous phase was extracted once more with 50 ml EtOAc, and the combined organic phase was dried over sodium sulfate and concentrated in vacuo. The resulting crude acid was azeotroped with 10 ml of anhydrous toluene. To a 100-ml round-bottom flask containing the crude acid were added anhydrous DMF (20 ml), Cs2C03 (4.11 g), and methyl iodide (3.58 g) sequentially. The mixture was heated at 40 C for 1 hour under N2, cooled to room temperature, diluted with 200 ml saturated NH4Cl solution, and extracted two times with 200 ml EtOAc/hexanes (1/1). The combined organic phase was dried over Na2S04, concentrated in vacuo, and purified by column chromatography on silica gel (25% EtOAc/hexanes) to provide the desired product. ¹H NMR (CDCl3) : 8.22 (s, 1H), 8.01 (d, J=8 Hz, 1H), 7.83 (d, J=8 Hz, 1H), 7.44 (t, J=8 Hz, 1H), 4.0 (s, 3H) MS: m/e 243/245 (M+1)+

References: [1]Patent: WO2005/97136,2005,A1 .Location in patent: Page/Page column 28-29.

10
[ 2142-63-4 ]
[ 7194-78-7 ]

Yield	Reaction Conditions	Operation in experiment
		A 100-ml round-bottom flask fitted with a stirbar, condenser, and septum was flushed with N2 and charged with 3-bromoacetophenone (2.50 g) and anhydrous pyridine (20 mL), followed by selenium dioxide (2.8 g). The reaction mixture was heated to 100 C. After one hour, the reaction was cooled to room temperature and pyridine was distilled off under reduced pressure. The resulting thick oil was partitioned between 50 ml 1N HCl and 50 ml EtOAc. The aqueous phase was extracted once more with 50 ml EtOAc, and the combined organic phase was dried over sodium sulfate and concentrated in vacuo. The resulting crude acid was azeotroped with 10 ml of anhydrous toluene. To a 100-ml round-bottom flask containing the crude acid were added anhydrous DMF (20 ml), Cs2C03 (4.11 g), and methyl iodide (3.58 g) sequentially. The mixture was heated at 40 C for 1 hour under N2, cooled to room temperature, diluted with 200 ml saturated NH4Cl solution, and extracted two times with 200 ml EtOAc/hexanes (1/1). The combined organic phase was dried over Na2S04, concentrated in vacuo, and purified by column chromatography on silica gel (25% EtOAc/hexanes) to provide the desired product. ¹H NMR (CDCl3) : 8.22 (s, 1H), 8.01 (d, J=8 Hz, 1H), 7.83 (d, J=8 Hz, 1H), 7.44 (t, J=8 Hz, 1H), 4.0 (s, 3H) MS: m/e 243/245 (M+1)+
	With pyridine; selenium(IV) oxide; at 100℃; for 16h;	[000969] A suspension of Compound 261 A (6.00 g, 30.15 mmol) and Se02 (5.02 g, 45.22 mmol) in pyridine (50 mL) was stirred at 100 C for 16 h. It was filtered to remove the resultant solid and the filtrate was evaporated to remove pyridine. The residue was dissolved in aqueous NaOH solution (5% w/w, 200 mL) and extracted with diethyl ether (100 mL x 2). The aqueous was adjusted to pH 1 with con. HCl to form a solid, which was filtered and dried to afford Compound 261B.

References: [1]Organic Letters,2019,vol. 21,p. 2663 - 2667.
[2]Patent: WO2005/97136,2005,A1 .Location in patent: Page/Page column 28-29.
[3]Chemical Communications,2013,vol. 49,p. 3640 - 3642.
[4]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1517 - 1522.
[5]Chemistry - A European Journal,2014,vol. 20,p. 7241 - 7244.
[6]Patent: WO2015/42397,2015,A1 .Location in patent: Paragraph 000969.
[7]Chemical Communications,2015,vol. 51,p. 10524 - 10527.
[8]Organic and Biomolecular Chemistry,2017,vol. 15,p. 4320 - 4327.
[9]Advanced Synthesis and Catalysis,2017,vol. 359,p. 2390 - 2395.
[10]Organic Letters,2017,vol. 19,p. 4556 - 4559.
[11]Advanced Synthesis and Catalysis,2019,vol. 361,p. 1798 - 1802.
[12]Green Chemistry,2019,vol. 21,p. 3796 - 3801.

11
[ 875781-21-8 ]
[ 7194-78-7 ]
[ 1071454-55-1 ]

Yield	Reaction Conditions	Operation in experiment
46%		To a mixture of 3-(2-Methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine (1.0 g, 2.1 mmol) and the crude (3-Bromo-phenyl)-oxo-acetic acid obtained in last step (0.49 g, 2.1 mmol) in a 20 mL microwave reaction flask was added THF (6 mL), acetonitrile (6 mL), and sodium carbonate (1 N in water, 6 mL, 6 mmol). The resulting suspension was purged with nitrogen for 1 minute. Dichloro[1,1'-bis(diphenylphoshino)ferrocene]palladium(II) dichloromethane adduct (73 mg, 89 mumol) was added and the purging was continued for another minute. The flask was sealed and was irradiated in a microwave reactor to 90 C. for 10 minutes. The reaction mixture was adjusted to pH 4 by addition of 1 N hydrochloric acid, extracted with ethyl acetate (10 mL×3). The combine organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel using a gradient of methanol in dichloromethane to afford {3-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-oxo-acetic acid as a off white solid (490 mg, 46%). MS: m/z 504 (M+H+).

References: [1]Patent: US2008/261921,2008,A1 .Location in patent: Page/Page column 105-106.

12
[ 62123-80-2 ]
[ 7194-78-7 ]

Yield	Reaction Conditions	Operation in experiment
89%		To a solution of (3-Bromo-phenyl)-oxo-acetic acid ethyl ester (1 g, 3.9 mmol) in methanol (10 mL) was added potassium hydroxide (2 mL, 50% w/v in water) and the resulting mixture was stirred at room temperature for 30 minutes. Hydrochloric acid (1 N) was added to adjust to pH 4. The mixture was extracted with ethyl acetate (5 mL×4) and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was used in next step without further purification (0.8 g, 89% yield). MS: m/z 230 (M-H+).

References: [1]Patent: US2008/261921,2008,A1 .Location in patent: Page/Page column 105-106.

13
[ 7194-78-7 ]
[ 585-76-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid;pH 7.4;Kinetics;	A series of compounds were synthesized and kinetically analyzed (Table 1). The measured rate constants correlate well with the Hammett ? parameters giving a p value of 3.80 (Figure 4). Many of the compounds display faster reactivity with Eta202 than BFA.

References: [1]Patent: WO2012/27274,2012,A2 .Location in patent: Page/Page column 29; 30.

14
[ 7194-78-7 ]
[ 68-12-2 ]
[ 1426249-30-0 ]

References: [1]Chemical Communications,2013,vol. 49,p. 3640 - 3642.

15
[ 7194-78-7 ]
[ 121-44-8 ]
[ 1438283-01-2 ]

Yield	Reaction Conditions	Operation in experiment
55%	With Bromotrichloromethane; Ir(dF(CF3)ppy)2(bpy)PF6; caesium carbonate; In dichloromethane; at 20℃; for 20h;Sealed tube; Irradiation;	General procedure: The 10-mL round-bottom flask was equipped with a magnetic stirrer bar. Afterwards Triamine1 (0.4 mmol), Benzoylformic Acids 2 (0.2 mmol), [Ir{dFCF3ppy}2(bpy)]PF6 (0.006 mmol), BrCCl3 (0.6 mmol), Cs2CO3 (0.4 mmol) and DCM (2 mL) were added. Then the reaction mixture was sealed with stopper and placed in room temperature. A 5w blue LED was placed at a distance of about 5 cm from the reaction vessel. After the reaction was complete (as judged by TLC plate). The solvent was removed under reduced pressure directly. The crude product was purified by flash chromatography on silica gel to afford the desired product 3.

References: [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 3649 - 3654.
[2]Tetrahedron Letters,2019,vol. 60.

16
[ 7194-78-7 ]
[ 4783-68-0 ]
(3-bromophenyl)(2-(pyridin-2-yloxy)phenyl)methanone [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 1517 - 1522.

17
[ 7194-78-7 ]
[ 495-48-7 ]
[ 1456728-75-8 ]

References: [1]Chemical Communications,2013,vol. 49,p. 9170 - 9172.

18
[ 7194-78-7 ]
[ 1227476-15-4 ]
C₁₉H₁₃BrN₂O [ No CAS ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 14432 - 14436.

19
[ 7194-78-7 ]
[ 1227476-15-4 ]
(E)-(3-bromophenyl)(2-(phenyldiazenyl)phenyl)methanone [ No CAS ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 10414 - 10420.

20
[ 120-72-9 ]
[ 7194-78-7 ]
[ 1096981-81-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	With iodine; oxygen; palladium diacetate; caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 45℃; for 12h;Schlenk technique; Sealed tube;	General procedure: A 10 mL oven-dried Schlenk tube was charged with phenylglyoxylic acid 1a (49.5mg, 0.33mmol), indole 2a (35.1mg, 0.3mmol), I2 (164.5mg, 0.65mmol), Pd(OAc)2 (10mol%, 6.7mg, 0.03mmol), Cs2CO3 (292mg, 0.9mmol). The tube was evacuated and filled with O2 (this procedure was repeated three times). Then NMP (1.5mL) were added with a syringe under a counter flow of O2. The tube was sealed with a screw cap. The reaction was stirred at 45C for 12h, and was then allowed to cool to ambient temperature. The mixture was added 20mL EtOAc, and filtered, washed with water. The organic layers were dried over Na2SO4 and filtered. Solvents were evaporated under reduced pressure. The residue was purified by flash column chromatography with hexane/ethyl acetate to give the corresponding product 3.

References: [1]Chinese Chemical Letters,2014,vol. 25,p. 90 - 92.

21
[ 273-53-0 ]
[ 7194-78-7 ]
[ 1327274-44-1 ]

References: [1]Chemistry - A European Journal,2014,vol. 20,p. 7241 - 7244.
[2]Journal of Organic Chemistry,2015,vol. 80,p. 11065 - 11072.

22
[ 38210-35-4 ]
[ 7194-78-7 ]
(3-bromophenyl)(2-(pyridin-2-yl)benzo[b]thiophen-3-yl)methanone [ No CAS ]

References: [1]Tetrahedron,2015,vol. 71,p. 1269 - 1275.

23
[ 7194-78-7 ]
[ 7035-05-4 ]
(3-bromophenyl)(2-(pyridin-2-yl)benzofuran-3-yl)methanone [ No CAS ]

References: [1]Tetrahedron,2015,vol. 71,p. 1269 - 1275.

24
[ 100954-03-8 ]
[ 7194-78-7 ]
3-(3-bromobenzoyl)-4-phenyl-2H-chromen-2-one [ No CAS ]

References: [1]Journal of Organic Chemistry,2015,vol. 80,p. 1550 - 1556.
[2]Advanced Synthesis and Catalysis,2017,vol. 359,p. 443 - 453.

25
[ 20984-26-3 ]
[ 7194-78-7 ]
3-(3-bromobenzoyl)-6-methyl-4-phenyl-2H-chromen-2-one [ No CAS ]