122394-38-1|Methyl 2-(2-bromophenyl)-2-oxoacetate| Ambeed

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Quality Control of [ 122394-38-1 ] Purity: 97% SDS Specification

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Product Details of [ 122394-38-1 ]

CAS No. :	122394-38-1
Formula :	C₉H₇BrO₃
M.W :	243.05
SMILES Code :	O=C(OC)C(C1=CC=CC=C1Br)=O
MDL No. :	MFCD18206246
InChI Key :	SCPBADGYTPFIQF-UHFFFAOYSA-N
Pubchem ID :	10890094

Safety of [ 122394-38-1 ]

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

Computational Chemistry of [ 122394-38-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.11
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	50.43
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	43.37 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.05
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	2.35
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.8
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.	1.73
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	2.26
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.04

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.97
Solubility	0.26 mg/ml ; 0.00107 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.	-2.9
Solubility	0.306 mg/ml ; 0.00126 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	-3.28
Solubility	0.127 mg/ml ; 0.000524 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.	-6.11 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	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 [ 122394-38-1 ]

* 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 [ 122394-38-1 ]

[ 122394-38-1 ] Synthesis Path-Downstream 1~29

1
[ 20763-19-3 ]
[ 122394-38-1 ]
[ 122283-38-9 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 8213 - 8216.

2
[ 21165-13-9 ]
[ 122394-38-1 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 8213 - 8216.
[2]Organic Letters,2015,vol. 17,p. 3810 - 3813.

3
[ 264882-02-2 ]
[ 122394-38-1 ]

References: [1]Organic Letters,2018,vol. 20,p. 776 - 779.
[2]Synlett,2006,p. 2486 - 2488.
[3]Tetrahedron Letters,2005,vol. 46,p. 3927 - 3929.

4
[ 57486-69-8 ]
[ 122394-38-1 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 3927 - 3929.
[2]Advanced Synthesis and Catalysis,2011,vol. 353,p. 3335 - 3339.

5
[ 6630-33-7 ]
[ 122394-38-1 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 8213 - 8216.
[2]Organic Letters,2015,vol. 17,p. 3810 - 3813.

6
[ 122394-38-1 ]
(E)-3-Methoxy-2-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-phenyl]-acrylic acid methyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 8213 - 8216.

7
[ 122394-38-1 ]
(E)-3-Methoxy-2-[2-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-phenyl]-acrylic acid methyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 8213 - 8216.

8
[ 122394-38-1 ]
[ 1066-54-2 ]
[ 158036-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	With nitrogen; triphenylphosphine;palladium diacetate; copper(I) iodide; In ethyl acetate; triethylamine;	Example 1 Preparation of methyl 2-ethynylphenylglyoxylate O-methyloxime (compound 1, Table 2) 33.3 g (0.35 mol) of trimethylsilylacetylene, 3.8 g of palladium(II) acetate, 3.2 g of copper(I) iodide and 8.9 g of triphenylphosphine are added to a solution of 55.4 g (0.23 mol) of <strong>[122394-38-1]methyl 2-bromophenylglyoxylate</strong> in 415 ml of triethylamine, and nitrogen is then passed through the solution for 30 minutes. The reaction mixture is then heated at 90 C. for 45 minutes, is allowed to cool and is filtered off. The filtrate is evaporated down, the residue is taken up in ethyl acetate and the solution is washed with water. The organic phase is dried and evaporated down. 56.8 g of alpha-ketoester remain as a black oil. The crude product prepared in this manner is dissolved in 50 ml of methanol, 38.9 g (0.37 mol) of O-methylhydroxylamine hydrochloride are added and heating is carried out for 15 minutes at 60 C.

References: [1]Patent: US5449809,1995,A .

9
0-methylhydroxylamine hydrochloride [ No CAS ]
[ 122394-38-1 ]
[ 1066-54-2 ]
[ 158036-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	With nitrogen; triphenylphosphine;palladium diacetate; copper(I) iodide; In methanol; ethyl acetate; triethylamine;	EXAMPLE 6 2-Ethynylphenylglyoxylic acid methyl ester-O-methyloxime (Compound F) 33.3 g (0.35 mol) of trimethylsilylacetylene, 3.8 g of palladium(II) acetate, 3.2 g of copper(I) iodide and 8.9 g of triphenylphosphine are added to a solution of 55.4 g (0.23 mol) of <strong>[122394-38-1]methyl 2-bromophenylglyoxylate</strong> in 415 ml of triethylamine, and nitrogen is passed through the solution for 30 minutes. The reaction mixture is then heated for 45 minutes at 90 C. The mixture is cooled and filtered. The filtrate is evaporated down, taken up in ethyl acetate and washed with water. The organic phase is dried and evaporated down. There remains 56.8 g of the alpha-keto ester as a black oil. The crude product prepared in this way is dissolved in 50 ml of methanol, 38.9 g (0.37 mol) of 0-methylhydroxylamine hydrochloride is added and the mixture is heated for 15 minutes at 60 C. The mixture is evaporated down, and the residue is taken up in ethyl acetate and washed with water. The organic phase is dried and evaporated down. There remains 52.4 g of the trimethylsilyl compound as a black oil. 1 H-NMR (CDCl3 /TMS): delta=0.22 (s,9H,SiMe3); 3.86; 4.06 (s,3H,OCH3); 7.25-7.61 ppm (m, 4H,aryl).

References: [1]Patent: US5594020,1997,A .

10
[ 766-47-2 ]
[ 122394-38-1 ]
methyl 2-(2-methylphenyl)-ethynylphenylglyoxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With nitrogen; triphenylphosphine;palladium diacetate; copper(I) iodide; In dichloromethane; triethylamine;	a) Preparation of methyl 2-(2-methylphenyl)-ethynylphenylglyoxylate O-methyloxime (European Patent 253,213, No. 136) 300 mg of palladium(II) acetate, 1.5 g of triphenylphosphine and 100 mg of copper(I) iodide and 11 g (0.095 mol) of 2-methylphenylacetylene are added to a solution of 10 g (0.041 mol) of <strong>[122394-38-1]methyl 2-bromophenylglyoxylate</strong> in 50 ml of triethylamine. Nitrogen is passed through the solution for 30 minutes, after which the solution is heated for 3 hours at 80 C. After cooling, methylene chloride is added and the solution is washed with water. The organic phase is dried and evaporated down. 16.5 g of methyl 2-(2-methylphenyl)-ethynylphenylglyoxylate remain as a black oil. 1 H-NMR (CDCl3 /TMS): delta=2.53 (s, 3H, CH3); 3.81 (s, 3H, OCH3); 7.13-7.88 ppm (m, 8H, aryl).

References: [1]Patent: US5449809,1995,A .

11
[ 57486-69-8 ]
[ 4009-98-7 ]
[ 122394-38-1 ]
(E)-methyl 3-methoxy-2-[2-(3-methylphenoxy)phenyl]propenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With selenium(IV) oxide; potassium tert-butylate; In hexane;	EXAMPLE 3 This Example illustrates an alternative synthesis of (E)-methyl 3-methoxy-2-[2-(3-methylphenoxy)phenyl]propenoate. A mixture of methyl ortho-bromophenylacetate (4.10 g, prepared as described in Example 1) and selenium dioxide (4.92 g) was stirred for 25 hours at 190 C. After cooling, the mixture was diluted with dichloromethane (100 ml) then filtered through `Supercel`. The filtrate was washed successively with saturated aqueous sodium bicarbonate (2) and brine, then dried and concentrated to give a yellow liquid (3.60 g) containing (52% by GC-MS) <strong>[122394-38-1]methyl (2-bromobenzoyl)formate</strong> and unreacted methyl ortho-bromophenylacetate. Potassium tert-butoxide (2.33 g) was added to a vigorously-stirred suspension of (methoxymethyl)triphenylphosphonium chloride (7.90 g) in ether (80 ml) at room temperature. After 15 minutes, a solution of the crude <strong>[122394-38-1]methyl (2-bromobenzoyl)formate</strong> (3.60 g) in ether (10 ml) was added in a single portion. After a further 15 minutes, the reaction mixture was poured into water (150 ml), the aqueous and organic layers were separated, and the former was extracted with a further portion of ether (100 ml). The combined ether layers were washed successively with water (2) and brine, then dried and concentrated to give a yellow oil (5.81 g) containing, in a ratio of about 6:5, the (E)- and (Z)-isomers respectively of methyl 2-(2-bromophenyl)-3-methoxypropenoate. Chromatography using ether:hexane (1:1) as eluant allowed the pure (Z)-isomer (0.450 g) to be isolated as a pale yellow oil, IR (film) 1712, 1638 cm-1, 1 H n.m.r delta 3.71 (3H, s), 3.95 (3H, s), 6.57 (1H, s) p.p.m.

References: [1]Patent: US4937374,1990,A .

12
[ 1059607-62-3 ]
[ 122394-38-1 ]
(4R,5S)-methyl 5-(2-bromophenyl)-4-(4,4-dimethyl-2-oxooxazolidine-3-carbonyl)-2-thioxooxazolidine-5-carboxylate [ No CAS ]
[ 1219925-40-2 ]

References: [1]Organic Letters,2010,vol. 12,p. 1544 - 1547.

13
[ 1218951-02-0 ]
[ 122394-38-1 ]

References: [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 3335 - 3339.

14
[ 18698-97-0 ]
[ 122394-38-1 ]

References: [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 3335 - 3339.

15
[ 43063-97-4 ]
[ 122394-38-1 ]

References: [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 3335 - 3339.

16
[ 70-55-3 ]
[ 122394-38-1 ]
C₁₆H₁₄BrNO₄S [ No CAS ]
C₁₆H₁₄BrNO₄S [ No CAS ]

References: [1]Chemical Communications,2013,vol. 49,p. 8392 - 8394.

17
[ 67-56-1 ]
[ 2142-69-0 ]
[ 122394-38-1 ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 17711 - 17714.
[2]Organic Letters,2017,vol. 19,p. 5920 - 5923.

18
[ 456-22-4 ]
[ 122394-38-1 ]
1-(2-bromophenyl)-2-methoxy-2-oxoethyl 4-fluorobenzoate [ No CAS ]