[ CAS No. 1192172-68-1 ] {[proInfo.proName]}

Name: 1192172-68-1|Ethyl 5-bromo-4-methylbenzofuran-2-carboxylate|98%
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SKU: A438565
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Quality Control of [ 1192172-68-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1192172-68-1 ]

SDS Specification

Alternatived Products of [ 1192172-68-1 ]

Product Details of [ 1192172-68-1 ]

CAS No. :	1192172-68-1	MDL No. :	MFCD21607419
Formula :	C₁₂H₁₁BrO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FSIUXWVJERJNOX-UHFFFAOYSA-N
M.W :	283.12	Pubchem ID :	67200885
Synonyms :

Calculated chemistry of [ 1192172-68-1 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.25
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	64.97
TPSA :	39.44 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.13
Log Po/w (XLOGP3) :	3.93
Log Po/w (WLOGP) :	3.68
Log Po/w (MLOGP) :	2.63
Log Po/w (SILICOS-IT) :	3.73
Consensus Log Po/w :	3.42

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.29
Solubility :	0.0145 mg/ml ; 0.0000513 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.46
Solubility :	0.00987 mg/ml ; 0.0000349 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.0
Solubility :	0.00281 mg/ml ; 0.00000993 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.79

Safety of [ 1192172-68-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H302-H317	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1192172-68-1 ]

* 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.

Upstream synthesis route of [ 1192172-68-1 ]
Downstream synthetic route of [ 1192172-68-1 ]

[ 1192172-68-1 ] Synthesis Path-Upstream 1~1

1
[ 137644-94-1 ]
[ 105-36-2 ]
[ 1192172-68-1 ]

Yield	Reaction Conditions	Operation in experiment
69.6%	With potassium carbonate In N,N-dimethyl-formamide at 0 - 100℃;	5-Bromo-4-methyl-benzofuran-2-carboxylic acid ethyl ester; [Show Image] To a solution of 3-Bromo-6-hydroxy-2-methyl-benzaldehyde (6.8 g, 0.032 mol)) in anhydrous DMF (50 ml) was added potassium carbonate (13.1 g, 0.095 mol) and cooled to 0°C. Bromo ethyl acetate (7.1 ml, 0.063 mol) was added slowly. The reaction mixture was stirred for one hour at 0°C. The completion of the reaction was confirmed by TLC. The reaction mixture was then heated to 100°C and maintained for 2 hours. After cooling to room temperature, ice water (250 ml) was added and the mixture was stirred for 20 minutes. The solid separated was filtered, washed with water (100 ml) and dried under vacuum, to get crude product. Column chromatography using 2/5 ethyl acetate/hexane yielded 5-Bromo-4-methyl-benzofuran-2-carboxylic acid ethyl ester (6.2 g, 69.6 percent) ¹H NMR (300MHz, CDCl₃), δ 1.4 (3H, t), 2.60 (3H, s), 4.4 (2H, qt), 7.30(1H, d), 7.44 (2H, m).

Reference： [1] Patent: EP2110374, 2009, A1, . Location in patent: Page/Page column 27-28

[ 1192172-68-1 ] Synthesis Path-Downstream 1~9

1
[ 137644-94-1 ]
[ 105-36-2 ]
[ 1192172-68-1 ]

Yield	Reaction Conditions	Operation in experiment
69.6%	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 100℃;	5-Bromo-4-methyl-benzofuran-2-carboxylic acid ethyl ester; [Show Image] To a solution of 3-Bromo-6-hydroxy-2-methyl-benzaldehyde (6.8 g, 0.032 mol)) in anhydrous DMF (50 ml) was added potassium carbonate (13.1 g, 0.095 mol) and cooled to 0C. Bromo ethyl acetate (7.1 ml, 0.063 mol) was added slowly. The reaction mixture was stirred for one hour at 0C. The completion of the reaction was confirmed by TLC. The reaction mixture was then heated to 100C and maintained for 2 hours. After cooling to room temperature, ice water (250 ml) was added and the mixture was stirred for 20 minutes. The solid separated was filtered, washed with water (100 ml) and dried under vacuum, to get crude product. Column chromatography using 2/5 ethyl acetate/hexane yielded 5-Bromo-4-methyl-benzofuran-2-carboxylic acid ethyl ester (6.2 g, 69.6 %) 1H NMR (300MHz, CDCl3), delta 1.4 (3H, t), 2.60 (3H, s), 4.4 (2H, qt), 7.30(1H, d), 7.44 (2H, m).
60.5%	With potassium carbonate; In N,N-dimethyl-formamide; for 1.0h;Reflux;	The compound 3-bromo-6-hydroxy-2-methylbenzaldehyde (7 g, 32.7 mmol), potassium carbonate (13.5 g, 98.1 mmol) wasdissolved in N,N-dimethylformamide (100 mL). Ethyl bromoacetate (10.9 g, 65.4 mmol) was slowly added dropwise, and the mixture waswarmed to reflux to continue the reaction for 1 hour.After the reaction was completed, ice water (150 mL) was added, suction filtered, and the filter cake was washed with water and dried to give a product(5.6 g, yield: 60.5%).

Reference： [1]Patent: EP2110374,2009,A1 .Location in patent: Page/Page column 27-28
[2]Patent: CN109265471,2019,A .Location in patent: Paragraph 0496; 0513; 0514; 0515

2
[ 1192172-68-1 ]
[ 57260-71-6 ]
[ 1192172-70-5 ]

Yield	Reaction Conditions	Operation in experiment
34.1%	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 20℃;Inert atmosphere; Reflux;	4-(2-ethoxycarbonyl-4-methyl-benzofuran-5-yl)-piperazine-1-carboxylic acid tert-butyl ester ; [Show Image] Toluene (30 ml) was stirred under argon atmosphere for 30 minutes at room temperature. Cesium carbonate (4.83 g, 0.015 mol), palladium acetate (0.19 g, 0.0008 mol), BINAP (0.66 g, 0.001 mol), 5-Bromo-4-methyl-benzofuran-2-carboxylic acid ethyl ester (3 g, 0.010 mol ) and piperazine-1-carboxylic acid tert-butyl ester (2.16 g, 0.001 mol) was added with a regular interval of 30 minutes under argon atmosphere. The reaction mixture was stirred for 30 minutes at room temperature and then heated to reflux. The mixture was maintained at reflux for 16 hours. The reaction mixture was diluted with ethyl acetate (50 ml) and the inorganic material was filtered. The filtrate was then washed with water (2 x 15 ml), brine solution (50 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to get crude product as dark brown solid. Column chromatography using 5/95 ethyl acetate/hexane yielded 4-(2-ethoxycarbonyl-4-methyl-benzofuran-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (1.4 g, 34.1 %) 1H NMR (300 MHz, CDCl3), delta 1.5 (3H, t), 1.5 (9H, s), 2.5(3H, s), 2.8(4H, t), 3.5 (4H, t), 4.4 (2H, qt), 7.18 (1H, d), 7.38 (1 H, d), 7.56 (1H, s).

Reference： [1]Patent: EP2110374,2009,A1 .Location in patent: Page/Page column 28

3
[ 6161-65-5 ]
[ 1192172-68-1 ]