[ CAS No. 932-87-6 ] {[proInfo.proName]}

Name: 932-87-6|(Bromoethynyl)benzene|95%
Brand: Ambeed
SKU: A197823
Price: 46.0 USD
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Structure of 932-87-6 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 932-87-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 932-87-6 ]

SDS Specification

Alternatived Products of [ 932-87-6 ]

Product Details of [ 932-87-6 ]

CAS No. :	932-87-6	MDL No. :	MFCD00015715
Formula :	C₈H₅Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BPVHWNVBBDHIQU-UHFFFAOYSA-N
M.W :	181.03	Pubchem ID :	136737
Synonyms :

Calculated chemistry of [ 932-87-6 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.25
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.32
Log Po/w (XLOGP3) :	3.57
Log Po/w (WLOGP) :	2.47
Log Po/w (MLOGP) :	3.32
Log Po/w (SILICOS-IT) :	2.86
Consensus Log Po/w :	2.91

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.7
Solubility :	0.0357 mg/ml ; 0.000197 mol/l
Class :	Soluble
Log S (Ali) :	-3.26
Solubility :	0.1 mg/ml ; 0.000555 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.33
Solubility :	0.0845 mg/ml ; 0.000467 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.22

Safety of [ 932-87-6 ]

Signal Word:	Danger	Class:	N/A
Precautionary Statements:	P280-P304+P340+P312-P305+P351+P338+P310	UN#:	N/A
Hazard Statements:	H318-H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 932-87-6 ]

* 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 [ 932-87-6 ]
Downstream synthetic route of [ 932-87-6 ]

[ 932-87-6 ] Synthesis Path-Upstream 1~3

1
[ 932-87-6 ]
[ 39136-63-5 ]

Reference： [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 7, p. 1208 - 1212

2
[ 932-87-6 ]
[ 75-05-8 ]
[ 20662-93-5 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 11, p. 2672 - 2675
[2] Organic Letters, 2017, vol. 19, # 10, p. 2506 - 2509

3
[ 672-13-9 ]
[ 932-87-6 ]
[ 26964-24-9 ]

Reference： [1] Journal of Organic Chemistry, 2017, vol. 82, # 10, p. 5481 - 5486

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Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; 1,10-Phenanthroline; copper(II) sulphate hydrate; In toluene; at 80℃; for 15h;Inert atmosphere;	To a solution of bromoethynylbenzene (1.4 g, 8.0 mmol) in 24 mL of anhydrous toluene in a reaction vial were added methyl phenylcarbamate (1.5 g, 9.6 mmol), K3PO4 (3.4 g, 16 mmol), copper sulfate-pentahydrate (400 mg, 16 mmol), and 1,10-phenanthroline (577 mg, 3.2 mmol). The reaction mixtures was capped under an argon atmosphere, and heated in an oil bath at 80 ºC for 15 h. The progress of the reaction was monitored using TLC analysis. Upon completion, the reaction mixture was allowed to cool to room temperature, and diluted with 15 mL of ethyl acetate. The mixture was filtered through a pad of celite, and the filtrate was concentrated in vacuo. The crude residue was purified by column chromatography with eluent of Hexane/ ethyl acetate = 19/1 to give 1.6 g of 1 in 80 percent yield as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.55 (dd, J = 1.2, 8.6 Hz, 2H), 7.45-7.40 (m, 4H), 7.33-7.28 (m, 4H), 3.92 (s, 3H). 13C NMR. (100 MHz, CDCl3) delta 154.9, 139.7, 131.5, 129.1, 128.4, 128.0, 127.2, 124.8, 123.0, 83.0, 70.3, 54.5.#10;
	With 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; potassium carbonate; In toluene; at 80℃;Inert atmosphere;	General procedure: Procedure 1: To a solution of alkyne (9.80 mmol, 1.0 equiv) in acetone (10 mL) was added NBS (10.78 mmol, 1.1 equiv) and AgNO3 (0.98 mmol, 0.1 equiv). The resulting solution was stirred under nitrogen at room temperature for 4 h. After removing excess acetone the reaction was quenched with water and extracted with petroleum ether three times, dried over MgSO4, and concentrated under reduced pressure. The residue was eluted through a short silica column (petroleum ether) to obtain the bromoalkyne. To a dried flask was added 2-oxazolidone (4.8 mmol, 1.2 equiv), CuSO4·5H2O (100 mg, 0.4 mmol, 0.1 equiv), 1,10-phenanthroline (144 mg, 0.8 mmol, 0.2 equiv) and K2CO3 (1.38 g, 10.0 mmol, 2.5 equiv), bromoalkyne (4.0 mmol, 1.0 equiv) and this mixture was subsequently treated with anhydrous toluene (10 mL). The flask was charged with nitrogen, and the solution was heated at 80 °C overnight. After completion, the crude reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. Purification of the crude residue using silica gel flash column chromatography yielded the pure ynamides.

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; 1,10-Phenanthroline; copper(II) sulphate hydrate; In toluene; at 80℃; for 15h;Inert atmosphere;	To a solution of bromoethynylbenzene (1.4 g, 8.0 mmol) in 24 mL of anhydrous toluene in a reaction vial were added methyl phenylcarbamate (1.5 g, 9.6 mmol), K3PO4 (3.4 g, 16 mmol), copper sulfate-pentahydrate (400 mg, 16 mmol), and 1,10-phenanthroline (577 mg, 3.2 mmol). The reaction mixtures was capped under an argon atmosphere, and heated in an oil bath at 80 ºC for 15 h. The progress of the reaction was monitored using TLC analysis. Upon completion, the reaction mixture was allowed to cool to room temperature, and diluted with 15 mL of ethyl acetate. The mixture was filtered through a pad of celite, and the filtrate was concentrated in vacuo. The crude residue was purified by column chromatography with eluent of Hexane/ ethyl acetate = 19/1 to give 1.6 g of 1 in 80 % yield as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.55 (dd, J = 1.2, 8.6 Hz, 2H), 7.45-7.40 (m, 4H), 7.33-7.28 (m, 4H), 3.92 (s, 3H). 13C NMR. (100 MHz, CDCl3) δ 154.9, 139.7, 131.5, 129.1, 128.4, 128.0, 127.2, 124.8, 123.0, 83.0, 70.3, 54.5.
	With 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; potassium carbonate; In toluene; at 80℃;Inert atmosphere;	General procedure: Procedure 1: To a solution of alkyne (9.80 mmol, 1.0 equiv) in acetone (10 mL) was added NBS (10.78 mmol, 1.1 equiv) and AgNO3 (0.98 mmol, 0.1 equiv). The resulting solution was stirred under nitrogen at room temperature for 4 h. After removing excess acetone the reaction was quenched with water and extracted with petroleum ether three times, dried over MgSO4, and concentrated under reduced pressure. The residue was eluted through a short silica column (petroleum ether) to obtain the bromoalkyne. To a dried flask was added 2-oxazolidone (4.8 mmol, 1.2 equiv), CuSO4·5H2O (100 mg, 0.4 mmol, 0.1 equiv), 1,10-phenanthroline (144 mg, 0.8 mmol, 0.2 equiv) and K2CO3 (1.38 g, 10.0 mmol, 2.5 equiv), bromoalkyne (4.0 mmol, 1.0 equiv) and this mixture was subsequently treated with anhydrous toluene (10 mL). The flask was charged with nitrogen, and the solution was heated at 80 C overnight. After completion, the crude reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. Purification of the crude residue using silica gel flash column chromatography yielded the pure ynamides.
	With 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; potassium carbonate; In toluene; at 60℃;Schlenk technique; Inert atmosphere;	General procedure: A Schlenk flask charged with a stirring bar, sulfonamide (12mmol, 1.2 equiv), K2CO3 (20mmol, 2.0 equiv), CuSO45H2O (1.0mmol, 10mol%), and 1,10-phenanthroline (2.0mmol, 20mol%) was vacuumed and backfilled with N2, repeatedly for 3 times, and then a solution of alkynyl bromide [26] (10mmol, 1.0 equiv) in toluene (10mL, 1M) was added to the mixture by a syringe. The resulting mixture was heated to 60C for 24-48h. After completion, the mixture was filtered through celite pad, and the filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel (PE/EtOAc=20/1-5/1) to give the ynamide product.

Yield	Reaction Conditions	Operation in experiment
92%	With 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; potassium carbonate; In toluene; at 60℃; under 760.051 Torr; for 40h;Inert atmosphere;	The reaction mixture, which was prepared from Bromoethynylbenzene (1.38 g, 7.31mmol), <strong>[640-61-9]N-Methyl-p-toluenesulfonamide</strong> (1.23 g, 6.65 mmol), K2CO3 (1.83 g, 13.3mmol), CuSO4?5H2O (0.17 g, 0.66 mmol) and 1,10-Phenanthroline (0.24 g, 1.33mmol) in Toluene (8 mL), was stirred at 60 C for 40 h. After cooled to rt, the resulting mixture was filtered on celite, and the volatiles were removed under reduce pressure. The residue was separated by column chromatograpy on silica gel(Hexane/EtOAc = 3:1) to provide 1f (1.74 g, 92%). IR (KBr) nu 2233, 1339, 1189 cm-1; 1H NMR (400 MHz, CDCl3) delta 2.46 (s, 3H), 3.15(s, 3H), 7.07-7.32 (m, 3H), 7.32-7.64 (m, 4H) 7.84 (d, J = 8.2 Hz, 2H); 13C NMR(100 MHz, CDCl3) delta 21.6, 39.2, 68.9, 83.9, 122.6, 127.7, 127.8, 128.2, 129.7, 131.3,133.1, 144.8; EI-LRMS m/z 285 (M+), 130, 105, 89; EI-HRMS m/z calcd for C16H15NO2S (M+) 285.0823, found 285.0817.
	With potassium phosphate; 1,10-Phenanthroline; copper(II) sulphate hydrate; In toluene; at 80℃; for 15h;Inert atmosphere;	To a solution of bromoethynylbenzene (1.4 g, 8.0 mmol) in 24 mL of anhydrous toluene in a reaction vial were added methyl phenylcarbamate (1.5 g, 9.6 mmol), K3PO4 (3.4 g, 16 mmol), copper sulfate-pentahydrate (400 mg, 16 mmol), and 1,10-phenanthroline (577 mg, 3.2 mmol). The reaction mixtures was capped under an argon atmosphere, and heated in an oil bath at 80 ºC for 15 h. The progress of the reaction was monitored using TLC analysis. Upon completion, the reaction mixture was allowed to cool to room temperature, and diluted with 15 mL of ethyl acetate. The mixture was filtered through a pad of celite, and the filtrate was concentrated in vacuo. The crude residue was purified by column chromatography with eluent of Hexane/ ethyl acetate = 19/1 to give 1.6 g of 1 in 80 % yield as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.55 (dd, J = 1.2, 8.6 Hz, 2H), 7.45-7.40 (m, 4H), 7.33-7.28 (m, 4H), 3.92 (s, 3H). 13C NMR. (100 MHz, CDCl3) delta 154.9, 139.7, 131.5, 129.1, 128.4, 128.0, 127.2, 124.8, 123.0, 83.0, 70.3, 54.5.
	With 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; potassium carbonate; In toluene; at 60℃;Schlenk technique; Inert atmosphere;	General procedure: A Schlenk flask charged with a stirring bar, sulfonamide (12mmol, 1.2 equiv), K2CO3 (20mmol, 2.0 equiv), CuSO45H2O (1.0mmol, 10mol%), and 1,10-phenanthroline (2.0mmol, 20mol%) was vacuumed and backfilled with N2, repeatedly for 3 times, and then a solution of alkynyl bromide [26] (10mmol, 1.0 equiv) in toluene (10mL, 1M) was added to the mixture by a syringe. The resulting mixture was heated to 60C for 24-48h. After completion, the mixture was filtered through celite pad, and the filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel (PE/EtOAc=20/1-5/1) to give the ynamide product.

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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
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[ CAS No. 932-87-6 ] {[proInfo.proName]}

Quality Control of [ 932-87-6 ]

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Product Details of [ 932-87-6 ]