[ CAS No. 5111-34-2 ] {[proInfo.proName]}

Name: 5111-34-2|1-Bromo-3-methoxynaphthalene|95%
Brand: Ambeed
SKU: A258746
Price: 13.0 USD
Availability: InStock
Rating: 94 (26 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 5111-34-2 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 5111-34-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5111-34-2 ]

SDS Specification

Alternatived Products of [ 5111-34-2 ]

Product Details of [ 5111-34-2 ]

CAS No. :	5111-34-2	MDL No. :	MFCD18410560
Formula :	C₁₁H₉BrO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GPVSVDNPAVXAQT-UHFFFAOYSA-N
M.W :	237.09	Pubchem ID :	13025837
Synonyms :

Safety of [ 5111-34-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 5111-34-2 ]

* 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 [ 5111-34-2 ]

[ 5111-34-2 ] Synthesis Path-Downstream 1~51

1
[ 5111-34-2 ]
[ 544-92-3 ]
[ 147397-59-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	In N,N-dimethyl-formamide for 6h; Heating;
	In N,N-dimethyl-formamide

Reference： [1]DeCosta, Dayal P.; Pincock, James A. [Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2180 - 2190]
[2]Tsuno,Y. et al. [Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 3347 - 3355]

2
[ 5498-31-7 ]
[ 77-78-1 ]
[ 5111-34-2 ]

Yield	Reaction Conditions	Operation in experiment
41%	With sodium hydroxide; In water; for 24h;	To a suspension of naphthol 31o (1.77 g, 7.93 mmol) in water (20 mL) at room temperature was added NaOH (dissolved in 50 mL water, 634 mg, 15.9 mmol). The contents were stirred until all solids were dissolved before the dropwise addition of dimethyl sulfate (1.50 mL, 15.9 mmol). After 24 hours of stirring, the reaction mixture was washed with diethyl ether (125 mL). The organic phase was dried over anhydrous Na2S04 and concentrated under reduced pressure. Purification by flash column chromatography (hexanes to 90: 10 hexanes/EtOAc) afforded 32o as a white solid (766 mg, 41% yield). Rf= 0.48 (hexanes/EtOAc 90: 10 v/v).1H NMR (400 MHz, CDCl3) delta 8.14 (d, J= 8.1 Hz, 1H), 7.72 (d, J= 7.7 Hz, 1H), 7.50 (d, = 2.3 Hz, 1H), 7.49-7.41 (m, 2H), 7.12 (d, J= 2.1 Hz, 1H), 3.92 (s, 3H).13C NMR (101 MHz, CDCl3) delta 157.3, 135.3, 127.8, 127.3, 127.3, 127.1, 125.1,123.6, 122.8, 106.2, 55.7.

Reference： [1]ChemMedChem,2018,vol. 13,p. 1092 - 1097
[2]Patent: WO2019/178480,2019,A1 .Location in patent: Page/Page column 102; 103
[3]Bulletin of the Chemical Society of Japan,1975,vol. 48,p. 3347 - 3355

3
[ 5343-99-7 ]
[ 5111-34-2 ]
[ 83710-51-4 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N,N,N,-tetramethylethylenediamine; magnesium 1.) THF, reflux, 2 h, 2.) RT, overnight; Yield given. Multistep reaction;

Reference： [1]Platt, Karl L.; Oesch, Franz [Journal of Organic Chemistry, 1982, vol. 47, # 27, p. 5321 - 5326]

4
C₁₅H₁₉N₃O [ No CAS ]
[ 5111-34-2 ]

Yield	Reaction Conditions	Operation in experiment
	With molecular sieve; Amberlyst XN-1010 resin; potassium iodide In N,N-dimethyl-formamide; acetonitrile at 70℃;

Reference： [1]Edwards, B.; Sparks, A.; Voyta, J. C.; Strong, R.; Murphy, O.; Bronstein, I. [Journal of Organic Chemistry, 1990, vol. 55, # 25, p. 6225 - 6229]

5
[ 5111-34-2 ]
(3- methoxynaphthalen- 1-yl)boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-bromo-3-methoxy-naphthalene With n-butyllithium In diethyl ether; hexane at 0℃; for 1h; Stage #2: With Trimethyl borate In diethyl ether; hexane at -78 - 20℃; Stage #3: With hydrogenchloride In diethyl ether; hexane; water at 20℃; for 0.75h;

Reference： [1]Spivey, Alan C.; Fekner, Tomasz; Spey, Sharon E.; Adams, Harry [Journal of Organic Chemistry, 1999, vol. 64, # 26, p. 9430 - 9443]

6
[ 52358-73-3 ]
[ 124-41-4 ]
[ 5111-34-2 ]
[ 10075-61-3 ]
1-methoxy-3-bromonaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 32% 2: 48% 3: 4%	With copper(l) iodide In methanol; N,N-dimethyl-formamide at 100℃; for 5h;

Reference： [1]Demirtas, Ibrahim; Erenler, Ramazan; Cakmak, Osman [Journal of Chemical Research - Part S, 2002, # 10, p. 524 - 526]

7
[ 5111-34-2 ]
3-methoxy-1-(1-methyl(2-pyrrolino[2,3-d]pyridin-7-yl))naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / diethyl ether; hexane / 1 h / 0 °C 1.2: trimethyl borate / diethyl ether; hexane / -78 - 20 °C 1.3: HCl / diethyl ether; hexane; H₂O / 0.75 h / 20 °C 2.1: 93 percent / Na₂CO₃; Pd(PPh₃)4 / toluene; ethanol; H₂O / Heating

Reference： [1]Spivey, Alan C.; Fekner, Tomasz; Spey, Sharon E.; Adams, Harry [Journal of Organic Chemistry, 1999, vol. 64, # 26, p. 9430 - 9443]

8
[ 5111-34-2 ]
[ 107098-25-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 70 percent / dimethylformamide / 6 h / Heating 2: 95 percent / 2.5 M NaOH / ethanol / 24 h / Heating 3: BH₃ / tetrahydrofuran / 1 h / Ambient temperature

Reference： [1]DeCosta, Dayal P.; Pincock, James A. [Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2180 - 2190]

9
[ 5111-34-2 ]
[ 147397-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 70 percent / dimethylformamide / 6 h / Heating 2: 95 percent / 2.5 M NaOH / ethanol / 24 h / Heating
	Multi-step reaction with 2 steps 1: dimethylformamide 2: aq. H₂SO₄ / acetic acid

10
[ 5111-34-2 ]
[ 112929-93-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 70 percent / dimethylformamide / 6 h / Heating 2: 95 percent / 2.5 M NaOH / ethanol / 24 h / Heating 3: BH₃ / tetrahydrofuran / 1 h / Ambient temperature 4: 1.) NaH₄ / 1.) DMF, 2.) DMF
	Multi-step reaction with 4 steps 1: 1) Mg / 1) ether, 2) ether, benzene, reflux, 1 h 2: 92 percent / conc. HCl / 2 h / Heating 3: diethyl ether / 3 h 4: Irradiation; substiuent effect investigated
	Multi-step reaction with 4 steps 1: 1) Mg / 1) ether, 2) ether, benzene, reflux, 1 h 2: 92 percent / conc. HCl / 2 h / Heating 3: diethyl ether / 3 h 4: methanol / Irradiation

Reference： [1]DeCosta, Dayal P.; Pincock, James A. [Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2180 - 2190]
[2]Foster, B.; Gaillard, B.; Mathur, N.; Pincock, A. L.; Pincock, J. A.; Sehmbey, C. [Canadian Journal of Chemistry, 1987, vol. 65, p. 1599 - 1607]
[3]Foster, B.; Gaillard, B.; Mathur, N.; Pincock, A. L.; Pincock, J. A.; Sehmbey, C. [Canadian Journal of Chemistry, 1987, vol. 65, p. 1599 - 1607]

11
[ 5111-34-2 ]
[ 123674-44-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 70 percent / dimethylformamide / 6 h / Heating 2: 95 percent / 2.5 M NaOH / ethanol / 24 h / Heating 3: BH₃ / tetrahydrofuran / 1 h / Ambient temperature 4: pyridine / benzene / 6 h

Reference： [1]DeCosta, Dayal P.; Pincock, James A. [Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2180 - 2190]

12
[ 5111-34-2 ]
3-methoxy-1-naphthylmethyl 3-phenylpropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 70 percent / dimethylformamide / 6 h / Heating 2: 95 percent / 2.5 M NaOH / ethanol / 24 h / Heating 3: BH₃ / tetrahydrofuran / 1 h / Ambient temperature 4: pyridine / benzene / 6 h

Reference： [1]DeCosta, Dayal P.; Pincock, James A. [Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2180 - 2190]

13
[ 5111-34-2 ]
[ 57404-87-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1) Mg / 1) ether, 2) ether, benzene, reflux, 1 h 2: 92 percent / conc. HCl / 2 h / Heating 3: diethyl ether / 3 h 4: 50 percent / Irradiation; substiuent effect investigated
	Multi-step reaction with 4 steps 1: 1) Mg / 1) ether, 2) ether, benzene, reflux, 1 h 2: 92 percent / conc. HCl / 2 h / Heating 3: diethyl ether / 3 h 4: 50 percent / methanol / Irradiation

Reference： [1]Foster, B.; Gaillard, B.; Mathur, N.; Pincock, A. L.; Pincock, J. A.; Sehmbey, C. [Canadian Journal of Chemistry, 1987, vol. 65, p. 1599 - 1607]
[2]Foster, B.; Gaillard, B.; Mathur, N.; Pincock, A. L.; Pincock, J. A.; Sehmbey, C. [Canadian Journal of Chemistry, 1987, vol. 65, p. 1599 - 1607]

14
[ 5111-34-2 ]
[ 112929-83-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1) Mg / 1) ether, 2) ether, benzene, reflux, 1 h 2: 92 percent / conc. HCl / 2 h / Heating 3: diethyl ether / 3 h

Reference： [1]Foster, B.; Gaillard, B.; Mathur, N.; Pincock, A. L.; Pincock, J. A.; Sehmbey, C. [Canadian Journal of Chemistry, 1987, vol. 65, p. 1599 - 1607]

15
[ 5111-34-2 ]
[ 130199-29-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1) ether, 0 deg C, 2) ether, warm to RT 2: Jones reagent / acetone / 0 °C

Reference： [1]Edwards, B.; Sparks, A.; Voyta, J. C.; Strong, R.; Murphy, O.; Bronstein, I. [Journal of Organic Chemistry, 1990, vol. 55, # 25, p. 6225 - 6229]

16
[ 50885-12-6 ]
[ 5111-34-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1) aq. HCl, NaNO₂, 2) K₂CO₃ / 1) H₂O, 0 deg C, 1 h, 2) H₂O 2: KI, Amberlyst XN-1010 resin, ground molecular sieve / acetonitrile; dimethylformamide / 70 °C

Reference： [1]Edwards, B.; Sparks, A.; Voyta, J. C.; Strong, R.; Murphy, O.; Bronstein, I. [Journal of Organic Chemistry, 1990, vol. 55, # 25, p. 6225 - 6229]

17
[ 33670-68-7 ]
[ 5111-34-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: alkaline aqueous sodium stannite solution / 80 - 90 °C
	Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 3 h / 0 °C 2: sodium hydroxide / water / 24 h / 20 °C
	Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 3 h / 0 °C 2: sodium hydroxide / water / 24 h

Reference： [1]Hodgson; Birtwell [Journal of the Chemical Society, 1943, p. 468]
[2]Trivedi-Parmar, Vinay; Robertson, Michael J.; Cisneros, José A.; Krimmer, Stefan G.; Jorgensen, William L. [ChemMedChem, 2018, vol. 13, # 11, p. 1092 - 1097]
[3]Current Patent Assignee: YALE UNIVERSITY - WO2019/178480, 2019, A1

18
[ 5111-34-2 ]
[ 58149-63-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dimethylformamide 2: aq. H₂SO₄ / acetic acid

Reference： [1]Tsuno,Y. et al. [Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 3347 - 3355]

19
[ 7499-65-2 ]
[ 5111-34-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: (reduction) 2: (i) NaNO₂, (ii) aq. H₂SO₄ 3: OH^-

Reference： [1]Tsuno,Y. et al. [Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 3347 - 3355]

20
[ 90767-01-4 ]
[ 5111-34-2 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1975,vol. 48,p. 3347 - 3355

21
[ 5111-34-2 ]
[ 1363155-94-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride / toluene / 24 h / Inert atmosphere; Reflux 2.1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 1 h / 0 °C 2.2: 0 °C 2.3: Neat (no solvent)

Reference： [1]Ettaoussi, Mohamed; Sabaouni, Ahmed; Rami, Marouan; Boutin, Jean A.; Delagrange, Philippe; Renard, Pierre; Spedding, Michael; Caignard, Daniel-Henri; Berthelot, Pascal; Yous, Saïd [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 310 - 323]

22
[ 5111-34-2 ]
[ 1363155-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: bis-triphenylphosphine-palladium(II) chloride / toluene / 24 h / Inert atmosphere; Reflux 2.1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 1 h / 0 °C 2.2: 0 °C 2.3: Neat (no solvent) 3.1: potassium carbonate / water; ethyl acetate / 20 °C 3.2: 1 h / 0 - 20 °C

23
[ 5111-34-2 ]
[ 17729-59-8 ]
[ 1261452-53-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With bis-triphenylphosphine-palladium(II) chloride In toluene for 24h; Inert atmosphere; Reflux;	4.1.29. 2-(3-Methoxy-naphthalen-1-yl)acetonitrile (35) To a solution of compound B (3.5 g, 14.5 mmol) in 40 mL of anhydrous toluene under an inert atmosphere, was added dropwise palladium dichloro-di(triphenylphosphine) (0.5 g, 0.7 mmol) and tributyl cyanomethyltin (5.5 g, 16.5 mmol) freshly prepared in 20 mL of anhydrous toluene. The reaction mixture was refluxed for 24 h, cooled and hydrolyzed with saturated solution of potassium fluoride then filtered on celite. The filtrate was extracted with ethyl acetate and the organic phase was washed with water, dried and evaporated to give the desired product after purification on a silica gel column eluted by a mixture of ethyl acetate-cyclohexane (1/9); Brown solid (2.66 g, 93% yield); m.p. 81-83 °C; 1H NMR (300 MHz, CDCl3): δH 3.94 (s, 3H, OCH3), 4.08 (s, 2H, CH2-a), 7.14 (d, J = 2.4, 1H, H-2), 7.30 (d, J = 2.4, 1H, H-4), 7.43-7.55 (m, 2H, H-6 and 7), 7.75-7.82 (m, 2H, H-5 and 8); IR (neat, cm-1): 2251 (CN); LC/MS m/z 198.2 (M + 1).

Reference： [1]Location in patent: experimental part Ettaoussi, Mohamed; Sabaouni, Ahmed; Rami, Marouan; Boutin, Jean A.; Delagrange, Philippe; Renard, Pierre; Spedding, Michael; Caignard, Daniel-Henri; Berthelot, Pascal; Yous, Saïd [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 310 - 323]

24
[ 5111-34-2 ]
[ 107-13-1 ]
(Z)-3-(3-methoxy-naphthalen-1-yl)acrylonitrile [ No CAS ]
(E)-3-(3-methoxy-naphthalen-1-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 5h; Inert atmosphere; optical yield given as %de;	4.1.30. (Z/E) 3-(3-methoxy-naphthalen-1-yl)acrylonitrile (36) To a solution of 1-bromo-3-methoxy-naphthalene (4.0 g, 16.9 mmol) in 150 mL of dry DMF was added dropwise acrylonitrile (1.7 mL, 25.3 mmol), palladium acetate (0.2 g, 0.8 mmol), triphenylphosphine (0.4 g, 1.7 mmol) and triethylamine (3.5 mL, 25.3 mmol). The reaction mixture was allowed to stir and heated at 100 °C for 5 h. After cooling, the mixture was taken up with saturated solution of NaHCO3 and extracted with ethyl acetate. The organic phase was washed with water, dried over MgSO4 and evaporated under reduced pressure to give the desired product after purification on silica gel column eluted by a mixture of ethyl acetate-cyclohexane (1/9); Yellow solid (3.46 g, 98% yield); m.p. 72-74 °C; 1H NMR (300 MHz, DMSO-d6): δH 3.93 (s, 3H, OCH3), 6.58 (d, J = 16.5, 1H, CH2-a), 7.41-7.57 (m, 3H, H-4,6 and 7), 7.60 (d, J = 2.4, 1H, H-2), 7.88 (d, J = 8.1, 1H, H-5), 8.22 (d, J = 9.1, 1H, H-8), 8.48 (d, J = 16.5, 1H, H-b); IR (neat, cm-1): 2216 (CN); LC/MS m/z 210.2 (M + 1).

25
[ 20191-76-8 ]
[ 5111-34-2 ]

Reference： [1]ChemMedChem,2018,vol. 13,p. 1092 - 1097
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 7089 - 7110
[3]Patent: WO2019/178480,2019,A1

26
[ 134-32-7 ]
[ 5111-34-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: acetic acid; bromine / 0.33 h / 0 - 60 °C 2: acetic acid; sodium nitrite / propionic acid / 0.17 h / 0 °C 3: sodium tetrahydroborate / ethanol / 3 h / 0 °C 4: sodium hydroxide / water / 24 h / 20 °C
	Multi-step reaction with 4 steps 1.1: bromine / acetic acid / 0.25 h / 0 - 60 °C 2.1: sodium nitrite; acetic acid; propionic acid / 0.17 h / 8 - 10 °C 3.1: sodium tetrahydroborate / ethanol / 0 - 10 °C 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / Inert atmosphere 4.2: 3 h / 20 °C
	Multi-step reaction with 4 steps 1: acetic acid; bromine / 0.33 h / 0 - 60 °C 2: acetic acid; propionic acid; sodium nitrite / 0.17 h / 0 °C 3: sodium tetrahydroborate / ethanol / 3 h / 0 °C 4: sodium hydroxide / water / 24 h

Reference： [1]Trivedi-Parmar, Vinay; Robertson, Michael J.; Cisneros, José A.; Krimmer, Stefan G.; Jorgensen, William L. [ChemMedChem, 2018, vol. 13, # 11, p. 1092 - 1097]
[2]Cerchia, Carmen; Nasso, Rosarita; Mori, Matteo; Villa, Stefania; Gelain, Arianna; Capasso, Alessandra; Aliotta, Federica; Simonetti, Martina; Rullo, Rosario; Masullo, Mariorosario; De Vendittis, Emmanuele; Ruocco, Maria Rosaria; Lavecchia, Antonio [Journal of Medicinal Chemistry, 2019, vol. 62, # 15, p. 7089 - 7110]
[3]Current Patent Assignee: YALE UNIVERSITY - WO2019/178480, 2019, A1

27
[ 5111-34-2 ]
2-((4-ethylnaphthalen-2-yl)oxy)-5-(3-fluoro-1H-pyrazol-4-yl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 2: boron tribromide / dichloromethane 3: caesium carbonate; copper(I) trifluoromethanesulfonate benzene; 1-naphthalenecarboxylic acid / toluene / 18 h / 110 °C / Molecular sieve; Sealed tube; Inert atmosphere 4: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; 1,4-dioxane / 3 h / 100 °C / Microwave irradiation; Inert atmosphere 5: sodium hydroxide; water / ethanol / 48 h / 20 °C