35615-97-5|Methyl 4-bromonaphthalene-1-carboxylate| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 35615-97-5 ] Purity: 97% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 35615-97-5 ]

CAS No. :	35615-97-5
Formula :	C₁₂H₉BrO₂
M.W :	265.10
SMILES Code :	O=C(OC)C1=C2C=CC=CC2=C(Br)C=C1
MDL No. :	MFCD09475914
InChI Key :	NSWYFJWAOXYZDF-UHFFFAOYSA-N
Pubchem ID :	22711886

Safety of [ 35615-97-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 35615-97-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	10
Fraction Csp3	0.08
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	62.93
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.65
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	3.72
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.39
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.	3.59
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	3.5
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.37

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.19
Solubility	0.0172 mg/ml ; 0.0000648 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.96
Solubility	0.0288 mg/ml ; 0.000109 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	-5.0
Solubility	0.00263 mg/ml ; 0.00000993 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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.	-5.28 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	0.0 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)	1.44

Application In Synthesis of [ 35615-97-5 ]

* 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 [ 35615-97-5 ]

[ 35615-97-5 ] Synthesis Path-Downstream 1~35

1
[ 67-56-1 ]
[ 81-86-7 ]
[ 35615-97-5 ]
[ 59866-97-6 ]

References: [1]Tetrahedron,2006,vol. 62,p. 4690 - 4697.

2
[ 35615-97-5 ]
(2-amino-4,5-dimethyl-thiophen-3-yl)-(4-bromo-naphthalen-1-yl)-methanone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 794 - 809.

3
[ 35615-97-5 ]
(2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(4-bromonaphthalen-1-yl)-methanone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 794 - 809.

4
[ 35615-97-5 ]
(2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(4-bromonaphthalen-1-yl)-methanone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 794 - 809.

5
[ 35615-97-5 ]
(2-amino-6-benzyl-4,5,6,7-tetrahydro-thieno[2,3-<i>c</i>]pyridin-3-yl)-(4-bromo-naphthalen-1-yl)-methanone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 794 - 809.

6
[ 83-53-4 ]
[ 35615-97-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2769 - 2773.

7
[ 16650-55-8 ]
[ 35615-97-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2769 - 2773.

8
[ 35615-97-5 ]
[ 3839-19-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2769 - 2773.
[2]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1737 - 1746.

9
[ 35615-97-5 ]
[ 661-69-8 ]
[ 332398-25-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	tetrakis(triphenylphosphine) palladium(0); In toluene; for 3h;Heating / reflux;	A stirred solution of methyl 4-bromo-I-naphthoate (Collect. Czech. Chem. Commun. 1997, 62(11), 1737; 7.3g, 28mmole) in degassed toluene (300ml) was treated with hexamethylditin (10g, 31mmole) and tetrakis(triphenylphosphine)palladium(0) (720mg) and heated at reflux under argon for 3h.. On cooling, the mixture was filtered through Celite (Diatomaceous Earth), concentrated under vacuum and the residue chromatographed on silica gel eluding with 0-3% ether/60-80 petrol to afford the title compound as a colourless oil (9.06g, 94%)

References: [1]Patent: EP1216239,2004,B1 .Location in patent: Page 8-9.

Yield	Reaction Conditions	Operation in experiment
97%		Step 2 4-Bromo-naphthalene-1-carboxylic acid methyl ester To a solution of 4-Bromo-naphthylene-1-carboxylic acid (8.6 g, 34.3 mmol) in MeOH (175 mL) at room temperature was added concentrated sulfuric acid (3.5 mL). The reaction was heated to reflux for 7 h. The reaction was then cooled to room temperature and the methanol partially evaporated. The reaction mixture was diluted with 300 mL H2O. The dilution was extracted with ethyl acetate and then with ether. The organic extractions were combined and washed with saturated sodium bicarbonate and brine, dried over MgSO4, filtered and concentrated to yield 8.86 g of a light yellow liquid (97%). 1H NMR (400 mHz) CDCl3 8.86 (m, 1H), 8.31 (m, 1H), 7.98 (d, 1H), 7.87 (d, 1H), 7.66 (m, 2H), 3.97 (s, 3H).

11
[ 35615-97-5 ]
[ 24850-33-7 ]
[ 475216-19-4 ]

Yield	Reaction Conditions	Operation in experiment
	tetrakis(triphenylphosphine)palladium (0); In toluene;	Step 3 4-Allylnaphthalene-1-carboxylic Acid Methyl Ester To a solution of <strong>[35615-97-5]4-bromo-naphthalene-1-carboxylic acid methyl ester</strong> (2.0 g, 7.9 mmol) in toluene (20 mL) was added allyltributyltin (2.7 mL), tetrakis(triphenylphosphine)palladium(0) (183 mg, 0.16 mmol) and 2 crystals of BHT. The system was purged under vacuum and nitrogen and allowed to heat to 120 C. under N2 for 4 h. TLC analysis (silica, 1:1 ethyl acetate-hexanes) showed the reaction to be completed with only one new fluorescent spot present. The mixture was diluted with ether, washed with H2O, 10% HCl, and then saturated sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (SiO2, 9:1 hexanes-ether) to give (1.6 g, 89%) 4-allylnaphthalene-1-carboxylic acid methyl ester as a colorless liquid. MS m/z 227.1 (M+1). 1H NMR (400 mHz) CDCl3 8.95(d 1H), 8.11(d, 1H), 8.08(d, 1H), 7.58(m, 2H), 7.37(d, 1H), 6.09(m, 1H), 5.11(m, 2H), 3.99(s, 3H), 3.88(d, 2H).

References: [1]Patent: US2003/96826,2003,A1 .

12
[ 79-37-8 ]
[ 16650-55-8 ]
[ 35615-97-5 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; N,N-dimethyl-formamide;	(a) Methyl 4-bromo-1-naphthoate. A solution of 4-bromo-1-naphthoic acid (Fischer, A; et al, J. Chem. Soc., 1426 (1958)) oxalyl chloride (2.56 g), and DMF (5 muL) in DCM (100 mL) was stirred for 3 h, concentrated, then redissolved in DCM (5 mL). Methanol was added and stirring continued overnight. Following concentration and purification by chromatography (DCM) the product was afforded as a white solid (4.85 g). 1H NMR (DMSO-d6): delta 8.83-8.77 (m, 1H), 8.31-8.25 (m, 1 H), 8.01 (s, 1 H), 7.82-7.75 (m, 2H), 3.96 (s, 3 H); MS m/z 265 (M+H).
	In methanol; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; N,N-dimethyl-formamide;	(a) Methyl 4-bromo-1-naphthoate. A solution of 4-bromo-1-naphthoic acid (Fischer, A; et al, J. Chem. Soc., 1426 (1958)) oxalyl chloride (2.56 g), and DMF (5 muL) in DCM (100 mL) was stirred for 3 h, concentrated, then redissolved in DCM (5 mL). Methanol was added and stirring continued overnight. Following concentration and purification by chromatography (DCM) the product was afforded as a white solid (4.85 g). 1H NMR (DMSO-d6): delta 8.83-8.77 (m, 1H), 8.31-8.25 (m, 1 H), 8.01 (s, 1 H), 7.82-7.75 (m, 2H), 3.96 (s, 3 H); MS m/z 265 (M+H).

References: [1]Patent: US6365602,2002,B1 .
[2]Patent: US6365602,2002,B1 .

13
aqueous concentrated NH₄OH [ No CAS ]
[ 35615-97-5 ]
[ 3839-19-8 ]
[ 39088-39-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In N,N-dimethyl-formamide;	(b) 4-cyano-1-naphthoic acid. A solution of <strong>[35615-97-5]methyl 4-bromo-1-naphthoate</strong> (0.509 g) copper (I) cyanide, (0.174 g), 1 drop of pyridine, and DMF (5 mL) was heated under reflux at 180 C. for 5 h. The hot solution was poured into 10 mL of aqueous concentrated NH4OH and extracted with DCM. The organic phase was washed successively with 1N HCl (20 mL) and brine (40 mL), dried (Na2SO4), filtered, and concentrated to afford methyl 4-cyano-1-naphthoate a colorless oil (0.213 g). MS m/z 196 (M-1). 1H NMR (DMSO6): delta 8.74-8.69 (m, 1 H), 8.29-8.15 (m, 3 H), 7.92-7.83 (m, 2H), 3.99 (s, 3 H).
	With pyridine; In N,N-dimethyl-formamide;	(b) 4-cyano-1-naphthoic acid. A solution of <strong>[35615-97-5]methyl 4-bromo-1-naphthoate</strong> (0.509 g) copper (I) cyanide, (0.174 g), 1 drop of pyridine, and DMF (5 mL) was heated under reflux at 180 C. for 5 h. The hot solution was poured into 10 mL of aqueous concentrated NH4OH and extracted with DCM. The organic phase was washed successively with 1N HCl (20 mL) and brine (40 mL), dried (Na2SO4), filtered, and concentrated to afford methyl 4-cyano-1-naphthoate a colorless oil (0.213 g). MS m/z 196 (M-1). 1H NMR (DMSO-d6): delta 8.74-8.69 (m, 1 H), 8.29-8.15 (m, 3 H), 7.92-7.83 (m, 2H), 3.99 (s, 3 H).

References: [1]Patent: US6365602,2002,B1 .
[2]Patent: US6365602,2002,B1 .

14
[ 35615-97-5 ]
[ 62855-40-7 ]