[ CAS No. 98453-60-2 ] {[proInfo.proName]}

Name: 98453-60-2|6-Bromo-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one|97%
Brand: Ambeed
SKU: A422122
Rating: 90 (26 reviews)

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Quality Control of [ 98453-60-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 98453-60-2 ]

SDS Specification

Alternatived Products of [ 98453-60-2 ]

Product Details of [ 98453-60-2 ]

CAS No. :	98453-60-2	MDL No. :	MFCD22041940
Formula :	C₁₂H₁₃BrO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HWRLTYBJEKHTJG-UHFFFAOYSA-N
M.W :	253.14	Pubchem ID :	11831935
Synonyms :

Calculated chemistry of [ 98453-60-2 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	61.49
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.3 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.58
Log Po/w (XLOGP3) :	3.59
Log Po/w (WLOGP) :	3.7
Log Po/w (MLOGP) :	3.25
Log Po/w (SILICOS-IT) :	4.17
Consensus Log Po/w :	3.46

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.99
Solubility :	0.026 mg/ml ; 0.000103 mol/l
Class :	Soluble
Log S (Ali) :	-3.64
Solubility :	0.0587 mg/ml ; 0.000232 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.01
Solubility :	0.00245 mg/ml ; 0.00000966 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.04

Safety of [ 98453-60-2 ]

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

Application In Synthesis of [ 98453-60-2 ]

* 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.

Upstream synthesis route of [ 98453-60-2 ]
Downstream synthetic route of [ 98453-60-2 ]

[ 98453-60-2 ] Synthesis Path-Upstream 1~7

1
[ 98453-58-8 ]
[ 98453-60-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	With chromium(VI) oxide; tert.-butylhydroperoxide In dichloromethane at 20℃; for 8 h;	6-Bromo-4, 4-dimethyl-3, 4-dihydro-2H-naphthalen-1-one (Compound 3) To a solution of 7-bromo-1, 1-dimethyl-1, 2,3, 4-tetrahydro-naphthalene (Compound 2, 1. 1 g, 4.62 mmol) in 10 mL of dichloromethane was added chromium (VI) oxide (72 mg, 0.46 mmol) and 5 mL of ter-butyl hydroperoxide solution (TBHP). After stirring at room temperature for 8 h, the mixture was diluted with water (20 mL), extracted with diethyl ether (3x 10 mL), washed with brine (1 x 10 mL), dried (MgS04) and concentrated at reduced pressure. Purification by flash chromatography (90: 10 hexane/ethyl acetate) yielded the title compound (920 mg, 79 percent yield) as a white solid: 1H NMR (CDC13, 300 MHz) 8 7.87 (d, J = 8. 1 Hz, 1H), 7.54 (d, J = 2.1 Hz, 1H), 7.42 (dd, J = 2.1, 8.1 Hz, 1H), 2.70 (dd, J = 6.3, 7.5 Hz, 2H), 2.01 (dd, J = 6.3, 7.5 Hz, 2H), 1.38 (s, 6H).
79%	With chromium(VI) oxide; tert.-butylhydroperoxide In dichloromethane at 20℃; for 8 h;	To a solution of 7-bromo-1,1-dimethyl-1,2,3,4-tetrahydro-naphthalene (Compound 15, 1.1 g, 4.62 mmol) in 10 mL of dichloromethane was added chromium (VI) oxide (72 mg, 0.46 mmol) and 5 mL of tert-butyl hydroperoxide solution (TBHP). After stirring at room temperature for 8 h, the mixture was diluted with water (20 mL), extracted with diethyl ether (310 mL), washed with brine (110 mL), dried (MgSO₄) and concentrated at reduced pressure. Purification by flash chromatography (90:10 hexane/ethyl acetate) yielded the title compound (920 mg, 79percent yield) as a white solid: ¹H NMR (CDCl₃, 300 MHz) δ 7.87 (d, J=8.1 Hz, 1H), 7.54 (d, J=2.1 Hz, 1H), 7.42 (dd, J=2.1, 8.1 Hz, 1H), 2.70 (dd, J=6.3, 7.5 Hz, 2H), 2.01 (dd, J=6.3, 7.5 Hz, 2H), 1.38 (s, 6H).
53%	With chromium(VI) oxide In water; acetic acid for 15 h;	c. 6-BROMO-4, 4-DIMETHYL-3, 4-DIHYDRO-2H-NAPHTHALEN-1-ONE A solution of 8.1 g (81 mmol) of chromium trioxide in 74 ml of acetic acid and 3.9 ml of water is added slowly to 14.3 g (60 mmol) of 7-BROM-1, 1- dimethyl-1, 2,3, 4-TETRAHYDRONAPHTHALENE dissolved in 1.5 1 of acetic acid. The reaction medium is stirred for 15 hours, reduced to a volume of 500 ml by concentration, hydrolysed with ice, extracted with ethyl ether and neutralized with 35percent sodium hydroxide solution. The solid obtained is washed with heptane. A pink-white powder is obtained (8 g; 53percent).

Reference： [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4345 - 4359
[2] Patent: WO2005/66115, 2005, A2, . Location in patent: Page/Page column 19; 21
[3] Patent: US2005/148590, 2005, A1, . Location in patent: Page/Page column 23; 24
[4] Tetrahedron, 1985, vol. 41, # 8, p. 1509 - 1516
[5] Patent: WO2004/46096, 2004, A2, . Location in patent: Page 24
[6] Patent: US2005/4213, 2005, A1, . Location in patent: Page 13

2
[ 108-86-1 ]
[ 98453-60-2 ]

Reference： [1] Tetrahedron, 1985, vol. 41, # 8, p. 1509 - 1516

3
[ 35656-89-4 ]
[ 98453-60-2 ]

Reference： [1] Tetrahedron, 1985, vol. 41, # 8, p. 1509 - 1516

4
[ 6340-79-0 ]
[ 98453-60-2 ]

Reference： [1] Tetrahedron, 1985, vol. 41, # 8, p. 1509 - 1516

5
[ 87077-85-8 ]
[ 98453-60-2 ]

Reference： [1] Tetrahedron, 1985, vol. 41, # 8, p. 1509 - 1516

6
[ 98453-57-7 ]
[ 98453-60-2 ]

Reference： [1] Tetrahedron, 1985, vol. 41, # 8, p. 1509 - 1516

7
[ 105986-54-7 ]
[ 98453-60-2 ]

Reference： [1] Patent: US6344561, 2002, B2, . Location in patent: Page column 72

[ 98453-60-2 ] Synthesis Path-Downstream 1~26

1
[ 98453-58-8 ]
[ 98453-60-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	With chromium(VI) oxide; tert.-butylhydroperoxide; In dichloromethane; at 20℃; for 8h;	6-Bromo-4, 4-dimethyl-3, 4-dihydro-2H-naphthalen-1-one (Compound 3) To a solution of 7-bromo-1, 1-dimethyl-1, 2,3, 4-tetrahydro-naphthalene (Compound 2, 1. 1 g, 4.62 mmol) in 10 mL of dichloromethane was added chromium (VI) oxide (72 mg, 0.46 mmol) and 5 mL of ter-butyl hydroperoxide solution (TBHP). After stirring at room temperature for 8 h, the mixture was diluted with water (20 mL), extracted with diethyl ether (3x 10 mL), washed with brine (1 x 10 mL), dried (MgS04) and concentrated at reduced pressure. Purification by flash chromatography (90: 10 hexane/ethyl acetate) yielded the title compound (920 mg, 79 percent yield) as a white solid: 1H NMR (CDC13, 300 MHz) 8 7.87 (d, J = 8. 1 Hz, 1H), 7.54 (d, J = 2.1 Hz, 1H), 7.42 (dd, J = 2.1, 8.1 Hz, 1H), 2.70 (dd, J = 6.3, 7.5 Hz, 2H), 2.01 (dd, J = 6.3, 7.5 Hz, 2H), 1.38 (s, 6H).
79%	With chromium(VI) oxide; tert.-butylhydroperoxide; In dichloromethane; at 20℃; for 8h;	To a solution of 7-bromo-1,1-dimethyl-1,2,3,4-tetrahydro-naphthalene (Compound 15, 1.1 g, 4.62 mmol) in 10 mL of dichloromethane was added chromium (VI) oxide (72 mg, 0.46 mmol) and 5 mL of tert-butyl hydroperoxide solution (TBHP). After stirring at room temperature for 8 h, the mixture was diluted with water (20 mL), extracted with diethyl ether (310 mL), washed with brine (110 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (90:10 hexane/ethyl acetate) yielded the title compound (920 mg, 79percent yield) as a white solid: 1H NMR (CDCl3, 300 MHz) delta 7.87 (d, J=8.1 Hz, 1H), 7.54 (d, J=2.1 Hz, 1H), 7.42 (dd, J=2.1, 8.1 Hz, 1H), 2.70 (dd, J=6.3, 7.5 Hz, 2H), 2.01 (dd, J=6.3, 7.5 Hz, 2H), 1.38 (s, 6H).
53%	With chromium(VI) oxide; In water; acetic acid; for 15h;	c. 6-BROMO-4, 4-DIMETHYL-3, 4-DIHYDRO-2H-NAPHTHALEN-1-ONE A solution of 8.1 g (81 mmol) of chromium trioxide in 74 ml of acetic acid and 3.9 ml of water is added slowly to 14.3 g (60 mmol) of 7-BROM-1, 1- dimethyl-1, 2,3, 4-TETRAHYDRONAPHTHALENE dissolved in 1.5 1 of acetic acid. The reaction medium is stirred for 15 hours, reduced to a volume of 500 ml by concentration, hydrolysed with ice, extracted with ethyl ether and neutralized with 35percent sodium hydroxide solution. The solid obtained is washed with heptane. A pink-white powder is obtained (8 g; 53percent).

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 4345 - 4359
[2]Patent: WO2005/66115,2005,A2 .Location in patent: Page/Page column 19; 21
[3]Patent: US2005/148590,2005,A1 .Location in patent: Page/Page column 23; 24
[4]Tetrahedron,1985,vol. 41,p. 1509 - 1516
[5]Patent: WO2004/46096,2004,A2 .Location in patent: Page 24
[6]Patent: US2005/4213,2005,A1 .Location in patent: Page 13

2
[ 98453-60-2 ]
[ 98453-62-4 ]