[ CAS No. 305798-02-1 ] {[proInfo.proName]}

Name: 305798-02-1|2-Bromo-6-(bromomethyl)naphthalene|95%
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SKU: A178855
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Quality Control of [ 305798-02-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 305798-02-1 ]

Product Details of [ 305798-02-1 ]

CAS No. :	305798-02-1	MDL No. :	MFCD09842471
Formula :	C₁₁H₈Br₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KNCXTOYNERTOJO-UHFFFAOYSA-N
M.W :	299.99	Pubchem ID :	19762395
Synonyms :

Calculated chemistry of [ 305798-02-1 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.09
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	64.48
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.82
Log Po/w (XLOGP3) :	4.64
Log Po/w (WLOGP) :	4.35
Log Po/w (MLOGP) :	4.72
Log Po/w (SILICOS-IT) :	4.64
Consensus Log Po/w :	4.23

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.13
Solubility :	0.00224 mg/ml ; 0.00000748 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.37
Solubility :	0.0129 mg/ml ; 0.000043 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.17
Solubility :	0.000202 mg/ml ; 0.000000675 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.59

Safety of [ 305798-02-1 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P260-P270-P271-P264-P280-P362+P364-P303+P361+P353-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405	UN#:	3261
Hazard Statements:	H302+H312+H332-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 305798-02-1 ]

* 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 [ 305798-02-1 ]
Downstream synthetic route of [ 305798-02-1 ]

[ 305798-02-1 ] Synthesis Path-Upstream 1~3

1
[ 100751-63-1 ]
[ 305798-02-1 ]

Yield	Reaction Conditions	Operation in experiment
99.2%	With phosphorus tribromide In chloroform at 20℃; for 1 h;	169 g of (6-bromo-2-naphthyl) methanol and 1250 g of chloroform were placed in a reacting flask. phosphorus tribromide was dissolved in 180 ml of chloroform and slowly dropped into the reacting flask at room temperature in a nitrogen atmosphere to compose a mixture. The mixture was stirred for one-hour, and a white solid was precipitated after the mixture become transparent. Then, 750 ml of methanol was added to the mixture. After cold bathing and filtering, the solid obtained was further mixed with 750 ml of methanol solution again and stirred for 10 min. The solid was obtained by filtering the methanol solution and dried at 100° C. 110 g of (6-bromo-2bromomethyl) naphthalene was obtained (yield: 48.6percent; purity: 99.2percent). Third Act: Synthesization of Compound A, 2-[4-(N,N-diphenylamino)styryl]-6-bromo-naphthalene
85%	With phosphorus tribromide In diethyl ether at 0 - 20℃; for 3 h;	Preparation of starting material 2-bromo-6-(bromomethyl)naphthalene (1d) To a solution of (6-bromonaphthalen-2-yl)methanol (1.19 g, 5 mmol) in anhydrous Et₂O (40 mL) at 0 °C, PBr₃ (1.52 g, 22 mmol) was added dropwise, and the resulting solution was stirred at room temperature for 3 h. The resultant mixture was neutralized with an aq. NaHCO₃, and the product was extracted with Et₂O (40 mL * 2). The organic layers were dried over Na₂SO₄, filtered and concentrated. Then, the crude product was purified by flash silica gel chromatography (eluent: petroleum ether) to afford 1d (1.27 g, 85percent yield) as a white solid.

Reference： [1] Patent: US2006/159953, 2006, A1, . Location in patent: Page/Page column 4
[2] Journal of Organometallic Chemistry, 2013, vol. 745-746, p. 177 - 185

2
[ 37796-78-4 ]
[ 305798-02-1 ]

Reference： [1] Journal of the American Chemical Society, 1948, vol. 70, p. 2843,2945
[2] Patent: EP2159217, 2010, A1, . Location in patent: Page/Page column 56-57

3
[ 37796-79-5 ]
[ 305798-02-1 ]

Reference： [1] Journal of the American Chemical Society, 1948, vol. 70, p. 2843,2945

[ 305798-02-1 ] Synthesis Path-Downstream 1~29

1
[ 37796-78-4 ]
[ 305798-02-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 3h;Reflux;	In a stream of argon, 15.0 g of Intermediate 7, 12.1 g of N-bromosuccinimide, 100 mg of azobisisobutyronitrile, and carbon tetrachloride were loaded into a 300-mL eggplant flask, and the mixture was subjected to a reaction under reflux for 3 hours. After the resultant had been cooled, clean water and methylene chloride were added to the resultant for separation and extraction. After that, an organic layer was washed with clean water and a saturated salt solution, and was dried with sodium sulfate. A coarse product obtained by concentrating the dried product was purified by silica gel chromatography (methylene chloride and hexane). The resultant solid was dried under reduced pressure. As a result, 16.2 g of a white solid were obtained. The solid was identified as Intermediate 8 by FD-MS.

Reference： [1]Journal of the American Chemical Society,1948,vol. 70,p. 2843,2945
[2]Patent: EP2159217,2010,A1 .Location in patent: Page/Page column 56-57

2
[ 305798-02-1 ]
[ 151-50-8 ]
[ 32721-06-5 ]

Reference： [1]Journal of the American Chemical Society,1948,vol. 70,p. 2843,2945

3
[ 37796-79-5 ]
[ 305798-02-1 ]

Reference： [1]Journal of the American Chemical Society,1948,vol. 70,p. 2843,2945

4
[ 100751-63-1 ]
[ 305798-02-1 ]

Yield	Reaction Conditions	Operation in experiment
99.2%	With phosphorus tribromide; In chloroform; at 20℃; for 1h;	169 g of (6-bromo-2-naphthyl) methanol and 1250 g of chloroform were placed in a reacting flask. phosphorus tribromide was dissolved in 180 ml of chloroform and slowly dropped into the reacting flask at room temperature in a nitrogen atmosphere to compose a mixture. The mixture was stirred for one-hour, and a white solid was precipitated after the mixture become transparent. Then, 750 ml of methanol was added to the mixture. After cold bathing and filtering, the solid obtained was further mixed with 750 ml of methanol solution again and stirred for 10 min. The solid was obtained by filtering the methanol solution and dried at 100 C. 110 g of (6-bromo-2bromomethyl) naphthalene was obtained (yield: 48.6%; purity: 99.2%). Third Act: Synthesization of Compound A, 2-[4-(N,N-diphenylamino)styryl]-6-bromo-naphthalene
85%	With phosphorus tribromide; In diethyl ether; at 0 - 20℃; for 3h;	Preparation of starting material 2-bromo-6-(bromomethyl)naphthalene (1d) To a solution of (6-bromonaphthalen-2-yl)methanol (1.19 g, 5 mmol) in anhydrous Et2O (40 mL) at 0 C, PBr3 (1.52 g, 22 mmol) was added dropwise, and the resulting solution was stirred at room temperature for 3 h. The resultant mixture was neutralized with an aq. NaHCO3, and the product was extracted with Et2O (40 mL * 2). The organic layers were dried over Na2SO4, filtered and concentrated. Then, the crude product was purified by flash silica gel chromatography (eluent: petroleum ether) to afford 1d (1.27 g, 85% yield) as a white solid.

Reference： [1]Patent: US2006/159953,2006,A1 .Location in patent: Page/Page column 4
[2]Journal of Organometallic Chemistry,2013,vol. 745-746,p. 177 - 185

Yield	Reaction Conditions	Operation in experiment
		Using a procedure analogous to Example 1, 4-benzoylureidopiperidine is reacted with the following compounds: 2-(naphth-2-yl)ethyl tosylate, 6-cyanonaphth-2-ylmethyl bromide, 6-fluoronaphth-2-ylmethyl bromide, 6-bromonaphth-2-ylmethyl bromide, 1-(naphth-2-yl)propyl chloride, di-(naphth-2-ylmethyl)sulphate, 6-chloromethylquinoxaline, 3-chloromethylcinnoline, 6-chloromethylisoquinoline,

6
[ 305798-02-1 ]
[ 122-52-1 ]
[ 1093403-10-1 ]

Yield	Reaction Conditions	Operation in experiment
	Inert atmosphere;	Synthesis Example (2-3) In a stream of argon, 16.0 g of Intermediate 8 and 14 g of triethyl phosphite were loaded into a 300-mL eggplant flask, and the temperature of the mixture was increased. Ethyl bromide produced in the foregoing was removed by distillation, and then unreacted triethyl phosphite was removed by distillation under reduced pressure. As a result, 19.2 g of a white solid were obtained. The solid was identified as Intermediate 9 by field desorption mass spectrometry (FD-MS).

Reference： [1]Patent: EP2159217,2010,A1 .Location in patent: Page/Page column 58

7
[ 2700-22-3 ]
[ 305798-02-1 ]
[ 24850-33-7 ]
[ 1477473-36-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	With tris-(dibenzylideneacetone)dipalladium(0); tetrabutylammomium bromide; In tetrahydrofuran; at 60℃; for 24h;Inert atmosphere;	General procedure: An oven-dried reaction tube (25 mL) was charged with Pd2(dba)3 (22.9 mg, 0.025 mmol), arylethylidene malononitrile (2, 0.5 mmol), and 2-(bromomethyl)naphthalene (1, 0.6 mmol). The tube was evacuated and purged with nitrogen gas for three times. Then, TBAB (248 mg, 0.75 mmol), freshly distilled THF (2 mL), and allyltributylstannane (198.6 mg, 0.6 mmol) were sequentially added. The reaction mixture was heated to 60 C for 24 h. After the reaction completed, the resultant mixture was evaporated in vacuo to give the crude product, which was then purified via basic Al2O3 chromatography (eluent: ethyl acetate/petroleum ether = 1:30 to 1:20) to afford alpha-benzyl-beta-allylation products 3.

Reference： [1]Journal of Organometallic Chemistry,2013,vol. 745-746,p. 177 - 185

8
[ 2700-22-3 ]
[ 305798-02-1 ]
[ 24850-33-7 ]
[ 1477473-67-8 ]
[ 1477473-76-9 ]

Yield	Reaction Conditions	Operation in experiment
49%; 50%	With tetrakis(triphenylphosphine) palladium(0); In toluene; at 70℃; for 24h;Inert atmosphere;	General procedure: An oven-dried reaction tube (25 mL) was charged with Pd(PPh3)4 (57.8 mg, 0.05 mmol), arylethylidene malononitrile (2, 0.5 mmol), and 2-(bromomethyl)naphthalene (1, 0.6 mmol). The tube was evacuated and purged with nitrogen gas for three times. Then, freshly distilled toluene (2 mL) and allyltributylstannane (198.6 mg, 0.6 mmol) were sequentially added. The reaction mixture was heated to 70 C for 24 h. After the reaction completed, the resultant mixture was evaporated in a vacuum to give the crude product, which was then purified via basic Al2O3 chromatography (eluent: ethyl acetate/petroleum ether = 1:30 to 1:20) to afford alpha-allyl-beta-benzylation products 4.

Reference： [1]Journal of Organometallic Chemistry,2013,vol. 745-746,p. 177 - 185

9
(1S,3R)-3-[difluoro(phenylsulfonyl)methyl]-3-phenyl-2,3-dihydrobenzo[d]isothiazole 1-oxide [ No CAS ]
[ 305798-02-1 ]
(1S,3R)-2-[(6-bromonaphthalen-2-yl)methyl]-3-[difluoro(phenylsulfonyl)methyl]-3-phenyl-2,3-dihydrobenzo[d]isothiazole 1-oxide [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 10596 - 10599

10
[ 305798-02-1 ]
3-phenylnaphtho[1,2-b]quinolizinium bromide [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 854 - 862

11
[ 305798-02-1 ]
3-(4-methylphenyl)naphtho[1,2-b]quinolizinium bromide [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 854 - 862

12
[ 305798-02-1 ]
3-(naphth-1-yl)naphtho[1,2-b]quinolizinium bromide [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 854 - 862

13
[ 305798-02-1 ]
3-(naphth-2-yl)naphtho[1,2-b]quinolizinium bromide [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 854 - 862

14
[ 305798-02-1 ]
3-(phenanthrene-9-yl)naphtho[1,2-b]quinolizinium bromide [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 854 - 862

15
[ 305798-02-1 ]
3-bromonaphtho[1,2-b]quinolizinium bromide [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 854 - 862

16
[ 5693-54-9 ]
[ 305798-02-1 ]
1-[(6-bromonaphth-2-yl)methyl]-2-(1,3-dioxolan-2-yl)pyridinium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In dimethyl sulfoxide; at 20℃; for 168h;Inert atmosphere;	A solution of <strong>[305798-02-1]2-bromo-6-(bromomethyl)naphthalene</strong> (2) (2.38 g, 7.99 mmol) and 2-(1,3-dioxolane-2-yl)pyridine (1.33 g, 8.80 mmol) in DMSO (60 mL) was stirred under an inert gas atmosphere for 7 d at room temperature. The reaction mixture was added dropwise under vigorous stirring to EtOAc (1 L). The white precipitate was filtered, washed with EtOAc (50 mL) and Et2O (50 mL) and dried in vacuo to give the pure product as white amorphous solid which was used without further purification (2.81 g, 6.23 mmol, 78%). For analytical purposes a sample was recrystallized from MeOH/EtOAc to give the product 3 as bright beige-colored microcrystalline solid; mp = 193-195 C (dec.). - 1H-NMR (400 MHz, DMSO-d6): = 4.11-4.13 (m, 4 H, 2 x CH2), 6.16 (s, 2 H, CH2), 6.56 (s, 1 H, CH), 7.55 (dd, 3J = 8.8 Hz, 4J = 1.8 Hz, 1 H, 3-H), 7.69 (dd, 3J = 8.8 Hz, 4J = 2.0 Hz, 1 H, 7-H), 7.87 (s, 1 H, 1-H), 7.90 (d, 3J = 8.8 Hz, 1 H, 8-H), 7.99 (d, 3J = 8.8 Hz, 1 H, 4-H), 8.20-8.23 (m, 1 H, 5?-H), 8.27 (d, 4J = 1.8 Hz, 1 H, 5-H), 8.36 (dd, 3J = 7.9 Hz, 4J = 1.2 Hz, 1 H, 3?-H), 8.73-8.77 (m, 1 H, 4?-H), 9.11 (dd, 3J = 6.1 Hz, 4J = 0.9 Hz, 1 H, 6?-H). - 13C-NMR (100 MHz, DMSO-d6): = 59.9 (CH2), 65.7 (2 x CH2), 97.2 (CH), 120.2 (6-C), 126.1 (3?-C), 126.6 (3-C), 127.5 (1-C), 128.1 (4-C), 128.7 (5?-C), 129.6 (5-C), 129.8 (7-C), 130.3 (8-C), 131.2 (8a-C), 132.1 (2-C), 133.9 (4a-C), 147.3 (4?-C), 147.4 (6?-C), 152.2 (2?-C). - MS (ESI+): m/z = 370 (100) [M-Br]+ - El. Anal. for Anal. for C19H17Br2NO2 (451.16), calcd (%): C 50.58, H 3.80, N 3.10, found (%): C 50.54, H 3.75, N 3.04.

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 854 - 862

17
[ 305798-02-1 ]
[ 37610-80-3 ]
C₁₆H₁₇BrO₂ [ No CAS ]