[ CAS No. 49660-57-3 ] {[proInfo.proName]}

Name: 49660-57-3|6-Bromochroman-4-one|97%
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Quality Control of [ 49660-57-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 49660-57-3 ]

Product Details of [ 49660-57-3 ]

CAS No. :	49660-57-3	MDL No. :	MFCD00546803
Formula :	C₉H₇BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PFLPVOXSUCCZDH-UHFFFAOYSA-N
M.W :	227.05	Pubchem ID :	4197451
Synonyms :

Calculated chemistry of [ 49660-57-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.71
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
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) :	-6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.11
Log Po/w (XLOGP3) :	2.07
Log Po/w (WLOGP) :	2.41
Log Po/w (MLOGP) :	1.76
Log Po/w (SILICOS-IT) :	3.08
Consensus Log Po/w :	2.29

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.92
Solubility :	0.272 mg/ml ; 0.0012 mol/l
Class :	Soluble
Log S (Ali) :	-2.25
Solubility :	1.27 mg/ml ; 0.0056 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.72
Solubility :	0.0437 mg/ml ; 0.000192 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.05

Safety of [ 49660-57-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 49660-57-3 ]

* 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 [ 49660-57-3 ]
Downstream synthetic route of [ 49660-57-3 ]

[ 49660-57-3 ] Synthesis Path-Upstream 1~9

1
[ 49660-57-3 ]
[ 80096-64-6 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 7, p. 1968 - 1972[2] Angew. Chem., 2018, vol. 130, p. 1986 - 1990,5

2
[ 93670-18-9 ]
[ 49660-57-3 ]

Yield	Reaction Conditions	Operation in experiment
64%	With sulfuric acid In water at 20℃; for 1 h;	Keep at room temperature, compound IV (150 g, 0.61 mol) is added to the 1.0 rises thickly sulfuric acid and stirred 1 hour. The reaction mixture is poured into ice in 500 g, the generation of a white solid. Filtering collecting white solid and air drying. The crude product is ethanol by recrystallization to obtain a white solid product 89 g (64percent).

Reference： [1] E-Journal of Chemistry, 2012, vol. 9, # 3, p. 1251 - 1256
[2] Patent: CN106699716, 2017, A, . Location in patent: Paragraph 0022; 0035
[3] Australian Journal of Chemistry, 2010, vol. 63, # 11, p. 1582 - 1593
[4] Journal of the American Chemical Society, 1951, vol. 73, p. 4205,4207
[5] Tetrahedron, 2017, vol. 73, # 27-28, p. 3913 - 3922

3
[ 491-37-2 ]
[ 49660-57-3 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: at 20℃; for 0.166667 h; Stage #2: at 0 - 80℃; for 0.333333 h;	To mechanically stirred neat aluminum trichloride (18.0 g, 135 mmol, 2.50 equiv) was added 4-chromanone (8.00 g, 54.0 mmol) portionwise at room temperature. The resulting brown oil was stirred for 10 minutes and bromine (3.34 mL, 65.8 mmol, 1.20 equiv) was added portionwise. The mixture was stirred for 10 minutes, heated to 80 C for 10 minutes, cooled to 0 C and quenched with careful addition of ice. The mixture was then diluted with ether and water, the organic layer was washed with 1M hydrochloric acid (3x), brine, dried over sodium sulfate, filtered and concentrated. The resulting residue was purified on a 40M Biotage column (0 to 10percent ethyl acetate in hexanes over 30 minutes) to give 7.61 g of 6-BROMO-CHROMAN-4-ONE (Yield: 62percent). The isolated product contains 21percent DIBROMIDE. HL NMR (400 MHz, CDC13) : 8 2.80 (t, 2H), 4.53 (t, 2H), 6.85 (d, 1H), 7.53 (dd, 1H), 7.98 (d, 1H).

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 16, p. 4405 - 4409
[2] Patent: WO2004/69244, 2004, A1, . Location in patent: Page/Page column 98

4
[ 106-41-2 ]
[ 32019-08-2 ]
[ 292638-85-8 ]
[ 49660-57-3 ]

Reference： [1] Patent: US4548948, 1985, A,

5
[ 106-41-2 ]
[ 7664-93-9 ]
[ 49660-57-3 ]

Reference： [1] Patent: US4548948, 1985, A,

6
[ 106-41-2 ]
[ 49660-57-3 ]

Reference： [1] Australian Journal of Chemistry, 2010, vol. 63, # 11, p. 1582 - 1593
[2] Tetrahedron Letters, 2011, vol. 52, # 38, p. 4824 - 4826
[3] Russian Journal of General Chemistry, 2016, vol. 86, # 12, p. 2900 - 2905[4] Zh. Obshch. Khim.,
[5] Tetrahedron, 2017, vol. 73, # 27-28, p. 3913 - 3922

7
[ 108-95-2 ]
[ 49660-57-3 ]

Reference： [1] Patent: CN106699716, 2017, A,

8
[ 3055-86-5 ]
[ 49660-57-3 ]

Reference： [1] Patent: CN106699716, 2017, A,

9
[ 49660-57-3 ]
[ 1373215-15-6 ]

Reference： [1] Patent: US2012/95020, 2012, A1,
[2] Patent: US2012/95020, 2012, A1,
[3] Patent: US2012/95020, 2012, A1,
[4] Patent: US2012/95020, 2012, A1,

[ 49660-57-3 ] Synthesis Path-Downstream 1~88

1
[ 50-00-0 ]
[ 49660-57-3 ]
[ 506-59-2 ]
6-bromo-3-dimethylaminomethyl-chroman-4-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 4205,4207

2
[ 49660-57-3 ]
[ 151-50-8 ]
[ 66892-61-3 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 230 - 243

3
[ 49660-57-3 ]
[ 93670-10-1 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 894 - 898

4
toluene-4-sulfonic acid 2-(4-bromo-2-formyl-phenoxy)-ethyl ester [ No CAS ]
[ 49660-57-3 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 4637 - 4640

5
[ 491-37-2 ]
[ 49660-57-3 ]

Yield	Reaction Conditions	Operation in experiment
62%		To mechanically stirred neat aluminum trichloride (18.0 g, 135 mmol, 2.50 equiv) was added 4-chromanone (8.00 g, 54.0 mmol) portionwise at room temperature. The resulting brown oil was stirred for 10 minutes and bromine (3.34 mL, 65.8 mmol, 1.20 equiv) was added portionwise. The mixture was stirred for 10 minutes, heated to 80 C for 10 minutes, cooled to 0 C and quenched with careful addition of ice. The mixture was then diluted with ether and water, the organic layer was washed with 1M hydrochloric acid (3x), brine, dried over sodium sulfate, filtered and concentrated. The resulting residue was purified on a 40M Biotage column (0 to 10% ethyl acetate in hexanes over 30 minutes) to give 7.61 g of 6-BROMO-CHROMAN-4-ONE (Yield: 62%). The isolated product contains 21% DIBROMIDE. HL NMR (400 MHz, CDC13) : 8 2.80 (t, 2H), 4.53 (t, 2H), 6.85 (d, 1H), 7.53 (dd, 1H), 7.98 (d, 1H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4405 - 4409
[2]Patent: WO2004/69244,2004,A1 .Location in patent: Page/Page column 98

6
[ 49660-57-3 ]
[ 79-19-6 ]
C₁₀H₁₀BrN₃OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4405 - 4409

7
[ 49660-57-3 ]
2-(6-bromo-3,4-dihydro-2H-chromen-4-yl)malononitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 3584 - 3591

8
[ 49660-57-3 ]
2-(6-bromo-3,4-dihydro-2H-chromen-4-yl)malononitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 3584 - 3591

9
[ 49660-57-3 ]
6-bromo-4-chloro-chroman [ No CAS ]