[ CAS No. 1036724-54-5 ] {[proInfo.proName]}

Name: 1036724-54-5|2-(Benzyloxy)-4-bromo-1-fluorobenzene|97%
Brand: Ambeed
SKU: A131591
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Quality Control of [ 1036724-54-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1036724-54-5 ]

SDS Specification

Alternatived Products of [ 1036724-54-5 ]

Product Details of [ 1036724-54-5 ]

CAS No. :	1036724-54-5	MDL No. :	MFCD11520671
Formula :	C₁₃H₁₀BrFO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CBYWJXRBIPEDSX-UHFFFAOYSA-N
M.W :	281.12	Pubchem ID :	73553470
Synonyms :

Calculated chemistry of [ 1036724-54-5 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.08
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	65.08
TPSA :	9.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.99
Log Po/w (XLOGP3) :	4.18
Log Po/w (WLOGP) :	4.44
Log Po/w (MLOGP) :	4.4
Log Po/w (SILICOS-IT) :	4.47
Consensus Log Po/w :	4.09

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.57
Solubility :	0.00751 mg/ml ; 0.0000267 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.08
Solubility :	0.0232 mg/ml ; 0.0000827 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.19
Solubility :	0.000182 mg/ml ; 0.000000649 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.92

Safety of [ 1036724-54-5 ]

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

Application In Synthesis of [ 1036724-54-5 ]

* 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.

Upstream synthesis route of [ 1036724-54-5 ]
Downstream synthetic route of [ 1036724-54-5 ]

[ 1036724-54-5 ] Synthesis Path-Upstream 1~2

1
[ 100-39-0 ]
[ 112204-58-7 ]
[ 1036724-54-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate In acetone for 16 h; Heating / reflux	To a solution of the product of step a) (0.802 g, 4. 20 mmol) and benzyl bromide (0.755 ml, 6.30 mmol) in acetone (10 ml) was added potassium carbonate (1.16 g, 8.40 mmol) and the mixture was heated at reflux for 16 h at 60C. The solid was filtered off washing with acetone and the filtrate evaporated. The residue was purified by flash chromatography eluting with 0-20percent ETOAC/ISOHEXANE to leave 1.04 (88percent) of the title compound as an oil that crystallized after cooling: AH (400 MHz, CDCL3) 5.08 (2 H, s), 6. 98 (2 H, m), 7.13 (1 H, dd, J7. 4,2. 2 Hz), 7.37 (5 H, m).
73%	With potassium carbonate In acetonitrile at 20℃; for 12 h; Large scale	Two reactions were carried out in parallel and combined for work-up. A mixture of 9 5-bromo-2-fluorophenol (1-1) (850 g, 4.5 mol), 10 benzyl bromide (837 g, 4.9 mol) and 11 potassium carbonate (923 g, 6.7 mol) in 12 ACN (5 L) was stirred at 20° C. for 12 h. The reactions were combined and concentrated, diluted with water (8 L), and extracted with EtOAc (3×3 L). The organic layer was separated, washed with brine (3 L), dried over sodium sulfate and concentrated. The crude product was purified through a silica gel pad (eluted with 3:1 petroleum ether:EtOAc) to give the title intermediate (1.83 kg, 73percent yield) as a white 13 solid. ¹H NMR (400 MHz, CDCl₃) δ 7.38-7.46 (m, 5H), 7.15 (dd, J=7.6, 2.0 Hz, 1H), 6.98-7.15 (m, 1H), 5.12 (s, 2H)

Reference： [1] Patent: WO2004/65388, 2004, A1, . Location in patent: Page 47
[2] Patent: US2018/311255, 2018, A1, . Location in patent: Paragraph 0204-0205

2
[ 348-61-8 ]
[ 100-51-6 ]
[ 1036724-54-5 ]
[ 133057-82-6 ]

Reference： [1] Tetrahedron Letters, 2008, vol. 49, # 31, p. 4588 - 4590

[ 1036724-54-5 ] Synthesis Path-Downstream 1~18

1
[ 100-39-0 ]
[ 112204-58-7 ]
[ 1036724-54-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate; In acetone; for 16h;Heating / reflux;	To a solution of the product of step a) (0.802 g, 4. 20 mmol) and benzyl bromide (0.755 ml, 6.30 mmol) in acetone (10 ml) was added potassium carbonate (1.16 g, 8.40 mmol) and the mixture was heated at reflux for 16 h at 60C. The solid was filtered off washing with acetone and the filtrate evaporated. The residue was purified by flash chromatography eluting with 0-20% ETOAC/ISOHEXANE to leave 1.04 (88%) of the title compound as an oil that crystallized after cooling: AH (400 MHz, CDCL3) 5.08 (2 H, s), 6. 98 (2 H, m), 7.13 (1 H, dd, J7. 4,2. 2 Hz), 7.37 (5 H, m).
73%	With potassium carbonate; In acetonitrile; at 20℃; for 12h;Large scale;	Two reactions were carried out in parallel and combined for work-up. A mixture of 9 <strong>[112204-58-7]5-bromo-2-fluorophenol</strong> (1-1) (850 g, 4.5 mol), 10 benzyl bromide (837 g, 4.9 mol) and 11 potassium carbonate (923 g, 6.7 mol) in 12 ACN (5 L) was stirred at 20 C. for 12 h. The reactions were combined and concentrated, diluted with water (8 L), and extracted with EtOAc (3×3 L). The organic layer was separated, washed with brine (3 L), dried over sodium sulfate and concentrated. The crude product was purified through a silica gel pad (eluted with 3:1 petroleum ether:EtOAc) to give the title intermediate (1.83 kg, 73% yield) as a white 13 solid. 1H NMR (400 MHz, CDCl3) delta 7.38-7.46 (m, 5H), 7.15 (dd, J=7.6, 2.0 Hz, 1H), 6.98-7.15 (m, 1H), 5.12 (s, 2H)
73%	With potassium carbonate; In acetonitrile; at 20℃; for 12h;Large scale;	Two reactions were carried out in parallel and combined for work-up. A mixture of <strong>[112204-58-7]5-bromo-2-fluorophenol</strong> (1-1) (850 g, 4.5 mol), benzyl bromide (837 g, 4.9 mol) and potassium carbonate (923 g, 6.7 mol) in ACN (5 L) was stirred at 20 C. for 12 h. The reactions were combined and concentrated, diluted with water (8 L), and extracted with EtOAc (3×3 L). The organic layer was separated, washed with brine (3 L), dried over sodium sulfate and concentrated. The crude product was purified through a silica gel pad (eluted with 3:1 petroleum ether:EtOAc) to give the title intermediate (1.83 kg, 73% yield) as a white solid. 1H NMR (400 MHz, CDCl3) delta 7.38-7.46 (m, 5H), 7.15 (dd, J=7.6, 2.0 Hz, 1H), 6.98-7.15 (m, 1H), 5.12 (s, 2H).

Reference： [1]Patent: WO2004/65388,2004,A1 .Location in patent: Page 47
[2]Patent: US2018/311255,2018,A1 .Location in patent: Paragraph 0204-0205
[3]Patent: US2020/131178,2020,A1 .Location in patent: Paragraph 0155

2
[ 348-61-8 ]
[ 100-51-6 ]
[ 1036724-54-5 ]
[ 133057-82-6 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 4588 - 4590

3
[ 1036724-54-5 ]
1-(benzyloxy)-4-bromo-5-ethyl-2-fluorobenzene [ No CAS ]