[ CAS No. 185331-69-5 ] {[proInfo.proName]}

Name: 185331-69-5|4-Bromo-3-fluoronitrobenzene|97%
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SKU: A327671
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Quality Control of [ 185331-69-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 185331-69-5 ]

Product Details of [ 185331-69-5 ]

CAS No. :	185331-69-5	MDL No. :	MFCD05865088
Formula :	C₆H₃BrFNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AZYQMHQOHNGPRR-UHFFFAOYSA-N
M.W :	220.00	Pubchem ID :	2756994
Synonyms :

Calculated chemistry of [ 185331-69-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.92
TPSA :	45.82 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) :	-5.71 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.64
Log Po/w (XLOGP3) :	2.72
Log Po/w (WLOGP) :	2.92
Log Po/w (MLOGP) :	2.06
Log Po/w (SILICOS-IT) :	0.81
Consensus Log Po/w :	2.03

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.26
Solubility :	0.122 mg/ml ; 0.000556 mol/l
Class :	Soluble
Log S (Ali) :	-3.34
Solubility :	0.101 mg/ml ; 0.000461 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.92
Solubility :	0.266 mg/ml ; 0.00121 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.95

Safety of [ 185331-69-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 185331-69-5 ]

* 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 [ 185331-69-5 ]
Downstream synthetic route of [ 185331-69-5 ]

[ 185331-69-5 ] Synthesis Path-Upstream 1~3

1
[ 1072-85-1 ]
[ 701-45-1 ]
[ 185331-69-5 ]

Reference： [1] Journal of Organic Chemistry, 1998, vol. 63, # 23, p. 8448 - 8454
[2] Journal of Organic Chemistry, 1998, vol. 63, # 23, p. 8448 - 8454

2
[ 1072-85-1 ]
[ 701-45-1 ]
[ 185331-69-5 ]

Reference： [1] Journal of Organic Chemistry, 1998, vol. 63, # 23, p. 8448 - 8454
[2] Journal of Organic Chemistry, 1998, vol. 63, # 23, p. 8448 - 8454

3
[ 185331-69-5 ]
[ 188975-15-7 ]

Reference： [1] Patent: WO2014/26242, 2014, A1,

[ 185331-69-5 ] Synthesis Path-Downstream 1~88

1
[ 75-85-4 ]
[ 185331-69-5 ]
2-(tert-pentyloxy)-1-bromo-4-nitrobenzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 14570 - 14571

2
[ 77-74-7 ]
[ 185331-69-5 ]
2-(3-methylpentan-3-yloxy)-1-bromo-4-nitrobenzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 14570 - 14571

3
[ 507-52-8 ]
[ 185331-69-5 ]
2-(1,1,1-trifluoro-2-methylpropan-2-yloxy)-1-bromo-4-nitrobenzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 14570 - 14571

4
[ 100-86-7 ]
[ 185331-69-5 ]
1-(2-(2-bromo-5-nitrophenoxy)-2-methylpropyl)benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 14570 - 14571

5
[ 590-67-0 ]
[ 185331-69-5 ]
2-(1-methylcyclohexyloxy)-1-bromo-4-nitrobenzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 14570 - 14571

6
[ 617-94-7 ]
[ 185331-69-5 ]
1-(2-(2-bromo-5-nitrophenoxy)propan-2-yl)benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 14570 - 14571

7
[ 53853-65-9 ]
[ 185331-69-5 ]
1-(1,1,1,3,3,3-hexadeuterated-2-methylpropoxy)-2-bromo-5-nitrobenzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 14570 - 14571

8
[ 185331-69-5 ]
[ 75-65-0 ]
[ 1369876-72-1 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 14570 - 14571

9
[ 108-59-8 ]
[ 185331-69-5 ]
[ 188975-47-5 ]

Yield	Reaction Conditions	Operation in experiment
73%		Synthesis of ND-7 and ND-8Dimethyl 2-(2-fluoro-4-nitrophenyl)malonate (86); To a suspension of sodium hydride (NaH, 60%, 0.40 g, 10.0 mmol) in dry DMF (10 mL) under ice cooling was added dimethyl malonate (1.04 mL, 9.1 mmol) dropwise followed by a solution of <strong>[185331-69-5]1-bromo-2-fluoro-4-nitrobenzene</strong> (1.00 g, 4.55 mmol) in dry DMF (3 mL) under an argon atmosphere. The resulting mixture was stirred at 70 C. overnight and then allowed to cool to 21 C. The reaction mixture was quenched with saturated NH4Cl and extracted with ethyl acetate (2×50 mL). The organic layer was dried over MgSO4, concentrated and the residue was purified with silica gel column chromatography (hexane:ethyl acetate, 2:1) to give Dimethyl 2-(2-fluoro-4-nitrophenyl)malonate (86) (0.90 g, 73%) as a light yellowish solid: 1H NMR delta 8.07 (dd, 1H, J=8.6, 2.2 Hz), 7.98 (dd, 1H, J=9.3, 2.2 Hz), 7.74 (dd, 1H, J=8.6, 7.1 Hz), 5.08 (s, 1H), 3.81 (s, 6H).
67%		Preparation of dimethyl 2-(2-fluoro-4-nitrophenyl)malonate 65.[00357] To a suspension of NaH (3.8 g, 95 mmol, 60%) in dry DMF (50 mL) was added dropwise dimethyl malonate (9.9 mL, 86 mmol) at OoC with stirring. The mixture was stirred at OoC for 30min, then to the mixture was added dropwise a solution of the compound 64 in DMF (100 mL) under N2. The mixture was stirred at 70oC for overnight and then allowed to cool to room temperature. The reaction mixture was quenched with saturated NH4C1 and the resulting solid was collected by filtration to give compound 65 (7.8 g, 67%) as a white solid. 1H NMR (400 MHz, CDC13) 58.07 (dd, 1H, J= 8.6, 2.2Hz), 7.98 (dd, 1H, J= 9.3, 2.2 Hz), 7.74 (dd, 1H, J= 8.6, 7.1 Hz), 5.08 (s, 1H), 3.81 (s, 6H).

Reference： [1]Patent: US2009/111864,2009,A1 .Location in patent: Page/Page column 9; 11-12
[2]Patent: WO2012/119559,2012,A1 .Location in patent: Page/Page column 112

10
[ 185331-69-5 ]
[ 761446-44-0 ]
[ 1079178-18-9 ]

Yield	Reaction Conditions	Operation in experiment
69%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 110℃; for 12h;Inert atmosphere;	General procedure: Dioxane (40 mL), H2O (10 mL) and Na2CO3 (3.2 equiv.) were combined in a 250 mL round-bottomed flask equipped with a stir bar under argon atmosphere and then degassed using argon for about 15 min. Both <strong>[185331-69-5]1-bromo-2-fluoro-4-nitrobenzene</strong> (1.0 equiv.) and boronic esters (1.4 equiv.) were then added to the round-bottomed flask under argon and degassed for another 15 min. Finally Pd(PPh3)4 catalyst (0.033 equiv.) was added and after degassing for 5 min, the reaction placed in pre-heated oil bath to 110 C for 12 h with vigorous stirring. The reaction was cooled to room temperature, the mixture diluted with EtOAc (2 × 25 mL) and washed with water (100 mL) and brine (50 mL). The combined organic layers were dried (Na2SO4) and concentrated under vacuum in a rotary evaporator. The pure nitrobenzene intermediates were obtained by trituration using EtOAc and Hexanes.
	With cesium fluoride;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 100℃; for 8h;Inert atmosphere; Sealed tube;	Example A7 a) Preparation of intermediate 17l-Methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrazole (2.83 g, 13.63 mmol), CsF (3.11 g, 20.45 mmol) and [l,l '-bis(diphenylphosphino) ferrocene]dichloropalladium(II) (1.99 g, 13.64 mmol) were added to a solution of 4- bromo-3-fluoronitrobenzene (3.0 g, 4.81 mmol) in DMF (60 ml). The reaction mixture was flushed with N2, sealed and stirred for 8 h at 100 0C. After cooling, the solvent was evaporated. The residue was dissolved in DCM and the organic phase was washed with H2O, dried (MgSO4), filtered and the filtrate was concentrated under reduced pressure to give intermediate 17. This fraction was used as a crude in the next reaction step without further purification.

Reference： [1]Patent: WO2020/51572,2020,A1 .Location in patent: Page/Page column 42-43
[2]Patent: WO2010/145883,2010,A1 .Location in patent: Page/Page column 50-51

11
[ 135-19-3 ]
[ 185331-69-5 ]
[ 1314114-59-4 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 5403 - 5413

12
[ 185331-69-5 ]
[ 1314114-49-2 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 5403 - 5413

13
[ 185331-69-5 ]
3-fluoro-4-(naphthalen-2-yloxy)aniline [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 5403 - 5413

14
potassium (2-chloro-6-fluorophenyl)trifluoroborate [ No CAS ]
[ 185331-69-5 ]
[ 1369584-81-5 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3923 - 3933

15
potassium (2-chloro-6-fluorophenyl)trifluoroborate [ No CAS ]
[ 185331-69-5 ]
[ 1369584-84-8 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3923 - 3933

16
[ 185331-69-5 ]
2,6-difluorophenyltrifluoroborate potassium salt [ No CAS ]
[ 1369584-78-0 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3923 - 3933

17
[ 185331-69-5 ]
2,6-difluorophenyltrifluoroborate potassium salt [ No CAS ]
[ 1369584-82-6 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3923 - 3933

18
[ 185331-69-5 ]
[ 1146975-36-1 ]