[ CAS No. 98545-64-3 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 98545-64-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 98545-64-3 ]

SDS Specification

Alternatived Products of [ 98545-64-3 ]

Product Details of [ 98545-64-3 ]

CAS No. :	98545-64-3	MDL No. :	MFCD00859376
Formula :	C₈H₈BrNO₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	KZOQVTUWEHNNMH-UHFFFAOYSA-N
M.W :	230.06	Pubchem ID :	5244418
Synonyms :

Calculated chemistry of [ 98545-64-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	49.83
TPSA :	52.32 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.41 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.83
Log Po/w (XLOGP3) :	1.82
Log Po/w (WLOGP) :	1.83
Log Po/w (MLOGP) :	2.06
Log Po/w (SILICOS-IT) :	1.65
Consensus Log Po/w :	1.84

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.65
Solubility :	0.514 mg/ml ; 0.00223 mol/l
Class :	Soluble
Log S (Ali) :	-2.54
Solubility :	0.666 mg/ml ; 0.00289 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.97
Solubility :	0.244 mg/ml ; 0.00106 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 98545-64-3 ]

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

Application In Synthesis of [ 98545-64-3 ]

* 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.

Downstream synthetic route of [ 98545-64-3 ]

[ 98545-64-3 ] Synthesis Path-Downstream 1~10

1
[ 100959-22-6 ]
[ 98545-64-3 ]

Yield	Reaction Conditions	Operation in experiment
94.2%	With tin(II) chloride dihdyrate; In ethyl acetate; for 4h;Reflux;	To a solution of compound 20 (4.5g, 17.0mmol) in EtOAc (100mL) was added SnCl2·2H2O (38.3g, 0.17mol). The mixture was heated to reflux and stirred for 4h. The mixture was poured into saturated NaHCO3 (500mL) and EtOAc (370mL). The organic layer was washed with brine (300mL), and dried over anhydrous MgSO4. The residue after rotary evaporation was purified by column chromatography over silica gel to give compound 21 as a solid (3.68g, 94.2% yield). 1H NMR (400MHz, CDCl3): delta 7.75 (d, J=8.5 Hz, 1H), 6.92 (d, J=2.2Hz, 1H), 6.57 (dd, J=8.5, 2.2Hz, 1H), 4.04 (brs, 2H) and 3.86 (s, 3H) ppm; mp: 96-98C.
		To a suspension of 2-bromo-4-nitro-benzoic acid methyl ester [100959-22-6] (350 mg, 1.35 mmol) in MeOH (60 mL) were subsequently added tin powder (1.6 g, 13.5 mmol) and 3N aqueous HCI (27.8 mL, 83 mmol). The mixture was stirred overnight at RT. The liquid phase was decanted from the excess tin and neutralized by adding a saturated aqueous NaHC03 solution. An equal amount of water by volume was added and the water phase was extracted with EtOAc (3x). The combined organics were dried (Phase Separator) and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (eluent: EtOAc/c-hexane 1 :4) to give the title compound as yellow solid. MS (LC/MS): 230 [M+H]+; tR (HPLC conditions b): 2.89 min.

Reference： [1]Organic Letters,2013,vol. 15,p. 3234 - 3237
[2]Chinese Chemical Letters,2011,vol. 22,p. 1411 - 1414
[3]European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75
[4]Organic Process Research and Development,2019,vol. 23,p. 1686 - 1694
[5]Academia Republicii Populare Romine, Baza de Cercetari Stiintifice, Timisoara, Studii si Cercetari, Stiinte Chimice,1956,vol. 4,p. 175,178
[6]Patent: WO2012/93101,2012,A1 .Location in patent: Page/Page column 236-237

Yield	Reaction Conditions	Operation in experiment
36%	With sodium tetrahydroborate; nickel(II) acetate tetrahydrate; In water; acetonitrile; at 10 - 20℃;	General procedure: Variant C: Adapting a literature known protocol (Setamdideh, et al., Orient. J. Chem., 2011, 27(3), 991-996), to a solution of the aromatic nitro compound (10 mmol) in acetonitrile (MeCN) (20 mL) is added a solution of nickel(II) acetate tetrahydrate (Ni(OAc)2 4H20) (1.0 mmol) in water (2 mL). The reaction mixture is stirred vigorously at room temperature and subsequently cooled to about 10C (water/ice bath). Solid sodium borohydride (NaBH4) (40 mmol) is added in small portions upon which a black nickelboride precipitates (NiB2) (Note: The reaction is strongly exothermic and copious amounts of hydrogen gas are generated). The reaction mixture is stirred with warming to room temperature for 1-4 hours (TLC reaction control). Upon completion, the reaction mixture is diluted with ethyl acetate (EtOAc) (30 mL) and the organic solution is filtered over a short plug of Celite. The filtrate is washed with saturated aqueous sodium hydrogencarbonate (NaHC03) (1 x) and the aqueous layer is extracted with EtOAc (lx). The combined organic extracts are washed with brine, dried over anhydrous magnesium sulfate (MgS04), filtered, and the combined filtrates are evaporated under reduced pressure using a rotary evaporator. The crude material is purified as described under Variant A.; Following the General Procedure of Description 6 (Variant C), 4-ethyl-3-iodo- aniline (40b) was prepared from l-ethyl-2-iodo-4-nitro-benzene (40a) (9.0 g, 32.0 mmol), nickel(II) acetate tetrahydrate (Ni(OAc)2 4H20) (1.08 g, 4.3 mmol), and sodium borohydride (NaBH4) (7.0 g, 185 mmol) in a mixture of acetonitrile (MeCN)/water (110 mL, 10: 1, v/v). After extractive work-up and purification by silica gel column chromatography using an ethyl acetate (EtOAc)/hexane gradient as eluent (EtOAc/hexane = 1 :5? EtOAc/hexane = 1 :4, v/v), 5.2 g (65% yield) of the target compound (40b) were obtained as a yellow solid. M.p.: 35.2-38.0C. Rf. -0.30 (EtOAc/hexane = 1 :4, v/v). 1H MR (300 MHz, CDC13): delta 7.18 (d, J = 2.7 Hz, 1H), 6.98 (d, J= 8.4 Hz, 1H), 6.62 (dd, J= 8.1, 2.7 Hz, 1H), 2.62 (q, J= 7.5 Hz, 2H), 2.54 (br. s, 2H), 1.15 (t, J= 7.2 Hz, 3H) ppm. LC/MS: Rt = 2.040 min; -100% purity by AUC at lambda = 254 nm; ESI (pos.) mlz = 248.10 (M+H+)+.
		methyl 4-amino-2-bromobenzoate m.p. 93-95 C.

3
[ 100959-22-6 ]
[ 7439-89-6 ]
[ 98545-64-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With ammonium chloride; In aqueous 2-propanol;	Example 54C methyl-2-bromo-4-aminobenzoate A solution of methyl 2-bromo-4-nitrobenzoate (970 mg, 3.73 mmol), iron powder 1.25 g (22.4 mmol) and ammonium chloride (239 mg, 4.48 mmol) in aqueous 2-propanol (20%, 15 mL) was heated to reflux for 30 minutes, cooled, filtered, and concentrated under reduced pressure. The residue was partitioned between diethyl ether (20 mL) and water (5 mL). The organic layer was washed with brine (1*5 mL), dried (MgSO4), filtered, and concentrated to provide the titled compound (813 mg, 95%).

Reference： [1]Patent: US2002/35137,2002,A1

4
[ 181132-65-0 ]
[ 98545-64-3 ]
[ 200879-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; triethylamine; In dichloromethane;	Step b) Methyl 2-Bromo-4-[(2-pyridin-2-yl-benzoyl)amino]benzoate A solution of <strong>[98545-64-3]methyl 2-bromo-4-amino benzoate</strong> (3 g, 13 mmol) and triethylamine (2.5 ml, 18 mmol) in dichloromethane (50 ml) was cooled to 0 and was treated with a slurry of 2-(pyridin-2-yl)benzoyl chloride in dichloromethane (20 ml). Stirring at room temperature was maintained for 4 hours. The reaction was quenched with 20% acetic acid, wash sequentially with saturated aqueous sodium bicarbonate, water then saturated brine solution. The solution was dried (MgSO4), filtered and concentrated in vacuo to give 5.23 g of a white foam. MS (+FAB) m/z 411/413 (M+H)+. Analysis for: C20H15BrN2O3 Calcd: C, 58.41; H, 3.68; N, 6.81. Found: C, 57.73; H, 3.66; N, 6.54.
5.23 g (97%)	With acetic acid; triethylamine; In dichloromethane;	Step b) Methyl 2-Bromo-4-[(2-pyridin-2-yl-benzoyl)amino]benzoate A slurry of 2-(pyridin-2-yl)benzoyl chloride in dichloromethane (20 ml) was added to a solution of <strong>[98545-64-3]methyl 2-bromo-4-amino benzoate</strong> (3 g, 13 mmol) and triethylamine (2.5 ml, 18 mmol) in dichloromethane (50 ml) which was cooled to 0 C. Stirring at room temperature was maintained for 4 hours. The reaction was quenched with 20% acetic acid, wash sequentially with saturated aqueous sodium bicarbonate, water then saturated brine solution. The solution was dried (MGSO4), filtered and concentrated in vacuo to give 5.23 g (97%) of a colorless foam. MS (+FAB) m/z: 411/413 (M+H)+.
5.23 g (97%)	With acetic acid; triethylamine; In dichloromethane;	Step b) Methyl 2-Bromo-4-[(2-pyridin-2-yl-benzoyl)amino]benzoate A slurry of 2-(pyridin-2-yl)benzoyl chloride in dichloromethane (20 ml) was added to a solution of <strong>[98545-64-3]methyl 2-bromo-4-amino benzoate</strong> (3 g, 13 mmol) and triethylamine (2.5 ml, 18 mmol) in dichloromethane (50 ml) which was cooled to 0 C. Stirring at room temperature was maintained for 4 hours. The reaction was quenched with 20% acetic acid, wash sequentially with saturated aqueous sodium bicarbonate, water then saturated brine solution. The solution was dried (MgSO4), filtered and concentrated in vacuo to give 5.23 g (97%) of a colorless foam. MS (+FAB) m/z: 411/413 (M+H)+. Analysis for: C20H15BrN2O3 Calcd: C, 58.41; H, 3.68; N, 6.81. Found: C, 57.73; H, 3.66; N, 6.54.

In dichloromethane; at 0 - 20℃; for 4h;

A solution of <strong>[98545-64-3]methyl 2-bromo-4-amino benzoate</strong> (3 g, 13 mmol) and triethylamine (2.5 ml, 18 mmol) in dichloromethane (50 ml) was cooled to 0 and was treated with a slurry of 2-(pyridin-2-yl)benzoyl chloride in dichloromethane (20 ml). Stirring at room temperature was maintained for 4 hours. The reaction was quenched with 20% acetic acid, wash sequentially with saturated aqueous sodium bicarbonate, water then saturated brine solution. The solution was dried (MgSO4), filtered and concentrated in vacuo to give 5.23 g of a white foam. MS (+FAB) m/z 411/413 (M+H)+. Analysis for: C20H15BrN2O3 Calcd: C, 58.41; H, 3.68; N, 6.81. Found: C, 57.73; H, 3.66; N, 6.54

Reference： [1]Patent: US5880122,1999,A
[2]Patent: US5700796,1997,A
[3]Patent: US5753648,1998,A
[4]Patent: EP1021444,2003,B1 .Location in patent: Page/Page column 29

5
[ 696-59-3 ]
[ 98545-64-3 ]
[ 1344109-43-8 ]