[ CAS No. 116435-77-9 ]

Name: 116435-77-9|2-Amino-3-bromophenol|97%
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Quality Control of [ 116435-77-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 116435-77-9 ]

CAS No. :	116435-77-9	MDL No. :	MFCD08445676
Formula :	C₆H₆BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JBNSVEGZVHJLMS-UHFFFAOYSA-N
M.W :	188.02	Pubchem ID :	21702252
Synonyms :

Calculated chemistry of [ 116435-77-9 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	40.57
TPSA :	46.25 Å²

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 :	Yes
Log Kp (skin permeation) :	-6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.38
Log Po/w (XLOGP3) :	1.58
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	1.58
Log Po/w (SILICOS-IT) :	1.34
Consensus Log Po/w :	1.53

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.49
Solubility :	0.602 mg/ml ; 0.0032 mol/l
Class :	Soluble
Log S (Ali) :	-2.16
Solubility :	1.29 mg/ml ; 0.00689 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.32
Solubility :	0.906 mg/ml ; 0.00482 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.26

Safety of [ 116435-77-9 ]

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 [ 116435-77-9 ]

* 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 [ 116435-77-9 ]
Downstream synthetic route of [ 116435-77-9 ]

[ 116435-77-9 ] Synthesis Path-Upstream 1~5

1
[ 5473-01-8 ]
[ 116435-77-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With boron tribromide In methanol; dichloromethane	Step B: 2-Amino-3-bromophenol. To an ice cooled solution of 6-bromo-2-anisidine (1.01 g, 5 mmol) in methylene chloride (30 mL) was slowly added a 1.0 M solution of boron tribromide in methylene chloride (10 mL, 10 mmol) via syringe. The reaction was slowly warmed to room temperature and stirred overnight. Methanol (10 mL) was added and the solvents removed by rotoevaporation to give the title compound (0.87 g, 92percent yield).

Reference： [1] Patent: US6291511, 2001, B1,

2
[ 1431458-17-1 ]
[ 116435-77-9 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 10, p. 2334 - 2337

3
[ 76361-99-4 ]
[ 116435-77-9 ]

Reference： [1] Journal of the Chemical Society, 1928, p. 2703

4
[ 116435-77-9 ]
[ 863870-87-5 ]

Reference： [1] Journal of the Chemical Society, 1934, p. 137

5
[ 116435-77-9 ]
[ 855836-52-1 ]

Reference： [1] Journal of the Chemical Society, 1934, p. 137

[ 116435-77-9 ] Synthesis Path-Downstream 1~43

1
[ 116435-77-9 ]
[ 863870-87-5 ]

Reference： [1]Journal of the Chemical Society,1934,p. 137

2
[ 116435-77-9 ]
[ 855836-52-1 ]

Reference： [1]Journal of the Chemical Society,1934,p. 137

3
[ 76361-99-4 ]
[ 116435-77-9 ]

Reference： [1]Journal of the Chemical Society,1928,p. 2703

4
[ 75-44-5 ]
[ 116435-77-9 ]
[ 14022-96-9 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1966,vol. 33,p. 144 - 148

6
[ 116435-77-9 ]
[ 872277-20-8 ]

Reference： [1]Journal of the Chemical Society,1934,p. 137

7
[ 116435-77-9 ]
[ 13603-97-9 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1966,vol. 33,p. 144 - 148

8
polyphosphoric ester [ No CAS ]
[ 116435-77-9 ]
4-bromo-2-trifluoromethyl-benzoxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With trifluoroacetic acid; In dichloromethane;	Step A: 4-Bromo-2-trifluoromethyl-benzoxazole. A solution of <strong>[116435-77-9]2-amino-3-bromophenol</strong> (480 mg, 2.6 mmol), polyphosphoric ester (PPE, 3.4 g) and trifluoroacetic acid (0.88 mL, 11.5 mmol) was heated to 100 C. under a nitrogen atmosphere overnight. A reflux condenser was added as was fresh PPE and the reaction heated to 120 C. for 8 hr. The reaction was cooled and diluted with methylene chloride. The solvent was removed by rotoevaporation. The residue was dissolved in fresh methylene chloride and successively washed with 2N sodium hydroxide solution and saturated salt solution. After drying over anhydrous magnesium sulfate and filtering, the solvent was removed by rotoevaporation. The residue was purified by flash column chromatography in silica gel eluted with 15% acetone in hexanes to yield the title compound (110 mg, 16% yield).

Reference： [1]Patent: US6291511,2001,B1

9
[ 5473-01-8 ]
[ 116435-77-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With boron tribromide; In methanol; dichloromethane;	Step B: 2-Amino-3-bromophenol. To an ice cooled solution of 6-bromo-2-anisidine (1.01 g, 5 mmol) in methylene chloride (30 mL) was slowly added a 1.0 M solution of boron tribromide in methylene chloride (10 mL, 10 mmol) via syringe. The reaction was slowly warmed to room temperature and stirred overnight. Methanol (10 mL) was added and the solvents removed by rotoevaporation to give the title compound (0.87 g, 92percent yield).

Reference： [1]Patent: US6291511,2001,B1

10
[ 116435-77-9 ]
[ 446-52-6 ]
C₁₃H₉BrFNO [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 1461 - 1467

11
[ 1260544-00-0 ]
[ 116435-77-9 ]
C₁₆H₁₇BrN₄O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 4788 - 4805

12
[ 116435-77-9 ]
[ 1374772-47-0 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 4788 - 4805

13
[ 116435-77-9 ]
[ 1374772-48-1 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 4788 - 4805

14
[ 116435-77-9 ]
[ 1374772-50-5 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 4788 - 4805

15
[ 116435-77-9 ]
[ 1374772-52-7 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 4788 - 4805

16
[ 116435-77-9 ]
[ 1374772-53-8 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 4788 - 4805

17
[ 1431458-17-1 ]
[ 116435-77-9 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2334 - 2337

18
[ 116435-77-9 ]
4-bromo-3-(4-methoxybenzyl)-3H-benzoxazol-2-one [ No CAS ]

Reference： [1]Patent: WO2014/153055,2014,A2

19
[ 116435-77-9 ]
3-(4-methoxybenzyl)-4-(2-nitrophenyl)-3H-benzooxazol-2-one [ No CAS ]

Reference： [1]Patent: WO2014/153055,2014,A2

20
[ 116435-77-9 ]
1-(4-methoxybenzyl)-1H,6H-3-oxa-1,6-diazacyclopenta[c]fluoren-2-one [ No CAS ]

Reference： [1]Patent: WO2014/153055,2014,A2

21
[ 116435-77-9 ]
1-(4-methoxybenzyl)-6-(3-fluoropropyl)-1H,6H-3-oxa-1,6-diazacyclopenta[c]fluoren-2-one [ No CAS ]

Reference： [1]Patent: WO2014/153055,2014,A2

22
[ 116435-77-9 ]
6-(3-fluoropropyl)-1H,6H-3-oxa-1,6-diazacyclopenta[c]fluoren-2-one [ No CAS ]

Reference： [1]Patent: WO2014/153055,2014,A2

23
[ 116435-77-9 ]
[ 530-62-1 ]
[ 14022-96-9 ]

Yield	Reaction Conditions	Operation in experiment
Ca. 100%	With triethylamine; In tetrahydrofuran; at 60℃; for 2.5h;	[0118] To a solution of <strong>[116435-77-9]2-amino-3-bromophenol</strong> (700 mg, 3.72 mmol) in tetrahydrofuran (60 mL) was added 1 , l'-carbonyldiimidazole (1.21 g, 7.44 mmol) and triethylamine (1.04 mL, 7.44 mmol) and the mixture stirred at 60 C for 2.5 h. The reaction mixture was evaporated and diluted with dichloromethane (60 mL). The organic layer was washed with 1 M hydrochloric acid (2 x 30 mL) and water (30 mL). The organic layer was dried over sodium sulfate and evaporated to give the title compound (800 mg, 3.74 mmol, ca. 100%) as a light brown powder. LCMS: 100%, Rt 1.191, ESMS m/z 214 (M+H)+.
96.64%	With triethylamine; In tetrahydrofuran; at 60℃; for 18.0h;	TEA (1.5 mL, 10.64 mmol) was added to the mixture of <strong>[116435-77-9]2-amino-3-bromophenol</strong> (l g, 5.32 mmol) and CDI (1.72 g, 10.64 mmol) in THF (20 mL). The mixturewas stirred at 60 oc for l8h. The reaction mixture was evaporated and diluted withdichloromethane (60 mL). Tiw organic layer was washed with 1M hydrochloric acid (2 x 30 mL) and water (30 mL). The organic layer was dried over sodium sulfate, filtered andconcentrated under vacuo. Compound 35A (1.1 g, 96.64% yield) was obtained as a red solid, which was used for next step directly. 1H NMR ( 400 MHz, DMSO-d6) 8 12.19 (br s, 1 H),7.37-7.29 (m, 2H), 7.08-7.01 (m, 1H).
96.64%	With triethylamine; In tetrahydrofuran; at 60℃; for 18.0h;	TEA (1.5 mL, 10.64 mmol) was added to the mixture of <strong>[116435-77-9]2-amino-3-bromophenol</strong> (1 g, 5.32 mmol) and CDI (1.72 g, 10.64 mmol) in THF (20 mL). The mixture was stirred at 60 C for l8h. The reaction mixture was evaporated and diluted with dichloromethane (60 mL). The organic layer was washed with 1M hydrochloric acid (2 x 30 mL) and water (30 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under vacuo. Compound 35A (1.1 g, 96.64% yield) was obtained as a red solid, which was used for next step directly. 1H NMR (400 MHz, DMSO -de) d 12.19 (br s, 1H), 7.37 - 7.29 (m, 2H), 7.08 - 7.01 (m, 1H).

Reference： [1]Patent: WO2014/153055,2014,A2 .Location in patent: Paragraph 0117-0118
[2]Patent: WO2019/190885,2019,A1 .Location in patent: Paragraph 0365
[3]Patent: WO2020/6294,2020,A1 .Location in patent: Paragraph 0309
[4]Journal of Medicinal Chemistry,2015,vol. 58,p. 9258 - 9272

24
[ 116435-77-9 ]
2-oxo-4-phenyl-N-(4-phenylbutyl)-1,3-benzoxazole-3-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9258 - 9272

25
[ 116435-77-9 ]
[ 1396795-79-1 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9258 - 9272

26
[ 116435-77-9 ]
[ 122-51-0 ]
4-bromobenzo[d]-oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51.7%	With pyridine; yttrium(III) trifluoromethanesulfonate; In dimethyl sulfoxide; at 60℃; for 18.0h;	Yttrium tris (trifluoromethanesulfonate) (249 mg, 0.5 mmol) and Triethylorthoformate (15 mL, 93.1 mmol) were combined. To this mixture was added a solution of <strong>[116435-77-9]2-amino-3-bromophenol</strong> (1.8 g, 9.31 mmol) in DMSO (20 mL) and Pyridine (1.5 mL, 18.6 mmol). The reaction mixture was stirred in a heat block at 60 C for l8h. The mixture was added H20 (200 mL) and extracted with EA (50 mL). The organic phase was washed with brine (20 mL) and dried over Na2S04, filtered and concentrated under vacuum. The product was purified by FCC (0 - 50% EA/PE) to afford compound 68A (1 g, yield 51.7%) as a red solid. ' H NMR (400 MHz, DMSO-c/r,) d 8.96 (s, 1H), 7.90 (d, / = 8.2 Hz, 1H), 7.73 (d, / = 7.6 Hz, 1H), 7.53 - 7.44 (m, 1H). MS (ESI) m/z (M+H)+ 198.0.
0.19 g	With pyridine; yttrium(III) trifluoromethanesulfonate; In dimethyl sulfoxide; at 70℃; for 4.0h;	Step 1: Yttrium tris(trifluoromethanesulfonate) (35.64 mg; 0.07 mmol; 0.05 eq.) and(diethoxymethoxy)ethane (2.2 mL; 13.3 mmol; 10 eq.) were combined. To this mixture wasadded a solution of <strong>[116435-77-9]2-amino-3-bromophenol</strong> (0.25 g; 1.33 mmol; 1 eq.) in pyridine (215 jiL;2.66 mmol; 2 eq.) and DMSO (1 mL). The reaction mixture was stirred in a heat block at 70C for 4 h. After cooling the reaction mixture was taken up in ethyl acetate and water. Thephases were separated, the aqueous phase was extracted with ethyl acetate, the combinedorganic phases were washed with water and brine, and then dried over sodium sulfate. Afterevaporation of solvent, the residue was purified by silica gel chromatography (ethyl acetate/hexanes gradient) to give 4-bromobenzo[dj-oxazole (0.19 g) as an off-white crystalline solid.
	With pyridine; ytterbium(III) triflate; In dimethyl sulfoxide; at 60℃; for 18.0h;	Yttrium tris (trit1uoromethanesulfonate) (249 mg, 0.5 mrno1) andTriethylorthoformate (15 mL, 93.1 mmol) were combined. To this mixture was added asolution of2-amino-3-bromopheno1 (1.8 g, 9.31 mmol) in DMSO (20 mL) and Pyridine (L5mL, 18.6 mmol). The reaction mixture was stirred in a heat block at 60 oc for 18h. Themixture was added H20 (200 mL) and extracted with EA (50 mL). T11e organic phase waswashed with brine (20 mL) and dried over Na2S04, filtered and concentrated under vacuum.The product was purified by FCC (0 - 50% EAJPE) to afford compound 68A (1 g, yield51.7%) as a red solid. 1H NMR (400 MHz, DMSO-d6) 8 8.96 (s, lH), 7.90 (d, J '" 8.2 Hz,lH), 7.73 (d, J = 7.6 Hz, lH), 7.53- 7.44 (m, lH). MS (ESI) m/z (M+Ht 198.0.

Reference： [1]Patent: WO2020/6294,2020,A1 .Location in patent: Paragraph 0306
[2]Patent: WO2016/201052,2016,A1 .Location in patent: Page/Page column 221
[3]Patent: WO2019/190885,2019,A1 .Location in patent: Paragraph 0362

27
[ 116435-77-9 ]
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole [ No CAS ]

Reference： [1]Patent: WO2016/201052,2016,A1

28
[ 506-68-3 ]
[ 116435-77-9 ]
4-bromobenzo[d]oxazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane; at 20℃; for 4.0h;	A mixture of <strong>[116435-77-9]2-amino-3-bromophenol</strong> (5 g, 26.6 mmol) and cyanic bromide (1.673 ml, 31.9 mmol) in Dichloromethane (25 ml) and MeOH (50 ml) was stirred at ambient temperature for 4 hr. The resulting mixture was quenched with aqueous sodium hydrogen carbonate (500 mL), diluted with water (20 mL) and extracted with dichloromethane (3 x 20 mL). The combined organic layers were washed with water (3 x 10 mL) and brine (3 x 10 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the title compound as asolid. LCMS (ESI) calc?d forC7H5BrN2O: [M + 1] 213, found :2 13; ?H NMR (DMSO-d6, 400 MHZ): 7.70 (s, 2H), 7.35 (s, J= 7.6 Hz, 1H), 7.30 (s, J= 8.4 Hz, 1H), 6.93-6.89 (m, 1H).

Reference： [1]Patent: WO2016/206101,2016,A1 .Location in patent: Page/Page column 64

29
[ 116435-77-9 ]
ethyl 4-(4-(N-(2-aminoethyl)sulfamoyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-3-(N-(4-methoxybenzyl)sulfamoyl)phenyl)benzo[d]oxazole-2-carboxylate [ No CAS ]