[ CAS No. 91983-31-2 ] {[proInfo.proName]}

Name: 91983-31-2|Methyl 5-bromo-2-hydroxy-3-nitrobenzoate|95%
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SKU: A100789
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Quality Control of [ 91983-31-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 91983-31-2 ]

SDS Specification

Alternatived Products of [ 91983-31-2 ]

Product Details of [ 91983-31-2 ]

CAS No. :	91983-31-2	MDL No. :	MFCD00458681
Formula :	C₈H₆BrNO₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YGVJGAVKLPOPMS-UHFFFAOYSA-N
M.W :	276.04	Pubchem ID :	970238
Synonyms :

Calculated chemistry of [ 91983-31-2 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	3
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.27
TPSA :	92.35 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.72
Log Po/w (XLOGP3) :	2.9
Log Po/w (WLOGP) :	1.85
Log Po/w (MLOGP) :	1.03
Log Po/w (SILICOS-IT) :	-0.19
Consensus Log Po/w :	1.46

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.48
Solubility :	0.0922 mg/ml ; 0.000334 mol/l
Class :	Soluble
Log S (Ali) :	-4.5
Solubility :	0.00873 mg/ml ; 0.0000316 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.13
Solubility :	2.05 mg/ml ; 0.00741 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.25

Safety of [ 91983-31-2 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501	UN#:	3077
Hazard Statements:	H302-H315-H317-H318-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 91983-31-2 ]

* 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 [ 91983-31-2 ]
Downstream synthetic route of [ 91983-31-2 ]

[ 91983-31-2 ] Synthesis Path-Upstream 1~6

1
[ 91983-31-2 ]
[ 35748-34-6 ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium acetate In water; ethyl acetate at 25℃; for 16 h;	Example 114 Cmethyl 3-amino-2-hydroxybenzoate; A suspension of methyl 5-bromo-2-hydroxy-3-nitrobenzoate (38.4 g, 0.14 mol), sodium acetate (19.63 g, 0.24 mol) and 10percent Pd/C (3.84 g) in ethyl acetate (500 mL) and water (30 mL) was stirred at 25° C. under 1 atm of hydrogen for 16 hr. The mixture was filtered and the filtrate was washed with water (500 mL.x.2), brine (300 mL), dried over anhydrous sodium sulfate and concentrated to give crude product. The crude product was washed with methanol at 0° C. to give methyl 3-amino-2-hydroxybenzoate (13.67 g, yield 59percent) as a light yellow solid. ¹H-NMR (400 MHz, CDCl₃-d) δ 3.88-3.94 (s, br, 2H), 3.91 (s, 3H), 6.70-6.74 (t, J=7.8 Hz, 1H), 6.88-6.90 (m, 1H), 7.24-7.26 (m, 1H), 10.91 (s, 1H); LC-MS (ESI) m/z 168 [M+1]^-.

Reference： [1] Patent: US2009/197863, 2009, A1, . Location in patent: Page/Page column 56

2
[ 4068-76-2 ]
[ 91983-31-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	at 0 - 20℃; for 3.5 h;	Methyl 5-bromo-2-hydroxybenzoate (231 g, 1 mol) was dissolved in concentrated sulfuric acid (500 mL).The ice bath is cold to 0°C.A mixture of concentrated nitric acid (108 g, 1.1 mol) and concentrated sulfuric acid (120 mL), which had been cooled to 0°C, was slowly added.The dropping rate was controlled so that the temperature of the reaction system was not higher than 5°C.After the addition was complete, the ice bath was removed and the system allowed to naturally warm to room temperature and react at room temperature for 3.5 hours. After completion of the reaction monitored by TLC, the mixture was poured into crushed ice (2 L) and stirred until the crushed ice melted completely and the system precipitated a large amount of pale yellow solid. The solid was filtered, neutralized with stirring in ice water, and dried.Methyl yellow 5-bromo-2-hydroxy-3-nitrobenzoate (243 g) was obtained, yield 88percent.
85%	With sulfuric acid; nitric acid In water at 0 - 5℃;	Example 114 Bmethyl 5-bromo-2-hydroxy-3-nitrobenzoate; To a mixture of methyl 5-bromo-2-hydroxybenzoate (150 g, 0.65 mol) in concentrated H₂SO₄(320 mL) below 0° C. was added dropwise a mixture of concentrated HNO₃(69.2 g, 0.71 mol) and concentrated H₂SO₄(97 mL) with stirring below 5° C. After the addition, the mixture was stirred at this temperature for 3 hr. The reaction mixture was poured into crash ice and the precipitate was collected, washed with cold water, hot ethanol and dried to give methyl 5-bromo-2-hydroxy-3-nitrobenzoate (153 g, yield 85percent). ¹H-NMR (400 MHz,CDCl₃-d) δ 4.04 (s, 3H), 8.25 (d, J=2.4 Hz, 1H), 8.28 (d, J=2.4 Hz, 1H), 11.92 (s, 1H); LC-MS (ESI) m/z 278 [M+1]⁺.

Reference： [1] Patent: CN107573336, 2018, A, . Location in patent: Paragraph 0096; 0097; 0098
[2] Patent: US2009/197863, 2009, A1, . Location in patent: Page/Page column 56
[3] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 3, p. 624 - 630

3
[ 119-36-8 ]
[ 91983-31-2 ]

Reference： [1] Patent: CN107573336, 2018, A,

4
[ 69-72-7 ]
[ 91983-31-2 ]

Reference： [1] Patent: CN107573336, 2018, A,

5
[ 67-56-1 ]
[ 91983-31-2 ]
[ 141761-82-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	for 3 h; Reflux	After mixing methyl 5-bromo-2-hydroxy-3-nitrobenzoate (138.02 g, 0.5 mol) with methanol (1000 mL),One-time addition of activated iron powder (112g, 2mol),After heating to a slightly refluxed state, saturated ammonium chloride solution (80 g, 1.5 mol) was slowly added dropwise and refluxed for 3 hours.After the completion of the reaction by TLC, the system was cooled to room temperature, mixed with diatomaceous earth (200 g), and suction filtered to obtain a black filtrate. After the solids were thoroughly washed with hot methanol to the product, the black solids were discarded. All filtratesCombine, evaporate the solvent under reduced pressure and purify by flash chromatography on an 80-100 mesh silica gel column.The objective compound 5-bromo-2-hydroxy-3-aminobenzoic acid methyl ester 96.0 g was obtained in a yield of 78percent.

Reference： [1] Patent: CN107573336, 2018, A, . Location in patent: Paragraph 0099; 0100; 0101; 0102

6
[ 91983-31-2 ]
[ 141761-82-2 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 3, p. 624 - 630

[ 91983-31-2 ] Synthesis Path-Downstream 1~33

1
[ 91983-31-2 ]
[ 141761-82-2 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 624 - 630

2
[ 4068-76-2 ]
[ 91983-31-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sulfuric acid; nitric acid; at 0 - 20℃; for 3.5h;	Methyl 5-bromo-2-hydroxybenzoate (231 g, 1 mol) was dissolved in concentrated sulfuric acid (500 mL).The ice bath is cold to 0C.A mixture of concentrated nitric acid (108 g, 1.1 mol) and concentrated sulfuric acid (120 mL), which had been cooled to 0C, was slowly added.The dropping rate was controlled so that the temperature of the reaction system was not higher than 5C.After the addition was complete, the ice bath was removed and the system allowed to naturally warm to room temperature and react at room temperature for 3.5 hours. After completion of the reaction monitored by TLC, the mixture was poured into crushed ice (2 L) and stirred until the crushed ice melted completely and the system precipitated a large amount of pale yellow solid. The solid was filtered, neutralized with stirring in ice water, and dried.Methyl yellow 5-bromo-2-hydroxy-3-nitrobenzoate (243 g) was obtained, yield 88%.
85%	With sulfuric acid; nitric acid; In water; at 0 - 5℃;	Example 114 Bmethyl 5-bromo-2-hydroxy-3-nitrobenzoate; To a mixture of methyl 5-bromo-2-hydroxybenzoate (150 g, 0.65 mol) in concentrated H2SO4 (320 mL) below 0 C. was added dropwise a mixture of concentrated HNO3 (69.2 g, 0.71 mol) and concentrated H2SO4 (97 mL) with stirring below 5 C. After the addition, the mixture was stirred at this temperature for 3 hr. The reaction mixture was poured into crash ice and the precipitate was collected, washed with cold water, hot ethanol and dried to give methyl 5-bromo-2-hydroxy-3-nitrobenzoate (153 g, yield 85%). 1H-NMR (400 MHz,CDCl3-d) delta 4.04 (s, 3H), 8.25 (d, J=2.4 Hz, 1H), 8.28 (d, J=2.4 Hz, 1H), 11.92 (s, 1H); LC-MS (ESI) m/z 278 [M+1]+.

Reference： [1]Patent: CN107573336,2018,A .Location in patent: Paragraph 0096; 0097; 0098
[2]Patent: US2009/197863,2009,A1 .Location in patent: Page/Page column 56
[3]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 624 - 630
[4]Patent: WO2019/201283,2019,A1 .Location in patent: Page/Page column 390; 391

4
[ 91983-31-2 ]
[ 141761-85-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 624 - 630

5
[ 91983-31-2 ]
5-Bromo-3-(2-chloro-acetylamino)-2-hydroxy-benzoic acid methyl ester [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 624 - 630

6
[ 91983-31-2 ]
[ 141761-96-8 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 624 - 630

7
[ 91983-31-2 ]
6-Bromo-4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carbonyl chloride [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 624 - 630

8
[ 91983-31-2 ]
[ 141761-88-8 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 624 - 630

9
[ 91983-31-2 ]
[ 141762-16-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 624 - 630

10
[ 91983-31-2 ]
[ 35748-34-6 ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium acetate; In water; ethyl acetate; at 25℃; under 760.051 Torr; for 16.0h;	Example 114 Cmethyl 3-amino-2-hydroxybenzoate; A suspension of <strong>[91983-31-2]methyl 5-bromo-2-hydroxy-3-nitrobenzoate</strong> (38.4 g, 0.14 mol), sodium acetate (19.63 g, 0.24 mol) and 10% Pd/C (3.84 g) in ethyl acetate (500 mL) and water (30 mL) was stirred at 25 C. under 1 atm of hydrogen for 16 hr. The mixture was filtered and the filtrate was washed with water (500 mL×2), brine (300 mL), dried over anhydrous sodium sulfate and concentrated to give crude product. The crude product was washed with methanol at 0 C. to give methyl 3-amino-2-hydroxybenzoate (13.67 g, yield 59%) as a light yellow solid. 1H-NMR (400 MHz, CDCl3-d) delta 3.88-3.94 (s, br, 2H), 3.91 (s, 3H), 6.70-6.74 (t, J=7.8 Hz, 1H), 6.88-6.90 (m, 1H), 7.24-7.26 (m, 1H), 10.91 (s, 1H); LC-MS (ESI) m/z 168 [M+1]-.

Reference： [1]Patent: US2009/197863,2009,A1 .Location in patent: Page/Page column 56

11
[ 119-36-8 ]
[ 91983-31-2 ]

Reference： [1]Patent: CN107573336,2018,A

12
[ 69-72-7 ]
[ 91983-31-2 ]

Reference： [1]Patent: CN107573336,2018,A

13
[ 67-56-1 ]
[ 91983-31-2 ]
[ 141761-82-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	With iron; ammonium chloride; for 3.0h;Reflux;	After mixing <strong>[91983-31-2]methyl 5-bromo-2-hydroxy-3-nitrobenzoate</strong> (138.02 g, 0.5 mol) with methanol (1000 mL),One-time addition of activated iron powder (112g, 2mol),After heating to a slightly refluxed state, saturated ammonium chloride solution (80 g, 1.5 mol) was slowly added dropwise and refluxed for 3 hours.After the completion of the reaction by TLC, the system was cooled to room temperature, mixed with diatomaceous earth (200 g), and suction filtered to obtain a black filtrate. After the solids were thoroughly washed with hot methanol to the product, the black solids were discarded. All filtratesCombine, evaporate the solvent under reduced pressure and purify by flash chromatography on an 80-100 mesh silica gel column.The objective compound 5-bromo-2-hydroxy-3-aminobenzoic acid methyl ester 96.0 g was obtained in a yield of 78%.

Reference： [1]Patent: CN107573336,2018,A .Location in patent: Paragraph 0099; 0100; 0101; 0102

14
[ 91983-31-2 ]
methyl 5-bromo-2-hydroxy-3-cyclohexylaminobenzoate [ No CAS ]

Reference： [1]Patent: CN107573336,2018,A

15
[ 91983-31-2 ]
methyl 6-bromo-4-cyclohexyl-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylate [ No CAS ]

Reference： [1]Patent: CN107573336,2018,A

16
[ 91983-31-2 ]
6-bromo-4-cyclohexyl-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid [ No CAS ]

Reference： [1]Patent: CN107573336,2018,A

17
[ 91983-31-2 ]
8-(N-(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methylamino)formyl-6-bromo-4-cyclohexyl-3,4-dihydro-2H-benzo[1,4]oxazine [ No CAS ]

Reference： [1]Patent: CN107573336,2018,A

18
[ 91983-31-2 ]
4-cyclohexyl-6-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid (4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-ylmethyl)amide [ No CAS ]

Reference： [1]Patent: CN107573336,2018,A

19
[ 91983-31-2 ]
methyl 3-amino-5-bromo-2-(3-(dimethylamino)propoxy)benzoate [ No CAS ]

Reference： [1]Patent: WO2019/201283,2019,A1

20
[ 91983-31-2 ]
methyl 5-bromo-2-(3-(dimethylamino)propoxy)-3-(methylsulfonamido)benzoate [ No CAS ]

Reference： [1]Patent: WO2019/201283,2019,A1

21
[ 91983-31-2 ]
2-(3-(dimethylamino)propoxy)-5-(3'-methyl-2'-oxo-2',3'-dihydrospiro[cyclobutane-1,1'-pyrrolo[2,3-c]quinolin]-8'-yl)-3-(methylsulfonamido)benzoic acid [ No CAS ]

Reference： [1]Patent: WO2019/201283,2019,A1

22
[ 91983-31-2 ]
2-(3-(dimethylamino)propoxy)-5-(3'-methyl-2'-oxo-2',3'-dihydrospiro[cyclobutane-1,1'-pyrrolo[2,3-c]quinolin]-8'-yl)-3-(methylsulfonamido)benzamide [ No CAS ]

Reference： [1]Patent: WO2019/201283,2019,A1

23
[ 91983-31-2 ]
methyl 2-(3-(dimethylamino)propoxy)-5-(3'-methyl-2'-oxo-2',3'-dihydrospiro[cyclobutane-1,1'-pyrrolo[2,3-c]quinolin]-8'-yl)-3-(methylsulfonamido)benzoate [ No CAS ]

Reference： [1]Patent: WO2019/201283,2019,A1

24
[ 91983-31-2 ]
N-(3-cyano-2-(3-(dimethylamino)propoxy)-5-(3'-methyl-2'-oxo-2',3'-dihydrospiro[cyclobutane-1,1'-pyrrolo[2,3-c]quinolin]-8'-yl)phenyl)methanesulfonamide [ No CAS ]

Reference： [1]Patent: WO2019/201283,2019,A1

25
[ 3179-63-3 ]
[ 91983-31-2 ]
methyl 5-bromo-2-(3-(dimethylamino)propoxy)-3-nitrobenzoate [ No CAS ]

Reference： [1]Patent: WO2019/201283,2019,A1 .Location in patent: Page/Page column 390; 391

26
[ 91983-31-2 ]
[ 100-39-0 ]
methyl 2-(benzyloxy)-5-bromo-3-nitrobenzoate [ No CAS ]