[ CAS No. 121936-68-3 ] {[proInfo.proName]}

Name: 121936-68-3|2-Bromo-5-hydroxy-4-methoxybenzoic acid|98%
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SKU: A214489
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Quality Control of [ 121936-68-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 121936-68-3 ]

SDS Specification

Alternatived Products of [ 121936-68-3 ]

Product Details of [ 121936-68-3 ]

CAS No. :	121936-68-3	MDL No. :	MFCD16659606
Formula :	C₈H₇BrO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QOHWIPQTBHQOQW-UHFFFAOYSA-N
M.W :	247.04	Pubchem ID :	44139642
Synonyms :

Calculated chemistry of [ 121936-68-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	49.62
TPSA :	66.76 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 :	No
Log Kp (skin permeation) :	-6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	1.76
Log Po/w (WLOGP) :	1.86
Log Po/w (MLOGP) :	1.48
Log Po/w (SILICOS-IT) :	1.43
Consensus Log Po/w :	1.63

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.69
Solubility :	0.504 mg/ml ; 0.00204 mol/l
Class :	Soluble
Log S (Ali) :	-2.78
Solubility :	0.41 mg/ml ; 0.00166 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.18
Solubility :	1.62 mg/ml ; 0.00658 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 121936-68-3 ]

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 [ 121936-68-3 ]

* 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.

Upstream synthesis route of [ 121936-68-3 ]
Downstream synthetic route of [ 121936-68-3 ]

[ 121936-68-3 ] Synthesis Path-Upstream 1~8

1
[ 2973-59-3 ]
[ 121936-68-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: With aminosulfonic acid In water; ethyl acetate Stage #2: With sodium chlorite In water; ethyl acetate at -10 - 20℃; for 1 h;	Example 3; 2-bromo-5-hydroxy-4-methoxy benzoic acid (B13); 1 Kg of 2-bromo-5-hydroxy-4-methoxy benzaldehyde (B2) and 1.255 Kg of sulfamic acid were added with stirring into a mixture of 4.473 Kg of EtOAc and 8 L of water. The reaction mixture was stirred until all of the solid had dissolved. The reaction mixture was cooled to between -10 and 0° C. An aqueous solution of sodium chlorite was prepared by dissolving 505 g of sodium chlorite in 3 L of water. The sodium chlorite solution was added to the pre-cooled B2 solution at a rate that maintained the reaction temperature under 5° C. After the complete addition of sodium chlorite solution, the reaction mixture was stirred for another hour at 0° C. and was then allowed to warm up to room temperature. The reaction was monitored by TLC. After the TLC analysis showed completion of the reaction, the aqueous layer was separated. The aqueous layer was extracted with EtOAc (1.789 Kg) and the combined organic layer was transferred to another flask and EtOAc was removed by vacuum distillation at 40° C. 6.92 Kg of toluene was added at between 30 to 40° C., the slurry was cooled to between -10 to 0° C. and the precipitate was collected by filtration to give about 950 g (89percent (wt?)yield) of 2-bromo-5-hydroxy-4-methoxy benzoic acid (B13). ¹H NMR (CDCl₃) δ 3.95 (3H, s, CH₃), 7.22 (1H, s, CH), 7.46 (1H, s, CH).

Reference： [1] Patent: US2008/255347, 2008, A1, . Location in patent: Page/Page column 5

2
[ 850856-55-2 ]
[ 121936-68-3 ]

Reference： [1] Journal of Organic Chemistry, 1940, vol. 5, p. 204,208

3
[ 621-59-0 ]
[ 121936-68-3 ]

Reference： [1] Journal of Organic Chemistry, 1940, vol. 5, p. 204,208

4
[ 52805-46-6 ]
[ 121936-68-3 ]

Reference： [1] Journal of Organic Chemistry, 1940, vol. 5, p. 204,208

5
[ 51673-94-0 ]
[ 121936-68-3 ]

Reference： [1] Journal of Organic Chemistry, 1940, vol. 5, p. 204,208

6
[ 859767-02-5 ]
[ 121936-68-3 ]

Reference： [1] Journal of Organic Chemistry, 1940, vol. 5, p. 204,208

7
[ 6286-46-0 ]
[ 121936-68-3 ]

Reference： [1] Yakugaku Zasshi, 1956, vol. 76, p. 1122,1125[2] Chem.Abstr., 1957, p. 3505

8
[ 645-08-9 ]
[ 121936-68-3 ]

Reference： [1] Journal of Organic Chemistry, 1940, vol. 5, p. 204,208

[ 121936-68-3 ] Synthesis Path-Downstream 1~32

1
[ 6286-46-0 ]
[ 121936-68-3 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1956,vol. 76,p. 1122,1125
Chem.Abstr.,1957,p. 3505

2
[ 645-08-9 ]
[ 121936-68-3 ]

Reference： [1]Journal of Organic Chemistry,1940,vol. 5,p. 204,208

3
[ 850856-55-2 ]
[ 121936-68-3 ]

Reference： [1]Journal of Organic Chemistry,1940,vol. 5,p. 204,208

4
[ 621-59-0 ]
[ 121936-68-3 ]

Reference： [1]Journal of Organic Chemistry,1940,vol. 5,p. 204,208

5
[ 52805-46-6 ]
[ 121936-68-3 ]

Reference： [1]Journal of Organic Chemistry,1940,vol. 5,p. 204,208

6
[ 51673-94-0 ]
[ 121936-68-3 ]

Reference： [1]Journal of Organic Chemistry,1940,vol. 5,p. 204,208

7
[ 859767-02-5 ]
[ 121936-68-3 ]

Reference： [1]Journal of Organic Chemistry,1940,vol. 5,p. 204,208

8
[ 2973-59-3 ]
[ 121936-68-3 ]

Yield	Reaction Conditions	Operation in experiment
89%		Example 3; 2-bromo-5-hydroxy-4-methoxy benzoic acid (B13); 1 Kg of 2-bromo-5-hydroxy-4-methoxy benzaldehyde (B2) and 1.255 Kg of sulfamic acid were added with stirring into a mixture of 4.473 Kg of EtOAc and 8 L of water. The reaction mixture was stirred until all of the solid had dissolved. The reaction mixture was cooled to between -10 and 0 C. An aqueous solution of sodium chlorite was prepared by dissolving 505 g of sodium chlorite in 3 L of water. The sodium chlorite solution was added to the pre-cooled B2 solution at a rate that maintained the reaction temperature under 5 C. After the complete addition of sodium chlorite solution, the reaction mixture was stirred for another hour at 0 C. and was then allowed to warm up to room temperature. The reaction was monitored by TLC. After the TLC analysis showed completion of the reaction, the aqueous layer was separated. The aqueous layer was extracted with EtOAc (1.789 Kg) and the combined organic layer was transferred to another flask and EtOAc was removed by vacuum distillation at 40 C. 6.92 Kg of toluene was added at between 30 to 40 C., the slurry was cooled to between -10 to 0 C. and the precipitate was collected by filtration to give about 950 g (89% (wt?)yield) of 2-bromo-5-hydroxy-4-methoxy benzoic acid (B13). 1H NMR (CDCl3) delta 3.95 (3H, s, CH3), 7.22 (1H, s, CH), 7.46 (1H, s, CH).

Reference： [1]Patent: US2008/255347,2008,A1 .Location in patent: Page/Page column 5

9
[ 121936-68-3 ]
2-bromo-5-hydroxy-4-methoxybenzoyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;N,N-dimethyl-formamide; In ethyl acetate; at 45 - 50℃; for 1h;Product distribution / selectivity;	Example 4; N-methyl-N-(2-[4-hydroxyphenyl]ethyl)-2-bromo-5-hydroxy-4-methoxy benzene carboxamide (C2); Method 1; A mixture of <strong>[121936-68-3]2-bromo-5-hydroxy-4-methoxy benzoic acid</strong> (B13) (1.49 kg by purity), DMF (0.071 kg) and EtOAc (6.712 kg) was stirred and heated to about 45 to 50 C. under an atmosphere of nitrogen. To this was slowly added thionyl chloride (1.29 Kg) whilst maintaining the temperature at between 45 to 50 C. This was then stirred for about 1 hour. Thus formed 2-bromo-5-hydroxy-4-methoxy benzoyl chloride solution was concentrated under vacuum, cooled to about 30 C. and was then diluted with dichloromethane (9.95 kg) under an atmosphere of nitrogen.; Method 3; To a solution of 138 g <strong>[121936-68-3]2-bromo-5-hydroxy-4-methoxy benzoic acid</strong> (B13) in EA (690 mL) was added DMF (6.9 mL) and the reaction mixture was heated to 45-50 C. Thionyl chloride (120 g) was added to the solution and stirred at this temperature until TLC analysis indicated the complete disappearance of B13. The excess thionyl chloride and EA was removed by distillation at atmosphere pressure to give a liquid residue. The residue was cooled to 30 C. and was diluted with methylene chloride (690 mL) to give a B-13-Cl solution.
	With thionyl chloride;N,N-dimethyl-formamide; In 4-methyl-2-pentanone; at 80℃;Product distribution / selectivity;	Method 2; To a solution of 138 g <strong>[121936-68-3]2-bromo-5-hydroxy-4-methoxy benzoic acid</strong> (B13) in MIBK (690 mL) was added thionyl chloride (106 g) and DMF (13 mL) and the reaction mixture was heated to 80 C. and stirred at this temperature until TLC analysis indicated the complete disappearance of B13. The resulting mixture was subjected to distillation to remove the excess thionyl chloride. After distillation of thionyl chloride, the resulting acid chloride solution was cooled to room temperature and was added to a solution of 100 g of N-methyl-N-(2-[4-hydroxyphenyl]ethyl) amine HBr (A12 HBr) and 94 g Na2CO3 in 1000 mL of MIBK and 600 mL H2O pre-cooled to 0 C. A solution of NaOH (82.5 g) in 165 mL H2O was added slowly to maintain the temperature under 5 C. The reaction mixture was stirred at this temperature until TLC analysis showed the complete disappearance of B13 acid chloride. The pH of the reaction mixture was brought to 10-11 by adding more NaOH and the resulting mixture was heated to 50 C. and stirred at this temperature for another 1 h. The reaction mixture was cooled to room temperature and the aqueous layer was separated. The organic layer was concentrated to th of its volume. 500 mL of heptane was added. The precipitate was collected by filtration to give 163 g (65% yield) of N-methyl-N-(2-[4-hydroxyphenyl]ethyl)-2-bromo-5-hydroxy-4-methoxy benzene carboxamide (C2).
	With thionyl chloride; In dichloromethane; at 76℃; for 7h;	General procedure: To the respective 2-bromobenzoic acid (2-bromo-4,5- dimethoxybenzoic acid, <strong>[121936-68-3]2-bromo-5-hydroxy-4-methoxybenzoic acid</strong> or 2-bromo-3,4,5-trimethoxybenzoic acid) (1 eq) was added thionyl chloride (1 M in CH2Cl2, 2 mL per mmol carboxylic acid) and the reaction mixture was stirred at 76 C for 7 h. After cooling to room temperature, the volatiles were removed in vacuo and the amine (44 eq of conc. aqueous NH3 solution or methyl amine, respectively) was added at 0 C. The reaction mixture was stirred at 0 C for 1 h and allowed to warm up to room temperature while stirring overnight. The mixture was acidified with conc. HCl and extracted with EtOAc (3 20 mL). The combined organic layers were washed with water (20 mL) and brine (20 mL), dried over Na2SO4 and the solvents were removed in vacuo.

Reference： [1]Patent: US2008/255347,2008,A1 .Location in patent: Page/Page column 6
[2]Patent: US2008/255347,2008,A1 .Location in patent: Page/Page column 6
[3]Tetrahedron,2020

10
[ 121936-68-3 ]
[ 108-46-3 ]
[ 1006683-96-0 ]