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[ CAS No. 2973-59-3 ] {[proInfo.proName]}

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2D 3D

Chemical Structure| 2973-59-3

Chemical Structure| 2973-59-3

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Quality Control of [ 2973-59-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2973-59-3 ]

SDS Specification

Alternatived Products of [ 2973-59-3 ]

Product Citations

Product Details of [ 2973-59-3 ]

CAS No. :	2973-59-3	MDL No. :	MFCD00195552
Formula :	C₈H₇BrO₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	AHYSXUDLJOFNAB-UHFFFAOYSA-N
M.W :	231.04	Pubchem ID :	616068
Synonyms :

Calculated chemistry of [ 2973-59-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.04
TPSA :	46.53 ?2

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) :	-6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.8
Log Po/w (XLOGP3) :	1.69
Log Po/w (WLOGP) :	1.98
Log Po/w (MLOGP) :	1.25
Log Po/w (SILICOS-IT) :	2.18
Consensus Log Po/w :	1.78

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.58
Solubility :	0.615 mg/ml ; 0.00266 mol/l
Class :	Soluble
Log S (Ali) :	-2.28
Solubility :	1.21 mg/ml ; 0.00522 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.76
Solubility :	0.403 mg/ml ; 0.00175 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 2973-59-3 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P261-P264-P270-P272-P273-P280-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P362+P364-P391-P501	UN#:	3077
Hazard Statements:	H302-H317-H318-H411	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 2973-59-3 ]

* 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 [ 2973-59-3 ]
Downstream synthetic route of [ 2973-59-3 ]

[ 2973-59-3 ] Synthesis Path-Upstream 1~1

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

[ 2973-59-3 ] Synthesis Path-Downstream 1~3

1
[ 2973-59-3 ]
[ 770-05-8 ]
p-hydroxy-α-(2-bromo-5-hydroxy-4-methoxybenzylaminomethyl)benzyl alcohol [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1986,p. 2444 - 2470

2
[ 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

3
[ 2973-59-3 ]
[ 57497-39-9 ]
[ 1271303-77-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium sulfate; triethylamine; In tetrahydrofuran; at 80℃; for 3h;Microwave irradiation;	General procedure: In a 20 mL glass tube equipped with septa, the aldehyde, dry Na2SO4 (2.81 equiv) and triethylamine (2 equiv) were suspended in dry THF. Then, the hydroxylamine hydrochloride (2 equiv) was added. The mixture was stirred for 30 s, and then exposed to MWI (250 W) at 80 °C during the time indicated for each compound. When the reaction was over (TLC analysis), the reaction mixture was diluted with water, extracted with CH2Cl2, dried over anhydrous sodium sulphate, filtered and the solvent was evaporated. The resultant solid was purified by column chromatography to give pure compounds.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 951 - 960

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Technical Information

? Acidity of Phenols ? Alkyl Halide Occurrence ? Appel Reaction ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Chugaev Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Halogenation of Phenols ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Jones Oxidation ? Julia-Kocienski Olefination ? Kinetics of Alkyl Halides ? Knoevenagel Condensation ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Martin's Sulfurane Dehydrating Reagent ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mitsunobu Reaction ? Moffatt Oxidation ? Mukaiyama Aldol Reaction ? Nomenclature of Ethers ? Nozaki-Hiyama-Kishi Reaction ? Oxidation of Alcohols by DMSO ? Oxidation of Phenols ? Passerini Reaction ? Paternò-Büchi Reaction ? Pechmann Coumarin Synthesis ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Alcohols ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Preparation of Ethers ? Prins Reaction ? Reactions of Alcohols ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reactions of Ethers ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Reimer-Tiemann Reaction ? Ritter Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Sharpless Olefin Synthesis ? Stetter Reaction ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Swern Oxidation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

Pharmaceutical Intermediates of
[ 2973-59-3 ]

Avoralstat Intermediates

[ 24207-22-5 ]

2-Bromo-3-methoxy-6-methylpyridine

[ 6451-86-1 ]

5-Benzyloxy-2-bromo-4-methoxybenzaldehyde

[ 13682-77-4 ]

Potassium trifluoro(vinyl)borate

[ 23003-35-2 ]

2-Bromo-6-methylpyridin-3-ol

[ 1121-78-4 ]

5-Hydroxy-2-methylpyridine

Related Functional Groups of
[ 2973-59-3 ]

Aryls

[ 5392-10-9 ]

2-Bromo-4,5-dimethoxybenzaldehyde

Similarity: 1.00

[ 43192-31-0 ]

2-Bromo-4-methoxybenzaldehyde

Similarity: 0.94

[ 121936-68-3 ]

2-Bromo-5-hydroxy-4-methoxybenzoic acid

Similarity: 0.91

[ 262450-65-7 ]

3-Bromo-5-methoxybenzaldehyde

Similarity: 0.89

[ 2973-80-0 ]

2-Bromo-5-hydroxybenzaldehyde

Similarity: 0.87

Bromides

[ 5392-10-9 ]

2-Bromo-4,5-dimethoxybenzaldehyde

Similarity: 1.00

[ 43192-31-0 ]

2-Bromo-4-methoxybenzaldehyde

Similarity: 0.94

[ 121936-68-3 ]

2-Bromo-5-hydroxy-4-methoxybenzoic acid

Similarity: 0.91

[ 15930-53-7 ]

6-Bromobenzo[d][1,3]dioxole-5-carbaldehyde

Similarity: 0.91

[ 262450-65-7 ]

3-Bromo-5-methoxybenzaldehyde

Similarity: 0.89

Aldehydes

[ 5392-10-9 ]

2-Bromo-4,5-dimethoxybenzaldehyde

Similarity: 1.00

[ 43192-31-0 ]

2-Bromo-4-methoxybenzaldehyde

Similarity: 0.94

[ 15930-53-7 ]

6-Bromobenzo[d][1,3]dioxole-5-carbaldehyde

Similarity: 0.91

[ 262450-65-7 ]

3-Bromo-5-methoxybenzaldehyde

Similarity: 0.89

[ 2973-80-0 ]

2-Bromo-5-hydroxybenzaldehyde

Similarity: 0.87

Ethers

[ 5392-10-9 ]

2-Bromo-4,5-dimethoxybenzaldehyde

Similarity: 1.00

[ 43192-31-0 ]

2-Bromo-4-methoxybenzaldehyde

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[ 121936-68-3 ]

2-Bromo-5-hydroxy-4-methoxybenzoic acid

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[ 262450-65-7 ]

3-Bromo-5-methoxybenzaldehyde

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[ 20035-41-0 ]

6-Bromo-2-hydroxy-3-methoxybenzaldehyde

Similarity: 0.86

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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
P402	Store in a dry place.
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P411
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P422
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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
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P501	Dispose of contents/container to ...
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H240	Heating may cause an explosion
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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