79669-49-1

Basic information

• Product Name: 5-Bromo-2-methylbenzoic acid
• Synonyms: 5-BROMO-2-METHYLBENZOIC ACID,98%;5-Bromo-2-methylbenzoic acid ,97%;2,3,4,6-tetrakis-O-triMethylsilyl-D-guluconolactone;5-Bromo-o-toluic acid, 4-Bromo-2-carboxytoluene;5 - broMine - 2 - Methyl benzoic acid;5-Bromo-2-methylbenzoic acid 97%;5-Bromo-2-methylbenzoic acid≥ 99% (HPLC);5-BROMO-2-METHYLBENZOIC ACID
• CAS NO: 79669-49-1
• Molecular Formula: C₈H₇BrO₂
• Molecular Weight: 215.04
• EINECS: 1308068-626-2
• Product Categories: Carboxylic Acids;Phenyls & Phenyl-Het;Organic acids;Acids & Esters;Bromine Compounds;Carboxylic Acids;Phenyls & Phenyl-Het;C8;Carbonyl Compounds;Aromatic Nitriles
• Mol File: 79669-49-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: 167-171°C
• Boiling Point: 319.4 °C at 760 mmHg
• Flash Point: 147 °C
• Appearance: white or reddish powder
• Density: 1.599 g/cm³
• Vapor Pressure: 0.000141mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: 3.48±0.25(Predicted)
• CAS DataBase Reference: 5-Bromo-2-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-methylbenzoic acid(79669-49-1)
• EPA Substance Registry System: 5-Bromo-2-methylbenzoic acid(79669-49-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 79669-49-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-white Powder.

Uses

2-Methyl-5-bromobenzoic acid is used in organic synthesis and pharmaceutical intermediates. It is used in the synthesis of 5-bromo-2-methyl-N-(quinolin-8-yl)benzamide, (5-Bromo-2-methylphenyl)(thiophen-2-yl)-methanone and 2-(5-bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiophene.

Synthesis

In a reaction vessel equipped with a mechanical stirrer, a solution of 2-methylbenzoic acid (10.00 g, 73.45 mmol, 1.0 equivalent) in concentrated sulfuric acid (15 mL) at room temperature, bromine (17.6 g, 110.14 mmol, 1. 5 equivalents) was added dropwise over 10 minutes and stirred at 25 ° C. for 20 hours. The reaction solution was injected into ice water (60 ml), and the precipitated solid was filtered, washed with water (20 mL), and air-dried at 60 ° C. overnight to obtain a bromo compound (15.2 g, 97%, addition rate: 95.7).5-Br body / 3-Br body = 62: 38). The obtained crude bromo compound (3 g) was dissolved in ethanol (9 mL) at 70 ° C., cooled to 20 ° C., and stirred at the same temperature for 30 minutes at 10 ° C. or lower for 3 hours. The precipitated crystals were filtered and air-dried at 60 ° C. overnight to obtain 5-Bromo-2-methylbenzoic acid(1.19 g, 5-Br / 3-Br = 91: 9, total yield: 38.5%).

InChI:InChI=1/C8H7BrO2/c1-5-2-3-6(9)4-7(5)8(10)11/h2-4H,1H3,(H,10,11)

Synthetic route

ortho-methylbenzoic acid (118-90-1) → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid	88%
Stage #1: ortho-methylbenzoic acid With bromine; iron at 20℃; for 2h; Stage #2: With hydrogenchloride In methanol; water at 20℃;	19%
With bromine by/at 167 degree melting substance;

5-iodo-2-methylbenzoic acid (54811-38-0) → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
With trifluorormethanesulfonic acid; bromine; iron Concentration; Solvent; Molecular sieve;	85%

3-Bromo-6-methyl-benzonitrile (156001-51-3) → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
With sulfuric acid at 160 - 170℃;

4-Methyl-3-nitroanilin (119-32-4) → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
durch Austausch von NH2 gegen Br, Reduktion des Produkts zu 4-Brom-2-amino-toluol und Austausch von NH2 gegen CO2H; by/at 167 degree melting substance;

2,β,β-Tribrom-4-methyl-styrol → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
With pyridine; potassium permanganate

ortho-methylbenzoic acid (118-90-1) + bromine (7726-95-6) → 5-bromo-2-methylbenzoic acid (79669-49-1)

ortho-methylbenzoic acid (118-90-1) + water (7732-18-5) + bromine (7726-95-6) → 5-bromo-2-methylbenzoic acid (79669-49-1) + 2-bromophthalide

Conditions	Yield
at 140℃;

diethyl ether (60-29-7) + 2,4-dibromotoluene (31543-75-6) + magnesium → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
Behandlung mit CO2;

5-bromo-11-nitro-1.2-dimethyl-benzene → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
With potassium permanganate by/at 174-176 degree melting substance;

asymm. bromo-o-xylene → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
With nitric acid by/at 174-176 degree melting substance;

diazotized 5-amino-2-methyl-benzoic acid → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
With hydrogen bromide; copper(I) bromide

silver salt of/the/ o-toluic acid → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
With bromine by/at 167 degree melting substance;

2-benzofuran-1(3H)-one (87-41-2) → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydriodic acid; yellow phosphorus 2: water; bromine / 140 °C View Scheme

2-cyano-4-nitrotoluene (939-83-3) → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: palladium; methanol / Hydrogenation 2: aqueous potassium tetrabromocuprate (I)-solution 3: aqueous sulfuric acid / 160 - 170 °C View Scheme

3-cyano-4-methylaniline (50670-64-9) → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous potassium tetrabromocuprate (I)-solution 2: aqueous sulfuric acid / 160 - 170 °C View Scheme

ortho-methylbenzoic acid (118-90-1) → 3-bromo-2-methylbenzoic acid (76006-33-2) + 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
With bromine; iron at 0 - 20℃;
With bromine; iron at 0 - 20℃;
With bromine; iron at 20℃; for 24h; Title compound not separated from byproducts.;

ortho-methylbenzoic acid (118-90-1) + 3-bromo-4-methylbenzoic acid (7697-26-9) + iron (7439-89-6) → 5-bromo-2-methylbenzoic acid (79669-49-1)

Conditions	Yield
With bromine In dichloromethane
With bromine In dichloromethane

5-bromo-2-methylbenzoic acid (79669-49-1) → 5-bromo-2-methylbenzoyl chloride (21900-41-4)

Conditions	Yield
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;	100%
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 6h;	100%
With thionyl chloride; N,N-dimethyl-formamide for 7h; Reflux;	70%

5-bromo-2-methylbenzoic acid (79669-49-1) → (5-bromo-2-methylphenyl)methanol (258886-04-3)

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 25.5h;	100%
With borane-THF In tetrahydrofuran; diethyl ether at 50℃; Inert atmosphere;	95%
With borane-THF In tetrahydrofuran; diethyl ether at 50℃; for 3h;	95%

methanol (67-56-1) + 5-bromo-2-methylbenzoic acid (79669-49-1) → methyl 2-methyl-5-bromobenzoate (79669-50-4)

Conditions	Yield
Stage #1: methanol; 5-bromo-2-methylbenzoic acid With diazomethyl-trimethyl-silane In hexane at 20℃; for 1.16667h; Stage #2: With acetic acid In hexane for 0.75h;	99%
Stage #1: 5-bromo-2-methylbenzoic acid With thionyl chloride; N,N-dimethyl-formamide at 0℃; for 3h; Reflux; Inert atmosphere; Stage #2: methanol	98%
With sulfuric acid at 20℃; for 5h; Time; Cooling with ice; Reflux;	97%

5-bromo-2-methylbenzoic acid (79669-49-1) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 2-methyl-5-bromobenzoate (79669-50-4)

Conditions	Yield
With methanol In diethyl ether; toluene at 0 - 20℃; for 1h;	99%

5-bromo-2-methylbenzoic acid (79669-49-1) + methyl iodide (74-88-4) → methyl 2-methyl-5-bromobenzoate (79669-50-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;	99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;

2-aminopyridine (504-29-0) + 5-bromo-2-methylbenzoic acid (79669-49-1) → 5-bromo-2-methyl-N-(pyridin-2-yl)benzamide

Conditions	Yield
Stage #1: 5-bromo-2-methylbenzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 2-aminopyridine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 30℃; Inert atmosphere;	99%

4-amino-3,5-dimethyl-benzoic acid methyl ester (3095-48-5) + 5-bromo-2-methylbenzoic acid (79669-49-1) → methyl 4-[(5-bromo-2-methyl-benzoyl)amino]-3,5-dimethyl-benzoate (1529760-92-6)

Conditions	Yield
Stage #1: 4-amino-3,5-dimethyl-benzoic acid methyl ester; 5-bromo-2-methylbenzoic acid With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; ethyl acetate at 50℃; for 16h;	97%

5-bromo-2-methylbenzoic acid (79669-49-1) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → C9H10BrNO2

Conditions	Yield
Stage #1: 5-bromo-2-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 0 - 20℃;	97%

ethanol (64-17-5) + 5-bromo-2-methylbenzoic acid (79669-49-1) → ethyl 5-bromo-2-methylbenzoate (359629-91-7)

Conditions	Yield
With sulfuric acid In benzene Cooling with ice; Reflux;	96%
With sulfuric acid Reflux;	95%
With sulfuric acid Reflux;	95%
sulfuric acid at 0 - 100℃; for 15h; Inert atmosphere;	69%

3,5-dimethyl-4-aminobenzoic acid ethyl ester (3095-47-4) + 5-bromo-2-methylbenzoic acid (79669-49-1) → methyl 3-[(5-bromo-2-methyl-benzoyl)amino]-2,4-dimethyl-benzoate (1529760-86-8)

Conditions	Yield
Stage #1: 5-bromo-2-methylbenzoic acid With oxalyl dichloride In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 2h; Stage #2: 4-amino-3,5-dimethylbenzoic acid ethyl ester With pyridine; dmap In dichloromethane at 0 - 20℃; for 2h;	95.5%

5-bromo-2-methylbenzoic acid (79669-49-1) + 1-bromo-2-(triisopropylsilyl)acetylene (111409-79-1) → 3-bromo-6-methyl-2-((triisopropylsilyl)ethynyl)benzoic acid

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium hydrogencarbonate In tert-Amyl alcohol at 30℃; for 24h;	95%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium carbonate In tert-Amyl alcohol at 80℃; for 24h; Sealed tube; Schlenk technique;	88%

2-(4-fluorophenyl)thiophene (58861-48-6) + 5-bromo-2-methylbenzoic acid (79669-49-1) → (5-bromo-2-methylphenyl)[5-(p-fluorophenyl)thiophene-2-yl]methanone (1132832-75-7)

Conditions	Yield
Stage #1: 5-bromo-2-methylbenzoic acid With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 20 - 25℃; Stage #2: 2-(4-fluorophenyl)thiophene With aluminum (III) chloride In dichloromethane at 0 - 25℃; for 12.5h; Solvent; Reagent/catalyst;	93.2%
Stage #1: 5-bromo-2-methylbenzoic acid With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 0 - 35℃; Stage #2: 2-(4-fluorophenyl)thiophene With aluminum (III) chloride In dichloromethane; N,N-dimethyl-formamide at 0 - 35℃;	89%
Stage #1: 5-bromo-2-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 25 - 30℃; for 0.1h; Inert atmosphere; Stage #2: 2-(4-fluorophenyl)thiophene With aluminum (III) chloride In dichloromethane at 0 - 15℃; Inert atmosphere;	80.4%
Stage #1: 5-bromo-2-methylbenzoic acid With oxalyl dichloride In dichloromethane at 20℃; for 2h; Stage #2: 2-(4-fluorophenyl)thiophene With aluminum (III) chloride In dichloromethane at -15 - 35℃; for 4h;	80%

tributyl borane (122-56-5) + 5-bromo-2-methylbenzoic acid (79669-49-1) → 5-butyl-2-methylbenzoic acid

Conditions	Yield
In tetrahydrofuran Suzuki-Miyaura Coupling; Inert atmosphere;	92%

5-bromo-2-methylbenzoic acid (79669-49-1) + (3R,4S)-tert-butyl 3-amino-4-fluoropyrrolidine-1-carboxylate → tert-butyl (3R,4S)-3-(5-bromo-2-methylbenzamido)-4-fluoropyrrolidine-1-carboxylate

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h;	92%

5-bromo-2-methylbenzoic acid (79669-49-1) → 2-[D3]-methyl-5-bromobenzoic acid

Conditions	Yield
With [D]-sodium hydroxide In water-d2 at 20 - 160℃; for 6.5h;	90%

5-bromo-2-methylbenzoic acid (79669-49-1) + 4-Aminobenzonitrile (873-74-5) → C15H11BrN2O

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;	88%

triethyl borane (97-94-9) + 5-bromo-2-methylbenzoic acid (79669-49-1) → 5-ethyl-2-methylbenzoic acid

Conditions	Yield
In tetrahydrofuran Suzuki-Miyaura Coupling; Inert atmosphere;	87%

N-methylmaleimide (930-88-1) + 5-bromo-2-methylbenzoic acid (79669-49-1) → C12H12BrNO2

Conditions	Yield
With sodium dihydrogenphosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; water at 85℃; for 16h; Green chemistry; chemoselective reaction;	84%

5-bromo-2-methylbenzoic acid (79669-49-1) → 5-bromo-2-methyl-3-nitro-benzoic acid (107650-20-4)

Conditions	Yield
Stage #1: 5-bromo-2-methylbenzoic acid With sulfuric acid at -10℃; for 0.166667h; Stage #2: With potassium nitrate at -10℃; for 1h;	82.5%
With sulfuric acid; nitric acid In acetone at -5 - 0℃; for 2.25h; Cooling with acetone-ice;	52%

N-acetylpiperidine (13889-98-0) + 5-bromo-2-methylbenzoic acid (79669-49-1) → 1-[4-(5-bromo-2-methyl-benzoyl)-piperazin-1-yl]-ethanone (1431542-16-3)

Conditions	Yield
Stage #1: 5-bromo-2-methylbenzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.333333h; Stage #2: N-acetylpiperidine In dichloromethane at 20℃; for 1h;	82%
Stage #1: 5-bromo-2-methylbenzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.333333h; Stage #2: N-acetylpiperidine In dichloromethane at 20℃; for 1h;	82%
Stage #1: 5-bromo-2-methylbenzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.333333h; Stage #2: N-acetylpiperidine In dichloromethane at 20℃; for 1h;	82%

5-bromo-2-methylbenzoic acid (79669-49-1) + methyl 3-amino-2,4-dimethyl-benzoate (24812-89-3) → methyl 3-[(5-bromo-2-methyl-benzoyl)amino]-2,4-dimethyl-benzoate (1529760-86-8)

Conditions	Yield
Stage #1: 5-bromo-2-methylbenzoic acid; methyl 3-amino-2,4-dimethyl-benzoate With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; ethyl acetate at 50℃; for 16h;	80%

4-amino-3,5-dimethyl-benzoic acid methyl ester (3095-48-5) + 5-bromo-2-methylbenzoic acid (79669-49-1) → methyl 3-[(5-bromo-2-methyl-benzoyl)amino]-2,4-dimethyl-benzoate (1529760-86-8)

Conditions	Yield
Stage #1: 4-amino-3,5-dimethyl-benzoic acid methyl ester; 5-bromo-2-methylbenzoic acid With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.166667h; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In dichloromethane; ethyl acetate at 50℃; for 16h;	80%

2-amino-1-(4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)-3-phenylpropan-1-one + 5-bromo-2-methylbenzoic acid (79669-49-1) → 5-bromo-N-(1-(4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)-1-oxo-3-phenylpropan-2-yl)-2-methylbenzamide

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;	79%

5-bromo-2-methylbenzoic acid (79669-49-1) → 5-bromo-2-methylbenzoyl fluoride

Conditions	Yield
With (3,3-difluorocycloprop-1-ene-1,2-diyl)dibenzene In dichloromethane at 50℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;	79%
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 0 - 20 °C 2: cesium fluoride / acetonitrile / 80 °C View Scheme

3,5-dimethyl-4-aminobenzoic acid ethyl ester (3095-47-4) + 5-bromo-2-methylbenzoic acid (79669-49-1) → ethyl 4-[(5-bromo-2-methyl-benzoyl)amino]-3,5-dimethyl-benzoate (1529761-04-3)

Conditions	Yield
Stage #1: 5-bromo-2-methylbenzoic acid With oxalyl dichloride In tetrahydrofuran; dichloromethane at 0 - 20℃; for 2h; Stage #2: 4-amino-3,5-dimethylbenzoic acid ethyl ester With pyridine; dmap In dichloromethane at 0 - 20℃; for 5h;	75.2%

5-bromo-2-methylbenzoic acid (79669-49-1) + acetonitrile (75-05-8) → 2-acetyl-6-bromoisoindolin-1-one

Conditions	Yield
With iron(III)-acetylacetonate; copper(II) nitrate; Selectfluor at 80℃; for 8h; Schlenk technique; Inert atmosphere;	74%

5-bromo-2-methylbenzoic acid (79669-49-1) + 3-chlorophenylboronic acid (63503-60-6) → 3'-chloro-4-methylbiphenyl-3-carboxylic acid (1482106-89-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; acetonitrile at 80℃; for 18h; Inert atmosphere;	73.2%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; acetonitrile at 80℃; for 18h; Inert atmosphere;	73.2%

5-bromo-2-methylbenzoic acid (79669-49-1) → 5-bromo-2-(difluoromethyl)benzoic acid (1630983-04-8)

Conditions	Yield
With sodium persulfate; silver nitrate; Selectfluor In water; acetonitrile at 80℃; for 3h; Inert atmosphere; Schlenk technique; Cooling with liquid nitrogen;	73%

Upstream product

• 118-90-1 ortho-methylbenzoic acid 
• 156001-51-3 3-Bromo-6-methyl-benzonitrile 
• 119-32-4 4-Methyl-3-nitroanilin 
• 7726-95-6 bromine 
• 7732-18-5 water 
• 60-29-7 diethyl ether 
• 31543-75-6 2,4-dibromotoluene 
• 87-41-2 2-benzofuran-1(3H)-one 
• 7697-26-9 3-bromo-4-methylbenzoic acid 
• 7439-89-6 iron 
• 54811-38-0 5-iodo-2-methylbenzoic?acid 
• 50670-64-9 3-cyano-4-methylaniline 
• 939-83-3 2-cyano-4-nitrotoluene 

Downstream Products

• 106-38-7 para-bromotoluene 
• 79669-50-4 methyl 2-methyl-5-bromobenzoate 
• 258886-04-3 (5-bromo-2-methylphenyl)methanol 
• 99548-54-6 methyl 3-bromo-2-methylbenzoate 
• 19725-82-7 5-Bromo-2-carboxymethyl-benzoic acid 
• 1202551-75-4 5-bromo-2-methyl-benzoic acid tert-butyl ester 
• 1201908-18-0 C₂₇H₂₅F₄NO₄ 
• 1286178-48-0 2-(phenylthiomethyl)-5-ethylbenzoic acid 
• 1286176-82-6 2-(benzenesulphonylmethyl)-5-ethylbenzoic acid 
• 79670-17-0 methyl 2-bromomethyl-5-bromobenzoate 
• 1313582-20-5 (S)-methyl 2-(6-(4-benzamidophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate 
• 1313576-65-6 (S)-2-(6-(4-benzamidophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoic acid 
• 1313579-16-6 (S)-methyl 3-methyl-2-(6-(4-nitrophenyl)-1-oxoisoindolin-2-yl)butanoate 
• 1313579-17-7 (S)-methyl 2-(6-(4-aminophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate 

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PROBLEM TO BE SOLVED: To provide a method for producing 5-bromo-2-alkylbenzoic acid, which is useful as a synthetic intermediate of a drug substance such as an antidiabetic, in an industrially inexpensive and efficient manner. SOLUTION: The present disclosure provides a method for producing 5-bromo-2-alkylbenzoic acid by bringing 2-alkylbenzoic acid and bromine into contact with each other, in the presence of sulfuric acid. Particularly if 2-alkylbenzoic acid is 2-methylbenzoic acid, the inventive production method enables efficient production of 5-bromo-2-methylbenzoic acid to be a raw material for producing canagliflozin, one of antidiabetics. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Synthesis, computational, and spectroscopic analysis of tunable highly fluorescent BN-1,2-azaborine derivatives containing the N-BOH moiety

Nine new polycyclic aromatic BN-1,2-azaborine analogues containing the N-BOH moiety were synthesized using a convenient two-step, one-pot procedure. Characterization of the prepared compounds show the luminescence wavelength and the quantum yields of the azaborines were tunable by controlling the power and location of the donor and acceptor substituents on the chromophore. UV-visible spectroscopy and density functional theory (DFT) computations revealed that the addition of electron-donating moieties to the isoindolinone hemisphere raised the energy of the HOMO, resulting in the reduction of the HOMO-LUMO gap. The addition of an electron-accepting moiety to the isoindolinone hemisphere and an electron-donating group to the boronic acid hemisphere decreased the HOMO-LUMO gap considerably, leading to emission properties from partial intramolecular charge transfer (ICT) states. The combined effect of an acceptor on the isoindolinone side and a donor on the boronic acid side (strong acceptor-π-donor) gave the most red-shifted absorption. The polycyclic aromatic BN-1,2-azaborines emitted strong fluorescence in solution and in the solid-state with the largest red-shifted emission at 640 nm and a Stokes shift of Δλ = 218 nm, or Δν = 8070 cm-1.

Series of structural and functional models for the ES (enzyme-substrate) complex of the Co(II)-containing quercetin 2,3-dioxygenase

A series of mononuclear CoII-flavonolate complexes [Co IILR(fla)] (LRH = 2-{[bis(pyridin-2-ylmethyl) amino]methyl}-p/m-R-benzoic acid; R = p-OMe (1), p-Me (2), m-Br (4), and m-NO2 (5); fla = flavonolate) were designed and synthesized as structural and functional models for the ES (enzyme-substrate) complexes to mimic the active site of the Co(II)-containing quercetin 2,3-dioxygenase (Co-2,3-QD). The metal center Co(II) ion in each complex shows a similar distorted octahedral geometry. The model complexes display high enzyme-type dioxygenation reactivity (oxidative O-heterocyclic ring opening of the coordinated substrate flavonolate) at low temperature, presumably due to the attached carboxylate group in the ligands. The reactivity exhibits a substituent group dependent order of -OMe (1) > -Me (2) > -H (3)14b > -Br (4) > -NO2 (5), and the Hammett plot is linear (ρ = -0.78). This can be explained as the electronic nature of the substituent group in the ligands may influence the conformation and redox potential of the bound flavonolate and finally bring different reactivity. The structures, properties, and reactivity of the model complexes show some dependence on the substituent group in the supporting model ligands, and there is some relationship among them. This study is the first example of a series of structural and functional ES models of Co-2,3-QD, with focus on the effects of the electronic nature of substituted groups and the carboxylate group of the ligands to the dioxygenation reactivity, that will provide important insights into the structure-property-reactivity relationship and the catalytic role of Co-2,3-QD.