21739-92-4

Basic information

• Product Name: 5-Bromo-2-chlorobenzoic acid
• Synonyms: Benzoic acid, 5-bromo-2-chloro-;2-CHLORO-5-BROMOBENZOIC ACID;5-BROMO-2-CHLOROBENZOIC ACID;5-Bromo-2-chlorobenzoic acid, 98+%;5-Bromo-2-Chlorobenzoic Acid (BCBA);5-Bromo-2-chlorobenzoic acid ,99%;5-BROMO-2-CHLOROBENZOIC ACID FOR SYNTHES;5 - broMine - 2 - chlorobenzoic acid
• CAS NO: 21739-92-4
• Molecular Formula: C₇H₄BrClO₂
• Molecular Weight: 235.46
• EINECS: 244-558-5
• Product Categories: blocks;Bromides;Carboxes;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Organic acids;Miscellaneous;Acids & Esters;Bromine Compounds;Chlorine Compounds;C7;Carbonyl Compounds;Carboxylic Acids;Benzoic acid series;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 21739-92-4.mol
• Article Data: 20

Chemical Properties

• Melting Point: 154-156 °C(lit.)
• Boiling Point: 324.5 °C at 760 mmHg
• Flash Point: 150.1 °C
• Appearance: white to light yellow crystal powder
• Density: 1.7312 (rough estimate)
• Vapor Pressure: 0.0001mmHg at 25°C
• Refractive Index: 1.5590 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 2.63g/l
• PKA: 2.49±0.25(Predicted)
• Water Solubility: Soluble in water 2.63 g/L @20°C.
• BRN: 2691432
• CAS DataBase Reference: 5-Bromo-2-chlorobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-chlorobenzoic acid(21739-92-4)
• EPA Substance Registry System: 5-Bromo-2-chlorobenzoic acid(21739-92-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 21739-92-4(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

5-Bromo-2-chlorobenzoic acid was used to evaluate the homogeneity of organic powder. It can be used to produce 2-chloro-5-deuteriobenzoic acid.

InChI:InChI=1/C7H4BrClO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,(H,10,11)/p-1

Synthetic route

2-chloro-5-bromobenzaldehyde (189628-37-3) → 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;	99%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;	99%

tert-butyl 5-bromo-2-chloro-benzoate → 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
In hexafluoropropan-2-ol at 100℃; for 2h; Microwave irradiation;	96%

2-chlorobenzotrichloride (2136-89-2) → 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
Stage #1: 2-chlorobenzotrichloride With ferric(III) bromide; ferrocenyl methyl trimethyl ammonium bromide; copper(I) bromide; iron(II) bromide at 20℃; for 15h; Stage #2: With aminosulfonic acid In water at 80℃; for 8h;	92.5%
Stage #1: 2-chlorobenzotrichloride With bromine; iron for 6h; Stage #2: With sulfuric acid at 100℃; for 5h;	90%
Stage #1: 2-chlorobenzotrichloride With ferric(III) bromide; bromine In dichloromethane at 25 - 30℃; for 6h; Stage #2: With acetic acid at 110℃; for 15h; Reagent/catalyst; Temperature;

5-bromosalicyclic acid (89-55-4) → 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
With tetrachloromethane; molybdenum hexacarbonyl In dimethyl sulfoxide at 150℃; for 6h; Reagent/catalyst; Solvent; Autoclave;	92.1%

5-bromo-2-chloro-benzoyl chloride (21900-52-7) → 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide at 0 - 20℃; for 12h;	89.1%

ortho-chlorobenzoic acid (118-91-2) → 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
Stage #1: ortho-chlorobenzoic acid With aluminum (III) chloride In chloroform for 0.5h; Large scale; Stage #2: With bromine In chloroform at 25℃; for 48.5h; Solvent; Large scale;	88%
With sodium periodate; sulfuric acid; sodium bromide In water; acetic acid at 30 - 65℃;	87.8%
Stage #1: ortho-chlorobenzoic acid With sodium sulfide; sulfuric acid at 30℃; for 0.333333h; Stage #2: With N-Bromosuccinimide at 30℃; for 0.166667h; Temperature; Reagent/catalyst;	85%

5-bromo-2-chlorobenzyl alcohol (149965-40-2) → 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
With potassium phosphate; carbon dioxide; CrH6Mo6O24(3-)*3H3N*3H(1+) In dimethyl sulfoxide at 80℃; under 750.075 Torr; for 24h; Green chemistry;	80%

2-(2-chloro-5-bromophenyl)-4,5-dihydro-4,4-dimethyloxazole → 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
With hydrogenchloride In water; acetonitrile at 60 - 70℃; for 3h; Time;	75.1%

bromochlorobenzene (106-39-8) + carbon dioxide (124-38-9) → 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -75℃; for 2h;	52%

bromochlorobenzene (106-39-8) + carbon dioxide (124-38-9) → 2-bromo-5-chlorobenzoic acid (21739-93-5) + 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -100℃;	A 20% B n/a

2-chloro-5-bromotoluene (54932-72-8) → 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
With alkaline aqueous potassium permanganate solution
With nitric acid

5-Bromo-2-aminobenzoic acid (5794-88-7) → 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
With hydrogenchloride; copper(l) chloride; sodium nitrite Diazotization.weiteres Reagens: wss. Salzsaeure;

2-chloro-benzoate silver → 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
With bromine

2-methyl-4-nitro-benzenamine (99-52-5) → 5-bromo-2-chlorobenzoic acid (21739-92-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: man ersetzt die NH2-Gruppe durch Chlor, reduziert mit Zinn und Salzsaeure und ersetzt die neugebildete NH2-Gruppe durch Brom 2: HNO3 View Scheme

5-bromo-2-chlorobenzoic acid (21739-92-4) → 5-bromo-2-chloro-benzoyl chloride (21900-52-7)

Conditions	Yield
With oxalyl dichloride In DMF (N,N-dimethyl-formamide); dichloromethane at 20 - 25℃;	100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 10h;	100%
With thionyl chloride In N,N-dimethyl-formamide; toluene at 0 - 100℃; for 4h; Inert atmosphere;	100%

5-bromo-2-chlorobenzoic acid (21739-92-4) + methylamine (74-89-5) → 5-bromo-2-chloro-N-methylbenzamide

Conditions	Yield
Stage #1: 5-bromo-2-chlorobenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Cooling with ice; Stage #2: methylamine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 0.333333h;	100%

5-bromo-2-chlorobenzoic acid (21739-92-4) → 5-bromo-2-chlorobenzyl alcohol (149965-40-2)

Conditions	Yield
With dimethylsulfide; borane In tetrahydrofuran at 20℃; for 24h;	98%
With borane dimethyl sulfide complex In tetrahydrofuran at 0 - 23℃; for 14h;	98%
Stage #1: 5-bromo-2-chlorobenzoic acid With sodium tetrahydroborate; iodine In tetrahydrofuran for 18h; Reflux; Stage #2: With sodium hydrogensulfite In ethyl acetate	97%

methanol (67-56-1) + 5-bromo-2-chlorobenzoic acid (21739-92-4) → methyl 5-bromo-2-chloro-benzoate (251085-87-7)

Conditions	Yield
With sulfuric acid for 72h; Heating;	98%
With sulfuric acid for 72h; Heating / reflux;	98%
With hydrogenchloride In water	98%

fluorobenzene (462-06-6) + 5-bromo-2-chlorobenzoic acid (21739-92-4) → (2-chloro-5-bromophenyl)(4-fluorophenyl)methanone (915095-85-1)

Conditions	Yield
Stage #1: fluorobenzene; 5-bromo-2-chlorobenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide at 0 - 25℃; Stage #2: With aluminum (III) chloride at 25℃;	96.94%
Stage #1: 5-bromo-2-chlorobenzoic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 10 - 30℃; for 2h; Stage #2: fluorobenzene With aluminum (III) chloride at 75℃;	78%
Stage #1: 5-bromo-2-chlorobenzoic acid With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 39 - 42℃; Stage #2: fluorobenzene With aluminum (III) chloride In dichloromethane Reflux;	265 g

5-bromo-2-chlorobenzoic acid (21739-92-4) + 4-methoxy-benzylamine (2393-23-9) → 5-bromo-2-chloro-N-(4-methoxybenzyl)benzamide

Conditions	Yield
With silica gel In neat (no solvent) at 120℃; for 8h; Inert atmosphere; Sealed tube;	94%

2,2,2-trifluoroethanol (75-89-8) + 5-bromo-2-chlorobenzoic acid (21739-92-4) → 2,5-di-(2,2,2-trifluoroethoxy)benzoic acid (35480-52-5)

Conditions	Yield
With C10H12N2O8(4-)*Cu(2+)*2H4N(1+) In N,N-dimethyl-formamide at 20℃; for 4h; Reagent/catalyst;	93.5%
With potassium tert-butylate; copper(I) bromide In tetrahydrofuran; water	45%

ethanol (64-17-5) + 5-bromo-2-chlorobenzoic acid (21739-92-4) → 5-Bromo-2-chloro-benzoic acid ethyl ester (76008-73-6)

Conditions	Yield
With sulfuric acid In benzene Cooling with ice; Reflux;	92%
sulfuric acid
With sulfuric acid Reflux;
In N,N-dimethyl-formamide at 80℃; for 8h;

5-bromo-2-chlorobenzoic acid (21739-92-4) + benzylamine (100-46-9) → N-benzyl-5-bromo-2-chlorobenzamide

Conditions	Yield
With silica gel In neat (no solvent) at 120℃; for 8h; Inert atmosphere; Sealed tube;	92%

5-bromo-2-chlorobenzoic acid (21739-92-4) + C8H12O → (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone (461432-22-4)

Conditions	Yield
Stage #1: 5-bromo-2-chlorobenzoic acid; C8H12O With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 10 - 30℃; Stage #2: With aluminum (III) chloride In dichloromethane for 1h; Cooling with ice;	92%

oxalyl dichloride (79-37-8) + 5-bromo-2-chlorobenzoic acid (21739-92-4) → methyl 5-bromo-2-chloro-benzoate (251085-87-7)

Conditions	Yield
In methanol; dichloromethane; N,N-dimethyl-formamide	91%

5-bromo-2-chlorobenzoic acid (21739-92-4) + Phenetole (103-73-1) → (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone (461432-22-4)

Conditions	Yield
With dipotassium peroxodisulfate; phosphorus; iron(III) oxide; sodium carbonate; sodium bromide In 1,4-dioxane at 40℃; Temperature; Solvent; Molecular sieve;	90%
Stage #1: 5-bromo-2-chlorobenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 3h; Stage #2: Phenetole With aluminum (III) chloride In dichloromethane at 4 - 5℃; for 1h;	70%
Stage #1: 5-bromo-2-chlorobenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; Stage #2: Phenetole With aluminum (III) chloride In dichloromethane at 20℃; for 2h; Cooling with ice;

5-bromo-2-chlorobenzoic acid (21739-92-4) → 2-chloro-5-deuteriobenzoic acid (121990-18-9)

Conditions	Yield
With Raney Cu-Al alloy; sodium carbonate In water-d2 at 65℃; for 8h;	88%

5-bromo-2-chlorobenzoic acid (21739-92-4) + phenol (108-95-2) → (5-bromo-2-chlorophenyl)(4-hydroxyphenyl)methanone (1360568-68-8)

Conditions	Yield
With polyphosphoric acid at 50 - 85℃;	87%

norepinephrine (48115-38-4) + 5-bromo-2-chlorobenzoic acid (21739-92-4) → 5-bromo-2-chloro-N-(1-hydroxy-1-phenylpropane-2-yl)benzamide (1150313-65-7)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;	86%

5-bromo-2-chlorobenzoic acid (21739-92-4) + 4-methoxy-aniline (104-94-9) → N-(4-methoxyphenyl)-4-bromoanthranilic acid

Conditions	Yield
With copper(I) oxide; copper; potassium carbonate In 2-ethoxy-ethanol at 130℃; for 24h;	85%

5-bromo-2-chlorobenzoic acid (21739-92-4) + tert-butyl alcohol (75-65-0) → tert-butyl (5-bromo-2-chlorophenyl)carbamate (740806-51-3)

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine for 3h; Heating / reflux;	85%

5-bromo-2-chlorobenzoic acid (21739-92-4) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → 5-bromo-2-chloro-N-methoxy-N-methyl-benzamide (842136-59-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 14h;	84%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 14h;	84%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h;	82%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 64h;
With diethylamine; dicyclohexyl-carbodiimide In dichloromethane at 5 - 10℃; for 0.5h;	88 g

5-bromo-2-chlorobenzoic acid (21739-92-4) + phenethylamine (64-04-0) → 5-bromo-N-phenethylanthranilic acid (1002965-88-9)

Conditions	Yield
With copper(I) oxide; copper; potassium carbonate In various solvent(s) at 130℃; for 24h;	84%

5-bromo-2-chlorobenzoic acid (21739-92-4) + 1-amino-2-propene (107-11-9) → N-allyl-5-bromo-2-chlorobenzamide

Conditions	Yield
Stage #1: 5-bromo-2-chlorobenzoic acid With thionyl chloride for 1h; Reflux; Stage #2: 1-amino-2-propene In dichloromethane at 20℃; for 2h;	83%
With silica gel In neat (no solvent) at 120℃; for 14h; Inert atmosphere; Sealed tube;	80%

5-bromo-2-chlorobenzoic acid (21739-92-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-chloro-5-formylbenzoic acid (1206625-81-1)

Conditions	Yield
Stage #1: 5-bromo-2-chlorobenzoic acid With isopropylmagnesium chloride In tetrahydrofuran at -45 - 20℃; for 16.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0 - 20℃; for 1.83333h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20 - 37℃; for 1.58333h; Inert atmosphere;	80%
Stage #1: 5-bromo-2-chlorobenzoic acid With isopropylmagnesium chloride In tetrahydrofuran at -30 - 20℃; Bouveault aldehyde synthesis; Inert atmosphere; Large scale reaction; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; Bouveault aldehyde synthesis; Inert atmosphere; Large scale reaction; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 10 - 20℃; Bouveault aldehyde synthesis; Large scale reaction;	80%

1-(aminomethyl)cycloheptanol (45732-95-4) + 5-bromo-2-chlorobenzoic acid (21739-92-4) → C15H19BrClNO2 (1227807-64-8)

Conditions	Yield
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 1h;	80%

5-bromo-2-chlorobenzoic acid (21739-92-4) + aniline (62-53-3) → 5-Bromo-N-phenylanthranilic acid (82762-60-5)

Conditions	Yield
With potassium carbonate; CuPy2Cl2 at 75℃; for 0.333333h; microwave irradiation;	79%

Upstream product

• 54932-72-8 2-chloro-5-bromotoluene 
• 57381-44-9 5-bromo-2-chlorobenzonitrile 
• 149965-40-2 5-bromo-2-chlorobenzyl alcohol 
• 21900-52-7 5-bromo-2-chloro-benzoyl chloride 
• 89-55-4 5-bromosalicyclic acid 
• 189628-37-3 2-chloro-5-bromobenzaldehyde 
• 2136-89-2 2-chlorobenzotrichloride 
• 503555-23-5 tert-butyl 5-bromo-2-chloro-benzoate 
• 99-52-5 2-methyl-4-nitro-benzenamine 
• 106-39-8 bromochlorobenzene 
• 124-38-9 carbon dioxide 
• 118-91-2 ortho-chlorobenzoic acid 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 

Downstream Products

• 728931-56-4 5-bromo-2-(4-bromo-anilino)-benzoic acid 
• 121990-18-9 2-chloro-5-deuteriobenzoic acid 
• 118-91-2 ortho-chlorobenzoic acid 
• 461432-22-4 (5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone 
• 301672-80-0 5-bromo-2-chloro-N-(tricyclo[3.3.1.1^3,7]dec-1-ylmethyl)benzamide 
• 1002965-88-9 5-bromo-N-phenethylanthranilic acid 
• 333361-49-2 (5-bromo-2-chlorophenyl)(4-methoxyphenyl)methanone 
• 871332-75-1 C₁₁H₁₃BClNO₃ 

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