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21739-92-4

Basic Information
CAS No.: 21739-92-4
Name: 5-Bromo-2-chlorobenzoic acid
Molecular Structure:
Molecular Structure of 21739-92-4 (5-Bromo-2-chlorobenzoic acid)
Formula: C7H4BrClO2
Molecular Weight: 235.46
Synonyms: 5-bromo-2-chloro-benzoate;5-bromo-2-chloro-benzoic acid;2-Chloro-5-bromobenzoic acid;5-Bromo-2-Chloro Benzoic Acid;2-Chloro-5-Bromo Benzoic Acid;
EINECS: 244-558-5
Density: 1.809 g/cm3
Melting Point: 154-156 °C(lit.)
Boiling Point: 324.5 °C at 760 mmHg
Flash Point: 150.1 °C
Solubility: Soluble in water 2.63 g/L @20°C.
Appearance: white to light yellow crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information:
PSA: 37.30000
LogP: 2.80070
Synthetic route
189628-37-3

2-chloro-5-bromobenzaldehyde

21739-92-4

5-bromo-2-chlorobenzoic acid

Conditions
ConditionsYield
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

21739-92-4

5-bromo-2-chlorobenzoic acid

Conditions
ConditionsYield
In hexafluoropropan-2-ol at 100℃; for 2h; Microwave irradiation;96%
2136-89-2

2-chlorobenzotrichloride

21739-92-4

5-bromo-2-chlorobenzoic acid

Conditions
ConditionsYield
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;
89-55-4

5-bromosalicyclic acid

21739-92-4

5-bromo-2-chlorobenzoic acid

Conditions
ConditionsYield
With tetrachloromethane; molybdenum hexacarbonyl In dimethyl sulfoxide at 150℃; for 6h; Reagent/catalyst; Solvent; Autoclave;92.1%
21900-52-7

5-bromo-2-chloro-benzoyl chloride

21739-92-4

5-bromo-2-chlorobenzoic acid

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide at 0 - 20℃; for 12h;89.1%
118-91-2

ortho-chlorobenzoic acid

21739-92-4

5-bromo-2-chlorobenzoic acid

Conditions
ConditionsYield
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%
149965-40-2

5-bromo-2-chlorobenzyl alcohol

21739-92-4

5-bromo-2-chlorobenzoic acid

Conditions
ConditionsYield
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

21739-92-4

5-bromo-2-chlorobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride In water; acetonitrile at 60 - 70℃; for 3h; Time;75.1%
106-39-8

bromochlorobenzene

124-38-9

carbon dioxide

21739-92-4

5-bromo-2-chlorobenzoic acid

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -75℃; for 2h;52%
106-39-8

bromochlorobenzene

124-38-9

carbon dioxide

A

21739-93-5

2-bromo-5-chlorobenzoic acid

B

21739-92-4

5-bromo-2-chlorobenzoic acid

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -100℃;A 20%
B n/a
54932-72-8

2-chloro-5-bromotoluene

21739-92-4

5-bromo-2-chlorobenzoic acid

Conditions
ConditionsYield
With alkaline aqueous potassium permanganate solution
With nitric acid
5794-88-7

5-Bromo-2-aminobenzoic acid

21739-92-4

5-bromo-2-chlorobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride; copper(l) chloride; sodium nitrite Diazotization.weiteres Reagens: wss. Salzsaeure;
2-chloro-benzoate silver

2-chloro-benzoate silver

21739-92-4

5-bromo-2-chlorobenzoic acid

Conditions
ConditionsYield
With bromine
99-52-5

2-methyl-4-nitro-benzenamine

21739-92-4

5-bromo-2-chlorobenzoic acid

Conditions
ConditionsYield
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
21739-92-4

5-bromo-2-chlorobenzoic acid

21900-52-7

5-bromo-2-chloro-benzoyl chloride

Conditions
ConditionsYield
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%
21739-92-4

5-bromo-2-chlorobenzoic acid

74-89-5

methylamine

5-bromo-2-chloro-N-methylbenzamide

Conditions
ConditionsYield
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%
21739-92-4

5-bromo-2-chlorobenzoic acid

149965-40-2

5-bromo-2-chlorobenzyl alcohol

Conditions
ConditionsYield
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%
67-56-1

methanol

21739-92-4

5-bromo-2-chlorobenzoic acid

251085-87-7

methyl 5-bromo-2-chloro-benzoate

Conditions
ConditionsYield
With sulfuric acid for 72h; Heating;98%
With sulfuric acid for 72h; Heating / reflux;98%
With hydrogenchloride In water98%
462-06-6

fluorobenzene

21739-92-4

5-bromo-2-chlorobenzoic acid

915095-85-1

(2-chloro-5-bromophenyl)(4-fluorophenyl)methanone

Conditions
ConditionsYield
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
21739-92-4

5-bromo-2-chlorobenzoic acid

2393-23-9

4-methoxy-benzylamine

5-bromo-2-chloro-N-(4-methoxybenzyl)benzamide

Conditions
ConditionsYield
With silica gel In neat (no solvent) at 120℃; for 8h; Inert atmosphere; Sealed tube;94%
75-89-8

2,2,2-trifluoroethanol

21739-92-4

5-bromo-2-chlorobenzoic acid

35480-52-5

2,5-di-(2,2,2-trifluoroethoxy)benzoic acid

Conditions
ConditionsYield
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; water45%
64-17-5

ethanol

21739-92-4

5-bromo-2-chlorobenzoic acid

76008-73-6

5-Bromo-2-chloro-benzoic acid ethyl ester

Conditions
ConditionsYield
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;
21739-92-4

5-bromo-2-chlorobenzoic acid

100-46-9

benzylamine

N-benzyl-5-bromo-2-chlorobenzamide

Conditions
ConditionsYield
With silica gel In neat (no solvent) at 120℃; for 8h; Inert atmosphere; Sealed tube;92%
21739-92-4

5-bromo-2-chlorobenzoic acid

C8H12O

461432-22-4

(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone

Conditions
ConditionsYield
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%
79-37-8

oxalyl dichloride

21739-92-4

5-bromo-2-chlorobenzoic acid

251085-87-7

methyl 5-bromo-2-chloro-benzoate

Conditions
ConditionsYield
In methanol; dichloromethane; N,N-dimethyl-formamide91%
21739-92-4

5-bromo-2-chlorobenzoic acid

103-73-1

Phenetole

461432-22-4

(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone

Conditions
ConditionsYield
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;
21739-92-4

5-bromo-2-chlorobenzoic acid

121990-18-9

2-chloro-5-deuteriobenzoic acid

Conditions
ConditionsYield
With Raney Cu-Al alloy; sodium carbonate In water-d2 at 65℃; for 8h;88%
21739-92-4

5-bromo-2-chlorobenzoic acid

108-95-2

phenol

1360568-68-8

(5-bromo-2-chlorophenyl)(4-hydroxyphenyl)methanone

Conditions
ConditionsYield
With polyphosphoric acid at 50 - 85℃;87%
48115-38-4

norepinephrine

21739-92-4

5-bromo-2-chlorobenzoic acid

1150313-65-7

5-bromo-2-chloro-N-(1-hydroxy-1-phenylpropane-2-yl)benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;86%
21739-92-4

5-bromo-2-chlorobenzoic acid

104-94-9

4-methoxy-aniline

N-(4-methoxyphenyl)-4-bromoanthranilic acid

Conditions
ConditionsYield
With copper(I) oxide; copper; potassium carbonate In 2-ethoxy-ethanol at 130℃; for 24h;85%
21739-92-4

5-bromo-2-chlorobenzoic acid

75-65-0

tert-butyl alcohol

740806-51-3

tert-butyl (5-bromo-2-chlorophenyl)carbamate

Conditions
ConditionsYield
With diphenyl phosphoryl azide; triethylamine for 3h; Heating / reflux;85%
21739-92-4

5-bromo-2-chlorobenzoic acid

6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

842136-59-8

5-bromo-2-chloro-N-methoxy-N-methyl-benzamide

Conditions
ConditionsYield
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
21739-92-4

5-bromo-2-chlorobenzoic acid

64-04-0

phenethylamine

1002965-88-9

5-bromo-N-phenethylanthranilic acid

Conditions
ConditionsYield
With copper(I) oxide; copper; potassium carbonate In various solvent(s) at 130℃; for 24h;84%
21739-92-4

5-bromo-2-chlorobenzoic acid

107-11-9

1-amino-2-propene

N-allyl-5-bromo-2-chlorobenzamide

Conditions
ConditionsYield
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%
21739-92-4

5-bromo-2-chlorobenzoic acid

68-12-2, 33513-42-7

N,N-dimethyl-formamide

1206625-81-1

2-chloro-5-formylbenzoic acid

Conditions
ConditionsYield
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%
45732-95-4

1-(aminomethyl)cycloheptanol

21739-92-4

5-bromo-2-chlorobenzoic acid

1227807-64-8

C15H19BrClNO2

Conditions
ConditionsYield
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%
21739-92-4

5-bromo-2-chlorobenzoic acid

62-53-3

aniline

82762-60-5

5-Bromo-N-phenylanthranilic acid

Conditions
ConditionsYield
With potassium carbonate; CuPy2Cl2 at 75℃; for 0.333333h; microwave irradiation;79%
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Standards and Recommendations

5-Bromo-2-Chlorobenzoic Acid
Appearance: White to off white powder
Packing: 25Kgs fiber drum
Assay: 99.5%

Specification

The IUPAC name of this chemical is 5-bromo-2-chlorobenzoic acid. With the CAS registry number 21739-92-4, it is also named as benzoic acid, 5-bromo-2-chloro-. The product's categories are 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. It is white to light yellow crystal powder which should be sealed in the container and stored in the cool and dry place.

The other characteristics of 5-Bromo-2-chlorobenzoic acid can be summarized as: (1)ACD/LogP: 2.79; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.02; (4)ACD/LogD (pH 7.4): -0.35; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.32; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.621; (13)Molar Refractivity: 45.76 cm3; (14)Molar Volume: 130 cm3; (15)Polarizability: 18.14×10-24 cm3; (16)Surface Tension: 55.9 dyne/cm; (17)Enthalpy of Vaporization: 59.81 kJ/mol; (18)Vapour Pressure: 0.0001 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 233.90832; (21)MonoIsotopic Mass: 233.90832; (22)Topological Polar Surface Area: 37.3; (23)Heavy Atom Count: 11; (24)Complexity: 163.

Preparation of 5-Bromo-2-chlorobenzoic acid: It can be obtained by 1-bromo-4-chloro-benzene and carbon dioxide. This reaction needs reagent 2,2,6,6-tetramethylpiperidine, butyllithium and solvent tetrahydrofuran and hexane at temperature of -75 °C. The reaction time is 2 hours. The yield is 52%.

Uses of 5-Bromo-2-chlorobenzoic acid: It can be used to produce 2-chloro-5-deuteriobenzoic acid. This reaction needs reagent sodium carbonate, Raney Cu-Al alloy and solvent D2O at temperature of 65 °C. The reaction time is 8 hours. The yield is 88%. 

When you are using this chemical, please be cautious about it as the following: 
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable gloves and eye/face protection.

People can use the following data to convert to the molecule structure. 
1. SMILES:Clc1c(C(=O)O)cc(Br)cc1
2. InChI:InChI=1/C7H4BrClO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,(H,10,11)
3. InChIKey:FGERXQWKKIVFQG-UHFFFAOYAG