5-Bromo-2-chlorobenzoic acid supplier

Name
5-Bromo-2-chlorobenzoic acid
EINECS 244-558-5
CAS No. 21739-92-4
Article Data24
CAS DataBase
Density 1.809 g/cm³
Solubility Soluble in water 2.63 g/L @20°C.
Melting Point 154-156 °C(lit.)
Formula C₇H₄BrClO₂
Boiling Point 324.5 °C at 760 mmHg
Molecular Weight 235.465
Flash Point 150.1 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
PSA 37.30000
LogP 2.80070

Synthetic route

: 189628-37-3
2-chloro-5-bromobenzaldehyde

: 21739-92-4
5-bromo-2-chlorobenzoic acid

Conditions

Conditions	Yield
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;	99%
With 4H3N4H(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

Conditions	Yield
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

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;

: 89-55-4
5-bromosalicyclic acid

: 21739-92-4
5-bromo-2-chlorobenzoic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

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%

: 149965-40-2
5-bromo-2-chlorobenzyl alcohol

: 21739-92-4
5-bromo-2-chlorobenzoic acid

Conditions

Conditions	Yield
With potassium phosphate; carbon dioxide; CrH6Mo6O24(3-)3H3N3H(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

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 54932-72-8
2-chloro-5-bromotoluene

: 21739-92-4
5-bromo-2-chlorobenzoic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With bromine

: 99-52-5
2-methyl-4-nitro-benzenamine

: 21739-92-4
5-bromo-2-chlorobenzoic acid

Conditions

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

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 21900-52-7
5-bromo-2-chloro-benzoyl chloride

Conditions

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%

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 74-89-5
methylamine

: 5-bromo-2-chloro-N-methylbenzamide

Conditions

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%

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 149965-40-2
5-bromo-2-chlorobenzyl alcohol

Conditions

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%

: 67-56-1
methanol

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 251085-87-7
methyl 5-bromo-2-chloro-benzoate

Conditions

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

: 462-06-6
fluorobenzene

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 915095-85-1
(2-chloro-5-bromophenyl)(4-fluorophenyl)methanone

Conditions

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

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 2393-23-9
4-methoxy-benzylamine

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

Conditions

Conditions	Yield
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

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%

: 64-17-5
ethanol

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 76008-73-6
5-Bromo-2-chloro-benzoic acid ethyl ester

Conditions

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;

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 100-46-9
benzylamine

: N-benzyl-5-bromo-2-chlorobenzamide

Conditions

Conditions	Yield
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

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%

: 79-37-8
oxalyl dichloride

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 251085-87-7
methyl 5-bromo-2-chloro-benzoate

Conditions

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

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 103-73-1
Phenetole

: 461432-22-4
(5-bromo-2-chlorophenyl)(4-ethyloxyphenyl)methanone

Conditions

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;

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 121990-18-9
2-chloro-5-deuteriobenzoic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 64-04-0
phenethylamine

: 1002965-88-9
5-bromo-N-phenethylanthranilic acid

Conditions

Conditions	Yield
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

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%

: 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

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%

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%

: 45732-95-4
1-(aminomethyl)cycloheptanol

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 1227807-64-8
C15H19BrClNO2

Conditions

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%

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 62-53-3
aniline

: 82762-60-5
5-Bromo-N-phenylanthranilic acid

Conditions

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

5-Bromo-2-chlorobenzoic acid Standards and Recommendations

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

5-Bromo-2-chlorobenzoic acid 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^-24cm³; (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

Product Name

5-Bromo-2-chlorobenzoic acid

Synthetic route

5-Bromo-2-chlorobenzoic acid Standards and Recommendations

5-Bromo-2-chlorobenzoic acid Specification

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