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21739-92-4

Basic Information
CAS No.: 21739-92-4
Name: 5-Bromo-2-chlorobenzoic acid
Article Data: 24
Cas Database
Molecular Structure:
Molecular Structure of 21739-92-4 (5-Bromo-2-chlorobenzoic acid)
Formula: C7H4BrClO2
Molecular Weight: 235.465
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: N/A
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
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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