3D Mol Similar

5-Bromo-2-chlorobenzoic acid

: Iupac Name：5-bromo-2-chlorobenzoic acid; CAS No.: 21739-92-4; Molecular Weight：235.461; Modify Date.: 2022-11-23 22:11; Introduction:
white to light yellow crystal powder
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1. Names and Identifiers

: 1.1 Name; 5-Bromo-2-chlorobenzoic acid; 1.2 Synonyms; 2-CHLORO-5-BROMOBENZOIC ACID 5-Brom-2-chlor-benzoesaeure 5-bromo-2-chloro benzoic acid 5-Bromo-2-Chlorobenzoic Acid (BCBA) 5-BROMO-2-CHLOROBENZOIC ACID FOR SYNTHES Benzoic acid, 5-bromo-2-chloro- Benzoic acid,5-bromo-2-chloro EINECS 244-558-5 MFCD00002415 QVR BG EE; View all

1.3 CAS No.: 21739-92-4

1.4 CID: 33127

1.5 EINECS(EC#): 244-558-5

1.6 Molecular Formula: C7H4BrClO2 (isomer)

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

1.8 InChIkey: FGERXQWKKIVFQG-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=C(C=C1Br)C(=O)O)Cl

1.10 Isomers Smiles: C1=CC(=C(C=C1Br)C(=O)O)Cl

2. Properties

2.1 Density: 1.809

2.1 Melting point: 157-160℃

2.1 Boiling point: 324.5 °C at 760 mmHg

2.1 Refractive index: 1.5590 (estimate)

2.1 Flash Point: 150.1 °C

2.1 Precise Quality: 233.90800

2.1 PSA: 37.30000

2.1 logP: 2.80070

2.1 Solubility: 2.63g/l

2.2 Appearance: White to beige powder.

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: white to light yellow crystal powder 5-Bromo-2-chlorobenzoic acid Preparation Products And Raw materials Preparation Products

2.5 Color/Form: Off white colored powder

2.6 pKa: 2.49±0.25(Predicted)

2.7 Water Solubility: soluble in water 2.63 g/L @20°C.

2.8 Stability: Stable at room temperature in closed containers under normal storage and handling conditions.

2.9 StorageTemp: Sealed in dry,Room Temperature

3. Use and Manufacturing

3.1 Methods of Manufacturing: First, sodium periodate solution was configured: 5.5 g (25.56 mmol) of sodium periodate was dissolved in 38 ml of water and 23 ml of acetic acid.Next, add 10 g (63.9 mmol) of 2-chlorobenzoic acid, 6.6 g (63.9 mmol) of sodium bromide and sodium periodate solution to the reaction flask and heat to 30°C.At this temperature, 5.6 ml of concentrated sulfuric acid was slowly added dropwise. After completion of the dropwise addition of concentrated sulfuric acid, the temperature was raised to 50-65°C and reacted at this temperature for 2-3 hours.Thin layer chromatography (TLC) detection reaction is completed, cooled, poured into ice water, solid precipitated, filtered, The filter cake was washed with water several times to obtain the product 2-chloro-5-bromobenzoic acid 13.2 g, yield 87.8percent.This example is the preparation of 2-chloro-5-bromo-benzoic acid, and the specific method is as follows:2.14 g of molybdenum hexacarbonyl (0.01 mol) was added to a 1 L autoclave.217.0 g of 2-hydroxy-5-bromobenzoic acid (1.0 mol), 185.0 g of carbon tetrachloride (1.2 mol) and 250 mL of dimethyl sulfoxide, Heat to 150 ° C, The reaction was stirred for 6 h.After the end of the controlled reaction in HPLC, Evaporate the solvent under reduced pressure.Then add 250 mL of acetonitrile, Warm up to 70 ° C and stir to dissolve.Then add neutral alumina for hot filtration.The filtrate was cooled to room temperature.A pale yellow solid precipitated.Then, 564 mL of an ethanol/water mixed solvent (volume ratio 1:3) was added.After heating and dissolving, Slowly cool to 60 ° C first, After a small amount of crystals are precipitated, Cooled to 50 ° C for 1 h, Finally, it was slowly cooled to 28 ° C and stirred for 3 h.filter, Collecting white solids, Washed twice in cold water and dried.217.0 g of white solid 2-chloro-5-bromo-benzoic acid were obtained.The yield was 92.1percent and the purity was 99.9percent (HPLC).into a 250ml reaction flask added the 46g O-chlorobenzotrichloride (0.2mol, 1eq) and 0.2g Fe powder. Stirring at room temperature, and added the drops of 35g Br2, after that maintain the reaction temperature at 35-40 ° C for 6 h. Ventilation with nitrogen will blow out excess Br2, and absorbed with alkali. Cooled at 10 ° C, and added the drops of 60 g of concentrated sulfuric acid (exothermic, dripping speed control to prevent the flow), after that heated at 100 ° C for 5 h; temperature get down at 60 ° C below, then slowly added the drops of 150mL water(intense heat, gas overflow, strictly control the drop speed to prevent the flow), and maintain 60-80 ° C stirring for 1h, than after gradually cooling to 15 ° C, the mixture has been filtered and washed with 100 mL of water, after that obtained the white crude, the purity of the crude product is 91percent and yield is 99percent. The crude product has been recrystallized with 60percent aqueous acetic acid, then obtained white solid 42.0g (yield 90percent, HPLC purity is 98.8percent).60.00 g (0.26 mol) of 5_bromo-2-chlorobenzoic acid (1) was added to 200 mL of dry dichloromethane. 1.5 mL (5.2 mol) of DMF was added dropwise, and 32 mL (0.39 mmol) of oxalyl chloride was slowly dropped into the reaction solution four times under ice-cold bath conditions, and the temperature of the reaction solution was required to be between 0 and 5 ° C. The solution was slowly warmed to room temperature for 12 h. The reaction was monitored by thin layer chromatography TLC until the reaction of the starting material was completed, and solvent and oxalyl chloride were evaporated under reduced pressure. The oxalyl chloride was distilled off three times with dichloromethane, and cooled to give a white solid (2) 53.5 g. Yield 89.1percent; View all

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xi

4.1 Signal Word: Warning

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Hazard Class: IRRITANT

4.1 Hazard Declaration: H315-H319-H335

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P261-P305 + P351 + P338

4.1 WGK Germany: 3

4.1 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

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

1H NMR : 400 MHz in DMSO-d6

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

21739-92-4Total: 6 Synthesis Route

99-52-5 82 Suppliers

21739-92-4 238 Suppliers

Literatures:
Journal of the Chemical Society, , vol. 85, p. 1269
Yield: null

118-91-2 255 Suppliers

21739-92-4 238 Suppliers

Literatures:
Journal of the Indian Chemical Society, , vol. 57, # 6 p. 640 - 642
Yield: null

5794-88-7 203 Suppliers

21739-92-4 238 Suppliers

Literatures:
Journal of the Chemical Society, , p. 232,236
Yield: null

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8. Precursor and Product

precursor:

124-38-9

5794-88-7

99-52-5

54932-72-8

106-39-8

118-91-2

product :

842136-59-8

21900-52-7

189628-37-3

921630-23-1

76008-73-6

871332-75-1

149965-40-2

149965-41-3

625470-33-9

28077-43-2

355142-36-8

1183702-65-9

461432-26-8

669734-35-4

82762-60-5

864070-18-8

461432-23-5

461432-22-4

View all

9. Other Information

9.0 Usage: 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.

9.1 BRN: 2691432

9.2 Chemical Properties: white to light yellow crystal powder

9.3 Storage Conditions: First, sodium periodate solution was configured: 5.5 g (25.56 mmol) of sodium periodate was dissolved in 38 ml of water and 23 ml of acetic acid.Next, add 10 g (63.9 mmol) of 2-chlorobenzoic acid, 6.6 g (63.9 mmol) of sodium bromide and sodium periodate solution to the reaction flask and heat to 30°C.At this temperature, 5.6 ml of concentrated sulfuric acid was slowly added dropwise. After completion of the dropwise addition of concentrated sulfuric acid, the temperature was raised to 50-65°C and reacted at this temperature for 2-3 hours.Thin layer chromatography (TLC) detection reaction is completed, cooled, poured into ice water, solid precipitated, filtered, The filter cake was washed with water several times to obtain the product 2-chloro-5-bromobenzoic acid 13.2 g, yield 87.8percent.This example is the preparation of 2-chloro-5-bromo-benzoic acid, and the specific method is as follows:2.14 g of molybdenum hexacarbonyl (0.01 mol) was added to a 1 L autoclave.217.0 g of 2-hydroxy-5-bromobenzoic acid (1.0 mol), 185.0 g of carbon tetrachloride (1.2 mol) and 250 mL of dimethyl sulfoxide, Heat to 150 ° C, The reaction was stirred for 6 h.After the end of the controlled reaction in HPLC, Evaporate the solvent under reduced pressure.Then add 250 mL of acetonitrile, Warm up to 70 ° C and stir to dissolve.Then add neutral alumina for hot filtration.The filtrate was cooled to room temperature.A pale yellow solid precipitated.Then, 564 mL of an ethanol/water mixed solvent (volume ratio 1:3) was added.After heating and dissolving, Slowly cool to 60 ° C first, After a small amount of crystals are precipitated, Cooled to 50 ° C for 1 h, Finally, it was slowly cooled to 28 ° C and stirred for 3 h.filter, Collecting white solids, Washed twice in cold water and dried.217.0 g of white solid 2-chloro-5-bromo-benzoic acid were obtained.The yield was 92.1percent and the purity was 99.9percent (HPLC).into a 250ml reaction flask added the 46g O-chlorobenzotrichloride (0.2mol, 1eq) and 0.2g Fe powder. Stirring at room temperature, and added the drops of 35g Br2, after that maintain the reaction temperature at 35-40 ° C for 6 h. Ventilation with nitrogen will blow out excess Br2, and absorbed with alkali. Cooled at 10 ° C, and added the drops of 60 g of concentrated sulfuric acid (exothermic, dripping speed control to prevent the flow), after that heated at 100 ° C for 5 h; temperature get down at 60 ° C below, then slowly added the drops of 150mL water(intense heat, gas overflow, strictly control the drop speed to prevent the flow), and maintain 60-80 ° C stirring for 1h, than after gradually cooling to 15 ° C, the mixture has been filtered and washed with 100 mL of water, after that obtained the white crude, the purity of the crude product is 91percent and yield is 99percent. The crude product has been recrystallized with 60percent aqueous acetic acid, then obtained white solid 42.0g (yield 90percent, HPLC purity is 98.8percent).60.00 g (0.26 mol) of 5_bromo-2-chlorobenzoic acid (1) was added to 200 mL of dry dichloromethane. 1.5 mL (5.2 mol) of DMF was added dropwise, and 32 mL (0.39 mmol) of oxalyl chloride was slowly dropped into the reaction solution four times under ice-cold bath conditions, and the temperature of the reaction solution was required to be between 0 and 5 ° C. The solution was slowly warmed to room temperature for 12 h. The reaction was monitored by thin layer chromatography TLC until the reaction of the starting material was completed, and solvent and oxalyl chloride were evaporated under reduced pressure. The oxalyl chloride was distilled off three times with dichloromethane, and cooled to give a white solid (2) 53.5 g. Yield 89.1percent; View all

9.4 Manufacturing Info: Benzoic acid, 5-bromo-2-chloro-: ACTIVE|PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

10. Computational chemical data

Molecular Weight: 235.461g/mol
Molecular Formula: C₇H₄BrClO₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 233.90832
Monoisotopic Mass: 233.90832
Complexity: 163
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 37.3
Heavy Atom Count: 11
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBgMAAEEAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgJACAABrAKAmCAwCIAAAgCIAiDSCAACAAAkBQQIiAEACugIJjKBFxCAcQAkwAEIn5eIyCCOAAAIEAABAAAAABAgAAIAAAAAAAAAAA==

11. Question & Answer

What is the synthesis method of 5-Bromo-2-chlorobenzoic acid? Dec 27 2022
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