2-Bromo-4,5-difluorobenzoic acid

Base Information

• Chemical Name: 2-Bromo-4,5-difluorobenzoic acid
• CAS No.: 64695-84-7
• Molecular Formula: C7H3BrF2O2
• Molecular Weight: 237
• Hs Code.: 29163990
• European Community (EC) Number: 629-562-0
• DSSTox Substance ID: DTXSID40382296
• Nikkaji Number: J510.175A
• Wikidata: Q72454347
• Mol file: 64695-84-7.mol

Synonyms:2-Bromo-4,5-difluorobenzoic acid;64695-84-7;2-Bromo-4,5-difluorobenzoicacid;Benzoic acid, 2-bromo-4,5-difluoro-;MFCD04973422;2-bromo-4,5-difluoro-benzoic Acid;SCHEMBL500029;DTXSID40382296;DGCBGBZYTNTZJH-UHFFFAOYSA-N;2-Bromo-4,5-Difluoro Benzoic Acid;BBL101259;CL8025;STL555055;AKOS005257928;AC-3907;AM61612;CS-W012865;DS-1514;2-Bromo-4,5-difluorobenzoic acid, 97%;SY014895;2-bromanyl-4,5-bis(fluoranyl)benzoic acid;A1759;B5722;FT-0651170;EN300-101332;A834853;Z1269235585

Chemical Property of 2-Bromo-4,5-difluorobenzoic acid

Chemical Property:

• Appearance/Colour: White to yellow crystalline powder
• Vapor Pressure: 0.000902mmHg at 25°C
• Melting Point: 118-122 °C(lit.)
• Refractive Index: 1.558
• Boiling Point: 291.3 °C at 760 mmHg
• PKA: 2.45±0.10(Predicted)
• Flash Point: 130 °C
• PSA: 37.30000
• Density: 1.872 g/cm³
• LogP: 2.42550
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 235.92845
• Heavy Atom Count: 12
• Complexity: 188

Purity/Quality:

97% ^*data from raw suppliers

2-Bromo-4,5-difluorobenzoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22
• Safety Statements: 36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=CC(=C1F)F)Br)C(=O)O

Technology Process of 2-Bromo-4,5-difluorobenzoic acid

There total 11 articles about 2-Bromo-4,5-difluorobenzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

1-bromo-3,4-difluorobenzene (348-61-8) + acetyl chloride (75-36-5) → 2-bromo-4,5-difluorobenzoic acid (64695-84-7)

Guidance literature:

aluminium trichloride; In water;

Reference yield:

2-Bromo-4,5-difluoro-α, α-dichloroacetophenone + sodium disulfite → 2-bromo-4,5-difluorobenzoic acid (64695-84-7)

Guidance literature:

With hydrogenchloride; In sodium hypobromide;

Reference yield:

4,5-dichlorophthalic anhydride (942-06-3) → 2-bromo-4,5-difluorobenzoic acid (64695-84-7)

Guidance literature:

Multi-step reaction with 5 steps

1: KF / tetrahydrothiophene 1,1-dioxide / 2 h / 185 °C

2: 2.) oxalyl chloride / 1.) 10 min, 2.) CH₂Cl₂, 16 h

3: 75 percent / tetrahydrofuran / 24 h

4: CCl₃Br, AIBN / 6 h / Heating

5: aq. LiOH / tetrahydrofuran / 3 h / Ambient temperature

With potassium fluoride; lithium hydroxide; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); Bromotrichloromethane; In tetrahydrofuran; sulfolane;

DOI:10.1080/00397919209409255

upstream raw materials:

2-bromo-4,5-difluorobenzonitrile

2-amino-4,5-difluorobenzoic acid

2-bromo-4,5-difluorobenzoic acid methyl ester

4,5-dichlorophthalic anhydride

Downstream raw materials:

2-Bromo-4-(4-chloro-phenylsulfanyl)-5-fluoro-benzoic acid

2-(4-Chloro-phenylsulfanyl)-4,5-difluoro-benzoic acid

2,4-Bis-(4-chloro-phenylsulfanyl)-5-fluoro-benzoic acid

N-(2-((3-(benzylthio)-2-(methylcarbamoyl)phenyl)carbamoyl)-3-bromophenyl)-2-bromo-4,5-difluorobenzamide

Refernces

Renin inhibitors for the treatment of hypertension: Design and optimization of a novel series of spirocyclic piperidines

10.1016/j.bmcl.2011.10.013

The research focuses on the discovery and structure-activity relationship (SAR) of a novel series of spirocyclic renin inhibitors for the treatment of hypertension. The study aimed to enhance renin potency and reduce hERG affinity and CYP3A4 inhibition through spirocyclization, which restricts the molecule to its bioactive conformation. Experiments involved the synthesis of various spirocyclic compounds, with compound 31 identified as an optimized renin inhibitor. Reactants used in the synthesis included 2-bromo-4,5-difluorobenzoic acid, TBSCl, imidazole, DMF, Pd(dppf)Cl2, Na2CO3, and other reagents for Suzuki coupling and cyclization reactions. Analytical methods employed in the study included buffer and plasma renin inhibition assays, hERG channel affinity measurements, and CYP3A4 inhibition assessments, which were used to evaluate the potency, safety, and metabolic profile of the synthesized compounds.