5-Bromo-3-fluorobenzene-1,2-diol

Base Information

• Chemical Name: 5-Bromo-3-fluorobenzene-1,2-diol
• CAS No.: 876861-29-9
• Molecular Formula: C6H4BrFO2
• Molecular Weight: 206.999
• Hs Code.: 2908190090
• European Community (EC) Number: 893-101-1
• DSSTox Substance ID: DTXSID90468877
• Wikidata: Q82296337
• Mol file: 876861-29-9.mol

Synonyms:5-Bromo-3-fluorobenzene-1,2-diol;876861-29-9;1,2-Benzenediol, 5-bromo-3-fluoro-;SCHEMBL2050124;DTXSID90468877;NTMLYGHAJRXVMB-UHFFFAOYSA-N;BKB86129;MFCD19441229;AKOS016007177;DS-16078;CS-0060186;EN300-746886;A928432;A1-16442

Chemical Property of 5-Bromo-3-fluorobenzene-1,2-diol

Chemical Property:

• Boiling Point: 263.2±35.0 °C(Predicted)
• PKA: 7.84±0.15(Predicted)
• PSA: 40.46000
• Density: 1.940±0.06 g/cm3(Predicted)
• LogP: 1.99940
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 205.93787
• Heavy Atom Count: 10
• Complexity: 122

Purity/Quality:

98% ^*data from raw suppliers

5-Bromo-3-fluorobenzene-1,2-diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1O)O)F)Br
• Uses: 5-Bromo-3-fluorobenzene-1,2-diol is used as a reagent in the synthesis of N-(hydroxy(pyrrolidinyl)propanyl)pyrrolidinecarboxamide derivatives as glucosylceramide synthase inhibitors.5-Bromo-3-fluorobenzene-1,2-diol is also used in the preparation of 5,5-disubstituted-2-iminopyrrolidine derivatives as thrombin receptor antagonists.

Technology Process of 5-Bromo-3-fluorobenzene-1,2-diol

There total 2 articles about 5-Bromo-3-fluorobenzene-1,2-diol 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: 98.0%

5-bromo-3-fluoro-2-hydroxybenzaldehyde (251300-28-4) → 5-bromo-3-fluoro-benzene-1,2-diol (876861-29-9)

Guidance literature:

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 6.5h; pH=10 - 11;

Reference yield:

3-fluorosalicylaldehyde (394-50-3) → 5-bromo-3-fluoro-benzene-1,2-diol (876861-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1: N-Bromosuccinimide; ammonium formate / acetonitrile / 2 h / 20 °C

2: sodium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 6.5 h / 0 - 20 °C / pH 10 - 11

With N-Bromosuccinimide; dihydrogen peroxide; ammonium formate; sodium hydroxide; In tetrahydrofuran; water; acetonitrile;

Reference yield: 87.0%

5-bromo-3-fluoro-benzene-1,2-diol (876861-29-9) + ethyl iodide (75-03-6) → 5-bromo-1,2-diethoxy-3-fluorobenzene (876861-32-4)

Guidance literature:

With potassium carbonate; In N,N-dimethylformamide (DMF); at 20 - 50 ℃; for 17h; Under a nitrogen atmosphere;

upstream raw materials:

5-bromo-3-fluoro-2-hydroxybenzaldehyde

3-fluorosalicylaldehyde

Downstream raw materials:

5-bromo-1,2-diethoxy-3-fluorobenzene

Refernces

• 1、 -. "GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES". Paragraph 000179. . Retrieved 2016/09/26.
• 2、 -. "N-(1-HYDROXY-3-(PYRROLIDINYL)PROPAN-2-YL)PYRROLIDINE-3-CARBOXAMIDE DERIVATIVES AS GLUCOSYLCERAMIDE SYNTHASE INHIBITORS". Paragraph 000213. . Retrieved 2015/05/19.