2,4,6-Tribromophenol

Base Information

• Chemical Name: 2,4,6-Tribromophenol
• CAS No.: 118-79-6
• Molecular Formula: C6H3Br3O
• Molecular Weight: 330.801
• Hs Code.: 29081990
• European Community (EC) Number: 204-278-6
• ICSC Number: 1563
• NSC Number: 2136
• UN Number: 2811,3082
• UNII: YS6K3EU393
• DSSTox Substance ID: DTXSID6021959
• Nikkaji Number: J5.307D
• Wikipedia: 2,4,6-Tribromophenol
• Wikidata: Q209180
• NCI Thesaurus Code: C87256
• Metabolomics Workbench ID: 43953
• ChEMBL ID: CHEMBL220087
• Mol file: 118-79-6.mol

Synonyms:2,4,6-tribromophenol;2,4,6-tribromophenol, bismuth (3+) salt;bismuth tribromophenate;Xeroform

Chemical Property of 2,4,6-Tribromophenol

Chemical Property:

• Appearance/Colour: Soft, long, white crystals with a bromine odor.
• Vapor Pressure: 0.0015mmHg at 25°C
• Melting Point: 90-94 °C(lit.)
• Refractive Index: 1.674
• Boiling Point: 286.8 °C at 760 mmHg
• PKA: 6.34±0.23(Predicted)
• Flash Point: 109.7 °C
• PSA: 20.23000
• Density: 2.55 g/cm³
• LogP: 3.67970
• Storage Temp.: 2-8°C
• Solubility.: water: soluble0.007g/100ml at 25°C
• Water Solubility.: 71 mg/L (15 ºC)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 329.77135
• Heavy Atom Count: 10
• Complexity: 108
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

2,4,6-Tribromophenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xi,N,Xn,T,F
• Statements: 36/37/38-51/53-20/22-39/23/24/25-23/24/25-11-63-43-45-50-36-67-40-22
• Safety Statements: 26-36-61-37/39-45-36/37-16-7-24/25-23-53-37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Phenols
• Canonical SMILES: C1=C(C=C(C(=C1Br)O)Br)Br
• Recent ClinicalTrials: Phage Therapy for the Prevention and Treatment of Wound Infections in Burned Patients
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the eyes.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Uses: 2,4,6-Tribromophenol is used as a certified reference standard for the determination of the analyte in multiple solid formulation drug products using gas chromatography coupled to tandem mass spectrometry. 2,4,6-Tribromophenol was used in analysis of nonylphenol, nonylphenol monoethoxylate and octylphenol in sediment, water and fish tissue.

Technology Process of 2,4,6-Tribromophenol

There total 186 articles about 2,4,6-Tribromophenol 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: 41.0%

phenol (108-95-2,27073-41-2) → 2,4-dibromophenol (615-58-7) + 2,4,6-tribromophenol (118-79-6)

Guidance literature:

With bromine; for 4h; Phase-vanishing reaction with phase screen; Neat (no solvent);

DOI:10.3762/bjoc.5.75

Reference yield: 37.0%

2,4,6-tribromoaniline (147-82-0) + copper(I) cyanide (544-92-3) → 1,3,5-trisbromobenzene (626-39-1) + 2,4,6-tribromonitrobenzene (3463-40-9) + 2,4,6-tribromobenzonitrile (35851-93-5) + 2,4,6-tribromophenol (118-79-6)

Guidance literature:

With tert.-butylnitrite; In dimethyl sulfoxide; at 60 ℃; for 1.5h; Further byproducts given;

DOI:10.1016/0040-4020(96)00331-6

Reference yield: 28.0%

4-bromo-phenol (106-41-2) → 2,4-dibromophenol (615-58-7) + 2,4,6-tribromophenol (118-79-6)

Guidance literature:

With aluminum tri-bromide; [bis(acetoxy)iodo]benzene; In acetonitrile; at 23 ℃;

DOI:10.1039/c8ra02982b

upstream raw materials:

methanol

tetrachloromethane

2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one

formic acid

Downstream raw materials:

2,4,6-tribromoanisole

benzoic acid-(2,4,6-tribromo-phenyl ester)

2,4,6-tribromophenyl acetate

(2,4,6-tribromo-phenoxy)-acetic acid

Refernces

• 1、 Grovenstein,Henderson. "". . p. 569,571, 572. Retrieved 1956.
• 2、 Borkowski,Ardanaz,Rossomando,Tonn. "Reaction mechanism for the cyclization of 3-[γ,γ-dimethylallyl] coumaric acid methyl ester in dimethyl sulfoxide (DMSO)". . p. 612 - 613. Retrieved 2000.
• 3、 Kemp. "-". . p. 202. Retrieved 1971.
• 4、 Van Kerrebroeck, Reinout,Naert, Pieter,Heugebaert, Thomas S.A.,D’hooghe, Matthias,Stevens, Christian V.. "Electrophilic bromination in flow: A safe and sustainable alternative to the use of molecular bromine in batch". . . Retrieved 2019.
• 5、 Bamberger,Kraus. "-". . p. 265. Retrieved 1922.
• 6、 Tsubota,M. et al.. "-". . p. 1252 - 1253. Retrieved 1972.
• 7、 Barton,Halley,Ozbalik,Mehl. "Benzylic oxidation by the GIF(IV) system". . p. 6615 - 6618. Retrieved 1989.
• 8、 Lauer,Langkammerer. "-". . p. 1628. Retrieved 1934.
• 9、 Lloyd. "-". . p. 8. Retrieved 1905.
• 10、 Wu, Yong-Qi,Lu, Hai-Jia,Zhao, Wen-Ting,Zhao, Hong-Yi,Lin, Zi-Yun,Zhang, Dong-Feng,Huang, Hai-Hong. "A convenient and efficient H2SO4-promoted regioselective monobromination of phenol derivatives using N-bromosuccinimide". supporting information. p. 813 - 822. Retrieved 2020/02/15.