3147-55-5

Basic information

• Product Name: 3,5-Dibromosalicylic acid
• Synonyms: 3,5-Dibromosalicylic acid, 98+%;3,5-Dibromosalicylic;3,5-BroMosalicylic acid;3,5-Dibromosalicylic acid, 2-Carboxy-4,6-dibromophenol;3,5-Dibromosalicylic acid 97%;3,5-dibromo-2-hydroxy-benzoicaci;Benzoic acid, 3,5-dibromo-2-hydroxy-;Salicylic acid, 3,5-dibromo-
• CAS NO: 3147-55-5
• Molecular Formula: C₇H₄Br₂O₃
• Molecular Weight: 295.91
• EINECS: 221-570-9
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Acids & Esters;Bromine Compounds;Phenols;Building Blocks;C7;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 3147-55-5.mol
• Article Data: 19

Chemical Properties

• Melting Point: 224-227 °C(lit.)
• Boiling Point: 341.3 °C at 760 mmHg
• Flash Point: 160.2 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 2.0591 (rough estimate)
• Vapor Pressure: 3.13E-05mmHg at 25°C
• Refractive Index: 1.4947 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 1.96±0.14(Predicted)
• Water Solubility: SLIGHTLY SOLUBLE
• Merck: 14,3028
• BRN: 2210805
• CAS DataBase Reference: 3,5-Dibromosalicylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dibromosalicylic acid(3147-55-5)
• EPA Substance Registry System: 3,5-Dibromosalicylic acid(3147-55-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 3147-55-5(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

InChI:InChI=1/C7H4Br2O3/c8-3-1-4(7(11)12)6(10)5(9)2-3/h1-2,10H,(H,11,12)/p-1

Upstream product

• 118-92-3 anthranilic acid 
• 69-72-7 salicylic acid 
• 87-25-2 2-ethoxycarbonylaniline 
• 21524-15-2 6,8-dibromo-2H-chromen-2-one 
• 46020-91-1 3',5'-dibromosalicylate 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 10035-10-6 hydrogen bromide 
• 7722-84-1 dihydrogen peroxide 
• 7553-56-2 iodine 
• 392-92-7 2,4-dibromo-6-trifluoromethyl-phenol 
• 1820-99-1 5,5'-thio-bis(2-hydroxy-benzoic acid) 

Downstream Products

• 53643-52-0 3,5-dibromo-2-hydroxy-benzoic acid-(4-bromo-phenyl ester) 
• 677321-44-7 3,5-dibromo-2-hydroxy-benzoic acid-[2]naphthyl ester 
• 79402-07-6 3,5-Dibromo-N-(2,4-difluoro-phenyl)-2-hydroxy-benzamide 
• 144181-06-6 trimesoyl tris(3,5-dibromosalicylate) 
• 46020-91-1 3',5'-dibromosalicylate 
• 90481-38-2 2-(2′-hydroxy-3′,5′-dibromophenyl)benzothiazole 
• 90425-99-3 3,5-Dibromo-N-(4-bromo-2-methyl-phenyl)-2-hydroxy-benzamide 
• 6548-90-9 3,5-Dibrom-3',4'-dichlor-salicylanilid 
• 2316-50-9 2-bromo-4,6-dinitrophenol 
• 118-79-6 2,4,6-tribromophenol 
• 615-58-7 2,4-dibromophenol 
• 95-56-7 2-hydroxybromobenzene 
• 15790-59-7 3,5-dibromo-2-methoxy-benzoic acid methyl ester 
• 108-95-2 phenol 

Relevant articles and documents

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A new process to prepare 3,6-dichloro-2-hydroxybenzoic acid, the penultimate intermediate in the synthesis of herbicide dicamba

Glyphosate [N-(phosphonomethyl)glycine] is a broad spectrum, post-emergent herbicide that is among the most widely used agrochemicals globally. Over the past 30 years, there has been a development of glyphosate-resistant weeds, which pose a significant challenge to growers and crop scientists, resulting in lower crop yields and increased costs. 3,6-Dichloro-2-methoxybenzoic acid (dicamba) is the active ingredient in XtendiMax a standalone herbicide developed by Bayer Crop Science to control broadleaf weeds, including glyphosate-resistant species. 3,6-Dichloro-2-hydroxybenzoic acid (3,6-DCSA) is the penultimate intermediate in the synthesis of dicamba. Existing dicamba manufacturing routes utilize a high temperature, high pressure Kolbe-Schmitt carboxylation to prepare 3,6-DCSA. Described in this Letter is a new, non-Kolbe-Schmitt process to prepare 3,6-DCSA from salicylic acid in four chemical steps.

Graphene Oxide Promoted Oxidative Bromination of Anilines and Phenols in Water

The mildly acidic and oxidative nature of graphene oxide, with its large surface area available for catalytic activity, has been explored in aromatic nuclear bromination chemistry for the first time. The versatile catalytic activity of graphene oxide (GO) has been used to selectively and rapidly brominate anilines and phenols in water. The best results were obtained at ambient temperatures using molecular bromine in a protocol promoted by oxidative bromination catalyzed by GO; these transformations proceeded with 100% atom economy with respect to bromine and high selectivities for the tribromoanilines and -phenols. Reduced graphene oxide (r-GO) was observed to form after the second recycle (third use) of GO. This technique is also effective with N-bromosuccinimide (NBS) as the brominating reagent. In the case of NBS, reactions were instantaneous and the GO displayed excellent recyclability without any loss of activity over several cycles.