618-58-6

Basic information

• Product Name: 3,5-Dibromobenzoic acid
• Synonyms: 3,5-dibromo-benzoicaci;Benzoic acid, 3,5-dibromo-;RARECHEM AL BO 0773;3,5-DIBROMOBENZOIC ACID;BUTTPARK 99\57-19;3,5-DibroMobenzoic Acid, 97+%
• CAS NO: 618-58-6
• Molecular Formula: C₇H₄Br₂O₂
• Molecular Weight: 279.91
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Acids & Esters;Bromine Compounds;Building Blocks for Dendrimers;Functional Materials;C7;Carbonyl Compounds;Carboxylic Acids;Benzoic acid series;OLED
• Mol File: 618-58-6.mol

Chemical Properties

• Melting Point: 218-220 °C(lit.)
• Boiling Point: 355.2 °C at 760 mmHg
• Flash Point: 168.6 °C
• Appearance: white to light yellow crystal powder
• Density: 1.9661 (rough estimate)
• Vapor Pressure: 1.17E-05mmHg at 25°C
• Refractive Index: 1.4970 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Very faint turbidity in methanol.
• PKA: 3.42±0.10(Predicted)
• BRN: 1940691
• CAS DataBase Reference: 3,5-Dibromobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dibromobenzoic acid(618-58-6)
• EPA Substance Registry System: 3,5-Dibromobenzoic acid(618-58-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: DG6290010
• HazardClass: IRRITANT
• Hazardous Substances Data: 618-58-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3,5-Dibromobenzoic acid is used as a key intermediate in the synthesis of various organic compounds for different applications. Its reactivity allows it to be a valuable building block in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
3,5-Dibromobenzoic acid is used as a starting material for the synthesis of (+)-menthyl 3,5-dibromobenzoate, which is an important compound in the development of pharmaceuticals. This ester derivative can be utilized in the formulation of drugs targeting specific medical conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 3,5-dibromobenzoic acid is used as a precursor for the synthesis of di-tert-butyl 4-[2-(tert-butoxycarbonyl)ethyl]-4-(3,5-dibromobenzamido)heptanedioate2. 3,5-Dibromobenzoic acid can be employed in the development of agrochemicals, such as pesticides or herbicides, to enhance crop protection and yield.
Used in Specialty Chemicals:
3,5-Dibromobenzoic acid is also used in the synthesis of (L)-methyl 2-(3,5-dibromobenzamido)-3-phenylpropanoate, which can be utilized in the production of specialty chemicals. These chemicals may have applications in various industries, such as coatings, adhesives, or polymers, where their unique properties can provide specific benefits.

Synthesis

3,5-Dibromobenzoic acid was synthesized from anthranilic acid by bromination, diazotization and additional reactions derived. The bromination reaction is carried out at about 20°C. After the reaction, the crystals are filtered, washed with hot water to remove anthranilic acid and hydrochloric acid, and recrystallized with acetic acid to obtain o-amino-3,5-dibromobenzoic acid; then use sodium nitrite to carry out diazotization in hydrochloric acid at about 0°C, then add the diazonium salt into ethanol containing calcium sulfate at 60-70°C in batches. After the addition is complete, continue stirring for 10 minutes, filter to obtain the crude product, and recrystallize with ethanol to obtain the finished product.

InChI:InChI=1/C7H4Br2O2/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3H,(H,10,11)/p-1

Upstream product

• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 626-39-1 1,3,5-trisbromobenzene 
• 1611-92-3 3,5-dibromotoluene 
• 4123-72-2 4-amino-3,5-dibromobenzoic acid 
• 51686-78-3 2,4-dibromonitrobenzene 
• 151-50-8 potassium cyanide 
• 97165-77-0 3,5-dibromobenzonitrile 
• 42237-85-4 3-amino-5-bromobenzoic acid 
• 606-00-8 2-amino-3,5-dibromo-benzoic acid methyl ester 
• 27003-05-0 3,5-dibromo-2-chloro-benzoic acid 
• 609-85-8 2-amino-3,5-dibromobenzoic acid 
• 51329-15-8 methyl 3,5-dibromobenzoate 
• 401-84-3 1,3-dibromo-5-(trifluoromethyl)benzene 

Downstream Products

• 51329-15-8 methyl 3,5-dibromobenzoate 
• 67973-33-5 3,5-dibromobenzoic acid ethyl ester 
• 23950-59-6 3,5-dibromobenzoyl chloride 
• 60912-52-9 3,5-dibromo-2-nitro-benzoic acid 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 37960-84-2 [3,5-D₂]benzoic acid 
• 67973-19-7 3,5-dibromo-2,6-dinitrobenzoic acid 
• 195134-70-4 tert-butyl (3,5-dibromophenyl)carbamate 
• 65-85-0 benzoic acid 
• 145691-59-4 (3,5-dibromophenyl)methanol 
• 1080603-07-1 3,5-dibromo-N-methoxy-N-methyl-benzamide 

Relevant articles and documents

Polyoxometalate built-in conjugated microporous polymers for visible-light heterogeneous photocatalysis

Herein, we report two novel Anderson-type polyoxometalate (POM) built-in conjugated microporous polymers (CMPs), Bn-Anderson-CMP and Th-Anderson-CMP prepared through Sonogashira-Hagihara cross-coupling of tetrabromo-bifunctionalized Anderson-type POMs and 1,3,5-triethynylbenzene. These two Anderson-CMPs exhibit outstanding heterogeneous photocatalytic activities towards degrading organic dyes in water. Control photocatalysis experiments with different radical scavengers demonstrate that hydrogen peroxide and singlet oxygen are the primary active catalytic species. Moreover, these two CMPs can be easily recycled at least five times without a noticeable decrease in photocatalytic performances.

INHIBITORS OF STEAROYL-COA DESATURASE

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity.

Buttressing Effects Rerouting the Deprotonation and Functionalization of 1,3-Dichloro- and 1,3-Dibromobenzene

A systematic comparison between 1,3-difluorobenzene, 1,3-dichlorobenzene, and 1,3-dibromobenzene did not reveal major differences in their behavior towards strong bases such as lithium diisopropylamide or lithium 2,2,6,6-tetramethyl-piperidide. Thus, all 2,6-dihalobenzoic acids 1 are directly accessible by consecutive treatment with a suitable base and dry ice. In contrast, (2,6-dichlorophenyl)- and (2,6-bromo-phenyl)triethylsilane (2a and 2b) were found to undergo deprotonation at the 5-position (affording acids 3 and, after deprotection, 4), whereas the 1,3-difluoro analog is known to react at the 4-position. The 2,4-dihalobenzoic acids 7 were selectively prepared from either the silanes 2 (by bromination at the 4-position, metalation and carboxylation of the neighboring position, followed by desilylation and debromination) or the 1,3-dihalo-2-iodobenzenes 8 (by base-promoted migration of iodine to the 4-position followed by iodine/magnesium permutation and subsequent carboxylation). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Marine Bacteria, I. - Synthesis of Pentabromopseudiline, a Cytotoxic Phenylpyrrole from Alteromonas luteo-violaceus

A new synthesis of 2,3,4-tribromo-5-(3,5-dibromo-2-hydroxyphenyl)pyrrole (1a, pentabromopseudiline), an antibiotic, enzymeinhibitory and cytotoxic active constituent of the marine bacterium Alteromonas luteo-violaceus, is described.For investigation of structure-activity relationships further 2-phenylpyrroles are investigated.Key step in their synthesis is the Grignard reaction of 2-(1,3-dioxan-2-yl)ethylmagnesium bromide (9d) with benzoyl chlorides yielding γ-phenyl-γ-ketoaldehydes 24, and the Paal-Knorr cyclisation of the latter. - Key Words: Alteromonas luteo-violaceus / Bromopyrrole / Marine bacteria / Pentabromopseudiline

Substitution Reactions of Phenylated Aza-Heterocycles. Part 2. Bromination of Some 2,5-Diaryl-1,3,4-oxadiazoles

Electrophilic bromination of the title compounds may be achieved using either bromine in oleum, or bromine and potassium bromate in a sulphuric-acetic acid mixture.Under the milder reaction conditions provided by the latter, 2-(p-nitrophenyl)-5-phenyl-1,3,4-oxadiazole (2), the model compound used in this study, is mono- and di-brominated in the phenyl ring.In the first bromination step, all three monobromo-isomers are produced in appreciable amount.The orientation of the second bromination is controlled entirely by the first bromine and not by the oxadiazole substituent: this is confirmed by a separate study of the bromination of the three monobromo-compounds (3a-3c).

1,3,5-TRISUBSTITUTED BENZENES I. SYNTHESIS AND REACTIONS OF 3,5-DIBROMOPHENYLLITHIUM

An improved method for the synthesis of 3,5-dibromophenyllithium (I) has been developed.The reactions between I and various substrates leads to a variety of substituted compounds e.g. (3,5-Br2C6H3)nX; when n = 1, X = -CO2H, -CHO, -Si(CH3)2Cl, -C(O)C3F7, -C(O)CF2(OCF2CF2)3OC2F5, -C(O)CF(CF3)OC3F7, -C(O)CF(CF3)2OC3F7, -C(CF3)2OH and C6F5; when n = 2, X = p-C6F4; when n = 3, X = P.The thermal stability of I is also reported.

Diester of 3,5,3',5'-tetrabromo-bisphenol A with halogenated aromatic carboxylic acid

A novel diester compound of the formula (I): STR1 wherein each of R1 and R2 represents a group of the formula (II): STR2 wherein n is an integer of 0 to 4; and m an integer of 1 to 5, is found to be capable of imparting excellent flame-retardancy to various inflammable polymeric materials such as polystyrene, polyester, polyamide, polyphenylene oxide, etc. without deleterious effects on other physical properties of such polymeric materials.