13731-82-3

Basic information

• Product Name: 2,5-Dibromoterephthalic acid
• Synonyms: 2,5-DIBROMOTEREPHTALIC ACID;2,5-DIBROMOTEREPHTHALIC ACID;2,5-dibromo-4-benzenedicarboxylicacid;2,5-Dibromo-1,4-PhenyldicarboxylicAcid;2,5-dibromotetrephthalic acid;2,5-Dibromoterephtha;1,4-DibroMo-2,5-benzenedicarboxylic acid;1,4-Benzenedicarboxylicacid, 2,5-dibroMo-
• CAS NO: 13731-82-3
• Molecular Formula: C₈H₄Br₂O₄
• Molecular Weight: 323.92
• EINECS: 237-300-8
• Product Categories: Phthalic Acids, Esters and Derivatives;Carboxylic Acids;Phenyls & Phenyl-Het;Organic acids;Carboxylic Acids;Phenyls & Phenyl-Het;Derivatives of phthalic acid
• Mol File: 13731-82-3.mol
• Article Data: 23

Chemical Properties

• Melting Point: 320-325°C
• Boiling Point: 445ºC at 760 mmHg
• Flash Point: 222.9°C
• Appearance: /
• Density: 2.205g/cm3
• Vapor Pressure: 1.06E-08mmHg at 25°C
• Refractive Index: 1.679
• Storage Temp.: Room temperature.
• Solubility: soluble in Methanol
• PKA: 1.75±0.10(Predicted)
• CAS DataBase Reference: 2,5-Dibromoterephthalic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dibromoterephthalic acid(13731-82-3)
• EPA Substance Registry System: 2,5-Dibromoterephthalic acid(13731-82-3)

Safety Data

• Hazard Codes: C,Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• Hazardous Substances Data: 13731-82-3(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

InChI:InChI=1/C8H4Br2O4/c9-5-1-3(7(11)12)6(10)2-4(5)8(13)14/h1-2H,(H,11,12)(H,13,14)

Synthetic route

2,5-dibromo-p-xylene (1074-24-4) → 2,5-dibromoterephtalic acid (13731-82-3)

Conditions	Yield
With pyridine; potassium permanganate In water	96%
With pyridine; potassium permanganate In water for 24h; Reflux;	91%
With chromium(VI) oxide; sulfuric acid In acetic acid at 20℃; for 24h;	90%

2,5-dibromo-4-methylbenzoic acid (20871-01-6) → 2,5-dibromoterephtalic acid (13731-82-3)

Conditions	Yield
With potassium permanganate; sodium hydrogencarbonate for 144h; Heating;	94%
With potassium permanganate In water for 144h; Reflux;	86%
With potassium permanganate; water for 144h; Reflux;	86%
With alkaline permanganate
With potassium permanganate; potassium carbonate

2,5-dibromobenzene-1,4-dinitrile (18870-11-6) → 2,5-dibromoterephtalic acid (13731-82-3)

Conditions	Yield
With sodium hydroxide

2.5-dibromo-1.4-bis-tribromomethyl-benzene → 2,5-dibromoterephtalic acid (13731-82-3)

Conditions	Yield
With sulfuric acid at 120 - 130℃;

2.5-dibromo-cymene → 2,5-dibromoterephtalic acid (13731-82-3)

Conditions	Yield
With nitric acid at 180℃; im geschlossenen Rohr;

methanol (67-56-1) + 2,5-dibromoterephtalic acid (13731-82-3) → dimethyl 2,5-dibromoterephthalate (18014-00-1)

Conditions	Yield
With thionyl chloride for 5h; Reflux;	100%
With sulfuric acid Heating;	95%
With sulfuric acid Heating; Reflux;	95%

2,5-dibromoterephtalic acid (13731-82-3) → 3,6-dibromo-2,5-phenylenedi(carboxylic acid chloride) (13815-90-2)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In benzene at 80℃;	100%
With oxalyl dichloride	100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 3h; Inert atmosphere; Reflux;	100%

biphenyl-2-ylcarbamic acid 1-[2-(methylamino)ethyl]piperidin-4-yl ester (743460-48-2) + 2,5-dibromoterephtalic acid (13731-82-3) → N-{2-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]ethyl}-2,5-dibromo-N-methylterephthalamic Acid (864751-39-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In DMF (N,N-dimethyl-formamide) at 20℃; for 3h;	100%

ethanol (64-17-5) + 2,5-dibromoterephtalic acid (13731-82-3) → 2,5-dibromo-terephthalic acid diethyl ester (18013-97-3)

Conditions	Yield
Stage #1: 2,5-dibromoterephtalic acid With thionyl chloride for 4h; Reflux; Stage #2: ethanol In tetrahydrofuran for 10h;	99%
sulfuric acid Reflux;	96%
With sulfuric acid for 48h; Reflux;	96%

2,5-dibromoterephtalic acid (13731-82-3) + N-(2-hexyldecyl)thiophene-3-amine (1401211-90-2) → 2,5-dibromo-N1,N4-bis(2-hexyldecyl)-N1,N4-di(thiophen-3-yl)terephthalamide

Conditions	Yield
Stage #1: 2,5-dibromoterephtalic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 20h; Schlenk technique; Inert atmosphere; Stage #2: N-(2-hexyldecyl)thiophene-3-amine With triethylamine In dichloromethane at 0 - 20℃; for 20h;	99%

2,5-dibromoterephtalic acid (13731-82-3) → 2,5-dihydroxy-1,4-benzenedicarboxylic acid (610-92-4)

Conditions	Yield
Stage #1: 2,5-dibromoterephtalic acid With water; sodium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine; copper(I) bromide In acetonitrile at 90℃; for 18h; Stage #2: With hydrogenchloride In water; acetonitrile at 25℃; Product distribution / selectivity;	98%
Stage #1: 2,5-dibromoterephtalic acid With water; sodium carbonate for 1h; Heating / reflux; Stage #2: With water; trans-N,N'-dimethylcyclohexane-1,2-diamine; copper(I) bromide at 90℃; for 2h; Stage #3: With hydrogenchloride In water at 25℃; Product distribution / selectivity;	97%
Stage #1: 2,5-dibromoterephtalic acid With water; sodium carbonate for 1h; Heating / reflux; Stage #2: 2,2,6,6-tetramethylheptane-3,5-dione; copper(I) bromide In water at 80℃; for 30h; Stage #3: With hydrogenchloride In water at 25℃;	92%

2,5-dibromoterephtalic acid (13731-82-3) + sodium methylate (124-41-4) → C10H8O6(2-)*2Na(1+)

Conditions	Yield
(±)-N,N-dimethyl-trans-1,2-diaminocyclohexane; copper(ll) bromide In methanol for 8h; Heating / reflux;	95%
2,2,6,6-tetramethylheptane-3,5-dione; copper(ll) bromide In methanol for 8h; Heating / reflux;
1,2-bis[(2,4,6-trimethylphenyl)imino]-1,2-dimethylethane; copper(ll) bromide In methanol for 8h; Heating / reflux;

2,5-dibromoterephtalic acid (13731-82-3) → 2,5-dibromobenzene-1,4-carboxamide (50880-39-2)

Conditions	Yield
Stage #1: 2,5-dibromoterephtalic acid With thionyl chloride; N,N-dimethyl-formamide for 3h; Inert atmosphere; Reflux; Stage #2: With ammonium hydroxide In 1,4-dioxane for 1h;	94%
Multi-step reaction with 2 steps 1: PCl5 2: diethyl ether; ammonia View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / 3 h / Reflux 2: ammonium hydroxide / 1,4-dioxane / 20 °C View Scheme

2,5-dibromoterephtalic acid (13731-82-3) → 2-hydroxyterephthalic acid (636-94-2) + 2,5-dihydroxy-1,4-benzenedicarboxylic acid (610-92-4)

Conditions	Yield
Stage #1: 2,5-dibromoterephtalic acid With sodium carbonate In water for 1h; Heating / reflux; Stage #2: With water; 2,2,6,6-tetramethylheptane-3,5-dione; copper(I) bromide at 80℃; for 30h; Stage #3: With hydrogenchloride In water at 25℃;	A n/a B 92%

2,5-dibromoterephtalic acid (13731-82-3) + butan-1-ol (71-36-3) → dibutyl 2,5-dibromoterephthalate (58613-36-8)

Conditions	Yield
With sulfuric acid at 120℃; for 12h;	89%
With sulfuric acid for 15h;	81%

cobalt(II) nitrate hexahydrate + 4,4'-methylenebis(3,5-dimethylpyrazole) (83524-76-9) + 2,5-dibromoterephtalic acid (13731-82-3) → {[Co(methylenebis(3,5-dimethylpyrazole))(Br-BDC)](H2O)0.5}

Conditions	Yield
In water at 120℃; for 24h; Autoclave;	82%

cadmium(II) nitrate tetrhydrate + 4,4'-methylenebis(3,5-dimethylpyrazole) (83524-76-9) + 2,5-dibromoterephtalic acid (13731-82-3) → [Cd(methylenebis(3,5-dimethylpyrazole))(Br-BDC)0.5(Br-HBDC)]

Conditions	Yield
In water at 120℃; for 48h; Autoclave;	79%

formic acid (64-18-6) + cobalt(II) nitrate hexahydrate + 2,5-dibromoterephtalic acid (13731-82-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → [Co2(2,5-dibromoterephthalate)(HCOO)2(dimethylformamide)2]

Conditions	Yield
at 150℃; for 24h; Autoclave; High pressure;	78.2%

2,2,3,3-tetrafluoropropanol (76-37-9) + 2,5-dibromoterephtalic acid (13731-82-3) → 2,5-bis(2,2,3,3-tetrafluoropropoxy)terephthalic acid (1268628-20-1)

Conditions	Yield
Stage #1: 2,2,3,3-tetrafluoropropanol With sodium hydride In tetrahydrofuran Stage #2: 2,5-dibromoterephtalic acid; cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(ll) bromide In tetrahydrofuran; 2,2,3,3-tetrafluoropropanol at 60℃; for 48h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	72%
Stage #1: 2,2,3,3-tetrafluoropropanol With sodium hydride In tetrahydrofuran Stage #2: 2,5-dibromoterephtalic acid; cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(ll) bromide In tetrahydrofuran; 2,2,3,3-tetrafluoropropanol at 60℃; for 48h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	72%
Stage #1: 2,2,3,3-tetrafluoropropanol With sodium hydride In tetrahydrofuran Stage #2: 2,5-dibromoterephtalic acid; N-Methylanthranilic acid; copper(ll) bromide In tetrahydrofuran; 2,2,3,3-tetrafluoropropanol at 60℃; for 48h; Stage #3: With hydrogenchloride In tetrahydrofuran; water
Stage #1: 2,2,3,3-tetrafluoropropanol With sodium hydride In tetrahydrofuran Stage #2: 2,5-dibromoterephtalic acid; 2,3-bis[N,N-(2-trifluoromethylphenyl)imino]butane; copper(ll) bromide In tetrahydrofuran; 2,2,3,3-tetrafluoropropanol at 60℃; for 48h; Stage #3: With hydrogenchloride In tetrahydrofuran; water
Stage #1: 2,2,3,3-tetrafluoropropanol With sodium hydride In tetrahydrofuran Stage #2: 2,5-dibromoterephtalic acid; acetylacetone; copper(ll) bromide In tetrahydrofuran; 2,2,3,3-tetrafluoropropanol at 60℃; for 48h; Stage #3: With hydrogenchloride In tetrahydrofuran; water

4,4'-bipyridine (553-26-4) + 2,5-dibromoterephtalic acid (13731-82-3) + calcium acetate hydrate (114460-21-8) → (4,4′-bpy)0.5[Ca(dbt)(H2O)2]n

Conditions	Yield
With potassium hydroxide In ethanol; water at 120℃; for 72h; Sealed tube; High pressure;	72%

+ 2,5-dibromoterephtalic acid + calcium acetate hydrate (114460-21-8)

Conditions	Yield
With potassium hydroxide In ethanol; water at 120℃; for 72h; Sealed tube; High pressure;	72%

+ 2,5-dibromoterephtalic acid → (2,5-dibromo-1,4-phenylene)bis((4-butylphenyl)methanone) (197370-00-6)

Conditions	Yield
Stage #1: 2,5-dibromoterephtalic acid With thionyl chloride for 10h; Reflux; Stage #2: 1-butylbenzene With aluminium trichloride In dichloromethane at 25℃; for 2h;	72%

2,2,2-trifluoroethanol (75-89-8) + 2,5-dibromoterephtalic acid (13731-82-3) → 2,5-bis(2,2,2-trifluoroethoxy)terephthalic acid (1268628-19-8)

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanol With sodium hydride In tetrahydrofuran Stage #2: 2,5-dibromoterephtalic acid; cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(ll) bromide In tetrahydrofuran; 2,2,2-trifluoroethanol at 60℃; for 96h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	71%
Stage #1: 2,2,2-trifluoroethanol With sodium hydride In tetrahydrofuran Stage #2: 2,5-dibromoterephtalic acid; cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(ll) bromide In tetrahydrofuran; 2,2,2-trifluoroethanol at 60℃; for 96h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	71%
Stage #1: 2,2,2-trifluoroethanol With sodium hydride In tetrahydrofuran Stage #2: 2,5-dibromoterephtalic acid; D,L-valine; copper(ll) bromide In tetrahydrofuran; 2,2,2-trifluoroethanol at 60℃; for 96h; Stage #3: With hydrogenchloride In tetrahydrofuran; water
Stage #1: 2,2,2-trifluoroethanol With sodium hydride In tetrahydrofuran Stage #2: 2,5-dibromoterephtalic acid; 1,2-bis[(2,4,6-trimethylphenyl)imino]-1,2-dimethylethane; copper(ll) bromide In tetrahydrofuran; 2,2,2-trifluoroethanol at 60℃; for 96h; Stage #3: With hydrogenchloride In tetrahydrofuran; water
Stage #1: 2,2,2-trifluoroethanol With sodium hydride In tetrahydrofuran Stage #2: 2,5-dibromoterephtalic acid; copper(ll) bromide In tetrahydrofuran; 2,2,2-trifluoroethanol at 60℃; for 96h; Stage #3: With hydrogenchloride In tetrahydrofuran; water

2,5-dibromoterephtalic acid (13731-82-3) + 1,3,5-trimethyl-benzene (108-67-8) → (2,5-dibromo-1,4-phenylene)bis(mesitylmethanone)

Conditions	Yield
Stage #1: 2,5-dibromoterephtalic acid With thionyl chloride In dichloromethane for 24h; Reflux; Stage #2: 1,3,5-trimethyl-benzene With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 12h;	70%
Stage #1: 2,5-dibromoterephtalic acid With thionyl chloride In dichloromethane for 12h; Reflux; Stage #2: 1,3,5-trimethyl-benzene With aluminum (III) chloride In dichloromethane Cooling with ice; Reflux;	65%

2-hexyldecan-1-ol (2425-77-6) + 2,5-dibromoterephtalic acid (13731-82-3) → 1,4-dibromo-2,5-bis(2-hexyldecanoate)benzene

Conditions	Yield
Stage #1: 2,5-dibromoterephtalic acid With thionyl chloride Reflux; Stage #2: 2-hexyldecan-1-ol With pyridine at 80℃; for 18h;	70%

4,4'-dimethyl-2,2'-bipyridines (1134-35-6) + zinc(II) nitrate hexahydrate + 2,5-dibromoterephtalic acid (13731-82-3) → C8H2Br2O4(2-)*C12H12N2*H2O*Zn(2+)

Conditions	Yield
In water; N,N-dimethyl-formamide at 120℃; for 72h; Sealed tube;	70%

2,5-dibromoterephtalic acid (13731-82-3) + calcium acetate hydrate (114460-21-8) + 1,4-bis-(1H-imidazol-1-yl)benzene (25372-07-0) → (H2-dib)[Ca3(dbt)4(H2O)4·2H2O]n

Conditions	Yield
With potassium hydroxide In ethanol; water at 120℃; for 72h; Sealed tube; High pressure;	69%

4,4'-bipyridine (553-26-4) + uranyl nirate hexahydrate + 2,5-dibromoterephtalic acid (13731-82-3) → [(uranyl)(2,5-dibromoterephthalate)(4,4′-bipyridine)0.5]

Conditions	Yield
In ethanol; water at 160℃; for 24h; Sealed tube; High pressure;	65%

[2,2]bipyridinyl (366-18-7) + cobalt(II) nitrate hexahydrate + 2,5-dibromoterephtalic acid (13731-82-3) → C8H2Br2O4(2-)*C10H8N2*H2O*Co(2+)

Conditions	Yield
In water; N,N-dimethyl-formamide at 120℃; for 72h; Sealed tube;	65%

2,4,6-triaminopyrimidine (1004-38-2) + 2,5-dibromoterephtalic acid (13731-82-3) → 2C4H7N5*C8H4Br2O4

Conditions	Yield
In ethanol; water for 0.5h;	63%

Upstream product

• 106-42-3 para-xylene 
• 63525-48-4 2,5-dibromoterephthalaldehyde 
• 69065-15-2 2,5-dibromo-p-cumene 
• 7697-37-2 nitric acid 
• 20871-01-6 2,5-dibromo-4-methylbenzoic acid 
• 1074-24-4 2,5-dibromo-p-xylene 
• 18870-11-6 2,5-dibromobenzene-1,4-dinitrile 

Downstream Products

• 1268628-20-1 2,5-bis(2,2,3,3-tetrafluoropropoxy)terephthalic acid 
• 1268628-19-8 2,5-bis(2,2,2-trifluoroethoxy)terephthalic acid 
• 1314135-89-1 bis(6-((4'-cyano-[1,1'-biphenyl]-4-yl)oxy)hexyl) 2,5-dibromoterephthalate 
• 1050611-59-0 C₁₈H₂₂Br₂N₂O₂ 
• 1333248-71-7 C₄₂H₅₈N₄O₆S₂ 
• 1333248-64-8 C₃₆H₅₀N₄O₂S₂ 
• 1333248-59-1 C₄₂H₆₆N₄O₂S₂Si₂ 
• 58613-36-8 dibutyl 2,5-dibromoterephthalate 
• 1391086-22-8 3,7-bis(dodecylthio)-2,6-(5-phenyl-2-thienyl)benzo[1,2-b;4,5-b']dithiophene 
• 19126-26-2 1,4-dibromo-2,5-bis(p-tolyl-methanoyl)benzene 

Relevant articles and documents

Unfolding ESIPT in Bis-2,5-(2-benzoxazolyl) Hydroquinone and 2,5-Bis(benzo[d]oxazol-2-yl)-4-methoxyphenol: a Comprehensive Computational Approach

The photo-physical behaviour of bis-2,5-(2-benzoxazolyl) hydroquinone and 2,5-bis (benzo[d]oxazol-2-yl)-4-methoxyphenol was studied using the Density Functional Theory (DFT) and Time-Dependent Density Functional Theory (TD-DFT). All the possible rotamers were optimized to obtain global minimum optimized structure. The theoretical absorption and emission values of rotamers estimated by using TD-DFT [TD-B3LYP/6–31G(d)] are in good agreement with experimental absorption and emission wavelengths. Based on the absorption values, the contribution of respective rotamer is determined theoretically.

A heterofunctional ligand approach for the preparation of high connectivity coordination polymers: Combining a "bridge" and "pillar" in one ligand

Two of the most successful strategies for the preparation of three-dimensional coordination polymers and MOFs are reticular synthesis and pillaring. Here we present a new approach which combines aspects of both of these by employing a heterofunctional dicarboxylic and dipyridyl ligand, 2,5-di(pyridin-4-yl)terephthalic acid (H2L). The reaction of H2L with zinc(ii) produces a non-interpenetrated 3D coordination polymer [ZnL(H2O)]n. This journal is

PREPARING METHOD OF SYNTHESIZING INDACENO DITHIENOTHIOPHENE COMPOUND

Provided is a manufacturing method of synthesizing an indaseno-dithienothiophene compound using, as a novel starting material, a bis(thieno[3,2-b] thiophen-2-yl)-bismethanone derivative. The manufacturing method of synthesizing the indaseno-dithienothiophene compound has an excellent synthetic yield and improves production efficiency.COPYRIGHT KIPO 2020

Substituent effect on redox potential of terephthalate-based electrode materials for lithium batteries

The substituent effect on the redox potential of lithium terephthalate was studied using symmetrical dilithium disubstituted-terephthalates incorporating bromo, methoxy and amino groups. All the terephthalate derivatives have been synthesized and evaluated as anode material for lithium-ion batteries. The electrochemical results revealed an increase in the reduction potential in the case of bromo and methoxy groups and almost the same in the case of amino group compared to unmodified dilithium terephthalate. In addition, a very first tendency between the 13C chemical shifts and FTIR signal of the carbonyl and the reduction potential of the studied disubstituted-terephthalates was formulated.