618-88-2

Basic information

• Product Name: 5-Nitroisophthalic acid
• Synonyms: NITROISOPHTHALIC-5 ACID;NITRO ISOPHTHALIC ACID;5-NIPA ;5-NITRO-ISO-PHTHALIC ACID PESTANAL;1,3-BENZENEDICARBOXYLIC ACID,5-NITRO;5-NITROISOPHTHALIC ACID 99+%;5-NITROISOPHTHALIC ACID5-NITRO-PHENYL-1,3-DICARBOXYLIC ACID;5-Nitro-m-phthalic acid
• CAS NO: 618-88-2
• Molecular Formula: C₈H₅NO₆
• Molecular Weight: 211.13
• EINECS: 210-568-3
• Product Categories: Phthalic Acids, Esters and Derivatives;Organic acids;Building Blocks;C8;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 618-88-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 259-261 °C(lit.)
• Boiling Point: 350.79°C (rough estimate)
• Flash Point: 120°C
• Appearance: light cream crystalline powder
• Density: 1.6342 (rough estimate)
• Vapor Pressure: 8.85E-10mmHg at 25°C
• Refractive Index: 1.5282 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Acetonitrile (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)
• PKA: 2.81±0.10(Predicted)
• Water Solubility: Soluble in water.1.5 g/L at 20°C
• BRN: 1976587
• CAS DataBase Reference: 5-Nitroisophthalic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitroisophthalic acid(618-88-2)
• EPA Substance Registry System: 5-Nitroisophthalic acid(618-88-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-40
• Safety Statements: 26-36-22
• RIDADR: 2811
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 618-88-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 618-88-2 differently. You can refer to the following data:
1. 5-Nitrobenzene-1,3-Dicarboxylic Acid is used in the synthesis of Glycopyrrolate, a novel pharmaceutical compound based on PDE IV inhibitors; used in the treatment of respiratory complaints. Also used in the synthesis of coordination polymers.
2. 5-Nitroisophthalic acid is used as an intermediate of medicine compound and as a disperser in dyes. It is used as an intermediate in organic synthesis,agrochemical,pharmaceutical and dyestuffs etc,.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C8H5NO6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H,(H,10,11)(H,12,13)/p-2

Synthetic route

isophthalic acid (121-91-5) → 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2)

Conditions	Yield
With sulfuric acid; nitric acid at 50 - 75℃; Temperature; Concentration;	90%
Stage #1: isophthalic acid With sulfuric acid at 75℃; for 0.5h; Stage #2: With nitric acid at 75 - 90℃; Temperature; Time;	88.3%
With fuming sulphuric acid; nitric acid at 25 - 90℃; for 4h;	83%

isophthalic acid (121-91-5) → 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + 4-nitroisophthalic acid (4315-09-7)

Conditions	Yield
With nitric acid at 30℃;

5-nitro-m-xylene (99-12-7) → 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2)

Conditions	Yield
With chromic acid

5-nitro-m-xylene (99-12-7) → 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + 5-Methyl-3-nitrobenzoic acid (113882-33-0)

Conditions	Yield
With nitric acid

isophthalic acid (121-91-5) + nitric acid (7697-37-2) → 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + 4-nitroisophthalic acid (4315-09-7)

3-(3-benzoyl-5-nitro-benzoyl)-benzoic acid + acetic acid (64-19-7) + chromium (VI)-oxide → 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2)

m-xylene (108-38-3) → 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: alkaline permanganate 2: concentrated nitric acid / 30 °C View Scheme
Multi-step reaction with 2 steps 1: potassium permanganate; sodium hydroxide / water / 144 h / Reflux 2: nitric acid; sulfuric acid / 24 h / Reflux View Scheme

3-nitrobenzoic acid (121-92-6) → 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2)

Conditions	Yield
	2.5 mol %

5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → 5-nitro-1,3-benzenedicarbonylchloride (13438-30-7)

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide for 6h; Heating;	100%
With thionyl chloride Reflux;	100%
With thionyl chloride In N,N-dimethyl-formamide at 6℃; Heating;	99.1%

methanol (67-56-1) + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → dimethyl 5-nitroisophthalate (13290-96-5)

Conditions	Yield
With sulfuric acid for 3h; Inert atmosphere; Reflux;	98%
With hydrogenchloride

zinc(II) nitrate hexahydrate + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + trans-1,2-bis(4-pyridyl)ethylene (1135-32-6) → [Zn(5-nitroisophthalate)(1,2-di(4-pyridyl)ethylene)]n

Conditions	Yield
In water; N,N-dimethyl-formamide at 120℃; for 6h;	97%
In water; N,N-dimethyl-formamide at 20℃; for 6h;	97%
In water; N,N-dimethyl-formamide at 120℃; for 6h;	97%
In N,N-dimethyl-formamide N2 atm., DMF-soln.;

5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + water (7732-18-5) + zinc(II) chloride (7646-85-7) → [Zn(5-nitroisophthalate)(H2O)](n) (710946-12-6)

Conditions	Yield
With NaOH In water High Pressure; mixt. of 5-nitroisophthalic acid, NaOH, and H2O heated till boiling; cooled; soln. put into bomb; ZnCl2 added; bomb sealed; heated at 142°C for 72 h; cooled to room temp.; crystals obtained; elem. anal.;	95.6%

5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → 5-aminoisophthalic acid (99-31-0)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; under 760 Torr; for 1h;	95%
Stage #1: 5-nitrobenzene-1,3-dicarboxylic acid With sodium hydroxide In water for 1h; Stage #2: With hydrazine hydrate In water at 30 - 35℃; for 1h; Concentration; Temperature;	95%
With hydrogenchloride; tin

5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + tert-butyl alcohol (75-65-0) → di-tert-butyl 5-nitroisophthalate

Conditions	Yield
Stage #1: 5-nitrobenzene-1,3-dicarboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 12h; Stage #2: tert-butyl alcohol With dmap In toluene at 20 - 25℃; for 4h;	95%
With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 23℃; Inert atmosphere;	64%

5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + 4-aminobenzene sulfonic acid (121-57-3) → 4,4'-[(5-nitrobenzene-1,3-diyl)bis(carbonylimino)]dibenzenesulfonic acid (792175-38-3)

Conditions	Yield
With pyridine; triphenyl phosphite In N,N-dimethyl acetamide at 75 - 115℃; Inert atmosphere;	94.7%

5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → 3,5,3',5'-azobenzenetetracarboxylic acid (365549-33-3)

Conditions	Yield
Stage #1: 5-nitrobenzene-1,3-dicarboxylic acid With sodium hydroxide In water at 60℃; for 1h; Stage #2: With D-glucose In water for 0.5h; Stage #3: In water at 20℃; for 16h;	92%
Stage #1: 5-nitrobenzene-1,3-dicarboxylic acid With sodium hydroxide In water at 60℃; for 1h; Stage #2: In water Heating; Stage #3: With oxygen In water at 20℃; for 16h;	92%
Stage #1: 5-nitrobenzene-1,3-dicarboxylic acid With sodium hydroxide In water at 60℃; for 0.5h; Stage #2: With D-Glucose Stage #3: With hydrogenchloride In water pH=1;	90%

1,10-Phenanthroline (66-71-7) + copper(II) choride dihydrate + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + water (7732-18-5) → [CuCl(1,10-phenanthroline)2](C8H4NO6)*2H2O

Conditions	Yield
at 160℃; for 72h; Autoclave;	92%

zinc dioxide + 1,2-bis(4'-pyridyl)ethane (4916-57-8) + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + trans-1,2-bis(4-pyridyl)ethylene (1135-32-6) → C8H3NO6(2-)*0.8C12H10N2*0.2C12H12N2*Zn(2+)

Conditions	Yield
With zirconia balls In water at 20℃; for 1h;	91%

5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → dimethyl 5-nitroisophthalate (13290-96-5)

Conditions	Yield
With thionyl chloride In methanol at 0 - 80℃; for 6h; Inert atmosphere;	90%
With hydrogenchloride
With sulfuric acid In methanol; water; toluene

5-t-butylisophthalic acid (2359-09-3) + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + zinc(II) oxide + trans-1,2-bis(4-pyridyl)ethylene (1135-32-6) → [Zn(NO2ip)0.95(tBuip)0.05(bpe)]

Conditions	Yield
In water at 25℃; for 1h;	90%

5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → 5-nitro-m-xylene-(α,α')-diol (71176-55-1)

Conditions	Yield
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 20℃; for 16h;	89%
Stage #1: 5-nitrobenzene-1,3-dicarboxylic acid In tetrahydrofuran at 0 - 20℃; for 49h; Stage #2: With methanol In tetrahydrofuran	88.6%
With borane-THF In tetrahydrofuran at 0 - 25℃; for 44.5h; Inert atmosphere;	83%

ethanol (64-17-5) + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → diethyl 5-nitro-isophthalate (10560-13-1)

Conditions	Yield
With sulfuric acid for 36h; Heating;	88%
With hydrogenchloride

1H-imidazole (288-32-4) + copper(II) nitrate trihydrate + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → [(copper)3(5-nitro-1,3-benzenedicarboxylate)2(hydoxy)2(imidazole)2]n

Conditions	Yield
In ethanol; water High Pressure; hydrothermal reaction of Cu(NO3)2*3H2O, 5-nitro-1,3-benzenedicarboxylic acid and imidazole in aqua-alcohol solution; crystn.;	88%

cadmium(II) nitrate tetrhydrate + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + 4-stilbazole → [Cd2(5-nitrobenzene-1,3-dicarboxylic acid)2(5-nitrobenzene-1,3-dicarboxylic acid)2(H2O)4]·(4-styrylpyridine-H)2

Conditions	Yield
In water at 150℃; for 72h; Autoclave; regiospecific reaction;	88%

1,2-bis(4'-pyridyl)ethane (4916-57-8) + zinc(II) nitrate hexahydrate + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → Zn(5-nitroisophthalic acid(-2H))(1,2-di(4-pyridyl)ethane)

Conditions	Yield
With potassium hydroxide In water at 160℃; for 72h;	88%

1,2-bis(4'-pyridyl)ethane (4916-57-8) + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + zinc(II) acetate dihydrate (5970-45-6) → Zn(5-nitroisophthalic acid(-2H))(1,2-di(4-pyridyl)ethane)

Conditions	Yield
With potassium hydroxide In water at 160℃; for 72h;	88%

zinc(II) nitrate (10196-18-6) + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + N4,N4′-di(pyridin-4-yl)-[1,1′-biphenyl]-4,4′- dicarboxamide (1381886-63-0) → Zn(N4,N4'-di(pyridin-4-yl)biphenyl-4,4'-dicarboxamide)(5-nitro-isophthalate)

Conditions	Yield
In water; N,N-dimethyl-formamide at 120℃; for 48h; Autoclave;	88%

nickel(II) nitrate hexahydrate + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + N-(pyridin-2-yl)-N-(4-(2-(pyridin-4-yl)vinyl)-phenyl)pyridin-2-amine + water (7732-18-5) + acetonitrile (75-05-8) → [Ni(dipyridin-2-yl-[4-(2-pyridin-4-yl-vinyl)-phenyl]amine)(5-nitroisophthalate)(H2O)]2*MeCN

Conditions	Yield
at 150℃; for 48h; Sealed tube; High pressure;	88%

1H-imidazole (288-32-4) + cobalt(II) nitrate hexahydrate + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → [cobalt(II)(5-nitro-1,3-benzenedicarboxylate)(imidazole)2]n

Conditions	Yield
In ethanol; water High Pressure; Co(NO3)2*6H2O, 5-nitro-1,3-benzenedicarboxylic acid and imidazole mixed in aqua-alcohol solution, hydrothermal conditions; crystn.;	85%

1,10-Phenanthroline (66-71-7) + copper(II) nitrate trihydrate + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → [Cu(5-nitroisophthalate)(1,10-phenanthroline)]n (781673-71-0)

Conditions	Yield
With NaOH In water High Pressure; mixture of Cu(NO3)2*3H2O, 5-nitroisophthalic acid, 1,10-phenanthroline, and NaOH stirred in air for 15 min, sealed, heated hydrothermally at 150°C for 5 d, cooled to room temp. at rate 5 °C/h; washed with water; elem. anal.;	85%

N,N'-dimethylpiperazine (106-58-1) + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → C8H5NO6*0.5C6H14N2

Conditions	Yield
With nitric acid In methanol; water; N,N-dimethyl-formamide pH=5;	85%

cadmium(II) nitrate tetrhydrate + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + 1,4-bis(1H-imidazol-4-yl)benzene (96982-29-5) + water (7732-18-5) → Cd(2+)*C12H10N4*C8H3NO6(2-)*3H2O

Conditions	Yield
With sodium hydroxide at 120℃; for 72h; High pressure;	85%

pyridine-4-carboxylic acid (55-22-1) + europium(III) nitrate hexahydrate + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + water (7732-18-5) + zinc(II) acetate dihydrate (5970-45-6) → [EuZn(5-nitroisophthalate)2(isonicotinate)(H2O)]n

Conditions	Yield
With triethylamine at 150℃; for 72h; pH=Ca. 3; Autoclave; High pressure;	85%

cobalt(II) nitrate hexahydrate + 1,2-bis(4'-pyridyl)ethane (4916-57-8) + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → [(Co(1,2-bis(4-pyridyl)ethylene)(5-nitro-1,3-benzenedicarboxylate))*0.5(1,2-bis(4-pyridyl)ethylene)](n)*nH2O

Conditions	Yield
With NaOH In water High Pressure; pH preadjusted to about 6, sealed in an autoclave, heated to 200°C for 72 h; crystallization on slow cooling; elem. anal.;	84%

2-ethyl-N-(2-ethylhexyl)-1-hexanamine (106-20-7) + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → C40H71N3O4 (1360595-64-7)

Conditions	Yield
Stage #1: 5-nitrobenzene-1,3-dicarboxylic acid With thionyl chloride In chloroform at 10 - 65℃; for 3h; Stage #2: 2-ethyl-N-(2-ethylhexyl)-1-hexanamine With triethylamine In chloroform at 64℃; for 3h;	83.4%

1,10-Phenanthroline (66-71-7) + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) + trimethyltin(IV)chloride (1066-45-1) + water (7732-18-5) → [(Me3Sn)2(5-nitroisophthalate)(H2O)]*1,10-phenanthroline

Conditions	Yield
With sodium ethoxide In methanol (N2); addn. of acid and EtONa to methanol, stirring for 10 min, addn. oftin compd., addn. of phen, heating to 40°C for 12 h, cooling to room temp.; filtration, gradual evapn. in vac., recrystn. (hexane/CH2Cl2); elem. anal.;	83%

1,2-bis(4'-pyridyl)ethane (4916-57-8) + aqueous cadmium chloride + 5-nitrobenzene-1,3-dicarboxylic acid (618-88-2) → Cd[1,2-bis(4-pyridyl)ethane]1.5[5-nitro-1,3-benzenedicarboxylate](H2O)0.25

Conditions	Yield
With NaOH In water High Pressure; hydrothermally, mixed, pH adjusted to 6 (aq.NaOH), in stainless autoclave at 180°C for 72 h; cooled to room temp, elem. anal.;	82%

Upstream product

• 121-92-6 3-nitrobenzoic acid 
• 108-38-3 m-xylene 
• 64-19-7 acetic acid 
• 121-91-5 isophthalic acid 
• 7697-37-2 nitric acid 
• 99-12-7 5-nitro-m-xylene 

Downstream Products

• 365549-33-3 3,5,3',5'-azobenzenetetracarboxylic acid 
• 110935-45-0 3,3',5,5'-Azoxybenzoltetracarbonsaeure-tetramethylester 
• 1299474-88-6 N,N'-bis[6-(2-ethylhexanoylamino)pyrid-2-yl]-5-nitroisophthalamide 
• 1299474-84-2 5-nitro-N,N'-bis[6-(pentanoylamino)pyrid-2-yl]isophthalamide 
• 1268162-29-3 poly[Zn(3,5-diamino-1,2,4-triazole)(5-nitroisophthalate) monohydrate] 
• 1287189-56-3 N₁,N₃-bis(3,5-bis(trifluoromethyl)phenyl)-5-nitrobenzene-1,3-dicarboxamide 

Relevant articles and documents

5-Nitroisophthalic acid hydrate

In the title compound, C8H5NO6·H2O, the carboxylic acid groups are coplanar with the phenyl ring, whereas the nitro group is twisted from it by 26.1 (3)°. In the crystal, the molecules are linked by O - H...O hydrogen bonds through the water molecules and by weak C -H...O hydrogen bonds involving the nitro groups, to form infinite zigzag sheets.

Synthesizing method of 5-nitroisophthalic acid

The invention discloses a synthesizing method of 5-nitroisophthalic acid. The synthesizing method comprises the following steps of reacting, washing by water, filtering, recrystallizing and purifying.The synthesizing method has the advantages that by using isophthalic acid as a raw material, a small amount of concentrated sulfuric acid and 60% of nitric acid are used for reacting and nitrifying,so as to synthesize the 5-nitroisophthalic acid; the usage amounts of sulfuric acid and nitric acid are reduced, the effective utilization rate of equipment is improved, the generation of waste liquidin production is reduced, the difficulty in treatment of the waste liquid is decreased, the problem of nitrifying difficulty is solved, and the economic benefit and environment-friendly social benefit of the product are improved.

Liquid-Crystalline Star-Shaped Supergelator Exhibiting Aggregation-Induced Blue Light Emission

A family of closely related star-shaped stilbene-based molecules containing an amide linkage are synthesized, and their self-assembly in liquid-crystalline and gel states was investigated. The number and position of the peripheral alkyl tails were systematically varied to understand the structure-property relation. Interestingly, one of the molecules with seven peripheral chains was bimesomorphic, exhibiting columnar hexagonal and columnar rectangular phases, whereas the rest of them stabilized the room-temperature columnar hexagonal phase. The self-assembly of these molecules in liquid-crystalline and organogel states is extremely sensitive to the position and number of alkoxy tails in the periphery. Two of the compounds with six and seven peripheral tails exhibited supergelation behavior in long-chain hydrocarbon solvents. One of these compounds with seven alkyl chains was investigated further, and it has shown higher stability and moldability in the gel state. The xerogel of the same compound was characterized with the help of extensive microscopic and X-ray diffraction studies. The nanofibers in the xerogel are found to consist of molecules arranged in a lamellar fashion. Furthermore, this compound shows very weak emission in solution but an aggregation-induced emission property in the gel state. Considering the dearth of solid-state blue-light-emitting organic materials, this molecular design is promising where the self-assembly and emission in the aggregated state can be preserved. The nonsymmetric design lowers the phase-transition temperatures.The presence of an amide bond helps to stabilize columnar packing over a long range because of its polarity and intermolecular hydrogen bonding in addition to promoting organogelation.