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1,4,5,8-Naphthalenetetracarboxylic acid

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Name

1,4,5,8-Naphthalenetetracarboxylic acid

EINECS 204-924-7
CAS No. 128-97-2 Density 1.751 g/cm3
PSA 149.20000 LogP 1.63260
Solubility Soluble in water Melting Point 180 °C
Formula C14H8O8 Boiling Point 737.9 °C at 760 mmHg
Molecular Weight 304.213 Flash Point 414 °C
Transport Information N/A Appearance Pale yellow solid
Safety 26-36 Risk Codes 36
Molecular Structure Molecular Structure of 128-97-2 (1,4,5,8-Naphthalenetetracarboxylic acid) Hazard Symbols IrritantXi
Synonyms

1,4,5,8-Tetracarboxynaphthalene;NSC 66207;Tetra acid;naphthalene-1,4,5,8-tetracarboxylic acid;

Article Data 36

1,4,5,8-Naphthalenetetracarboxylic acid Synthetic route

157100-92-0

cyclopenta[fg]acenaphthylene-1,2,5,6-tetraene

128-97-2

naphthalene-1,4,5,8-tetracarboxylic acid

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydroxide In 1,4-dioxane; water at 60℃; for 2h; Reagent/catalyst;91%
129-00-0

pyrene

128-97-2

naphthalene-1,4,5,8-tetracarboxylic acid

Conditions
ConditionsYield
With sodium dichromate; sulfuric acid
With chromium(III) oxide; sulfuric acid weitere Oxydation mit alkal. Chlorkalk-Loesung;
Multi-step reaction with 3 steps
1: SO2Cl2; nitrobenzene
2: fuming sulfuric acid; SO3 / 80 °C / Erhitzen der mit wss. Schwefelsaeure auf 98 prozentig. Saeure verduennten Reaktionsloesung auf 200grad und Erhitzen des Reaktionsprodukts mit Wasser auf Siedetemperatur
3: alkaline aqueous sodium hypochlorite
View Scheme
Multi-step reaction with 2 steps
1: bromine; nitrobenzene / 120 °C
2: concentrated sulfuric acid / 160 - 170 °C / Behandeln des Reaktionsgemisches mit Salpetersaeure bei 120-180grad
View Scheme
Multi-step reaction with 2 steps
1: chromic acid
2: KMnO4
View Scheme
36440-69-4

1,2-dihydro-cyclopenta[cd]phenalen-5-one

128-97-2

naphthalene-1,4,5,8-tetracarboxylic acid

Conditions
ConditionsYield
With chromic acid; acetic acid
6169-92-2

4-oxo-4H-phenalene-1,9-dicarboxylic acid

128-97-2

naphthalene-1,4,5,8-tetracarboxylic acid

Conditions
ConditionsYield
With potassium permanganate
128-63-2

1,3,6,8-tetrabromopyrene

128-97-2

naphthalene-1,4,5,8-tetracarboxylic acid

Conditions
ConditionsYield
With sulfuric acid at 160 - 170℃; Behandeln des Reaktionsgemisches mit Salpetersaeure bei 120-180grad;
With sulfuric acid at 160 - 170℃; Behandeln des Reaktionsgemisches mit Salpetersaeure bei 120-180grad;
5698-99-7

5,6-acenaphthenedicarboxylic acid

128-97-2

naphthalene-1,4,5,8-tetracarboxylic acid

Conditions
ConditionsYield
With alkaline permanganate
With copper(II) acetate dihydrate; manganese(II) acetate dihydrate; oxygen; acetic acid; potassium bromide at 140℃; under 15200.4 Torr; for 2h; Reagent/catalyst; Time; Temperature;
76662-39-0

1,2-dihydro-cyclopenta[cd]phenalene-5,7-dione

128-97-2

naphthalene-1,4,5,8-tetracarboxylic acid

Conditions
ConditionsYield
With nitric acid at 150℃; im Rohr;
With alkaline potassium permanganate
59320-81-9

5,7-diimino-2,5,6,7-tetrahydro-1H-cyclopenta[cd]phenalene

128-97-2

naphthalene-1,4,5,8-tetracarboxylic acid

Conditions
ConditionsYield
With sodium dichromate; sulfuric acid
6345-20-6

6,7-dihydrocycloheptacenaphthene-5,8-dione

128-97-2

naphthalene-1,4,5,8-tetracarboxylic acid

Conditions
ConditionsYield
With sodium dichromate; acetic acid
With sodium hydroxide; potassium permanganate
873385-36-5

pyrene-1,3,6,8-tetraol

128-97-2

naphthalene-1,4,5,8-tetracarboxylic acid

1,4,5,8-Naphthalenetetracarboxylic acid Consensus Reports

Reported in EPA TSCA Inventory.

1,4,5,8-Naphthalenetetracarboxylic acid Specification

The 1,4,5,8-Naphthalenetetracarboxylic acid, with the CAS registry number 128-97-2 and EINECS registry number 204-924-7, has the systematic name of naphthalene-1,4,5,8-tetracarboxylic acid. It is a kind of intermediates of Dyes and Pigments. And the molecular formula of this chemical is C14H8O8.

The physical properties of 1,4,5,8-Naphthalenetetracarboxylic acid are as following: (1)ACD/LogP: 1.37; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4.51; (4)ACD/LogD (pH 7.4): -4.78; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 8; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 105.2 Å2; (13)Index of Refraction: 1.765; (14)Molar Refractivity: 71.81 cm3; (15)Molar Volume: 173.6 cm3; (16)Polarizability: 28.46×10-24cm3; (17)Surface Tension: 107.8 dyne/cm; (18)Density: 1.751 g/cm3; (19)Flash Point: 414 °C; (20)Enthalpy of Vaporization: 112.98 kJ/mol; (21)Boiling Point: 737.9 °C at 760 mmHg; (22)Vapour Pressure: 7.33E-23 mmHg at 25°C.

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)c1ccc(c2c(ccc(C(=O)O)c12)C(=O)O)C(=O)O
(2)InChI: InChI=1/C14H8O8/c15-11(16)5-1-2-6(12(17)18)10-8(14(21)22)4-3-7(9(5)10)13(19)20/h1-4H,(H,15,16)(H,17,18)(H,19,20)(H,21,22)
(3)InChIKey: OLAPPGSPBNVTRF-UHFFFAOYAR

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 3800mg/kg (3800mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 90, 1982.
rat LD50 oral 7500mg/kg (7500mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 90, 1982.

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