52671-72-4

Basic information

• Product Name: 1,4,5,8-Naphthalenetetracarboxylic acid 1,8-monoanhydride
• Synonyms: 1,4,5,8-Naphthalenetetracarboxylic acid 1,8-monoanhydride;3-dihydrobenzo[de]isochroMene-6;3-dioxo-1;7-dicarboxylic acid;1,3-dioxo-1,3-dihydrobenzo[de]isochromene-6,7-dicarboxylic acid;1,3-Dioxo-1H,3H-naphtho[1,8-cd]pyran-6,7-dicarbonsure;1,4,5,8-Naphthalintetracarbonsure-1,8-monoanhydrid;1H,3H-Naphtho[1,8-cd]pyran-6,7-dicarboxylic acid, 1,3-dioxo-
• CAS NO: 52671-72-4
• Molecular Formula: C₁₄H₆O₇
• Molecular Weight: 286.194
• Mol File: 52671-72-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 692.8 °C at 760 mmHg
• Flash Point: 272.2 °C
• Appearance: /
• Density: 1.769
• Vapor Pressure: 3.75E-20mmHg at 25°C
• Refractive Index: 1.772
• PKA: 0.88±0.20(Predicted)
• CAS DataBase Reference: 1,4,5,8-Naphthalenetetracarboxylic acid 1,8-monoanhydride(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,5,8-Naphthalenetetracarboxylic acid 1,8-monoanhydride(52671-72-4)
• EPA Substance Registry System: 1,4,5,8-Naphthalenetetracarboxylic acid 1,8-monoanhydride(52671-72-4)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36-50
• Safety Statements: 26-36/37-61
• RIDADR: UN 3077
• Hazardous Substances Data: 52671-72-4(Hazardous Substances Data)

Usage

General Description

May contain varying amounts of tetracarboxylic acid

InChI:InChI=1/C14H6O7/c15-11(16)5-1-3-7-10-8(14(20)21-13(7)19)4-2-6(9(5)10)12(17)18/h1-4H,(H,15,16)(H,17,18)

Synthetic route

naphthalene-1,4,5,8-tetracarboxylic acid (128-97-2) → monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid (52671-72-4)

Conditions	Yield
at 30℃;	80%

C14H4O8(4-)*4K(1+) → monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid (52671-72-4)

Conditions	Yield
With phosphoric acid pH=6.2 - 6.4;

1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) → monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid (52671-72-4)

Conditions	Yield
With potassium hydroxide pH=6.4;
In water Equilibrium constant; Acid hydrolysis;

tetrasodium salt of 1,4,5,8-naphthalene tetracarbocyclic acid (17273-41-5, 93094-23-6, 96315-29-6) → monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid (52671-72-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH 2: 80 percent / 30 °C View Scheme

monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid (52671-72-4) + trimethyltin(IV)chloride (1066-45-1) → O(2-)*C14H4O7(2-)*2Sn(4+)*4CH3(1-)

Conditions	Yield
Stage #1: monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid; trimethyltin(IV)chloride With potassium hydroxide In water pH=Ca. 5 - 6; Autoclave; Stage #2: In water at 130℃; for 72h; Autoclave;	40%

monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid (52671-72-4) + Trimethylenediamine (109-76-2) → C31H18N2O12

Conditions	Yield
Stage #1: monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid; Trimethylenediamine With phosphoric acid In water for 24h; pH=6.2 - 6.4; Heating; Stage #2: With acetic acid pH=5.0;

monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid (52671-72-4) + methylamine hydrochloride (593-51-1) → 2-methyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-6,7-dicarboxylic acid

Conditions	Yield
With phosphoric acid at 110℃; pH=6.4;

monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid (52671-72-4) + benzyl N-(2-aminoethyl)carbamate hydrochloride (18807-71-1) → 2-(2-benzyloxycarbonylamino-ethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-6,7-dicarboxylic acid (849543-70-0)

Conditions	Yield
With phosphoric acid at 110℃; pH=6.4;

monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid (52671-72-4) + isobutylamine (78-81-9) → 2-isobutyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-6,7-dicarboxylic acid

Conditions	Yield
With phosphoric acid at 110℃; pH=6.4;

monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid (52671-72-4) → 1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1)

Conditions	Yield
In water Equilibrium constant; Acid hydrolysis;

monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid (52671-72-4) → 1,3-bis(1,8-naphthalene-tetracarboxylic-monoimide-4,5-monohydro)-propane (351999-12-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: phosphoric acid / H2O / 24 h / pH 6.2 - 6.4 / Heating 1.2: acetic acid / pH 5.0 2.1: 9.5 g / acetic anhydride / Heating View Scheme

monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid (52671-72-4) → C35H22N4O8

Conditions	Yield
Multi-step reaction with 3 steps 1.1: phosphoric acid / H2O / 24 h / pH 6.2 - 6.4 / Heating 1.2: acetic acid / pH 5.0 2.1: 9.5 g / acetic anhydride / Heating 3.1: 2.7 percent / 1,4-diaza[2.2.2]bicyclooctane / 1-methyl-pyrrolidin-2-one; dimethylformamide / 54 h / 100 °C View Scheme

monoanhydride of 1,4,5,8-naphthalenetetracarboxylic acid (52671-72-4) + naphthalene-1,4,5,8-tetracarboxylic acid (128-97-2) → 1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1)

Conditions	Yield
In N,N-dimethyl acetamide; toluene at 111℃; for 2h; Solvent; Temperature; Inert atmosphere;	73 g

Upstream product

• 17273-41-5 tetrasodium salt of 1,4,5,8-naphthalene tetracarbocyclic acid 
• 128-97-2 naphthalene-1,4,5,8-tetracarboxylic acid 
• 81-30-1 1,4,5,8-naphthalenetetracarboxylic dianhydride 

Downstream Products

• 849543-70-0 2-(2-benzyloxycarbonylamino-ethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-6,7-dicarboxylic acid 
• 81-30-1 1,4,5,8-naphthalenetetracarboxylic dianhydride 
• 83204-68-6 2,6-dibromo-1,4,5,8-naphthalenetetracarboxylic acid dianhydride 

Relevant articles and documents

Synthesis and characterization of [3,3]- and [3,4]-perinophane

Synthesis of [3,3]- and [3,4]-perinophanes is described via a novel route which will permit the synthesis of both symmetrical and unsymmetrical perinophanes and related cyclophane structures.

Modulating charge transfer through cyclic D,L-α-peptide self-assembly

We describe a concise, solid support-based synthetic method for the preparation of cyclic D,L-α-peptides bearing 1,4,5,8- naphthalenetetracarboxylic acid diimide (NDI) side chains. Studies of the structural and photoluminescence properties of these molecules in solution show that the hydrogen bond-directed self-assembly of the cyclic D,L-α-peptide backbone promotes intermolecular NDI excimer formation. The efficiency of NDI charge transfer in the resulting supramolecular assemblies is shown to depend on the length of the linker between the NDI and the peptide backbone, the distal NDI substituent, and the number of NDIs incorporated in a given structure. The design rationale and synthetic strategies described here should provide a basic blueprint for a series of self-assembling cyclic D,L-α-peptide nanotubes with interesting optical and electronic properties.