1,4,5,8-Naphthalenetetracarboxylic dianhydride

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Names

[ CAS No. ]:
81-30-1

[ Name ]:
1,4,5,8-Naphthalenetetracarboxylic dianhydride

[Synonym ]:
Isochromeno[6,5,4-def]isochromene-1,3,6,8-tetrone
MFCD00006915
NTCDA
Naphthalenetetracarboxylic dianhydride
QK3695000
UNII:L56XQD1V6Y
1,4,5,8-Naphthalenetetracarboxylic acid dianhydride
Naphthalene-1,4,5,8-tetracarboxylic dianhydride
1,4,5,8-Naphthalenetetracarboxylic dianhydride
[2]Benzopyrano[6,5,4-def][2]benzopyran-1,3,6,8-tetrone
Naphtho[1,8-cd:4,5-c'd']dipyran-1,3,6,8-tetrone
Isochromeno[6,5,4-def]isochromene-1,3,6,8-tetraone
EINECS 201-342-5
{[2]Benzopyrano[6,5,4-def][2]benzopyran-1,3,6,8-tetrone}

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
617.0±38.0 °C at 760 mmHg

[ Melting Point ]:
>300 °C(lit.)

[ Molecular Formula ]:
C₁₄H₄O₆

[ Molecular Weight ]:
268.178

[ Flash Point ]:
280.4±26.8 °C

[ Exact Mass ]:
268.000793

[ PSA ]:
86.74000

[ LogP ]:
0.06

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.782

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QK3695000

CAS REGISTRY NUMBER :: 81-30-1

BEILSTEIN REFERENCE NO. :: 0272788

LAST UPDATED :: 199709

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C14-H4-O6

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 7400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GMAT "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982 Volume(issue)/page/year: -,90,1982

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intratracheal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 50 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GMAT "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982 Volume(issue)/page/year: -,90,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GMAT "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982 Volume(issue)/page/year: -,90,1982

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
QK3695000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

pyrene-1,3,6,8-tetrone
1,4,5,8-Naphthalenetetracarboxylic acid
3-chloro-1,6-pyrenequinone
3-methoxypyrene-1,6-dione
1,6-Pyrenedione
pyrene-1,8-dione
Pyrene
Pyrene,1,3,6,8-tetrachloro-
1,3,6,8-Tetrabromopyrene

DownStream

4,9-Dibromo-2,7-bis(2-decyltetradecyl)benzo[lMn][3,8]phenanthroline-1,3,6,8-tetraone
1,4,5,8-Naphthalenetetracarboxylic acid 1,8-monoanhydride
Benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone
Vat Orange 7
Vat Red 15
naphthalene diimide
4,5,9,10-Tetrabromoisochromeno[6,5,4-def]isochromene-1,3,6,8- tetraone
2-Bromonaphthalene-1,4,5,8-tetracarboxylic 1,8:4,5-Dianhydride
4,9-DIBROMOISOCHROMENO[6,5,4-DEF]ISOCHROMENE-1,3,6,8-TETRAONE
4-Bromo-2,7-dihexylbenzo[lMn][3,8]phenanthroline-1,3,6,8-tetraone

Articles

Unexpected photoluminescence of fluorinated naphthalene diimides.

Chemistry 21(10) , 4133-40, (2015)

Two new amino core-substituted naphthalene diimides (cNDIs) bearing fluorinated side chains have been synthesised. Steady-state and time-resolved fluorescence spectroscopy reveals unprecedented optica...

NTCDA-TTF first axial fusion: emergent panchromatic, NIR optical, multi-state redox and high optical contrast photooxidation.

Chem. Commun. (Camb.) 48(52) , 6475-7, (2012)

The first synthetic entry into axially fused NTCDA/PMDA-TTF multipolar molecules demonstrates a high optical contrast photooxidation, panchromism, low HOMO-LUMO gap, generation of a stable radical cat...

Newman, C.R., et al.

Chem. Mater. 16 , 4436, (2004)

2-bromo-1,4,5,8-naphthalenetetracarboxylic dianhydride
1,4,5,8-Naphthalenetetracarboxylic acid tetrapotassium salt
1,4,5,8-Naphthalenetetracarboxylic acid 1,8-monoanhydride
1,4,5,8-Naphthalenetetracarboxylic acid
1,4,5,8-NAPHTHALENETETRACARBOXYLIC ACID HYDRATE
4,5,9,10-Tetrabromoisochromeno[6,5,4-def]isochromene-1,3,6,8- tetraone