1,5-Naphthalenediamine

1,5-Naphthalenediamine Basic information
Product Name:1,5-Naphthalenediamine
Synonyms:NCI-C03021;1,5-DIAMINONAPHTHALENE;1,5-NAPHTHALENEDIAMINE;1,5-NAPHTHYLENEDIAMINE;NAPHTHALENE-1,5-DIAMINE;1,5-DIAMINONAPHTHALENE, FOR FLUORESCENCE;Diaminonaphthalene;LABOTEST-BB LT00053486
CAS:2243-62-1
MF:C10H10N2
MW:158.2
EINECS:218-817-8
Product Categories:Amines;Aromatics;Benzoquinones, etc. (Charge Transfer Complexes);Charge Transfer Complexes for Organic Metals;Functional Materials;Mutagenesis Research Chemicals;Intermediates of Dyes and Pigments
Mol File:2243-62-1.mol
1,5-Naphthalenediamine Structure
1,5-Naphthalenediamine Chemical Properties
Melting point 185-187 °C(lit.)
Boiling point 200-210°C 5mm
density 1.4
vapor pressure 0Pa at 20℃
refractive index 1.6441 (estimate)
Fp 200-210°C/5mm
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility 0.04g/l
pka4.59±0.10(Predicted)
form Powder
color Gray to dark brown
Water Solubility <0.1 g/100 mL at 20.5 ºC
BRN 907947
LogP0.91
Dissociation constant4.21 at 25℃
CAS DataBase Reference2243-62-1(CAS DataBase Reference)
IARC3 (Vol. 27, Sup 7) 1987
NIST Chemistry Reference1,5-Naphthalenediamine(2243-62-1)
EPA Substance Registry System1,5-Naphthalenediamine (2243-62-1)
Safety Information
Hazard Codes Xn,N
Risk Statements 40-50/53
Safety Statements 36/37-60-61
RIDADR UN 3077 9/PG 3
WGK Germany 2
RTECS QJ3400000
HazardClass 9
PackingGroup III
HS Code 29215990
Hazardous Substances Data2243-62-1(Hazardous Substances Data)
MSDS Information
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1,5-Diaminonaphthalene English
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1,5-Naphthalenediamine Usage And Synthesis
Chemical PropertiesGREY TO DARK BROWN POWDER
UsesAromatic amines likely to have high carcinogenic potency. QSARs of aromatic amines.
Uses1,5-naphthalenediamine be used as intermediates for the synthesis of materials.
Uses1,5-Naphthalenediamineis an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs. The reducing properties of 1,5-diaminonaphthalene (1,5-DAN) as a MALDI matrix ( matrix-assisted laser desorption ionization) to amino acid sequencing and disulfide bond mapping of human urotensin II possessing one disulfide bond, and human guanylin possessing two disulfide bonds.
Production MethodsThe 1979 estimated production volume was 50,000 kg in Germany and Japan. The major use of the compound is for the manufacture of 1,5-naphthalene diisocyanate and in the production of polyurethane elastomers.
The potential for exposure to 1,5-naphthalenediamine may be greatest for workers involved in the manufacture of 1,5- naphthalene diisocyanate, which is known to hydrolyze readily to 1,5-naphthalenediamine upon contact with water.
DefinitionChEBI: A naphthalenediamine compound having amino substituents in the 1- and 5-positions.
General DescriptionColorless to pale purple crystals or lavender powder.
Air & Water Reactions1,5-Naphthalenediamine is sensitive to prolonged exposure to air. Insoluble in water.
Reactivity Profile1,5-Naphthalenediamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
HazardQuestionable carcinogen.
Fire HazardFlash point data for 1,5-Naphthalenediamine are not available. 1,5-Naphthalenediamine is probably combustible.
Safety ProfileSuspected carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic data. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Purification MethodsRecrystallise the amino-naphthalene from boiling H2O, but this is wasteful due to poor solubility. Boil it in chlorobenzene (charcoal), filter hot and cool the filtrate (preferably under N2). This gives colourless crystals. Dry it in a vacuum till free from chlorobenzene (odour), and store it in sealed ampoules under N2 away from light. [Beilstein 13 IV 340.]
1,5-Naphthalenediamine Preparation Products And Raw materials
Raw materials1,4,5-TRINITRONAPHTHALENE-->Naphthalene, 1,4,5,8-tetranitro--->5-nitronaphthalen-1-amine
Preparation Products1,5-Naphthalene diisocyanate-->5-Amino-1-naphthol
2,6-DICHLORO-1,5-DINITRONAPHTHALENE BIO-FARMA BF003747 SALOR-INT L166774-1EA 5-nitro-1-naphthalenamine 1,5-DINITRONAPHTHALENE-D6 2,6-DI-TERT-BUTYLNAPHTHALENE SULFONIC ACID SODIUM SALT SALOR-INT L166804-1EA 3,7-DI(TERT-BUTYL)-1,5-DINITRONAPHTHALENE 1,4,5-TRINITRONAPHTHALENE 4-CHLORO-1,5-DINITRONAPHTHALENE 4,8-DICHLORO-1,5-DINITRONAPHTHALENE 2,6-DIMETHYLNAPHTHALENE Solvent Black 3 DIRECT BROWN 74 1,5-Naphthalenediamine 3-[5-(3-CARBOXY-ACRYLOYLAMINO)-NAPHTHALEN-1-YLCARBAMOYL]-ACRYLIC ACID 1,5-Dinitronaphthalene NAPHTHALENE DIISOCYANATE

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