1,5-Naphthalenediamine supplier

Name
1,5-Naphthalenediamine
EINECS 218-817-8
CAS No. 2243-62-1
Article Data61
CAS DataBase
Density 1.234 g/cm³
Solubility <0.1 g/100 mL at 20.5 °C in water
Melting Point 185-187 °C(lit.)
Formula C₁₀H₁₀N₂
Boiling Point 381.4 °C at 760 mmHg
Molecular Weight 158.203
Flash Point 220.2 °C
Transport Information UN 3077 9/PG 3
Appearance Grey to dark brown powder
Safety 36/37-60-61
Risk Codes 40-50/53
Molecular Structure
Hazard Symbols Xn, N
Synonyms 1,5-DAN;1,5-Diamine naphthaline;1,5-Diaminonaphthalene;1,5-Naphthalindiamine;NSC 401110;
PSA 52.04000
LogP 3.16660

Synthetic route

: 2243-95-0
1,4,5-trinitronaphthalene

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 10h;	100%

: 3272-91-1
5-nitro-[1]naphthylamine

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With hydrogen In palladium; toluene	97.5%
With hydrogenchloride; titanium(III) chloride
(electrochemical reduction);
With hydrogen; palladium-containing anion exchanger AB-17-8-Pd In ethanol at 45℃; under 750.06 Torr; Kinetics; Further Variations:; Solvents; Catalysts;

: 83-55-6
5-amino-1-naphthol

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With ammonium hydrogen sulfite; ammonia In water at 150℃; for 6h;	93%
With ammonium hydrogen sulfite; ammonia In diethylene glycol dimethyl ether; water at 150℃; for 6h;	93.6%

: 605-71-0
1,5-dinitronaphthalene

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With sodium tetrahydroborate; diphenyl ditelluride In ethanol; benzene at 55℃; for 15h;	92%
With iodophosphorus; water
With sulfuric acid; acetic acid elektrolytische Reduktion an Bleikathoden;

: 4793-98-0
1,4,5,8-tetranitronaphthalene

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 25℃; for 15h;	90%

: ammonium bisulfite

: 90-15-3
α-naphthol

: 117-59-9
1-hydroxynaphthalene-5-sulphonic acid

: 83-56-7
1,5-dihydroxynaphthalene

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With sodium hydroxide; sulfur dioxide; ammonia In titanium; water	86%

...Expand

: 605-71-0
1,5-dinitronaphthalene

A: 3272-91-1
5-nitro-[1]naphthylamine

B: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With sodium sulfide; ammonium hydroxide at 80℃;	A 54% B 34%
With sodium sulfide; ammonium chloride In water at 80 - 85℃; for 4h;	A 54% B 34%
With nickel; hydrazine hydrate In ethanol; 1,2-dichloro-ethane at 50 - 60℃; for 8h;	A 20.33% B 47.26%

: 91-20-3
naphthalene

A: 134-32-7
1-amino-naphthalene

B: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; acetic acid In water at 80℃; for 4h; Catalytic behavior; Reagent/catalyst; Temperature;	A 11.6% B 52.3%
With sodium amide; phenol at 220℃;

: 134-32-7
1-amino-naphthalene

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With sodium metavanadate; hydroxylamine hydrochloride; acetic acid In water at 30 - 80℃; for 4.33333h; Reagent/catalyst; Solvent; Temperature;	9.8%
With naphthalene; sodium amide at 230℃;
With hydroxylamine hydrochloride; acetic acid In water at 80℃; for 4h;

: 91-20-3
naphthalene

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With sodium amide; phenol at 220℃;
Multi-step reaction with 2 steps 1: phenol; sodium amide / 220 °C 2: naphthalene; sodium amide / 230 °C View Scheme

: 90-15-3
α-naphthol

A: 83-55-6
5-amino-1-naphthol

B: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With naphthalene; sodium amide

: 83-56-7
1,5-dihydroxynaphthalene

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With ammonia at 150 - 180℃; schliesslich Erhitzen auf 250-300grad;
With ammonium sulfite; ammonia at 125℃;

: 1,5-diamino-naphthalene-2-sulfonic acid

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With diluted acid

: C10H9N2(1-)*K(1+)

: 75-33-2
2-propanethiol

A: 51042-72-9
KSiPr

B: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With dimethyl sulfoxide; dimsyl potassium salt at 25℃; Thermodynamic data;

...Expand

: C10H9N2(1-)*K(1+)

: 62-53-3
aniline

A: 19642-99-0
potassium anilide

B: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With dimethyl sulfoxide; dimsyl potassium salt at 25℃; Thermodynamic data;

...Expand

: C10H9N2(1-)*K(1+)

: 108-42-9
3-chloro-aniline

A: 146962-56-3
C6H5ClN(1-)*K(1+)

B: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With dimethyl sulfoxide; dimsyl potassium salt at 25℃; Thermodynamic data;

...Expand

: C10H9N2(1-)*K(1+)

: 479-27-6
naphthalene-1,8-diamine

A: C10H9N2(1-)*K(1+)

B: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With dimethyl sulfoxide; dimsyl potassium salt at 25℃; Thermodynamic data;

...Expand

: 1-[N-(tert-butyloxycarbonyl)amino]-5-aminonaphthalene

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
With methanol; Amberlyst 15; ammonia 1.) CH2Cl2, 25 deg C, 4 d, 2.) 50 min; Yield given. Multistep reaction;

: 91-20-3
naphthalene

: 134-32-7
1-amino-naphthalene

: sodium amide

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
at 230℃;

...Expand

: 91-20-3
naphthalene

: 134-32-7
1-amino-naphthalene

: sodium amide

A: 2243-62-1
1,5-diaminonaphthalene

B naphthalene hydride/s: naphthalene hydride/s

Conditions

Conditions	Yield
at 230℃; bei laengerem Erhitzen;

...Expand

: 605-71-0
1,5-dinitronaphthalene

acetic acid-H2SO4-solution: acetic acid-H2SO4-solution

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
bei elektrochemischer Reduktion an Bleikathoden;

: 605-71-0
1,5-dinitronaphthalene

ammonium sulfide: ammonium sulfide

: 2243-62-1
1,5-diaminonaphthalene

: 7732-18-5
water

: 605-71-0
1,5-dinitronaphthalene

iodophosphorus: iodophosphorus

: 2243-62-1
1,5-diaminonaphthalene

...Expand

: 7732-18-5
water

: iron(II) sulfate

: 605-71-0
1,5-dinitronaphthalene

iron-powder: iron-powder

: 2243-62-1
1,5-diaminonaphthalene

...Expand

: 7647-01-0
hydrogenchloride

: 605-71-0
1,5-dinitronaphthalene

tin dichloride: tin dichloride

: 2243-62-1
1,5-diaminonaphthalene

...Expand

: 7647-01-0
hydrogenchloride

: 605-71-0
1,5-dinitronaphthalene

tin: tin

: 2243-62-1
1,5-diaminonaphthalene

...Expand

: 91-20-3
naphthalene

: 90-15-3
α-naphthol

: sodium amide

: 2243-62-1
1,5-diaminonaphthalene

...Expand

: 83-56-7
1,5-dihydroxynaphthalene

: ammonium hydroxide

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
at 300℃;

: 83-56-7
1,5-dihydroxynaphthalene

: 7664-41-7
ammonia

ammonium sulfite: ammonium sulfite

: 2243-62-1
1,5-diaminonaphthalene

Conditions

Conditions	Yield
at 125℃;

...Expand

: 24677-78-9
2,3-dihydroxybenzaldehyde

: 2243-62-1
1,5-diaminonaphthalene

: C24H18N2O4

Conditions

Conditions	Yield
In methanol	100%

: 407-25-0
trifluoroacetic anhydride

: 2243-62-1
1,5-diaminonaphthalene

: 98332-03-7
1,5-bis(trifluoroacetamido)naphthalene

Conditions

Conditions	Yield
at 5 - 25℃; for 2h;	98%
With triethylamine In tetrahydrofuran; benzene at 60℃; for 0.5h;

: bis(acetylacetonato)palladium(II)

: 2243-62-1
1,5-diaminonaphthalene

: [Pd(CH3COCHCOCH3)(NH2C10H6NH)]2

Conditions

Conditions	Yield
In benzene benzene soln. contg. Pd(acac)2 and excess diamine refluxed for 30 min, cooled to room temp.; ppt. filtered, washed with petroleum ether, recrystd. from hot benzene;	98%

: 538-75-0
dicyclohexyl-carbodiimide

: 2243-62-1
1,5-diaminonaphthalene

: 1342886-14-9
C36H54N6

Conditions

Conditions	Yield
With [Li(THF)(DME)]3La[μ-η2η1(iPrN)2C(NC6H4p-Cl)]3 at 50℃; for 5h; Inert atmosphere;	98%

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 2243-62-1
1,5-diaminonaphthalene

: 183659-47-4
N,N'-bis(2-hydroxy-3-methoxybenzyliden)-1,5-diaminonaphthalene

Conditions

Conditions	Yield
In ethanol for 2.5h; Reflux;	98%
In methanol	83%
In methanol for 8h; Reflux;	62%
In ethanol for 2.5h; Reflux;

: 104-88-1
4-chlorobenzaldehyde

: 2243-62-1
1,5-diaminonaphthalene

: 1408310-87-1
(E,E)-N1,N5-di(4-chlorobenzylidene)naphthalene-1,5-diamine

Conditions

Conditions	Yield
In ethanol Reflux;	97%

: 123-54-6
acetylacetone

: 2243-62-1
1,5-diaminonaphthalene

: (Z)-4-(5-((Z)-4-oxopent-2-en-2-ylamino)naphthalen-1-ylamino)pent-3-en-2-one

Conditions

Conditions	Yield
With acetic acid In ethanol for 3h; Reflux;	96%

: 17920-90-0
3,3,7-trimethyl-oct-6-enal

: 2243-62-1
1,5-diaminonaphthalene

: N,N'-bis(3',3',7'-trimethyloct-6'-enylidene)naphthalene-1,5-diamine

Conditions

Conditions	Yield
With 4 Angstroem powdered MC In dichloromethane Ambient temperature;	95%

: 911649-50-8
2,3-di(isopropylmercapto)benzoic acid chloride

: 2243-62-1
1,5-diaminonaphthalene

: 1165947-30-7
1,5-bis[2,3-di(isopropylmercapto)benzamido]naphthalene

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;	95%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere; Schlenk technique;	1.06 g

: 693-13-0
diisopropyl-carbodiimide

: 2243-62-1
1,5-diaminonaphthalene

: 1342886-13-8
C24H38N6

Conditions

Conditions	Yield
With [Li(THF)(DME)]3La[μ-η2η1(iPrN)2C(NC6H4p-Cl)]3 at 25℃; for 2h; Inert atmosphere;	95%

: 90-02-8
salicylaldehyde

: 2243-62-1
1,5-diaminonaphthalene

: 1449790-51-5
3,3'-[naphthalene-1,5-diylidi(E)diazene-2,1-diyl]bis(6-hydroxybenzaldehyde)

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 0 - 20℃; for 1h;	95%

: 541-41-3
chloroformic acid ethyl ester

: 2243-62-1
1,5-diaminonaphthalene

: 51977-17-4
1,5-bis-(ethoxycarbonylamino)naphthalene

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water at 20℃; for 12h;	95%

: 50-00-0
formaldehyd

: 2243-62-1
1,5-diaminonaphthalene

: 10075-69-1
N1,N1,N5,N5-tetramethyl-1,5-diaminonaphthalene

Conditions

Conditions	Yield
Stage #1: formaldehyd; 1,5-naphthalenediamine In ethanol; water Stage #2: With platinum(IV) oxide; hydrogen In ethanol; water under 760.051 Torr;	95%

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 762-04-9
phosphonic acid diethyl ester

: 2243-62-1
1,5-diaminonaphthalene

: tetraethyl((naphthalene-1,5-diylbis(azanediyl))bis((3,4dimethoxyphenyl)methylene))bis(phosphonate)

Conditions

Conditions	Yield
With palladium diacetate In neat (no solvent) for 0.0833333h; Catalytic behavior; Reagent/catalyst; Time; Microwave irradiation; Green chemistry;	95%

...Expand

: 77-78-1
dimethyl sulfate

: 2243-62-1
1,5-diaminonaphthalene

: 10075-69-1
N1,N1,N5,N5-tetramethyl-1,5-diaminonaphthalene

Conditions

Conditions	Yield
With sodium carbonate In methanol for 5h;	94.7%
With sodium carbonate In water at 20℃;	65%

: 141-97-9
ethyl acetoacetate

: 2243-62-1
1,5-diaminonaphthalene

: 861575-93-1
ethyl 3-[[5-[3-ethoxy-1-methyl-3-oxo-prop-1-enylamino]-1-naphthyl]amino]but-2-enoate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol for 4h; Molecular sieve; Reflux;	94%
With toluene-4-sulfonic acid In ethanol; water for 18h; Inert atmosphere; Reflux; Dean-Stark;	83%

: 135672-63-8
N-(p-anisyldiphenylmethyl) β-alanine

: 2243-62-1
1,5-diaminonaphthalene

: N1,N5-bis[3-(N-monomethoxytrityl)aminopropionyl]-1,5-diaminonaphthalene

Conditions

Conditions	Yield
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃; for 20h;	93%

: C15H15NO6

: 2243-62-1
1,5-diaminonaphthalene

: C24H21N3O5

Conditions

Conditions	Yield
With 5,15,10,20-tetraphenylporphyrin; calcium chloride In pyridine; 1-methyl-pyrrolidin-2-one at 60 - 130℃; for 10.5h; Inert atmosphere;	93%

1,5-Naphthalenediamine Chemical Properties

Chemical Name: 1,5-Naphthalenediamine
IUPAC NAME: Naphthalene-1,5-diamine
CAS No.: 2243-62-1
EINECS: 218-817-8
RTECS: QJ3400000
Molecular Formula: C₁₀H₁₀N₂
Molecular Weight: 158.2 g/mol
Melting Point: 185-187 °C(lit.)
Density: 1.234 g/cm³
Flash Point: 220.2 °C
Boiling Point: 381.4 °C at 760 mmHg
Following is the structure of 1,5-Naphthalenediamine (2243-62-1):

Product Categories about 1,5-Naphthalenediamine (2243-62-1) are Intermediates of Dyes and Pigments ; Benzoquinones, etc. (Charge Transfer Complexes) ; Charge Transfer Complexes for Organic Metals ; Functional Materials
The chemical synonymous of 1,5-Naphthalenediamine (2243-62-1) are NCI-C03021 ; LABOTEST-BB LT00053486 ; 1,5-Diaminonaphthalene ; 1,5-Naphthalenediamine ; 1,5-Naphthylenediamine ; Naphthalene-1,5-diamine ; 1,5-Diaminonaphthalene, For Fluorescence ; Diaminonaphthalene

1,5-Naphthalenediamine Uses

1,5-Naphthalenediamine (2243-62-1) is mainly used in organic synthesis.

1,5-Naphthalenediamine Toxicity Data With Reference

1.	mma-sat 33,300 ng/plate	ENMUDM Environmental Mutagenesis. 7 (Suppl 5)(1985),1.
2.	mma-sat 33,300 ng/plate	ENMUDM Environmental Mutagenesis. 7 (Suppl 5)(1985),1.
3.	orl-rat TDLo:721 g/kg/1Y-C:CAR	IARC** IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (World Health Organization, Internation Agency for Research on Cancer, Lyon, France) 27 (1982),127.
4.	orl-rat TD:18 g/kg/88W-C:ETA,REP	NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-143 ,1978.
5.	orl-rat TDLo:54 g/kg/2Y-C:NEO	NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-143 ,1978.

1,5-Naphthalenediamine Consensus Reports

IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 27 ,1982,p. 127.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse, rat NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-143 ,1978. . EPA Genetic Toxicology Program.

1,5-Naphthalenediamine Safety Profile

Suspected carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic data. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x. See also AMINES.
Hazard Codes:
Xn: Harmful
N: Dangerous for the environment
Risk Statements about 1,5-Naphthalenediamine (2243-62-1):
R40 Limited evidence of a carcinogenic effect.
R50/53 Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements about 1,5-Naphthalenediamine (2243-62-1):
S36/37 Wear suitable protective clothing and gloves.
S60 This material and its container must be disposed of as hazardous waste.
S61 Avoid release to the environment. Refer to special instructions/safety data sheets.
Attentions:
1. Storage: Store in a cool, dry place. Store in a tightly closed container.
2. Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.

Product Name

1,5-Naphthalenediamine

Synthetic route

1,5-Naphthalenediamine Chemical Properties

1,5-Naphthalenediamine Uses

1,5-Naphthalenediamine Toxicity Data With Reference

1,5-Naphthalenediamine Consensus Reports

1,5-Naphthalenediamine Safety Profile

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