1465-25-4

Basic information

• Product Name: N-(1-Naphthyl)ethylenediamine dihydrochloride
• Synonyms: N-(α-Naphthyl)ethylene diamine dihydrochloride;NED 2HCL;N-(1-Naphthyl)ethylenediamine;N-(1-NAPHTHYL)ETHYLENEDIAMINE 2HCL;N-(1-NAPHTHYL)ETHYLENEDIAMINE DIHYDROCHLORIDE;N-1-NAPHTHYLETHYLENEDIAMINE DIHYDROCHLORIDE MONOMETHANOLATE;N-(1-NAPHTHYL)-ETHYLENEDIAMMONIUM DICHLORIDE;N-1-NAPHTHALENYL-1,2-ETHANEDI-AMINE DIHYDROCHLORIDE
• CAS NO: 1465-25-4
• Molecular Formula: C₁₂H₁₆N₂*2Cl
• Molecular Weight: 259.17
• EINECS: 215-981-2
• Product Categories: Nitrogen-containing compoundsDerivatization Reagents TLC;Sulfur-containing compoundsDerivatization Reagents TLC;TLC Reagents, N-RSpectroscopy;Derivatization Reagents TLC;TLC Visualization Reagents (alphabetic sort);TLC Visualization Reagents (by application);UV/Vis Reagents;UV/Visible (UV/VIS) Spectroscopy;Aromatic Amines;by Application;Derivatization Reagents;Derivatization Reagents HPLC;HPLC Derivatization Reagents;ACS Grade;Amine Salts;Analytical Reagents;Analytical/Chromatography;Building Blocks;Chemical Synthesis;Essential Chemicals;Inorganic Salts;Nitrogen Compounds;Organic Building Blocks;Research Essentials;Solutions and Reagents
• Mol File: 1465-25-4.mol
• Article Data: 0

Chemical Properties

• Melting Point: 200 °C
• Boiling Point: 370.7 °C at 760 mmHg
• Flash Point: 209.7 °C
• Appearance: White to beige or pink/Powder
• Vapor Pressure: 1.08E-05mmHg at 25°C
• Storage Temp.: Store at RT.
• Solubility: : passes test
• Water Solubility: soluble
• Sensitive: Light Sensitive & Hygroscopic
• Stability: Air Sensitive, Hygroscopic
• Merck: 14,6409
• BRN: 3707471
• CAS DataBase Reference: N-(1-Naphthyl)ethylenediamine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1-Naphthyl)ethylenediamine dihydrochloride(1465-25-4)
• EPA Substance Registry System: N-(1-Naphthyl)ethylenediamine dihydrochloride(1465-25-4)

Safety Data

• Hazard Codes: T,Xn,Xi
• Statements: 36/37/38-22-39/23/24/25-20/21/22
• Safety Statements: 36/37-45-37/39-26-36
• WGK Germany: 3
• RTECS: KV5330000
• F: 3-8-9-23
• TSCA: Yes
• Hazardous Substances Data: 1465-25-4(Hazardous Substances Data)

Usage

Chemical Properties

white to beige or pink powder

Uses

Different sources of media describe the Uses of 1465-25-4 differently. You can refer to the following data:
1. Coupling agent for the spectrophotometric determination of aminophenols, phenylenediamines, dinitroanilines, chloroanilines, thiols, and sulfonamides.1,2,3
2. Determination of sulfanilamide
3. Usually used as a coupling agent for spectrophotometric analysis.
4. N-(1-Naphthyl)ethylenediamine dihydrochloride acts as a coupling agent for the spectrophotometric determination of aromatic amines, aminophenols, phenylenediamines, dinitroanilines, chloroanilines, thiols and sulfonamides. It is also used in the quantitative analysis of nitrate and nitrite in water samples by colorimetry. It is involved in the preparation of (N-1-naphthyl-ethylenediamine)-dichloroplatinum(II) by reacting with potassium tetrachloroplatinate.

Definition

ChEBI: An ethylenediamine dihydrochloride compound having an N-(1-naphthyl) substituent.

General Description

White to light tan or gray crystalline solid or off-white powder.

Air & Water Reactions

N-(1-Naphthyl)ethylenediamine dihydrochloride is hygroscopic. Slightly soluble in water.

Reactivity Profile

N-(1-Naphthyl)ethylenediamine dihydrochloride may decompose on exposure to light. N-(1-Naphthyl)ethylenediamine dihydrochloride is incompatible with acids, acid chlorides, acid anhydrides and oxidizing agents.

Fire Hazard

Flash point data for N-(1-Naphthyl)ethylenediamine dihydrochloride are not available; however, N-(1-Naphthyl)ethylenediamine dihydrochloride is probably combustible.

Purification Methods

Crystallise the salt from water. [Beilstein 12 II 699.]

InChI:InChI=1/C12H14N2/c13-8-9-14-12-7-3-5-10-4-1-2-6-11(10)12/h1-7,14H,8-9,13H2/p+1

Synthetic route

ethyl trifluoroacetate, (383-63-1) + N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) → 2,2,2-trifluoro-N-(2-(naphthalen-1-ylamino)ethyl)acetamide (895775-85-6)

Conditions	Yield
With water; N-ethyl-N,N-diisopropylamine In acetonitrile Reflux;	86%

N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) + Thioctic acid (1077-28-7, 62-46-4) → 5-[1,2]dithiolan-3-yl-pentanoic acid [2-(naphthalene-1-ylamino)ethyl]amide (1151851-91-0)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane	85%

tetrafluoroterephthalonitrile (1835-49-0) + N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) → C20H13F3N4

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Sonication;	80%

potassium tetrachloroplatinate(II) (10025-99-7) + N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) → ((1-naphthyl)-NH2CH2CH2NH3)PtCl4 (467218-94-6)

Conditions	Yield
In water 1 equiv. of N-compd. in aq. soln. (30 °C) was added to warm (40 °C) of Pt-compd. under stirring; soln. was allowed to stand at 0 °C for 20 min, ppt. was filtered off, washed with small amt. of H2O and ether, dried in vac.;	75%

N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) + orthoformic acid triethyl ester (122-51-0) → C13H12N2*ClH

Conditions	Yield
Heating;	66%

N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → C23H20N2O

Conditions	Yield
With acetic acid In ethanol Reflux;	65%
With acetic acid In ethanol at 85℃; for 12h;	52%

benzene diazonium chloride (100-34-5) + N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) → N-(4-phenylazo-[1]naphthyl)-ethylenediamine (132472-74-3)

N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) → N-Aminoethyl-1,4-naphthylendiamin (87790-97-4)

Conditions	Yield
With sodium sulfanilate; acetic acid; zinc 2.) 1,4-dioxane; Multistep reaction;

N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) → N--ethylenediamine monohydrochloride

Conditions	Yield
beim Erhitzen unter vermindertem Druck;

N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) + 5'-Amino-3-methanesulfonyl-1'-methyl-4,5-dihydro-3H,1'H-[1,2']biimidazolyl-2-one → 5'-[4-(2-amino-ethylamino)-naphthalen-1-ylazo]-3-methanesulfonyl-1'-methyl-4,5-dihydro-3H,1'H-[1,2']biimidazolyl-2-one; compound with GENERIC INORGANIC NEUTRAL COMPONENT

Conditions	Yield
Stage #1: 5'-Amino-3-methanesulfonyl-1'-methyl-4,5-dihydro-3H,1'H-[1,2']biimidazolyl-2-one With hydrogenchloride; sodium nitrite Stage #2: N-(1-naphthyl)ethylenediamine dihydrochloride

N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) + 2-(4,7,10-tris(tert-butoxycarbonyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetic acid (247193-74-4) → 10-{[2-(naphthalen-1-ylamino)-ethylcarbamoyl]-methyl}-1,4,7,10tetraaza-cyclododecane-1,4,7-tricarboxylic acid tri-tert-butyl ester

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 24h;

N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) → N-[2-(naphthalen-1-ylamino)-ethyl]-2-(1,4,7,10tetraaza-cyclododec-1-yl)-acetamide; compound with GENERIC INORGANIC NEUTRAL COMPONENT

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N; HOBt; DCC / tetrahydrofuran / 24 h / 20 °C 2: 1.0 g / HCl / methanol / 20 °C View Scheme

N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) → 6-Acetylamino-benzochinoxalin (87790-99-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) sulfanilic acid sodium salt, 2.) Zn, acetic acid / 2.) 1,4-dioxane 2: PDC / dimethylformamide / 0.25 h 3: pyridine View Scheme

N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) → 6-Amino-benzoquinoxaline (87790-98-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) sulfanilic acid sodium salt, 2.) Zn, acetic acid / 2.) 1,4-dioxane 2: PDC / dimethylformamide / 0.25 h View Scheme

N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) → N-(1-naphthyl)ethylenediamine (551-09-7)

Conditions	Yield
With pyridine; dmap In dichloromethane

3-chloro-N-(naphthalen-1-yl)propanamide (22302-59-6) + N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) + butan-1-ol (71-36-3) → 3-[(1-naphthylamino)ethylamino]-N-(1-naphthyl)propionamide dihydrochloride

Conditions	Yield
With hydrogenchloride; potassium iodide; potassium carbonate

methanol (67-56-1) + 2-chloro-N-(1-naphthyl)acetamide (832-89-3) + N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) + butan-1-ol (71-36-3) → [2-(1-naphthylamino)ethylamino]-N-(1-naphthyl)acetamide monohydrochloride monohydrate

Conditions	Yield
With hydrogenchloride; potassium iodide; potassium carbonate In hexane	1.5 g (39.1%)

N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) + 3-(α-chloroacetylamino)quinoline (121221-07-6) → 2-(1-naphthylamino)ethylamino-N-(3-quinolyl)acetamide dihydrochloride monohydrate

Conditions	Yield
With hydrogenchloride; potassium iodide; potassium carbonate In N-methyl-acetamide

5-(α-chloroacetylamino)quinoline (121221-08-7) + N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) → [2-(1-naphthylamino)ethylamino]-N-(5-quinolyl)acetamide dihydrochloride monohydrate

Conditions	Yield
With hydrogenchloride; potassium iodide; potassium carbonate In N-methyl-acetamide	4 g (22.5%)

2-chloro-N-(naphthalen-1-yl)propanamide (22302-58-5) + N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) → 2-[2-(1-naphthylamino)ethylamino]-N-(1-naphthyl)propionamide monohydrate

Conditions	Yield
With potassium iodide; potassium carbonate In acetonitrile

N-(5-quinoxalyl)-2-chloroacetamide (33544-33-1) + N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) → [2-(1-naphthylamino)ethylamino]-N-(5-quinoxalyl)-acetamide dihydrochloride

Conditions	Yield
With hydrogenchloride; potassium iodide; potassium carbonate In N-methyl-acetamide

2-chloropropionyl chloride (7623-09-8) + N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) → N-[(1-naphthylamino)ethyl]-2-chloropropionamide

Conditions	Yield
With triethylamine In tetrahydrofuran

N-(1-naphthyl)ethylenediamine dihydrochloride (1465-25-4) + benzyl chloroformate (501-53-1) → phenylmethyl [2-(1-naphthalenylamino)ethyl]-carbamate (1146411-78-0)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;

Downstream Products

• 551-09-7 N-(1-naphthyl)ethylenediamine 
• 13231-94-2 4-[4-(2-Amino-ethylamino)-naphthalen-1-ylazo]-benzenesulfonamide 
• 1146411-78-0 phenylmethyl [2-(1-naphthalenylamino)ethyl]-carbamate 
• 87790-98-5 6-Amino-benzoquinoxaline 
• 132472-74-3 N-(4-phenylazo-[1]naphthyl)-ethylenediamine