131-73-7

Basic information

• Product Name: DIPICRYLAMINE
• Synonyms: CI 10360;DIPICRYLAMINE;Dipicrylamine ammonium salt;HNDP;HNDPH;HEXANITRODIPHENYLAMINE;HEXANITRODIPHENYLAMINE AMMONIUM SALT;HEXIL
• CAS NO: 131-73-7
• Molecular Formula: C₁₂H₅N₇O₁₂
• Molecular Weight: 439.21
• EINECS: 205-037-8
• Mol File: 131-73-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: about 238° with dec
• Boiling Point: 550.83°C (rough estimate)
• Flash Point: 275.9°C
• Appearance: /
• Density: 1.6613 (rough estimate)
• Refractive Index: 1.6400 (estimate)
• PKA: pK1:5.42(＋1) (25°C)
• Water Solubility: 2.4 mg l-1 (e)
• CAS DataBase Reference: DIPICRYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: DIPICRYLAMINE(131-73-7)
• EPA Substance Registry System: DIPICRYLAMINE(131-73-7)

Safety Data

• Hazard Codes: E,T+,N
• Statements: 2-26/27/28-33-51/53
• Safety Statements: 35-36-45-61
• RIDADR: 0079
• HazardClass: 1.1D
• Hazardous Substances Data: 131-73-7(Hazardous Substances Data)

Usage

Preparation

Dinitrodiphenylamine is treated with 98%?nitric acid. The starting material, dinitrodiphenylamine, is obtained from the reaction of?aniline, dinitrochlorobenzene, and soda ash.

Chemical Properties

Yellow solid.decomposes violently at higher temperatures. Insoluble in water and alcohol; soluble in alkalies and warm acetic or nitric acid.

Uses

Reagent for gravimetric determination of potassium.

Hazard

Explodes on shock or exposure to heat, dangerous.

InChI:InChI=1/C6H13/c1-3-5-6-4-2/h1,3-6H2,2H3

Synthetic route

N-phenyl-2,4-dinitroaniline (961-68-2) → Dipikrylamin (131-73-7)

Conditions	Yield
technische Gewinnung;
With nitric acid
Nitrierung;

picramide (489-98-5) → 1,2,3,5-tetranitrobenzene (3698-53-1) + Dipikrylamin (131-73-7)

Conditions	Yield
With nitric acid at -5 - 7℃; Einleiten von nitrosen Gasen;

N,N-diphenylurea (603-54-3) → Dipikrylamin (131-73-7)

Conditions	Yield
With sulfuric acid; nitric acid

(2,4-dinitro-phenyl)-picryl-amine (21565-22-0) → Dipikrylamin (131-73-7)

Conditions	Yield
With nitric acid at 70℃;

benzhydrylidene(methyl)amine (552-82-9) → Dipikrylamin (131-73-7)

Conditions	Yield
With nitric acid

trinitro-2,4,6 diphenylamine (2919-12-2) → Dipikrylamin (131-73-7)

Conditions	Yield
With nitric acid mit rauchender Salpetersaeure;
With nitric acid at 25℃; mit absol. Salpetersaeure;
With sulfuric acid; nitric acid at 70℃;
Multi-step reaction with 2 steps 1: nitric acid / 25 °C / mit Salpetersaeure (D:1.49) 2: nitric acid / 70 °C View Scheme

bis(2,4-dinitrophenyl)amine (2908-76-1) → Dipikrylamin (131-73-7)

Conditions	Yield
With nitric acid at 70 - 90℃; mit 93prozentiger Salpetersaeure;
With sulfuric acid; nitric acid at 20 - 32℃;
Nitrierung;

N-(p-nitrophenyl)picrylamine (38417-97-9) → Dipikrylamin (131-73-7)

Conditions	Yield
With sulfuric acid; nitric acid

bis-(2,4-dinitro-phenyl)-carbamic acid ethyl ester (871882-90-5) → Dipikrylamin (131-73-7)

Conditions	Yield
With sulfuric acid; nitric acid

trinitro-2,4,6 diphenylamine (2919-12-2) + acetic acid (64-19-7) + isopentyl nitrite (110-46-3) → (2,4-dinitro-phenyl)-picryl-amine (21565-22-0) + Dipikrylamin (131-73-7)

diphenylamine (122-39-4) → Dipikrylamin (131-73-7)

Conditions	Yield
Nitrierung;
With nitric acid
With sulfuric acid; nitric acid

pyridin-1-ium (16969-45-2) + Dipicrylamin-Anion (32817-38-2) → pyridine (110-86-1) + Dipikrylamin (131-73-7)

Conditions	Yield
for 11h; Rate constant;

2,4,6-trinitrochlorobenzene (88-88-0) + picramide (489-98-5) → Dipikrylamin (131-73-7)

Conditions	Yield
With sodium hydride; iodophenylbis(triphenylphosphine)palladium acetonitrile, 6 h; Yield given. Multistep reaction;

sulfuric acid (7664-93-9) + N,N-diphenylurea (603-54-3) + 10 part nitric acid → Dipikrylamin (131-73-7)

Conditions	Yield
in der Waerme;

N-phenyl-2,4-dinitroaniline (961-68-2) + nitric acid (7697-37-2) → Dipikrylamin (131-73-7)

trinitro-2,4,6 diphenylamine (2919-12-2) + nitric acid (7697-37-2) → Dipikrylamin (131-73-7)

Conditions	Yield
at 25℃; bei 24-stuendiger Einw.;
auf dem Wasserbad;

bis(2,4-dinitrophenyl)amine (2908-76-1) + HNO3+H2SO4 → Dipikrylamin (131-73-7)

bis(2,4-dinitrophenyl)amine (2908-76-1) + nitric acid (93 percent ) → Dipikrylamin (131-73-7)

Conditions	Yield
at 40 - 90℃;

sulfuric acid (7664-93-9) + trinitro-2,4,6 diphenylamine (2919-12-2) + nitric acid (D:1.49) → Dipikrylamin (131-73-7)

Conditions	Yield
at 70℃;

picramide (489-98-5) + nitric acid (7697-37-2) + nitrogen oxide → 1,2,3,5-tetranitrobenzene (3698-53-1) + Dipikrylamin (131-73-7)

sulfuric acid (7664-93-9) + N,N-diphenylurea (603-54-3) + 10 part nitric acid → Dipikrylamin (131-73-7) + N.N-bis-<2.4-dinitro-phenyl>-urea

Conditions	Yield
in der Kaelte;

1-methoxy-2,4,6-trinitrobenzene (606-35-9) → Dipikrylamin (131-73-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aniline; alcohol 2: nitric acid / mit rauchender Salpetersaeure View Scheme

2,4,6-trinitrochlorobenzene (88-88-0) → Dipikrylamin (131-73-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: alcohol 2: HNO3+H2SO4 View Scheme

4-nitro-aniline (100-01-6) → Dipikrylamin (131-73-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: alcohol 2: HNO3+H2SO4 View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; potassium nitrate 2: aqueous HNO3 / -5 - 7 °C / Einleiten von nitrosen Gasen View Scheme

1,3-diaminoguanidine hydrochloride (36062-19-8) + Dipikrylamin (131-73-7) → CH7N5*C12H5N7O12 (1352994-43-4)

Conditions	Yield
Stage #1: Dipikrylamin With sodium hydroxide In water at 80℃; for 0.5h; Stage #2: 1,3-diaminoguanidine hydrochloride In water at 20℃; for 1h;	97%

ammonium chloride (12125-02-9) + Dipikrylamin (131-73-7) → dipicryl-amin; ammonium salt (2844-92-0)

Conditions	Yield
Stage #1: Dipikrylamin With sodium hydroxide In water at 80℃; for 0.5h; Stage #2: ammonium chloride In water at 20℃; for 1h;	96%

hydrazine hydrochloride (2644-70-4) + Dipikrylamin (131-73-7) → C12H5N7O12*H4N2 (1352994-40-1)

Conditions	Yield
Stage #1: Dipikrylamin With sodium hydroxide In water at 80℃; for 0.5h; Stage #2: hydrazine hydrochloride In water at 20℃; for 1h;	93%

Dipikrylamin (131-73-7) + 1-amino-3-methyl-1,2,3-triazol-3-ium iodide → C3H7N4(1+)*C12H4N7O12(1-)

Conditions	Yield
Stage #1: Dipikrylamin With sodium hydroxide In water at 80℃; for 0.5h; Stage #2: 1-amino-3-methyl-1,2,3-triazol-3-ium iodide In water at 20℃; for 1h;	89%

1-methyl-3,4,5-triamino-1,2,4-triazolium iodide (1052012-46-0, 1173151-14-8) + Dipikrylamin (131-73-7) → C3H9N6(1+)*C12H4N7O12(1-)*H2O

Conditions	Yield
Stage #1: Dipikrylamin With sodium hydroxide In water at 80℃; for 0.5h; Stage #2: 1-methyl-3,4,5-triamino-1,2,4-triazolium iodide In water at 20℃; for 1h;	88%

Imidazole hydrochloride (1467-16-9) + Dipikrylamin (131-73-7) → C3H4N2*C12H5N7O12 (1352994-39-8)

Conditions	Yield
Stage #1: Dipikrylamin With sodium hydroxide In water at 80℃; for 0.5h; Stage #2: Imidazole hydrochloride In water at 20℃; for 1h;	87%

ethylenediamine hydrochloride (18299-54-2) + Dipikrylamin (131-73-7) → C2H8N2*2C12H5N7O12

Conditions	Yield
Stage #1: Dipikrylamin With sodium hydroxide In water at 80℃; for 0.5h; Stage #2: ethylenediamine hydrochloride In water at 20℃; for 1h;	86%

4,7-dimethyl-3-chloromethyl-2H-1-benzopyran-2-one (58476-20-3) + Dipikrylamin (131-73-7) → 3-{[Bis-(2,4,6-trinitro-phenyl)-amino]-methyl}-4,7-dimethyl-chromen-2-one (138719-90-1)

Conditions	Yield
In benzene for 4h; Heating;	50%

crystal violet carbinol base (467-63-0) + nitrobenzene (98-95-3) + Dipikrylamin (131-73-7) → dipicryl-(4,4',4''-tris-dimethylamino-trityl)-amine

pararosaniline (467-62-9) + acetone (67-64-1) + Dipikrylamin (131-73-7) → dipicryl-(4,4',4''-triamino-trityl)-amine

crystal violet carbinol base (467-63-0) + acetone (67-64-1) + Dipikrylamin (131-73-7) → dipicryl-(4,4',4''-tris-dimethylamino-trityl)-amine

pararosaniline (467-62-9) + Dipikrylamin (131-73-7) → dipicryl-(4,4',4''-triamino-trityl)-amine

Conditions	Yield
With acetone

crystal violet carbinol base (467-63-0) + Dipikrylamin (131-73-7) → dipicryl-(4,4',4''-tris-dimethylamino-trityl)-amine

Conditions	Yield
With acetone
With nitrobenzene

pyridine (110-86-1) + Dipikrylamin (131-73-7) → pyridin-1-ium (16969-45-2) + Dipicrylamin-Anion (32817-38-2)

Conditions	Yield
for 11h; Rate constant;

Dipikrylamin (131-73-7) → dipicryl-amine; sodium-salt (13474-21-0)

Conditions	Yield
With sodium hydride In acetonitrile for 3h;

Upstream product

• 2919-12-2 trinitro-2,4,6 diphenylamine 
• 64-19-7 acetic acid 
• 110-46-3 isopentyl nitrite 
• 7664-93-9 sulfuric acid 
• 603-54-3 N,N-diphenylurea 
• 88-88-0 2,4,6-trinitrochlorobenzene 
• 100-01-6 4-nitro-aniline 
• 606-35-9 1-methoxy-2,4,6-trinitrobenzene 
• 489-98-5 picramide 
• 7697-37-2 nitric acid 
• 2908-76-1 bis(2,4-dinitrophenyl)amine 
• 961-68-2 N-phenyl-2,4-dinitroaniline 
• 16969-45-2 pyridin-1-ium 
• 32817-38-2 Dipicrylamin-Anion 

Downstream Products

• 2844-92-0 dipicryl-amin; ammonium salt 
• 1352994-40-1 C₁₂H₅N₇O₁₂*H₄N₂ 
• 41721-50-0 silver(I) dipicrylaminate 
• 16969-45-2 pyridin-1-ium 
• 32817-38-2 Dipicrylamin-Anion 

Relevant articles and documents

POLYNITRO- AND POLY(TRIFLUOROMETHYLSULFONYL)SUBSTITUTED DIPHENYLAMINES

Diphenylamines containing nitro and trifluoromethylsulfonyl groups at the positions 2, 2', 4, 4', 6, and 6' were synthesized.The introduction of trifluoromethylsulfonyl groups into the diphenylamine derivatives led to a new analytical functional group.