Diethanolnitramine dinitrate

Base Information

• Chemical Name: Diethanolnitramine dinitrate
• CAS No.: 4185-47-1
• Molecular Formula: C4H8N4O8
• Molecular Weight: 240.13
• Hs Code.: 2921199090
• European Community (EC) Number: 691-398-0
• DSSTox Substance ID: DTXSID30194648
• Wikidata: Q15628370
• Mol file: 4185-47-1.mol

Synonyms:Diethanolnitramine dinitrate;DINA;Nitrodiethanolamine dinitrate;sym-Dinitroxydiethylnitramine;N-Nitrodiethanolamine dinitrate;Diethanol-N-nitramine dinitrate;4185-47-1;2,2'-Nitroiminodiethanol nitrate;2,2'-Nitroiminobis(ethylnitrate);2,2'-Dinitrato-N-nitrodiethylamine;2,2'-(Nitroimino)ethanol dinitrate;2-[nitro(2-nitrooxyethyl)amino]ethyl nitrate;BRN 1803252;Ethanol, 2,2'-(nitroimino)bis-, dinitrate (ester);2,2'-(Nitroimino)bisethanol dinitrate (ester);Ethanol, 2,2'-nitroiminodi-, dinitrate;N-Nitrobis(2-hydroxyethyl)-amine dinitrate;ETHANOL, 2,2'-NITROIMINODI-, DINITRATE (ester);Ethanol, 2,2'-(nitroimino)bis-, dinitrate (ester) (9CI);DINA (explosive);C4H8N4O8;SCHEMBL2681712;DTXSID30194648;2,2'-Nitroiminobis(ethyl nitrate);C4-H8-N4-O8;STK366161;AKOS000567452;(nitroimino)diethane-2,1-diyl dinitrate;LS-66985;Ethanol, 2,2'-(nitroimino)bis-, dinitrate;Ethanol, 2,2'-(nitroimino)di-, dinitrate (ester);2,2-bis[2-(nitrooxy)ethyl]-1-oxo-1-hydraziniumolate;Q15628370;2-(1-[2-(Nitrooxy)ethyl]-2-oxido-2-oxohydrazino)ethyl nitrate #

Chemical Property of Diethanolnitramine dinitrate

Chemical Property:

• Vapor Pressure: 2.45E-07mmHg at 25°C
• Melting Point: 49.5-50.5 °C
• Refractive Index: 1.8500 (estimate)
• Boiling Point: 434.2°Cat760mmHg
• PKA: -10.40±0.70(Predicted)
• Flash Point: 216.4°C
• PSA: 159.16000
• Density: 1.57g/cm³
• LogP: 0.46630
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 240.03421323
• Heavy Atom Count: 16
• Complexity: 232

Purity/Quality:

99% ^*data from raw suppliers

2,2'-DINITROXYDIETHYLNITRAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CO[N+](=O)[O-])N(CCO[N+](=O)[O-])[N+](=O)[O-]
• General Description: 2,2'-(Nitroimino)bisethanol dinitrate (DINA) is a nitramine explosive containing both O-nitro and N-nitro functional groups. It is synthesized through the nitration of diethanolamine hydrochloride using a fuming nitric acid/acetic anhydride system, with optimal yields achieved under conditions of excess acetic anhydride and low reaction temperatures (e.g., 5 °C). 2,2'-(Nitroimino)bisethanol dinitrate exhibits moderate thermal stability, with a calculated \( T_{D24} \) of 61.9 °C, indicating that decomposition is unlikely under controlled conditions. However, its nitration reaction mixture can pose thermal runaway risks if improperly handled, necessitating careful process optimization and safety measures. Mass spectrometry studies reveal characteristic fragmentation patterns, including β-fission relative to nitramine and nitrate ester groups, as well as prominent ions such as \([MH - 45]^+\) in chemical ionization. Overall, DINA combines high-energy performance with manageable synthesis safety when proper protocols are followed.

Technology Process of Diethanolnitramine dinitrate

There total 7 articles about Diethanolnitramine dinitrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

diethanolamine hydrochloride (14426-21-2) → nitro-bis-(2-nitryloxy-ethyl)-amine (4185-47-1)

Guidance literature:

With nitric acid; acetic anhydride; at 5 - 40 ℃; for 5.55556h; Concentration; Temperature; Thermodynamic data;

DOI:10.1021/acs.oprd.9b00300

Reference yield: 82.0%

diethanolamine hydrochloride → nitro-bis-(2-nitryloxy-ethyl)-amine (4185-47-1)

Guidance literature:

With nitric acid; In acetic anhydride; at 10 - 40 ℃; for 1.5h;

Reference yield: 60.0%

C4H10NO5S(1-) → nitro-bis-(2-nitryloxy-ethyl)-amine (4185-47-1)

Guidance literature:

With sulfuric acid; nitric acid; at -15 - -5 ℃;

DOI:10.1007/bf02496139

upstream raw materials:

2,2'-iminobis[ethanol]

2-(1-aziridine)ethanol

nitroso-bis-(2-nitryloxy-ethyl)-amine

nitric acid