125735-38-8

Basic information

• Product Name: 1-(1,1-Dimethylethyl)-3,3-dinitroazetidine
• Synonyms: 1-(1,1-Dimethylethyl)-3,3-dinitroazetidine;1-tert-Butyl-3,3-dinitroazetidine
• CAS NO: 125735-38-8
• Molecular Formula: C₇H₁₃N₃O₄
• Molecular Weight: 203.2
• Mol File: 125735-38-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(1,1-Dimethylethyl)-3,3-dinitroazetidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1,1-Dimethylethyl)-3,3-dinitroazetidine(125735-38-8)
• EPA Substance Registry System: 1-(1,1-Dimethylethyl)-3,3-dinitroazetidine(125735-38-8)

Safety Data

• Hazardous Substances Data: 125735-38-8(Hazardous Substances Data)

Usage

Uses

Used in Military Applications:
1-(1,1-Dimethylethyl)-3,3-dinitroazetidine is used as an explosive compound for the production of detonators and other explosive devices. Its high stability and safety in handling make it an ideal choice for military applications where explosive power and reliability are crucial.
Used in Industrial Applications:
In the industrial sector, 1-(1,1-Dimethylethyl)-3,3-dinitroazetidine is utilized as a component in the manufacturing of explosives for various purposes, such as mining, construction, and demolition. Its stability and safety characteristics ensure that it can be used effectively and securely in these applications.
Due to the explosive properties of TATB, it is subject to strict regulation and control by government authorities to prevent misuse and ensure safety in its production, handling, and use.

Upstream product

• 158669-93-3 N-tert-butyl-3-hydroxymethyl-3-nitroazetidine hydrochloride 
• 158669-96-6 1-tert-butyl-3-hydroxymethyl-3-nitroazetidine 
• 46236-54-8 1-(tert-butyl)azetidin-3-yl methanesulfonate 
• 125735-36-6 1-tert-butyl-3-nitroazetidine 

Downstream Products

• 97645-24-4 1,3,3-trinitroazetidine 
• 147636-85-9 1-(benzyloxycarbonyl)-3,3-dinitroazetidine 
• 115-11-7 isobutene 
• 925206-65-1 [14C]-Rrx-001 

Relevant articles and documents

Structure of 1-tert-butyl-3-hydroxymethyl-3-nitroazetidine and 1-bromoacetyl-3,3-dinitroazetidine, an investigative anticancer agent derived from energetic materials

The structures of a novel investigative anticancer agent 1-bromoacetyl-3,3-dinitro azetidine (ABDNAZ, 2) and its synthetic precursor 1-tert-butyl-3-hydroxymethyl-3-nitroazetidine (1) were determined by single crystal X-ray diffraction. The data show that the chemical transformation from 1 to 2 resulted in an increase in crystal density of 0.725 Mg/m3 (1 = 1.232 Mg/m3; 2 = 1.957 Mg/m3). The azetidine ring of 1 is puckered while 2 is planar, consistent with sp2 hybridization of the ring nitrogen following conversion of the tertiary amine to an amide. The structural information will aid in elucidating the biological activity of 2. Graphical Abstract: Single crystal X-ray diffraction studies revealed that conversion of 1-tert-butyl-3-hydroxymethyl-3-nitroazetidine to 1-bromoacetyl-3,3-dinitroazetidine results inflattening of the azetidine ring due to sp2 hybridization of the ring nitrogen, and a crystal density increase of 0.725 Mg/m3 (1.232 vs. 1.957 Mg/m3 respectively) is observed.

Development of a safe and efficient two-step synthesis for preparing 1-bromoacetyl-3,3-dinitroazetidine, a novel clinical anticancer candidate

An efficient process for synthesizing and isolating a new investigative anticancer agent, 1-bromoacetyl-3,3-dinitroazetidine, is described. The reaction entails a sequence of oxidative nitration followed by acylative dealkylation. The methods reported give 50-60-g batches of high-purity product without a designated purification step. The reaction conditions have been designed to mitigate the safety concerns associated with gem-dinitroazetidines. Some observations on the acylative dealkylation mechanism are discussed.

Discovery of RRx-001, a Myc and CD47 Downregulating Small Molecule with Tumor Targeted Cytotoxicity and Healthy Tissue Cytoprotective Properties in Clinical Development

After extensive screening of aerospace compounds in an effort to source a novel anticancer agent, RRx-001, a first-in-class dinitroazetidine small molecule, was selected for advancement into preclinical and clinical development. RRx-001 is a minimally tox

METHODS OF SYNTHESIZING AND ISOLATING N-(BROMOACETYL)-3,3-DINITROAZETIDINE AND A COMPOSITION INCLUDING THE SAME

A method of synthesizing and isolating N-(bromoacetyl)-3,3-dinitroazetidine (ABDNAZ) by reacting DNAZ with bromoacetyl bromide and boron trifluoride etherate to produce a mixture comprising ABDNAZ and a salt of DNAZ. Water and a solvent are added to the mixture to form an organic phase comprising the ABDNAZ and an aqueous phase comprising the salt of DNAZ. The organic phase and the aqueous phase are separated to produce an ABDNAZ/solvent solution comprising the ABDNAZ and the aqueous phase comprising the salt of DNAZ. A nonsolvent is added to the ABDNAZ/solvent solution to produce an ABDNAZ/solvent/nonsolvent mixture. The ABDNAZ is subsequently recovered. A composition comprising ABDNAZ is also disclosed.

1-GLYCIDYL-3,3-DINITROAZETIDINE CONTAINING EXPLOSIVE MOIETY AND PREPARATION METHOD THEREOF

Disclosed is a 1-glycidyl-3,3-dinitroazetidine(GDNAZ) of Formula I wherein dinitroazetidine group which is a high energy group having unit structure of explosive moiety is incorporated to a monomer, and the method thereof. By using the GDNAZ of the present invention in the synthesis of energetic binder for high-performance insensitive explosive, an energetic binder with enhanced thermal and storing stability and explosive power can be provided.

Synthesis of heterocyclic geminal nitro azides

The oxidative azidation reactions of C-nitro-substituted saturated heterocyclic compounds, viz., the nitro derivatives of oxetane, azetidine, 1,3-dioxane, tetrahydro-1,3-oxazine, and hexahydropyrimidine, were investigated. A novel representatives of the geminal nitro azides were prepared and their physicochemical properties were studied. The process of the formation of the geminal dinitro compounds upon oxidative azidation was analyzed.

Synthesis and X-ray Crystal Structure of 1,3,3-Trinitroazetidine

1,3,3-Trinitroazetidine (1) was synthesized and its structure elucidated by X-ray crystallography.Reaction of 1-tert-butyl-3-((methylsulfonyl)oxy)azetidine (3a) with sodium nitrite gave 1-tert-butyl-3-nitroazetidine (4a), which was converted to 1-tert-butyl-3,3-dinitroazetidine (5a) by oxidative nitration.Nitrolysis of 5a with acetyl nitrate gave 1. 1-Benzhydryl-3,3-dinitroazetidine (5b) did not undergo a similar nitrolysis.Single-crystal X-ray analysis of 1 showed that the ring is puckered, with a dihedral angle of 13.6(5) deg between the C-C-C and C-N-C planes, and that the nitramino group exhibits an unusually high (39.4 deg) out-of-plane deformation.A structural optimization with MNDO reproduced the ring pucker and the nitramino bend to within 5 deg.The large bend at the ring nitrogen atom indicates sp3 rather than sp2 for its hybridization.However, the N-N bond length, 1.351(6) Angstroem, falls in the normal range for planar (sp2) nitramines and is ca. 0.1 Angstroem shorter than N-N bonds previously observed in bent nitramines.