2,3-Dimethyl-2,3-dinitrobutane

Base Information

• Chemical Name: 2,3-Dimethyl-2,3-dinitrobutane
• CAS No.: 3964-18-9
• Molecular Formula: C6H12N2O4
• Molecular Weight: 176.172
• Hs Code.: 29042090
• European Community (EC) Number: 223-569-9
• NSC Number: 1156
• DSSTox Substance ID: DTXSID4063248
• Nikkaji Number: J149.892D
• Wikipedia: DMDNB
• Wikidata: Q3267064
• Mol file: 3964-18-9.mol

Synonyms:2,3-dimethyl-2,3-dinitrobutane;DMDNB

Chemical Property of 2,3-Dimethyl-2,3-dinitrobutane

Chemical Property:

• Appearance/Colour: white to off-white crystal or crystalline powder
• Vapor Pressure: 0.117mmHg at 25°C
• Melting Point: 214-215 °C (dec.)(lit.)
• Refractive Index: 1.458
• Boiling Point: 219.8 °C at 760 mmHg
• Flash Point: 80.2 °C
• PSA: 91.64000
• Density: 1.15 g/cm³
• LogP: 2.14340
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 176.07970687
• Heavy Atom Count: 12
• Complexity: 187

Purity/Quality:

99.9% ^*data from raw suppliers

2,3-Dinitro-2,3-dimethylbutane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C(C)(C)[N+](=O)[O-])[N+](=O)[O-]
• Uses: 2,3-Dimethyl-2,3-dinitrobutane (DMNB) is an additive required for commercial plastic explosives. The product has been used to develop a fast, square-wave voltammetric measurement protocol of taggant (DMNB explosive) at an unmodified carbon fiber electrode. This protocol used a phosphate buffer solution at pH 7.0.

Technology Process of 2,3-Dimethyl-2,3-dinitrobutane

There total 156 articles about 2,3-Dimethyl-2,3-dinitrobutane 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: 93.0%

2,3-Dihydro-2,2,3,3,5,6-hexamethylpyrazine-1,4-dioxide (14384-47-5) → 2,3-dimethyl-2,3-dinitrobutane (3964-18-9) + dimethylglyoxal (431-03-8)

Guidance literature:

With ozone; In chloroform-d1; at -78 ℃; for 0.25h;

DOI:10.1021/jo00076a034

Reference yield: 54.0%

lithium 2-nitropropane (3958-63-2) + (p-methylphenyl)phenyliodonium bromide (2665-60-3) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + iodobenzene (591-50-4) + 2,3-dimethyl-2,3-dinitrobutane (3964-18-9) + 4-tolyl iodide (624-31-7)

Guidance literature:

In methanol; at 30 ℃; for 48h; Further byproducts given;

DOI:10.1016/S0040-4039(00)85837-2

Reference yield: 43.0%

lithium 2-nitropropane (3958-63-2) + diphenyliodonium bromide (1483-73-4) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + iodobenzene (591-50-4) + biphenyl (92-52-4,1594-86-1) + 2,3-dimethyl-2,3-dinitrobutane (3964-18-9) + 2-nitro-2-phenylpropane (3457-58-7) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

In methanol; at 30 ℃; for 48h; Mechanism; Product distribution; other diaryliodonium bromides, other times, effect of light and oxygen;

DOI:10.1016/S0040-4039(00)85837-2

upstream raw materials:

methanol

2-iodo-2-nitropropane

2,3-Dimethyl-2-butene

2-nitrobutane

Downstream raw materials:

2,3-dimethyl-2,3-diaminobutane

isopropylamine

2,3-Dimethyl-2-butene

1,3-dihydroxyl-2-(4'-chlorophen-1'-yl)-4,4,5,5-tetramethylimidazolidine

Refernces

• 1、 Bowman, W. Russel,Brown, David S.,Leung, Christina T. W.,Stutchbury, Andrew P.. "A NOVEL SRN1 SUBSTITUTION: THE REACTION BETWEEN THE ANION OF 2-NITROPROPANE AND 3-BROMO-1-NITROCYCLOHEX-1-ENE". . p. 539 - 540. Retrieved 1985.
• 2、 Wade, Peter A.,Dailey, William P.,Carroll, Patrick J.. "Polynitro-Substituted Strained-Ring Compounds. Synthesis, Mechanism of Formation, and Structure of trans-Dinitrocyclopropanes". . p. 5452 - 5456. Retrieved 1987.
• 3、 Morin, Jesse B.,Sello, Jason K.. "Efficient synthesis of a peculiar vicinal diamine semiochemical from streptomyces natalensis". . p. 3522 - 3524. Retrieved 2010.
• 4、 Bolsman,T.A.B.M.,de Boer,T.J.. "-". . p. 1019 - 1023. Retrieved 1975.
• 5、 -. "Nitroxide free radical, and preparation method and application thereof". Paragraph 0034-0035; 0044-0045. . Retrieved 2020/03/02.
• 6、 Lu, Shi-Chao,Li, Hong-Shuang,Gong, Ya-Ling,Zhang, Shi-Peng,Zhang, Ji-Guo,Xu, Shu. "Combination of PhI(OAc)2 and 2-Nitropropane as the Source of Methyl Radical in Room-Temperature Metal-Free Oxidative Decarboxylation/Cyclization: Construction of 6-Methyl Phenanthridines and 1-Methyl Isoquinolines". . p. 15415 - 15425. Retrieved 2019/01/03.