1,1-Dimethylurea

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1,1-Dimethylurea
1,1-Dimethylurea.svg
Names
IUPAC name
1,1-Dimethylurea
Other names
N,N-Dimethylurea
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.053 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C3H8N2O/c1-5(2)3(4)6/h1-2H3,(H2,4,6)
    Key: YBBLOADPFWKNGS-UHFFFAOYSA-N
  • CN(C)C(=O)N
Properties
C3H8N2O
Molar mass 88.110 g·mol−1
Related compounds
Related compounds
 1,3-Dimethylurea
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).


1,1-Dimethylurea (DMU) is a urea derivative used as a polar solvent and a reagent in organic reactions. It is a solid, but forms a eutectic with a low melting point in combination with various hydroxylic additives that can serve as a environmentally sustainable solvent for various chemical reactions. [1] [2] [3] [4] The unsubstituted nitrogen, as an amine-like region, can serve as a nucleophile for a wide range of reactions, including reaction with acyl halides to form acylureas, [5] coupling with vinyl halides, [6] and multi-component condensation reaction with aldehydes. [7] The unsubstituted amide-like portion can undergo oxidative coupling with alkenes to give dihydrooxazoles. [8]

References

  1. ↑ Kotha, Sambasivarao; Ali, Rashid; Srinivas, Venu; Krishna, Nimita G. (2015). "Diversity-oriented approach to spirocycles with indole moiety via Fischer indole cyclization, olefin metathesis and Suzuki–Miyaura cross-coupling reactions". Tetrahedron. 71: 129–138. doi:10.1016/j.tet.2014.11.024.
  2. ↑ Lu, Jun; Li, Xiao-Tang; Ma, Er-Qian; Mo, Li-Ping; Zhang, Zhan-Hui (2014). "Superparamagnetic CuFeO2 Nanoparticles in Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Imidazo[1,2-a]pyridines". ChemCatChem. 6 (10): 2854–2859. doi:10.1002/cctc.201402415.
  3. ↑ Imperato, Giovanni; Eibler, Ernst; Niedermaier, Julia; König, Burkhard (2005). "Low-melting sugar–urea–salt mixtures as solvents for Diels–Alder reactions". Chem. Commun. (9): 1170–1172. doi:10.1039/b414515a. PMID   15726181.
  4. ↑ Ilgen, Florian; König, Burkhard (2009). "Organic reactions in low melting mixtures based on carbohydrates and L-carnitine—a comparison". Green Chemistry. 11 (6): 848. doi:10.1039/B816551C.
  5. ↑ Sobol, Eyal; Bialer, Meir; Yagen, Boris (2004). "Tetramethylcyclopropyl Analogue of a Leading Antiepileptic Drug, Valproic Acid. Synthesis and Evaluation of Anticonvulsant Activity of Its Amide Derivatives". Journal of Medicinal Chemistry. 47 (17): 4316–4326. doi:10.1021/jm0498351. PMID   15294003.
  6. ↑ Belfrage, Anna Karin; Gising, Johan; Svensson, Fredrik; Åkerblom, Eva; Sköld, Christian; Sandström, Anja (2015). "Efficient and Selective Palladium-Catalysed C-3 Urea Couplings to 3,5-Dichloro-2(1H)-pyrazinones". European Journal of Organic Chemistry (5): 978–986. doi:10.1002/ejoc.201403405.
  7. ↑ Ahamed, Anis; Arif, Ibrahim A.; Moydeen, Meera; Kumar, Radhakrishnan Surendra; Idhayadhulla, Akbar (2018). "In-Vitro Antibacterial and Cytotoxicity Evaluation of Some Novel Tetrazole Derivatives". International Journal of Pharmaceutical Sciences and Research. 9 (8): 3322–3327. doi: 10.13040/IJPSR.0975-8232.9(8).3322-27 .
  8. ↑ Wu, Fan; Alom, Nur-E; Ariyarathna, Jeewani P.; Naß, Johannes; Li, Wei (2019). "Regioselective Formal [3+2] Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation". Angewandte Chemie International Edition. 58 (34): 11676–11680. doi:10.1002/anie.201904662. PMID   31211504.


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