1,1-Dimethylurea

1,1-Dimethylurea

Names
IUPAC name 1,1-Dimethylurea
Other names N,N-Dimethylurea
Identifiers
CAS Number	598-94-7  Y
3D model (JSmol)	Interactive image
ChemSpider	11244
ECHA InfoCard	100.009.053
PubChem CID	11737
UNII	I988R763P3
CompTox Dashboard (EPA)	DTXSID0060515
InChI InChI=1S/C3H8N2O/c1-5(2)3(4)6/h1-2H3,(H2,4,6) Key: YBBLOADPFWKNGS-UHFFFAOYSA-N
SMILES CN(C)C(=O)N
Properties
Chemical formula	C3H8N2O
Molar mass	88.110 g·mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
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). Infobox references

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.