1,1-Dimethylurea: Difference between revisions

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			{{Orphan\|date=December 2024}}

	{{chembox		{{chembox
	\|ImageFile = 1,1-Dimethylurea.svg		\|ImageFile = 1,1-Dimethylurea.svg
	\|IUPACName = 1,1-Dimethylurea		\|IUPACName = 1,1-Dimethylurea
	\|OtherNames = ''N'',''N''-Dimethylurea		\|OtherNames = ''N'',''N''-Dimethylurea
			\|Section1={{Chembox Identifiers
			\| CASNo = 598-94-7
			\| CASNo_Ref = {{Cascite\|correct\|CAS}}
			\| ChemSpiderID = 11244
			\| PubChem = 11737
			\| UNII = I988R763P3
			\| StdInChI=1S/C3H8N2O/c1-5(2)3(4)6/h1-2H3,(H2,4,6)
			\| StdInChIKey = YBBLOADPFWKNGS-UHFFFAOYSA-N
			\| SMILES = CN(C)C(=O)N
			}}
			\|Section2={{Chembox Properties
			\| C=3\|H=8\|N=2\|O=1
			}}
			\|Section8={{Chembox Related
			\| OtherCompounds = ]
			}}
	}}		}}



	'''1,1-Dimethylurea''' ('''DMU''') is a ] derivative used as a ] and a ] in ] reactions. It is a solid, but forms a ] with a low ] in combination with various ] additives that can serve as a ] solvent for various chemical reactions.<ref>{{cite journal \|doi= 10.1016/j.tet.2014.11.024 \|title= Diversity-oriented approach to spirocycles with indole moiety via Fischer indole cyclization, olefin metathesis and Suzuki–Miyaura cross-coupling reactions \|date= 2015 \|last1= Kotha \|first1= Sambasivarao \|last2= Ali \|first2= Rashid \|last3= Srinivas \|first3= Venu \|last4= Krishna \|first4= Nimita G. \|journal= Tetrahedron \|volume= 71 \|pages= 129–138 }}</ref><ref>{{cite journal \|doi= 10.1002/cctc.201402415 \|title= Superparamagnetic CuFeO<sub>2</sub> Nanoparticles in Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Imidazopyridines \|date= 2014 \|last1= Lu \|first1= Jun \|last2= Li \|first2= Xiao-Tang \|last3= Ma \|first3= Er-Qian \|last4= Mo \|first4= Li-Ping \|last5= Zhang \|first5= Zhan-Hui \|journal= ChemCatChem \|volume= 6 \|issue= 10 \|pages= 2854–2859 }}</ref><ref>{{cite journal \|doi= 10.1039/b414515a \|title= Low-melting sugar–urea–salt mixtures as solvents for Diels–Alder reactions \|date= 2005 \|last1= Imperato \|first1= Giovanni \|last2= Eibler \|first2= Ernst \|last3= Niedermaier \|first3= Julia \|last4= König \|first4= Burkhard \|journal= Chem. Commun. \|issue= 9 \|pages= 1170–1172 \|pmid= 15726181 }}</ref><ref>{{cite journal \|doi= 10.1039/B816551C \|title= Organic reactions in low melting mixtures based on carbohydrates and <small>L</small>-carnitine—a comparison \|date= 2009 \|last1= Ilgen \|first1= Florian \|last2= König \|first2= Burkhard \|journal= Green Chemistry \|volume= 11 \|issue= 6 \|page= 848 }}</ref> The un] nitrogen, as an ]-like region, can serve as a ] for a wide range of reactions, including reaction with ]s to form ]s,<ref>{{cite journal \|doi= 10.1021/jm0498351 \|title= Tetramethylcyclopropyl Analogue of a Leading Antiepileptic Drug, Valproic Acid. Synthesis and Evaluation of Anticonvulsant Activity of Its Amide Derivatives \|date= 2004 \|last1= Sobol \|first1= Eyal \|last2= Bialer \|first2= Meir \|last3= Yagen \|first3= Boris \|journal= Journal of Medicinal Chemistry \|volume= 47 \|issue= 17 \|pages= 4316–4326 \|pmid= 15294003 }}</ref> ] with ]s,<ref>{{cite journal \|doi= 10.1002/ejoc.201403405 \|title= Efficient and Selective Palladium-Catalysed C-3 Urea Couplings to 3,5-Dichloro-2(1''H'')-pyrazinones \|date= 2015 \|last1= Belfrage \|first1= Anna Karin \|last2= Gising \|first2= Johan \|last3= Svensson \|first3= Fredrik \|last4= Åkerblom \|first4= Eva \|last5= Sköld \|first5= Christian \|last6= Sandström \|first6= Anja \|journal= European Journal of Organic Chemistry \|issue= 5 \|pages= 978–986 }}</ref> and ] ] with ]s.<ref>{{cite journal \|doi= 10.13040/IJPSR.0975-8232.9(8).3322-27 \|date= 2018 \|journal= International Journal of Pharmaceutical Sciences and Research \|volume= 9 \|issue= 8 \|pages= 3322–3327 \|first1= Anis \|last1= Ahamed \|first2= Ibrahim A. \|last2= Arif \|first3= Meera \|last3= Moydeen \|first4= Radhakrishnan Surendra \|last4= Kumar \|first5= Akbar \|last5= Idhayadhulla \|title= In-Vitro Antibacterial and Cytotoxicity Evaluation of Some Novel Tetrazole Derivatives }}</ref> The unsubstituted ]-like portion can undergo ] coupling with ]s to give dihydro]s.<ref>{{cite journal \|doi= 10.1002/anie.201904662 \|title= Regioselective Formal Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation \|date= 2019 \|last1= Wu \|first1= Fan \|last2= Alom \|first2= Nur-E \|last3= Ariyarathna \|first3= Jeewani P. \|last4= Naß \|first4= Johannes \|last5= Li \|first5= Wei \|journal= Angewandte Chemie International Edition \|volume= 58 \|issue= 34 \|pages= 11676–11680 \|pmid= 31211504 }}</ref>		'''1,1-Dimethylurea''' ('''DMU''') is a ] derivative used as a ] and a ] in ] reactions. It is a solid, but forms a ] with a low ] in combination with various ] additives that can serve as a ] solvent for various chemical reactions.<ref>{{cite journal \|doi= 10.1016/j.tet.2014.11.024 \|title= Diversity-oriented approach to spirocycles with indole moiety via Fischer indole cyclization, olefin metathesis and Suzuki–Miyaura cross-coupling reactions \|date= 2015 \|last1= Kotha \|first1= Sambasivarao \|last2= Ali \|first2= Rashid \|last3= Srinivas \|first3= Venu \|last4= Krishna \|first4= Nimita G. \|journal= Tetrahedron \|volume= 71 \|pages= 129–138 }}</ref><ref>{{cite journal \|doi= 10.1002/cctc.201402415 \|title= Superparamagnetic CuFeO<sub>2</sub> Nanoparticles in Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Imidazopyridines \|date= 2014 \|last1= Lu \|first1= Jun \|last2= Li \|first2= Xiao-Tang \|last3= Ma \|first3= Er-Qian \|last4= Mo \|first4= Li-Ping \|last5= Zhang \|first5= Zhan-Hui \|journal= ChemCatChem \|volume= 6 \|issue= 10 \|pages= 2854–2859 }}</ref><ref>{{cite journal \|doi= 10.1039/b414515a \|title= Low-melting sugar–urea–salt mixtures as solvents for Diels–Alder reactions \|date= 2005 \|last1= Imperato \|first1= Giovanni \|last2= Eibler \|first2= Ernst \|last3= Niedermaier \|first3= Julia \|last4= König \|first4= Burkhard \|journal= Chem. Commun. \|issue= 9 \|pages= 1170–1172 \|pmid= 15726181 }}</ref><ref>{{cite journal \|doi= 10.1039/B816551C \|title= Organic reactions in low melting mixtures based on carbohydrates and <small>L</small>-carnitine—a comparison \|date= 2009 \|last1= Ilgen \|first1= Florian \|last2= König \|first2= Burkhard \|journal= Green Chemistry \|volume= 11 \|issue= 6 \|page= 848 }}</ref> The un] nitrogen, as an ]-like region, can serve as a ] for a wide range of reactions, including reaction with ]s to form ]s,<ref>{{cite journal \|doi= 10.1021/jm0498351 \|title= Tetramethylcyclopropyl Analogue of a Leading Antiepileptic Drug, Valproic Acid. Synthesis and Evaluation of Anticonvulsant Activity of Its Amide Derivatives \|date= 2004 \|last1= Sobol \|first1= Eyal \|last2= Bialer \|first2= Meir \|last3= Yagen \|first3= Boris \|journal= Journal of Medicinal Chemistry \|volume= 47 \|issue= 17 \|pages= 4316–4326 \|pmid= 15294003 }}</ref> ] with ]s,<ref>{{cite journal \|doi= 10.1002/ejoc.201403405 \|title= Efficient and Selective Palladium-Catalysed C-3 Urea Couplings to 3,5-Dichloro-2(1''H'')-pyrazinones \|date= 2015 \|last1= Belfrage \|first1= Anna Karin \|last2= Gising \|first2= Johan \|last3= Svensson \|first3= Fredrik \|last4= Åkerblom \|first4= Eva \|last5= Sköld \|first5= Christian \|last6= Sandström \|first6= Anja \|journal= European Journal of Organic Chemistry \|issue= 5 \|pages= 978–986 }}</ref> and ] ] with ]s.<ref>{{cite journal \|doi= 10.13040/IJPSR.0975-8232.9(8).3322-27 \|date= 2018 \|journal= International Journal of Pharmaceutical Sciences and Research \|volume= 9 \|issue= 8 \|pages= 3322–3327 \|first1= Anis \|last1= Ahamed \|first2= Ibrahim A. \|last2= Arif \|first3= Meera \|last3= Moydeen \|first4= Radhakrishnan Surendra \|last4= Kumar \|first5= Akbar \|last5= Idhayadhulla \|title= In-Vitro Antibacterial and Cytotoxicity Evaluation of Some Novel Tetrazole Derivatives }}</ref> The unsubstituted ]-like portion can undergo ] coupling with ]s to give dihydro]s.<ref>{{cite journal \|doi= 10.1002/anie.201904662 \|title= Regioselective Formal Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation \|date= 2019 \|last1= Wu \|first1= Fan \|last2= Alom \|first2= Nur-E \|last3= Ariyarathna \|first3= Jeewani P. \|last4= Naß \|first4= Johannes \|last5= Li \|first5= Wei \|journal= Angewandte Chemie International Edition \|volume= 58 \|issue= 34 \|pages= 11676–11680 \|pmid= 31211504 }}</ref>
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	== References ==		== References ==
	{{reflist}}		{{reflist}}

⚫	{{organic-compound-stub}}

	]		]
	]		]
			]


		⚫	{{organic-compound-stub}}

Revision as of 08:08, 23 December 2024

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1,1-Dimethylurea
Names

IUPAC name 1,1-Dimethylurea
Other names N,N-Dimethylurea
Identifiers
CAS Number	598-94-7
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
Related compounds
Related compounds	1,3-Dimethylurea
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

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. 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, coupling with vinyl halides, and multi-component condensation reaction with aldehydes. The unsubstituted amide-like portion can undergo oxidative coupling with alkenes to give dihydrooxazoles.

References

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.
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 Imidazopyridines". ChemCatChem. 6 (10): 2854–2859. doi:10.1002/cctc.201402415.
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.
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.
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.
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.
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.
Wu, Fan; Alom, Nur-E; Ariyarathna, Jeewani P.; Naß, Johannes; Li, Wei (2019). "Regioselective Formal 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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