19055-93-7

Basic information

• Product Name: NNTETRAMETHYLENEUREA
• Synonyms: NNTETRAMETHYLENEUREA;1,3-Tetramethyleneurea;4,5,6,7-Tetrahydro-1H-1,3-diazepine-2(3H)-one;Hexahydro-1H-1,3-diazepin-2-one;Hexahydro-2H-1,3-diazepine-2-one
• CAS NO: 19055-93-7
• Molecular Formula: C₅H₁₀N₂O
• Molecular Weight: 0
• Mol File: 19055-93-7.mol

Chemical Properties

• Boiling Point: 335.1°Cat760mmHg
• Flash Point: 174.3°C
• Appearance: /
• Density: 1.012g/cm³
• Vapor Pressure: 0.000122mmHg at 25°C
• Refractive Index: 1.442
• CAS DataBase Reference: NNTETRAMETHYLENEUREA(CAS DataBase Reference)
• NIST Chemistry Reference: NNTETRAMETHYLENEUREA(19055-93-7)
• EPA Substance Registry System: NNTETRAMETHYLENEUREA(19055-93-7)

Safety Data

• Hazardous Substances Data: 19055-93-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H10N2O/c8-5-6-3-1-2-4-7-5/h1-4H2,(H2,6,7,8)

Upstream product

• 4538-37-8 1,4-diisocyanatobutane 
• 4515-19-9 piperidin-2-one oxime 
• 86119-84-8 phosphoric acid 
• 110-60-1 1,4-diaminobutane 
• 5564-73-8 1-(dimethoxymethyl)pyrrolidine 
• 124-38-9 carbon dioxide 
• 75506-70-6 4-Isocyanato-butyramide 
• 89026-70-0 N(pyrrolidinomethyliden)harnstoff 
• 64965-62-4 N,N-Tetramethylen-N'-cyanformamidin 
• 4736-71-4 N-pyrrolidinecarboxamide 
• 51250-16-9 S-aminobutyl-N-dithiocarbamic acid 
• 201230-82-2 carbon monoxide 
• 75548-99-1 tetrahydro-2H-1,3-diazepine-2,4(3H)-dione 
• 72331-40-9 1,3,4,7-tetrahydro-2H-1,3-diazepin-2-one 

Downstream Products

• 102552-55-6 N₁,N₂-bis(phenylacetyl)-1,4-butanediamide 
• 5700-04-9 1,3-diazacycloheptane-2-thione 
• 724423-26-1 2-oxo-[1,3]diazepane-1-carboxylic acid phenyl ester 
• 80963-17-3 C₃₄H₃₈N₂O₈Si 
• 80963-18-4 C₃₁H₃₀N₂O₈ 
• 74024-66-1 1-(β-D-Ribofuranosyl)-perhydro-1,3-diazepin-2-one 
• 77249-70-8 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)tetrahydro-2H-1,3-diazepine-2-one 
• 946123-61-1 C₂₃H₂₆N₂O₅ 
• 16597-38-9 1,3-dimethyl-1,3-diazacycloheptan-2-one 
• 946123-64-4 C₁₉H₁₈N₂O₅ 

Relevant articles and documents

1,3-Diazepinones. 1. Synthesis of 5-Hydroxyperhydro-1,3-diazepin-2-one

The synthesis of 5-hydroxyperhydro-1,3-diazepin-2-one (3) is accomplished by two different routes.The first route involves the reduction of the precursor ketone 2, which is synthesized in seven steps from levulinic acid (5).The second approach makes use of the hydration of the symmetrically unsaturated precursor 4 via the hydroboration-oxidation procedure.This precursor in turn is obtained by direct cyclization of cis-1,4-diamino-2-butene (12).

CO2-Fixation on Aliphatic α,ω-Diamines to Form Cyclic Ureas, Catalyzed by Ceria Nanoparticles that were Obtained by Templating with Alginate

Ceria nanoparticles (average particle size: 8nm) have been obtained by the calcination of alginate aerogel beads that were precipitated from aqueous solutions of (NH4)2Ce(NO3)6. These nanoparticles were considerably more active as a catalyst for CO2-insertion into aliphatic α,ω-diamines than the analogous commercial CeO2 with larger particle size (40nm). CeO2 that was obtained by templating with the natural alginate biopolymer afforded the cyclic urea of ethylenediamine in EtOH solvent at 160°C in 37% yield. This yield is remarkable for a process that involves CO2 as a feedstock. Other α,ω-diamines, such as diethylenetriamine, N,N′-dimethylethylenediamine, N-(2-aminoethyl)acetamide, and 1,4-diaminobutane, also formed their corresponding cyclic ureas in 4-36% yield. The catalyst lost activity upon reuse, thereby leading to severe deactivation that was only partially recovered by washing with aqueous acidic solutions.

Catalytic oxidative carbonylation of primary and secondary diamines to cyclic ureas. Optimization and substituent studies

W(CO)6-catalyzed oxidative carbonylation of 1,3-propanediamine to the corresponding urea has been examined under a variety of conditions. Following optimization, the Thorpe-Ingold effect on ring closure was studied using 2,2-dialkyl-1,3-propanediamines. For the 2,2-dimethyl- and 2,2-dibutyl-1,3-propanediamines, the yields were increased significantly as compared to that of the unsubstituted case. The eight-membered cyclic urea 5-butyl-5-ethyl-1,3-diazepan-2-one (5f) was formed in 38% yield, while only trace amounts of the cyclic urea were produced from the parent 1,5-pentanediamine. In a study of secondary diamines, yields from the carbonylation of N,N′-dialkyl-2,2-dimethyl-1,3-propanediamines were lower than those obtained from the primary diamines. The main byproducts from secondary diamines were tetrahydropyrimidine derivatives formed from a competitive reaction of the substrate with the oxidant and base.

Is there stereoelectronic control in hydrolysis of cyclic guanidinium ions?

To assess stereoelectronic effects in the cleavage of tetrahedral intermediates, a series of five-, six-; and seven-membered cyclic guanidinium salts was synthesized. If stereoelectronic control by antiperiplanar lone pairs is operative, these are expected to hydrolyze with endocyclic C-N cleavage to acyclic ureas. However, hydrolysis in basic media produces mixtures of cyclic and acyclic products, as determined by 1H NMR analysis. The results show that in the six-membered ring antiperiplanar lone pairs provide a weak acceleration of the breakdown of the tetrahedral intermediate, but in five- and seven-membered rings there is no evidence for such acceleration, which instead can be provided by syn lone pairs.

Catalytic oxidative carbonylation of primary and secondary α,ω-diamines to cyclic ureas

(matrix presented) Primary and secondary diamines can be catalytically carbonylated to cyclic ureas using W(CO)6 as the catalyst, I2 as the oxidant, and CO as the carbonyl source. Preparation of five-, six-, and seven-membered cyclic ureas from the diamines RNHCH2(CH2)nCH2NHR (n = 0-2; R = H, Me) and RNHCH2CH2NHR (R = Et, i-Pr, Bz) was achieved in moderate to good yields.

Process for producing cyclic ureas

A process for producing a cyclic urea is provided. The process comprises reacting a diamine expressed by the formula (II) wherein R represents hydrogen atom or a lower alkyl group and R' represent dimethylene group, a lower alkyl group-substituted dimethylene group, trimethylene group, a lower alkyl group-substituted trimethylene group, tetramethylene group, a lower alkyl group-substituted tetramethylene group, but a case where R represents hydrogen atom and R' represent dimethylene group, a case where R represents hydrogen atom and R' represents a lower alkyl group-substituted dimethylene group and a case where R represent methyl group and R' represents dimethylene group are excluded, with phosgene in the presence of a dehydrochlorinating agent. In the process, the diamine is first converted to its hydrochloride, followed by reacting the hydrochloride with phosgene in water solvent while maintaining a pH of the reaction liquid in the range of 5.0 to 8.0 by said dehydrochlorinating agent to obtain a cyclic urea expressed by the formula (I) STR1 wherein R and R' are each as defined above.

The Dehydration of Ureas by Two-Phase Dichlorocarbene Reaction, a Synthetic Access to Substituted Cyanamides

A wide variety of N,N-disubstituted ureas are dehydrated in the CHCl3/NaOH catalytic two-phase system under mild conditions.The sequence of urea-transamidation and dehydration thus offers a profitable approach to aprotic cyanamides.Among various tested PT-catalysts tertiary amines prove to be the most efficient and favourable ones.Tertiary amines may also be used advantageously in the transformation of carboxylic amides and thioamides to the corresponding nitriles.The application of the same technique is less suitable in the case of N-mono-substituted ureas, N,N'-disubstituted ureas as well as N(dialkylaminomethylidene)ureas, because consequent reactions of the primarily formed cyanamides predominate.Problems concerning the dehydration mechanism are elucidated in terms of HMO-perturbation theory.

Cyclic Urea and Thiourea Derivatives as Inducers of Murine Erythroleukemia Differentiation

A series of derivatives of tetramethylurea, a known inducer of the differentiation of Friend erythroleukemia cells, has been synthesized and tested for its capacity to induce erythroid maturation, as measured by the synthesis of hemoglobin.Cyclic urea and thiourea derivatives consisting of five-, six-, and seven-membered ring systems containing N-alkyl substituents were prepared.Most of these agents were relatively effective inducers of differentiation, with N-alkyl substitution appearing to be essential for maximum response.The most potent agents developed wereN,N'-dimethyl cyclic ureas.Exposure to concentrations of 2 to 4 mM of these derivatives resulted in more than 90percent of the cell population achieving a differentiated state.Under these conditions, the parent compound, tetramethylurea, was slightly less efficacious, causing differentiation of only 68percent of the population at its maximum effective level of 4 mM.

Seven-membered ring compounds as inhibitors of cytidine deaminase

Seven-membered heterocyclic nucleosides used to inhibit the deamination enzyme responsible for the inactivation of arabinosylcytosine (ara--C). Preferred nucleosides containing a seven-member aglycone are as follows: STR1 Preferred aglycones are as follow

1,3-Diazepinones. 2. The Correct Structure of Squamolone as 1-Carbamoyl-2-pyrrolidinone and Synthesis of Authentic Perhydro-1,3-diazepine-2,4-dione

The natural product squamolone,previously reported as 4-oxoperhydro-1,3-diazepin-2-one (1), was found to be instead 1-carbamoyl-2-pyrrolidinone (2).An unequivocal synthesis of the diazepinedione 1 starting from glutaric acid monoamide (6) produced the desired compound in five steps.Diborane reduction of 1 yielded the known perhydro-1,3-diazepin-2-one (10, tetramethyleneurea), confirming the seven-membered-ring structure of 1.A detailed analysis of the IR, NMR, and mass spectra of squamolone (2) and its isomer 1 is presented.A one-step synthesis of squamolone (2) starting with 4-aminobutyric acid 3 is reported.