N,N'-Dimethylurea
syM · N,N'-dimethylurea · symmetricdimethylurea · (CH3NH)2CO · AKOS B029718 · 1.3-DiMethyl u · N'-Dimethylurea · 1,3-dimethyl-ure
Identifiers & Physical Properties
| CAS No. | 96-31-1 |
|---|---|
| Molecular formula | C3H8N2O |
| Average molar mass | 88.11 g/mol |
| Monoisotopic mass | 88.06366288 g/mol |
| SMILES | CNC(=O)NC |
| InChIKey | MGJKQDOBUOMPEZ-UHFFFAOYSA-N |
| PubChem CID | 7293 |
| ChEMBL | CHEMBL1234380 |
| ChEBI | CHEBI:80472 |
| EC No. | 202-498-7 |
| DTXSID | DTXSID5025156 |
Chemical & Physical Properties
| XLogP | -0.5 |
|---|---|
| Topological polar surface area | 41.1 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 0 |
| Heavy atoms | 6 |
| Formal charge | 0 |
| Complexity | 46.8 |
| Chemical classes | Nitrogen Compounds -> Urea Compounds |
| SpringerMaterials Properties | Boiling point |
| LogP (partition coefficient) | -0.490-0.78 |
| Density | 1.142 (NTP, 1992) - Denser than waterwill sink1.1 g/cm³ |
| Color/Form | RHOMBIC BIPYRAMIDAL CRYSTALS FROM CHLOROFORM-ETHERCOLORLESS PRISMS |
| Solubility | greater than or equal to 100 mg/mL at 70 °F (NTP, 1992)VERY SOL IN WATER & ALCOHOLINSOL IN ETHERSolubility in water, g/100ml at 21.5 °C: 76.5 (good)H2O: 0.1 g/mL, clear, colorless765 g/L (21.5 ºC) |
| Flash point | 154 °C157 °C |
| Boiling point | 514 to 518 °F at 760 mmHg (NTP, 1992)268-270 °C269.00 °C. @ 760.00 mm Hg268-270 °C(lit.) |
| Melting point | 226 °F (NTP, 1992)108 °C108.00 °C. @ 760.00 mm Hg102-107 °C101-104 °C(lit.) |
| Vapor pressure | 0.54 [mmHg]Vapor pressure, Pa at 20 °C: 0.0426 hPa (115 °C) |
| Physical Description | N,n'-dimethylurea appears as colorless crystals. (NTP, 1992)Dry PowderColorless solid[Hawley] Sheet[Alfa Aesar MSDS] Colorless powder[OECD SIDS: 1,3-Dimethylurea - 2003]COLOURLESS-TO-WHITE CRYSTALLINE POWDER. |
| Autoignition temperature | 400 °C |
| Bulk density | 500kg/m3 |
| Refractive index | 1.4715 (estimate) |
| Storage conditions | Store below +30°C. |
| pKa (acidity coefficient) | 14.57±0.46(Predicted) |
| Physical state | Crystals |
| Color | White |
| pH | 9.0-9.5 (100g/l, H2O, 20℃) |
| BRN | 1740672 |
| Cosmetics Ingredients Functions | NAIL CONDITIONING |
| InChI | 1S/C3H8N2O/c1-4-3(6)5-2/h1-2H3,(H2,4,5,6) |
| InChIKey | MGJKQDOBUOMPEZ-UHFFFAOYSA-N |
| SMILES | CNC(=O)NC |
| LogP (partition coefficient) | -0.783 at 25℃ |
| CAS DataBase Reference | 96-31-1(CAS DataBase Reference) |
| FDA UNII | WAM6DR9I4X |
| NIST Chemistry Reference | Urea, N,N'-dimethyl-(96-31-1) |
| EPA Substance Registry System | 1,3-Dimethylurea (96-31-1) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS08 |
| Signal word | Warning |
| GHS hazard statements | H373 |
| GHS precautionary statements | P260-P314-P501 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Risk statements (R) | 62-63-68 |
| Safety statements (S) | 22-24/25 |
| Water hazard class (WGK) | 1 |
| RTECS number | YS9868000 |
| F | 10-21 |
| TSCA inventory status | TSCA listed |
| Customs code | 29241900 |
| Storage class | 11 - Combustible Solids |
| Hazardous substances data | 96-31-1(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 4000 mg/kg |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 98.8% (169 of 171) of all reports.Not ClassifiedAggregated GHS information provided per 171 reports by companies from 4 notifications to the ECHA C&L Inventory.WarningH373: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]P260, P319, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatory information | Chemical: Urea, N,N'-dimethyl-Urea, N,N'-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Urea, N,N'-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 13-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/10061Urea, N,N'-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Fire hazards | Flash point data for this chemical are not availableit is probably combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| Health hazards | ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992) |
| Hazards summary | No evidence of mutagenicity[HSDB] Not irritating to skin or eyes of rabbits[IUCLID] An irritant[Alfa Aesar MSDS] Causes tremor, cyanosis, and respiratory depression in intraperitoneal lethal-dose study of rats[RTECS] |
| Reactive group | Amides and Imides |
| Reactivity Profile | N,N'-DIMETHYLUREA is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). |
Applications & Uses
Description
1, 3-Dimethylurea is a urea derivative and used as an intermediate in organic synthesis. It is a colorless crystalline powder with little toxicity. It is also used for synthesis of caffeine, pharmachemicals, textile aids, herbicides and other. In the textile processing industry 1,3-dimethylurea is used as intermediate for the production of formaldehyde-free easy-care finishing agents for textiles. In the Swiss Product Register there are 38 products containing 1,3-dimethylurea, among them 17 products intended for consumer use. Product types are e.g. paints and cleaning agents. The content of 1,3-dimethylurea in consumer products is up to 10 % (Swiss Product Register, 2003). Use in cosmetics has been proposed, but there is no information available as to its actual use in such applications.
Uses
N,N′-Dimethylurea can be used:As a starting material to synthesize N,N′-dimethyl-6-amino uracil. In combination with β-cyclodextrin derivatives, to form low melting mixtures (LMMs), which can be used as solvents for hydroformylation and Tsuji-Trost reactions.To synthesize N,N′-disubstituted-4-aryl-3,4-dihydropyrimidinones via Biginelli condensation under solvent-free conditions.
General Description
Colorless crystals.