テトラメチル尿素
テトラメチル尿素 · 1,1,3,3-テトラメチル尿素 · テムル · N,N,N',N'-テトラメチル尿素 · 1,1,3,3‐テトラメチル尿素 · TMU · TETRAMETHYLUREA · N,N,N',N'-TETRAMETHYLUREA
識別子と物理属性
| CAS No. | 632-22-4 |
|---|---|
| 分子式 | C5H12N2O |
| 平均分子量 | 116.16 g/mol |
| 単同位体質量 | 116.094963 g/mol |
| SMILES | CN(C)C(=O)N(C)C |
| InChIKey | AVQQQNCBBIEMEU-UHFFFAOYSA-N |
| PubChem CID | 12437 |
| ChEMBL | CHEMBL11949 |
| ChEBI | CHEBI:84278 |
| EC No. | 211-173-9 |
| DTXSID | DTXSID1060893 |
| 現地名 | テトラメチル尿素 |
化学・物理的性質
| XLogP | 0.2 |
|---|---|
| 極性表面積 | 23.6 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 0 |
| 重原子数 | 8 |
| 形式電荷 | 0 |
| 複雑度 | 78.4 |
| 物質分類 | Nitrogen Compounds -> Urea Compounds |
| SpringerMaterials Properties | Schoenflies notation |
| LogP（分配係数） | log Kow = 0.19 |
| 臭い | FAINT, PLEASANTほのかな心地よい香り |
| 密度 | 0.9687 @ 20 °C/4 °C0.968 g/mL at 20 °C(lit.) |
| Color/Form | LIQUID |
| 溶解度 | MISCIBLE WITH WATER, PETROLEUM ETHER, ALL COMMON SOLVENTSSLIGHTLY SOL IN ALCOHOLwater solubility = 1X10+6 mg/l水、石油エーテル、および一般的な溶剤と混和します。H2O: 20 °C で 1 M、混和性 |
| 引火点 | ABOUT 75 °C150 °F |
| 沸点 | 176.5 °C177 °C(lit.) |
| 融点 | -1.2 °C−1 °C(lit.) |
| 蒸気圧 | vaopr pressure = 13.9 mm Hg @ 71 °C |
| 屈折率 | INDEX OF REFRACTION: 1.4493 @ 25 °C/Dn20/D 1.451(lit.) |
| 貯蔵条件 | Inert atmosphere,Room Temperature |
| 外観・状態 | 液体 |
| pKa（酸解離定数） | 2.0(at 25℃) |
| 色 | 無色透明～淡黄色 |
| pH | 5-8 (25℃, 1M in H2O) |
| Merck | 14,9230 |
| BRN | 773898 |
| 誘電率 | 24.460000000000001 |
| InChI | 1S/C5H12N2O/c1-6(2)5(8)7(3)4/h1-4H3 |
| InChIKey | AVQQQNCBBIEMEU-UHFFFAOYSA-N |
| SMILES | CN(C)C(=O)N(C)C |
| CAS データベース | 632-22-4(CAS DataBase Reference) |
| NISTの化学物質情報 | Urea, tetramethyl-(632-22-4) |
| EPAの化学物質情報 | Tetramethylurea (632-22-4) |
化学的特性
Tetramethylurea is a clear colorless to pale yellow liquid with mild aromatic odor that is miscible with water and many organic solvents. Unusual for an urea is the liquid state of tetramethylurea in a range of > 170 °C.
安全性と法規制
| GHS 分類 | DangerH302 (97.4%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 116 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H227: Combustible liquid [Warning Flammable liquids] |
|---|---|
| 規制情報 | Chemical: Urea, tetramethyl-Tetramethylurea: Does not have an individual approval but may be used under an appropriate group standard |
| 火災の可能性 | FIRE HAZARD: MODERATE, VIA HEAT, FLAME & OXIDIZERS. |
| 有害性の概要 | Teratogenic effects observed in mice dosed by SC injectionIV doses of 150 mg/kg daily for five days produced weight loss in dogs, monkeys, and mice[HSDB] A strong skin irritant, but not a sensitizer in guinea pigsTemporary kidney injury and possible liver injury observed in two week feeding study of male rats at 450 mg/kg[EPA] Causes general anesthesia and somnolence in IP lethal-dose study of mice[RTECS] Teratogenic effects and fetal loss observed in studies of rodentsNo human data on reproductive or lactation effects[REPROTOX] An irritant[Alfa Aesar MSDS] |
| Special Reports | REVIEW OF PREPN, MFR, PROPERTIES AND USE AS SOLVENT AND AS REAGENT: LUTTRINGHAUS, DIRKSEN, AGNEW CHEM INT ED 3, 260 (1964).[The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 1190] |
| Hazard Classes and Categories | Acute Tox. 4 (97.4%)Flammable liquids - Category 4 |
| 消火手順 | FOAM, MIST, SPRAY, DRY CHEMICALS. |
| 相互作用 | MIXING TETRAMETHYLUREA WITH MINERAL OIL INCREASED MATERNAL TMU TOXICITY WHEN APPLIED TO SKIN OF RATS.TETRAMETHYL UREA WAS CAPABLE OF ENHANCING THE TOXICITY OF MORPHINE AND CHLORPROMAZINE IN DOGS, MONKEYS, AND MICE.TETRAMETHYLUREA LOWERED YIELDS AND/OR INCIDENCES OF TUMORS PROMOTED BY RETINYL ACETATE OR CROTON OIL AFTER INITIATION BY 7,12-DIMETHYLBENZ(A)ANTHRACENE. TOPICAL APPLICATION OF INDUCERS MIGHT HAVE THERAPEUTIC POTENTIAL IN EPIDERMAL CARCINOMA. |
用途
使用
Tetramethylurea is used as a solvent in dyestuff industries, in condensation reaction and intermediates in surfactant. It is utilized for base catalyzed isomerization and alkylation hydrocyanation due to its low permittivity. It reacts with oxalyl chloride to prepare tetramethyl chloroformamidinium chloride, which is used for the conversion of carboxylic acids and dialkyl phosphates to anhydrides and pyrophosphates respectively.
製法・合成法
製造方法
The reaction of dimethylamine with phosgene in the presence of e. g. 50 % sodium hydroxide solution and subsequent extraction with 1,2-dichloroethane yields tetramethylurea in 95% yield.
純化方法
Dry it over BaO and distil it under nitrogen. It denatures proteins in H2O. [Elbaum & Herskovits Biochemistry 13 1268 1974, Kane Anal Biochem 53 350 1973, Beilstein 4 IV 225.]