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テトラメチル尿素

Tetramethylurea

HCID 12437
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
632-22-4
標準SMILES
CN(C)C(=O)N(C)C
InChIKey
AVQQQNCBBIEMEU-UHFFFAOYSA-N
分子式
C5H12N2O
平均分子量
116.16 g/mol
単同位体質量
116.094963

概要

1,1,3,3-tetramethylurea is a member of the class of ureas that is urea substituted by methyl groups at positions 1, 1, 3 and 3 respectively. Metabolite observed in cancer metabolism. It has a role as a human metabolite.

名称と識別子

優先名称
Tetramethylurea
IUPAC
1,1,3,3-tetramethylurea
現地名
テトラメチル尿素
英語名
1,1,3,3-Tetramethylurea
分子式
C5H12N2O
分子量
116.16

名称と別名

1,1,3,3-TetramethylureaTETRAMETHYLUREA632-22-4TemurUrea, tetramethyl-N,N,N',N'-TetramethylureaTetramethylureeUrea, 1,1,3,3-tetramethyl-NSC-914882O1EJ64031DTXSID1060893CHEBI:84278
名称をさらに表示
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tetramethyl-ureOlaparib Impurity 381,1,3,3-tetramethyl-ure((CH3)2N)2CO
RefChem:188798DTXCID1043750211-173-9TMUurea, N,N,N',N'-tetramethyl-Tetramethyl UreaNSC 91488BRN 0773898

データベース識別子

CAS
632-22-4
PubChem CID
12437
DTXSID
DTXSID1060893
ChEMBL
CHEMBL11949
ChEBI
CHEBI:84278
UNII
2O1EJ64031
EC Number
211-173-9
Nikkaji
J6.897G

物性

構造計算による物性補完中

XLogP
0.2
極性表面積
23.6 Ų
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

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Urea Compounds
SpringerMaterials PropertiesSchoenflies notation
LogP · 2 件

log Kow = 0.19

0.19

OdorFAINT, PLEASANT
Density0.9687 @ 20 °C/4 °C
Color/FormLIQUID
Solubility · 3 件

MISCIBLE WITH WATER, PETROLEUM ETHER, ALL COMMON SOLVENTS

SLIGHTLY SOL IN ALCOHOL

water solubility = 1X10+6 mg/l

Flash PointABOUT 75 °C
Boiling Point176.5 °C
Melting Point-1.2 °C
Vapor Pressurevaopr pressure = 13.9 mm Hg @ 71 °C
Refractive IndexINDEX OF REFRACTION: 1.4493 @ 25 °C/D

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H302 (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.

Danger

H227: Combustible liquid [Warning Flammable liquids]

危険有害性情報

Regulatory Information · 2 件

Chemical: Urea, tetramethyl-

Tetramethylurea: Does not have an individual approval but may be used under an appropriate group standard

Fire PotentialFIRE HAZARD: MODERATE, VIA HEAT, FLAME & OXIDIZERS.
Hazards Summary · 1 件

Teratogenic effects observed in mice dosed by SC injection; IV 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 pigs; Temporary 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 rodents; No human data on reproductive or lactation effects; [REPROTOX] An irritant; [Alfa Aesar MSDS]

Special ReportsREVIEW 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 · 2 件

Acute Tox. 4 (97.4%)

Flammable liquids - Category 4

安全と保護具

化学と産業

用途と製造

Uses · 2 件

Used as solvent and reagent; [Merck Index]

SOLVENT & REAGENT

U.S. Exports · 2 件

(1972) No Data

(1975) No Data

U.S. Imports · 2 件

(1972) No Data

(1975) No Data

U.S. Production · 2 件

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY LESS THAN 4.54X10+5 GRAMS

Methods of ManufacturingPREPN: LAWSON, CROOM, J ORG CHEM, 28, 232 (1963).
General Manufacturing InformationUrea, N,N,N',N'-tetramethyl-: ACTIVE
応用分野 · 1 件

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.

調製方法

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.]

上流・下流製品情報

関連反応

56 件
反応記録を作成
HRID 1705 の反応式
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HRID 7199 の反応式
HRID 7199反応物としてuspto-grants-2006_08
HRID 49885 の反応式
HRID 49885反応物としてuspto-grants-2004_03
HRID 191842 の反応式
HRID 191842反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 192386 の反応式
HRID 192386反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 281478 の反応式
HRID 281478反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 306830 の反応式
HRID 306830反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 408790 の反応式
HRID 408790生成物としてuspto-grants-2014_06
1 / 7 ページ

化合物ノート

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物理化学的性質

融点
1.2 °C · −1.2 °C (29.8 °F; 271.9 K)
沸点
176.5 °C · 176.5 °C (349.7 °F; 449.6 K)
比重(密度)
0.968 g/mL · 0.968 g/mL
屈折率
1.45 · 1.45
闪点
75 °C · 75 °C
貯蔵温度
Inert atmosphere,Room Temperature
溶解性
水、石油エーテル、および一般的な溶剤と混和します。
酸解離定数(Pka)
2 · 2.0(at 25℃)
外見
liquid
色
Colorless
PH
5 · 5-8 (25℃, 1M in H2O)
臭い (Odor)
ほのかな心地よい香り
水溶解度
2 O: · H2O: 20 °C で 1 M、混和性
Merck
14 · 14,9230
BRN
773898 · 773898
Dielectric constant
24.46 · 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 · 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)

化学的性質

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.

Fire Fighting ProceduresFOAM, MIST, SPRAY, DRY CHEMICALS.

毒性情報

Interactions · 3 件

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.

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Non-Human Toxicity Excerpts · 3 件

ONE SC INJECTION OF 5.6 OR 8.6 MMOL TETRAMETHYLUREA/KG OR REPEATED DAILY ADMIN OF 0.9 AND 1.7 MMOL/KG TO PREGNANT MICE HAD A TERATOGENIC EFFECT ON EMBRYOS. GREATEST EFFECT WAS BY SINGLE DOSES ON 8TH OR 11TH DAY OF GESTATION. WHEN GIVEN ON 8TH DAY IT PRODUCED MOSTLY CRANIAL EFFECTS & ON 22ND DAY PAW MALFORMATIONS.

TETRAMETHYLUREA WAS APPLIED TO SKIN OF RATS & RABBITS DURING ORGANOGENESIS. SLIGHT TERATOGENIC EFFECTS WERE DEMONSTRATED.

TETRAMETHYLUREA 150 MG/KG IV ACUTELY OR DAILY FOR 5 DAYS WAS NOT LETHAL & CAUSED ONLY WEIGHT LOSS IN DOGS, MONKEYS, & MICE. DOSES HIGHER THAN 100 MG/KG CAUSED HYPOTENSION IN DOGS.

Toxicity DataLCLo (rat) = 312 ppm/4h

安全データ

F
3-10
wgk
3
tsca
TSCA listed
rtecs
YU2625000
ridadr
NA 1993 / PGIII
毒性
LD50 i.v. in rats: 1.1 g/kg (Lüttringhaus, Dirksen)
hs_code
2924199090
risk_code
22-61
化審法
(2)-1735
消防法
危-4-3-III
hazard_code
Xn,T
safety_code
53-45
hazard_class
CBL
Hazard Classifications
Acute Tox. 4 OralEye Dam. 1Repr. 1BSkin Irrit. 2
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
有毒物質データの
632-22-4(Hazardous Substances Data)
危険度評価（NFPA 704基準/消防庁データ）
人的[青]=1

上流原料

テトラメチルチオ尿素1,2-ジクロロエタン塩化カルボニルジメチルアミン

下流製品

フルオロ-N,N,N',N'-テトラメチルホルムアミジニウムヘキサフルオロホスファート2-ブロモベンゼンチオール(bis-dimethylamino-methylene)-malononitrile4-メルカプト安息香酸メチル2-クロロベンゼンチオール

補足説明

定義ChEBI: 1,1,3,3-tetramethylurea is a member of the class of ureas that is urea substituted by methyl groups at positions 1, 1, 3 and 3 respectively. Metabolite observed in cancer metabolism. It has a role as a human metabolite.