1,1'-カルボニルジイミダゾール
1,1'-カルボニルジイミダゾール · ビス(1-イミダゾリル)ケトン · 1,1'-カルボニルビス(1H-イミダゾール) · ジ(1H-イミダゾール-1-イル)ケトン · 1,1'-カルボニルビス[1H-イミダゾール] · ビス(1H-イミダゾール-1-イル)ケトン · N,N'-カルボニルジイミダゾール · 1,1'-カルボニルジ(1H-イミダゾール)
識別子と物理属性
| CAS No. | 530-62-1 |
|---|---|
| 分子式 | C7H6N4O |
| 平均分子量 | 162.15 g/mol |
| 単同位体質量 | 162.05416083 g/mol |
| SMILES | O=C(n1ccnc1)n1ccnc1 |
| InChIKey | PFKFTWBEEFSNDU-UHFFFAOYSA-N |
| PubChem CID | 68263 |
| ChEMBL | CHEMBL3903881 |
| EC No. | 208-488-9 |
| DTXSID | DTXSID9038761 |
| 現地名 | 1,1'-カルボニルジイミダゾール |
化学・物理的性質
| XLogP | -0.2 |
|---|---|
| 極性表面積 | 52.7 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 0 |
| 重原子数 | 12 |
| 形式電荷 | 0 |
| 複雑度 | 166 |
| Physical Description | Solid[Merck Index] White crystalline powder[Alfa Aesar MSDS] |
| 融点 | 117-122 °C(lit.) |
| 沸点 | 288.83°C (rough estimate) |
| 密度 | 1.303 g/mL at 25 °C |
| 蒸気圧 | 0.006-0.012Pa at 20-25℃ |
| 屈折率 | n20/D1.434 |
| 貯蔵条件 | 2-8°C |
| 溶解度 | ジメチルホルムアミドに可溶。水に不溶 |
| pKa（酸解離定数） | 2.90±0.10(Predicted) |
| 外観・状態 | 結晶性粉末 |
| 色 | ホワイト～ライトクリーム |
| pH | 7.7 (50g/l, H2O, 20℃) |
| Merck | 14,1819 |
| BRN | 6826 |
| 安定性 | 安定していますが、水分に敏感です。酸、強力な酸化剤、水とは混和しません。 |
| InChI | 1S/C7H6N4O/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H |
| InChIKey | PFKFTWBEEFSNDU-UHFFFAOYSA-N |
| SMILES | O=C(n1ccnc1)n2ccnc2 |
| CAS データベース | 530-62-1(CAS DataBase Reference) |
| EPAの化学物質情報 | 1H-Imidazole, 1,1'-carbonylbis- (530-62-1) |
化学的特性
The substance appears as a white to slightly pale-yellow crystalline powder with a melting point range of 115.5-116°C. It exhibits poor solubility in water, while displaying solubility in alcohol and ether.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 0.4% (1 of 233) of reports.DangerH302 (84.1%): Harmful if swallowed [Warning Acute toxicity, oral]H314 (83.3%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H315 (15.9%): Causes skin irritation [Warning Skin corrosion/irritation]H318 (45.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H319 (15.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H360 (26.2%): May damage fertility or the unborn child [Danger Reproductive toxicity]H360D (16.3%): May damage the unborn child [Danger Reproductive toxicity]P203, P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P318, P321, P330, P332+P317, P337+P317, P362+P364, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 233 reports by companies from 28 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 233 reports by companies.There are 27 notifications provided by 232 of 233 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 規制情報 | Chemical: 1H-Imidazole, 1,1'-carbonylbis-Status: Active Update: 30-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/103641,1'-Carbonyldiimidazole: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | Hydrolyzed by water evolving carbon dioxide[Merck Index] Causes burnsInhalation may cause corrosive injuries to upper respiratory tract and lungsHarmful by ingestion[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (84.1%)Skin Corr. 1B (83.3%)Skin Irrit. 2 (15.9%)Eye Dam. 1 (45.9%)Eye Irrit. 2 (15.9%)Repr. 1B (26.2%)Repr. 1B (16.3%) |
| 有害作用 | Dermatotoxin - Skin burns.Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors. |
| F | 10-21 |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| 輸送番号（UN） | UN 3263 8/PG 2 |
| 毒性 | LD50 orally in Rabbit: 1071 mg/kg |
| 税関コード | 29332990 |
| 危険文句（R） | 22-34-36/37/38-40-36/38 |
| 化審法 | (5)-6491 |
| 危険表示 | C,Xi,Xn |
| hazard_note | Harmful/Corrosive/Moisture Sensitive |
| 安全措置（S） | 26-36/37/39-45-37/39-27-36/37 |
| 危険等級 | 8Acute Tox. 4 OralEye Dam. 1Skin Corr. 1B |
| 包装等級 | III |
| 貯蔵分類 | 8A - Combustible corrosive hazardous materials |
用途
用途
カルボニルジイミダゾール (carbonyldiimidazole) はペプチド合成におけるアミノ酸のカップリング剤など、有機合成に用いられる試薬である。CDIと略称される。イミダゾール環をImと略記し、Im2C=Oと表されることもある。
用途
イミダゾールの脱離能の高さを生かし、アルコールやアミンをカルバメート、エステル、尿素、炭酸エステルに変換するのに用いられる。
用途
有機合成用反応試薬。
使用
CDI, also known as 1,1'-carbonyldiimidazole, is a commonly used peptide coupling reagent in the synthesis of peptides and nucleoside triphosphates. It usually contains approximately 10% imidazole and reacts rapidly with carboxylic acids to produce acyl imidazoles. Later, it readily reacts with amines to create amides. In addition, CDI is useful in converting alcohols and amines into a range of chemical compounds, including carbamates, esters, and ureas.
一般的な説明
1,1′-Carbonyldiimidazole (N,N′-carbonyldiimidazole) is a versatile peptide-forming reagent.
製法・合成法
製造方法
1,1'-Carbonyldiimidazole has been prepared by the reaction of imidazole and phosgene in anhydrous benzene and anhydrous tetrahydrofuran. It has also been obtained by the reaction of 1-(trimethylsilyl)imidazole and phosgene in anhydrous benzene, but that method offers no advantages that justify the more extensive preparative effort required.DOI: 10.15227/orgsyn.048.0044
純化方法
Crystallise it from *benzene or tetrahydrofuran in a dry-box and store it dry. [Hearn Methods Enzymol 135 102 1987, Beilstein 23/4 V 245.]