1,1'-Carbonyldiimidazole (HCID 68263)

名称と識別子

優先名称: 1,1'-Carbonyldiimidazole
IUPAC: di(imidazol-1-yl)methanone
現地名: 1,1'-カルボニルジイミダゾール
英語名: 1,1'-Carbonyldiimidazole
分子式: C7H6N4O
分子量: 162.15

名称と別名

530-62-11,1'-CarbonyldiimidazoleN,N'-CarbonyldiimidazoleN,N-CarbonyldiimidazoleCarbonyl diimidazoleDiimidazol-1-yl ketone63A10X1FSPNSC-67203RefChem:821863208-488-9di(1H-imidazol-1-yl)methanoneCarbonyldiimidazole

名称をさらに表示

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)カルボニルビス(1,1’)-1Ｈ-ジイミダゾルN，N’カルボニルジイミダゾ-ル1,1′-カルボニルジイミダゾール1,1'-カルボニルビス-1H-イミダゾール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溶液1,1'-カルボニルジイミダゾール, 97%1-(1H-イミダゾール-1-カルボニル)-1H-イミダゾールジ(1-イミダゾリル)メタノン1,1′-カルボニルビス(1H-イミダゾール)N,N′-カルボニルジイミダゾールビス(1H-イミダゾール-1-イル)メタノンCDI1,1'-CARBONYLDIIMIDAZOLE (CDI)1,1-CARBONYL DIIMIDAZOLEDiimidazolyl ketoneDi-imidazol-1-yl-methanoneCARBODIIMIDAZOLE

1H-Imidazole, 1,1'-carbonylbis-1,1'-Carbonylbis-1H-imidazole1,1-Carbonyldiimidazoledi(imidazol-1-yl)methanone1-(1H-imidazole-1-carbonyl)-1H-imidazoleCDI CrosslinkerN,N'-Carbonylbis(imidazole)1-Oxomethylenebis(N-imidazole)

データベース識別子

CAS: 530-62-1
PubChem CID: 68263
DTXSID: DTXSID9038761
ChEMBL: CHEMBL3903881
UNII: 63A10X1FSP
EC Number: 208-488-9
Nikkaji: J182.298E

物性

構造計算による物性

XLogP: -0.2
極性表面積: 52.7 Å²
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

実験および物理化学的性質

Physical DescriptionSolid; [Merck Index] White crystalline powder; [Alfa Aesar MSDS]

物理化学的性質

融点: 117 · 117-122 °C(lit.)
沸点: 288.83 °C · 288.83°C (rough estimate)
比重(密度): 1.303 g/mL · 1.303 g/mL at 25 °C
蒸気圧: 0.006 · 0.006-0.012Pa at 20-25℃
屈折率: 20 · n20/D1.434
貯蔵温度: 2 · 2-8°C
溶解性: ジメチルホルムアミドに可溶。
酸解離定数(Pka): 2.9 · 2.90±0.10(Predicted)
外見: 結晶性粉末
色: ホワイト～ライトクリーム
PH: 7.7 · 7.7 (50g/l, H2O, 20℃)
水溶解度: 水に不溶
Merck: 14 · 14,1819
BRN: 6826 · 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 · 530-62-1(CAS DataBase Reference)
EPAの化学物質情報: 1 H-Imidazole, · 1H-Imidazole, 1,1'-carbonylbis- (530-62-1)

化学的性質

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.

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 0.4% (1 of 233) of reports.

Danger

H302 (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.

危険有害性情報

Regulatory Information · 3 件

Chemical: 1H-Imidazole, 1,1'-carbonylbis-

Status: Active Update: 30-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/10364

1,1'-Carbonyldiimidazole: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryHydrolyzed by water evolving carbon dioxide; [Merck Index] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Harmful by ingestion; [Alfa Aesar MSDS]

Hazard Classes and CategoriesAcute 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%)

毒性情報

Adverse EffectsDermatotoxin - Skin burns.；Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

法規制情報

Regulatory Information · 3 件

Chemical: 1H-Imidazole, 1,1'-carbonylbis-

Status: Active Update: 30-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/10364

1,1'-Carbonyldiimidazole: Does not have an individual approval but may be used under an appropriate group standard

安全データ

F: 10-21
wgk: 2
tsca: TSCA listed
ridadr: UN 3263 8/PG 2
毒性: LD50 orally in Rabbit: 1071 mg/kg
hs_code: 29332990
risk_code: 22-34-36/37/38-40-36/38
化審法: (5)-6491
hazard_code: C,Xi,Xn
hazard_note: Harmful/Corrosive/Moisture Sensitive
safety_code: 26-36/37/39-45-37/39-27-36/37
hazard_class: 8
packing_group: III
Hazard Classifications: Acute Tox. 4 OralEye Dam. 1Skin Corr. 1B
ストレージクラス: 8A - Combustible corrosive hazardous materials

化学と産業

用途と製造

UsesUsed to make peptides; [Merck Index]

General Manufacturing InformationMethanone, di-1H-imidazol-1-yl-: ACTIVE

応用分野 · 5 件

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.

調製方法 · 2 件

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.]

上流・下流製品情報

上流原料

イミダゾール N-トリメチルシリルイミダゾールキット塩化カルボニルベンゼン N,N-ジメチルホルムアミド (トリクロロメトキシ)ぎ酸クロリド

下流製品

2-(Boc-aminomethyl)-piperidine 3-oxo-3-phenyl-propanamide 5-(Pyridin-3-yl)-1H-pyrazole-3-carboxamide ,97%チオフェン-3-アセトニトリル 4-アミノカルボニルベンジルアミン 2,8-DICHLOROPYRIMIDO[5,4-D]PYRIMIDINE プロガビド 2-アミノ-5-ブロモベンズアミド臭化物 2-エチルピペラジン 6-FLUORO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBONITRILE パズフロキサシン 5-ブロモチオフェン-2-カルボニトリル臭化物

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1,1'-カルボニルジイミダゾール

基本情報