N,N'-羰基二咪唑

1,1'-Carbonyldiimidazole

HCID 68263CAS 530-62-1
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基本信息

标准SMILES
O=C(n1ccnc1)n1ccnc1
InChIKey
PFKFTWBEEFSNDU-UHFFFAOYSA-N
分子式
C7H6N4O
平均分子量
162.15 g/mol
单同位素质量
162.05416083

名称与标识

首选名称
1,1'-Carbonyldiimidazole
IUPAC
di(imidazol-1-yl)methanone
中文名
N,N'-羰基二咪唑
英文名
1,1'-Carbonyldiimidazole
分子式
C7H6N4O
分子量
162.15

名称与别名

530-62-11,1'-CarbonyldiimidazoleN,N'-CarbonyldiimidazoleN,N-CarbonyldiimidazoleCarbonyl diimidazoleDiimidazol-1-yl ketone63A10X1FSPNSC-67203RefChem:821863208-488-9di(1H-imidazol-1-yl)methanoneCarbonyldiimidazole
展开更多名称
羰基咪唑羟基咪唑碳二引咪唑羰基二咪唑-羰基二咪唑CDI杂质对照羰基咪唑/CDIN,N-羰基咪唑N'-羰基二咪唑1,1-碳酰二咪唑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)

数据库标识

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

性质

结构计算性质

XLogP
-0.2
极性表面积
52.7 Ų
氢键供体
0
氢键受体
3
可旋转键
0
重原子
12

实验与物化性质

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

物理化学性质

熔点
117 · 117-122 °C(lit.)
沸点
288.83 °C · 288.83°C (rough estimate)
密度
1.303 g/mL · 1.303 g/mL at 25 °C
蒸气压
0.006 · 0.006-0.012Pa at 20-25℃
折射率
20 · n20/D1.434
储存条件
2 · 2-8°C

化学性质

白色晶体。熔点115.5-116℃，不溶于水，溶于醇、醚。

安全与法规

GHS分类

GHS Classification · 6 条

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.

危害信息

Regulatory Information · 3 条

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%)

毒理信息

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

法规信息

Regulatory Information · 3 条

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

安全数据

F
10-21
wgk
2
tsca
TSCA listed
毒性
LD50 orally in Rabbit: 1071 mg/kg
hazard_note
Harmful/Corrosive/Moisture Sensitive
包装类别
III

化学与工业

用途与制造

UsesUsed to make peptides; [Merck Index]
General Manufacturing InformationMethanone, di-1H-imidazol-1-yl-: ACTIVE
应用领域 · 6 条

概述N,N′-羰基二咪唑(简称CDI)是咪唑的衍生物,其咪唑结构中具有一个闭合的大P键,且其中一个氮原子未成键的sp2轨道上有一对孤对电子。这些决定了CDI具有较强的化学反应活性,能与氨、醇、酸等官能团反应,合成许多用一般化学方法难以得到的化合物。广泛用作酶和蛋白质粘合剂,抗生素类合成药物中间体,特别是作为合成多肽化合物的键合剂。

应用N,N'-羰基二咪唑（CDI）作为活化剂表现出快速、简便的特点,因而在有机合成中应用广泛,在生化、制药方面有较多的报道。如采用CDI作为活化剂,可快速合成具有良好抗菌性能的两亲性脲类低聚体;可合成具有酰胺结构的可在固相条件下进行自组装的羟基喹咛衍生物;可通过单体自身环化,制备出具有脲结构的杂环类有机化合物。1

用途在非线性光学以及多肽应用中，合成偶极聚酰胺的偶联试剂；也用于制备β-酮类砜以及亚砜；铅螯合试剂；β-烯氨基酸衍生物；酸活化为咪唑啉的反应试剂；用于酯、胺、酮等的合成；固定酶或亲合配体的固定试剂；在最新应用于不同类杂环化合物的合成中，羰基转化试剂

用途多肽试剂，用于生化合成基团保护及蛋白质肽链的连接。作为合成三磷核苷、肽、和酯类的缩合剂；以及是合成酰基咪唑和吡藜酰胺的重要中间体。

用途用于有机合成。可用于合成多肽，含有高达 10% 的咪唑。

用途用作农药、医药中间体

制备方法

制备在带有搅拌、温度计和导气管的四口反应瓶中,加入甲苯、三正丁基胺、咪唑,加热至70℃ ,在20～ 30min内通入光气之后,维持反应温度,反应1.5h,冷却至20℃ ,反应45min。过滤分离出白色结晶沉淀,经甲苯洗涤,氨气清扫下干燥,得产品。

生产方法将咪唑与溶于苯的光气反应，滤除反应物中的咪唑盐酸盐，滤液浓缩至干，得1,1'-羰基二咪唑，产率91%。

上下游产品信息

试剂价格

A14688 · 250g
1,1'-羰基二咪唑, 97%1,1'-Carbonyldiimidazole, 97% — 4066元
15181 · 10g
1，1-羰基二咪唑1,1'-Carbonyldiimidazole, 97%, Thermo Scientific Chemicals — 459元

供应商50 家

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

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