1,1'-Carbonyldiimidazole

HCID 68263
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
530-62-1
Standard SMILES
O=C(n1ccnc1)n1ccnc1
InChIKey
PFKFTWBEEFSNDU-UHFFFAOYSA-N
Molecular formula
C7H6N4O
Average molar mass
162.15 g/mol
Monoisotopic mass
162.05416083

Names & identifiers

Preferred name
1,1'-Carbonyldiimidazole
IUPAC
di(imidazol-1-yl)methanone
English name
1,1'-Carbonyldiimidazole
Molecular formula
C7H6N4O
Molecular weight
162.15

Names & synonyms

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

Database identifiers

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

Properties

Computed structural properties

XLogP
-0.2
Topological polar surface area
52.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
12

Experimental & physicochemical properties

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

Physicochemical properties

Melting point
117 · 117-122 °C(lit.)
Boiling point
288.83 °C · 288.83°C (rough estimate)
Density
1.303 g/mL · 1.303 g/mL at 25 °C
vapor pressure
0.006 · 0.006-0.012Pa at 20-25℃
refractive index
20 · n20/D1.434
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 6 items

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.

Hazard information

Regulatory Information · 3 items

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%)

Toxicology

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

Regulatory information

Regulatory Information · 3 items

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

Safety data

F
10-21
wgk
2
tsca
TSCA listed
ridadr
UN 3263 8/PG 2
hs_code
29332990
Toxicity
LD50 orally in Rabbit: 1071 mg/kg

Chemistry & industry

Uses & manufacturing

UsesUsed to make peptides; [Merck Index]
General Manufacturing InformationMethanone, di-1H-imidazol-1-yl-: ACTIVE
Applications · 2 items

UsesCDI, 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.

General Description1,1′-Carbonyldiimidazole (N,N′-carbonyldiimidazole) is a versatile peptide-forming reagent.

Preparation methods · 1 item

Preparation1,1'-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

Upstream & downstream products

Downstream products

Suppliers100 total

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]

Related reactions

9,856 records
New reaction record

Compound notes

Loading…