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CAS RN: 1122-28-7 | Product Number: D2026

4,5-Dicyanoimidazole


Purity: >98.0%(HPLC)(N)
Synonyms:
  • 4,5-Imidazoledicarbonitrile
Documents:
25G
€86.00
6   ≥100 
250G
€644.00
8   ≥100 

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Product Number D2026
Purity / Analysis Method >98.0%(HPLC)(N)
Molecular Formula / Molecular Weight C__5H__2N__4 = 118.10 
Physical State (20 deg.C) Solid
Storage Temperature Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN 1122-28-7
Reaxys Registry Number 118208
PubChem Substance ID 87568478
MDL Number

MFCD00005194

Specifications
Appearance White to Light yellow powder to crystal
Purity(HPLC) min. 98.0 area%
Purity(with Total Nitrogen) min. 98.0 %
Properties (reference)
Melting Point 175 °C
GHS
Pictogram Pictogram
Signal Word Danger
Hazard Statements H301 + H311 + H331 : Toxic if swallowed, in contact with skin or if inhaled.
H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P261 : Avoid breathing dust.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection/ hearing protection.
P301 + P310 + P330 : IF SWALLOWED: Immediately call a POISON CENTER/doctor. Rinse mouth.
P302 + P352 + P312 : IF ON SKIN: Wash with plenty of water. Call a POISON CENTER/doctor if you feel unwell.
P403 + P233 : Store in a well-ventilated place. Keep container tightly closed.
Related Laws:
EC Number 214-344-6
Transport Information:
UN Number UN3439
Class 6.1
Packing Group III
HS Number 2933299090
Application
TCI Practical Example: Construction of the Phosphoramidite Using 4,5-Dicyanoimidazole (= DCI)

 TCI Practical Example: Construction of the Phosphoramidite Using 4,5-Dicyanoimidazole (= DCI)

Used Chemicals

Procedure

To an acetonitrile (2 mL) solution of 2-cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite (0.42 g, 1.4 mmol) and DCI (0.14 g, 1.2 mmol) were added a DMF solution of 1 (0.40 g, 1.2 mmol) under nitrogen atmosphere. The reaction mixture was stirred overnight at room temperature, then diluted with TBME and washed with H2O, DMF:H2O (1:1) solution, H2O and brine. The organic layer was concentrated under reduced pressure. The resulting crude product was purified by column chromatography (hexane:ethyl acetate:triethylamine = 1:2:0.03 on silica gel) to give 2 as a white powder (0.45 g, 68% yield).

Experimenter’s Comments

The reaction mixtures were monitored by LCMS.

Analytical Data

Compound 2

1H NMR (400 MHz, DMSO-d6); δ 11.36 (brs, 1H), 8.05-7.96 (m, 2H), 7.73-7.64 (m, 1H), 7.59-7.51 (m, 2H), 7.45-7.37 (m, 1H), 6.25-6.17 (m, 1H), 4.72-4.62 (m, 1H), 4.62-4.52 (m, 1H), 4.51-4.38 (m, 1H), 4.32-4.15 (m, 1H), 3.84-3.66 (m, 2H), 3.66-3.51 (m, 2H), 2.84-2.73 (m, 2H), 2.47-2.22 (m, 2H), 1.67-1.53 (m, 3H), 1.27-1.03 (m, 12H).

13C NMR (101 MHz, DMSO-d6); δ 165.5, 163.6, 150.4, 135.8, 133.7, 129.3 (3C), 128.9 (2C), 119.0, 109.9, 84.1, 82.8, 72.8, 64.9, 58.3 (2C), 42.7, 37.7, 24.3 (4C), 19.8, 11.9.

31P NMR (162 MHz, DMSO-d6); δ 147.89.

Lead Reference


PubMed Literature


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