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CAS RN: 25952-53-8 | Product Number: D1601

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide Hydrochloride [Coupling Agent for Peptides Synthesis]


Purity: >98.0%(T)
Synonyms:
  • 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Hydrochloride
  • EDC·HCl
  • EDAC·HCl
  • EDCI·HCl
Documents:
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25G
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Product Number D1601
Purity / Analysis Method >98.0%(T)
Molecular Formula / Molecular Weight C__8H__1__7N__3·HCl = 191.70  
Physical State (20 deg.C) Solid
Storage Temperature 0-10°C
Store Under Inert Gas Store under inert gas
Condition to Avoid Moisture Sensitive,Heat Sensitive
CAS RN 25952-53-8
Reaxys Registry Number 5764110
PubChem Substance ID 87568083
SDBS (AIST Spectral DB) 21309
MDL Number

MFCD00012503

Specifications
Appearance White powder to crystal
Purity(with Total Nitrogen) min. 97.0 %
Purity(Argentometric Titration) min. 98.0 %
Properties (reference)
Melting Point 115 °C
Solubility in water Completely soluble
Solubility (soluble in) Dimethylformamide,Alcohol
GHS
Pictogram Pictogram
Signal Word Warning
Hazard Statements H302 : Harmful if swallowed.
H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P270 : Do not eat, drink or smoke when using this product.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P301 + P312 + P330 : IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Rinse mouth.
Related Laws:
EC Number 247-361-2
RTECS# FF2200000
Transport Information:
HS Number 2925290020
Application
TCI Practical Example: Condensation

Used Chemicals

Procedure

1-(2-methoxyphenyl)piperazine (500 mg, 2.60 mmol) was dissolved in DMF (15 mL). To this solution was added N-benzyloxycarbonyl-L-phenylalanine (770 mg, 2.60 mmol) and HOBt·H2O (414 mg, 2.71 mmol). The reaction mixture was cooled to 0 °C, then EDC·HCl (515 mg, 2.71 mmol) was added. Reaction was allowed to warm to room temperature, then stirred for 20 h at room temperature. Complete of the reaction was confirmed by TLC. Reaction was quenched by adding H2O (20 mL). Reaction mixture was extracted by EtOAc (30 mL). Organic phase was washed with H2O (20 mL, twice) and brine (20 mL), dried over Na2SO4, concentrated under reduced pressure to afford the crude product (1.2 g) as pale yellow oil. The crude product was purified by column chromatography on silica gel (hexane : ethyl acetate = 40 : 60) to afford the product 1 as a white powder (1.10 g, 2.32 mmol, 90%).

Experimenter's Comments

The reaction mixture was monitored by TLC (hexane / ethyl acetate = 4 : 6, Rf = 0.40)

Analytical Data(Compound 1)

1H NMR (400 MHz, CDCl3); δ 7.39-7.16 (m, 10H), 6.99 (m, 1H), 6.91-6.84 (m, 2H), 6.78 (m, 1H), 5.73 (d, J = 8,2 Hz, 1H), 5.12-5.01 (m, 2H), 4.91 (dd, J= 7.7, 7.3 Hz, 1H), 3.82 (s, 3H), 3.71-3.63 (m, 2H), 3.51 (m, 1H), 3.31 (m, 1H), 3.07-2.78 (m, 5H), 2.51 (m, 1H).


Application
Formation of Peptide Bonds Using EDC·HCl /HOBt

Typical Procedure: To a solution of Boc-ΔTyr(Cl2Bzl)-OH (307 mg, 0.7 mmol), glycinamide hydrochloride (77.4 mg, 0.7 mmol) and Et3N (0.1 mL, 0.7 mmol) in DMF (7 mL) is added EDC·HCl (148 mg. 0.77 mmol) and HOBt (129 mg, 0.84 mmol) at -10°C. The reaction mixture is stirred for 2 h at 0°C. and overnight at room temperature. After the solution is evaporated, the residual is dissolved in EtOAc. The solution is washed with 4% NaHCO3, 10% citric acid and water. The solution is dried and evaporated. The purification is carried out by silica gel column chromatography to give Boc-ΔTyr(Cl2Bzl)-Gly-NH2 (317 mg, 85% yield).
(Δ means dehydro-form.)

References

  • Dehydro‐enkephalins

  • Application
    Water-soluble Condensation Reagent

    Typical Procedure: To a 50 mL round bottom flask equipped with a magnetic stir bar and septum is added 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride 2.54 g (13.3 mmol), 4-dimethylaminopyridine 1.62 g (13.3 mmol), carboxylic acid 1.02 g (2.46 mmol), alcohol 0.96 g (3.98 mmol) and CHCl3 (15 mL), and the reaction mixture is stirred at room temperature for 2.5 days. Acetic acid (0.5 mL) is added and the reaction mixture is stirred for 10 min to convert excess alcohol to a more easily separable acetate. The mixture is washed with saturated aqueous NH4Cl solution, diluted with Et2O, and the layers are dried, filtered and concentrated under reduced pressure. The crude material is chromatographed by silica gel column chromatography (hexane:ethyl acetate = 9:1) to give the desired product 1.25 g (1.96 mmol, 80%).

    References

Documents (Note: Some products will not have analytical charts available.)
Safety Data Sheet (SDS)
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