Diethyl azodicarboxylate
Synonym(s):1,2-Ethoxycarbonyl diazene solution;DEAD;Diethoxycarbonyldiazene solution;Diethyl azodiformate solution;
- CAS NO.:1972-28-7
- Empirical Formula: C6H10N2O4
- Molecular Weight: 174.15
- MDL number: MFCD00009103
- EINECS: 217-821-7
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-04-24 17:21:45
What is Diethyl azodicarboxylate?
Description
Our Halloween 2012 series begins with a molecule that has the acronym DEAD. It stands for diethyl azodicarboxylate, an orange–red liquid that becomes yellow when diluted in a solvent. DEAD is a strong electron acceptor; it oxidizes iodide to molecular iodine, hydrazine to molecular nitrogen, alcohols to aldehydes, and thiols to disulfides. DEAD’s principal use is as a reagent in the Mitsunobu condensation reaction, and it participates in Michael and Diels–Alder reactions. Because it explodes when heated, it cannot be shipped in pure form. Instead, it is transported in solution or adsorbed onto plastic particles.
Description
Diethyl azodicarboxylate (DEAD) is commonly used in Mitsunobu reactions. It is often used as a 40% solution in toluene. Similar reagents include DIAD, DtBAD, and ADDP.
The Uses of Diethyl azodicarboxylate
A fluorescent CDK inhibitor for treatment of cancer
The Uses of Diethyl azodicarboxylate
To a solution of A (400 mg, 1.54 mmol), B (621 mg, 3.09 mmol), and PPh3 (610 mg, 2.32 mmol) in THF (5.5 mL) at RT was added DEAD (404 mg, 2.32 mmol) in THF (0.5 mL). After 90 min, silica gel was added and the mixture was concentrated and purified on a flash column (25% EtOAc/hexane) to provide the product. [545 mg, 80%]
Properties of Diethyl azodicarboxylate
Melting point: | 6°C |
Boiling point: | 106°C (13 mmHg) |
Density | 1.106 |
Flash point: | 85°C |
storage temp. | 2-8°C |
solubility | Miscible with dichloromethane, diethyl ether and toluene. |
appearance | Red/orange liquid |
Sensitive | Air Sensitive |
Safety information for Diethyl azodicarboxylate
Signal word | Danger |
Pictogram(s) |
Flame Flammables GHS02 Exclamation Mark Irritant GHS07 Health Hazard GHS08 |
GHS Hazard Statements |
H226:Flammable liquids H242:Self-reactive substances and mixtures; and Organic peroxides H304:Aspiration hazard H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation H336:Specific target organ toxicity,single exposure; Narcotic effects H373:Specific target organ toxicity, repeated exposure H412:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P331:Do NOT induce vomiting. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. P370+P378:In case of fire: Use … for extinction. P403+P233:Store in a well-ventilated place. Keep container tightly closed. P403+P235:Store in a well-ventilated place. Keep cool. |
Computed Descriptors for Diethyl azodicarboxylate
InChIKey | FAMRKDQNMBBFBR-FPLPWBNLSA-N |
SMILES | N(C(OCC)=O)=NC(OCC)=O |
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