DIETHYL AZODICARBOXYLATE

PRODUCT IDENTIFICATION

CAS RN

EINECS RN

FORMULA

MOLE WEIGHT

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE

MELTING POINT

BOILING POINT

DENSITY

1.11

SOLUBILITY IN WATER

pH

VAPOR DENSITY

REFRACTIVE INDEX

FLASH POINT

85 C

INCOMPATIBLE MATERIALS

Carbon oxides, Nitrogen oxides. Nitrogen gas.

NFPA RATINGS

SAFETY

HAZARD NOTES

Harmful if swallowed. Harmful if inhaled. Toxic in contact with skin

EYE

SKIN

INGESTION

INHALATION

CHRONIC

TRANSPORT & REGULATORY INFORMATION

UN NO.

6.1

III

HAZARD SYMBOL

T XN

RISK PHRASES

5-25-36/37/38

SAFETY PHRASES

OTHER INFORMATION

The Mitsunobu Reaction allows the conversion of primary and secondary alcohols to esters, phenyl ethers, thioethers and various other compounds. The nucleophile employed should be acidic, since one of the reagents (DEAD, diethylazodicarboxylate) must be protonated during the course of the reaction to prevent from side reactions. (source: http://www.organic-chemistry.org/namedreactions/mitsunobu-reaction.shtm)

The Mitsunobu reaction is a unique dehydration-condensation reaction between alcohols and various nucleophiles using the redox system comprised of diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP).The reactions proceed under mild conditions, and a wide variety of compounds can be used as nucleophiles, for example, carboxylic acids, active methylenes, imides, thiols, etc. The reaction between secondary alcohols and nucleophiles yields products with Walden inversion. The Mitsunobu reaction has been used widely in organic synthesis. Due to its utility, efforts have been made to expand application of the Mitsunobu reaction, and modified reactions have been reported. For example, by using azodicarboxamides instead of azodicarboxylates the Mitsunobu reaction is being applied to weak-acidity nucleophiles with a higher pKa value. Methods have also been reported for the easy removal of phosphine oxide, a reaction by-product, by utilizing phosphines which have an intramolecular basic component and diphenylphosphino polystyrene resin. (source: http://www.tci-asiapacific.com/product/synthetic-chem/S004.shtml)

The Mitsunobu reaction has proven to be a useful, diverse and practical method for C-O, C-N, C-C and C-X bond formation, among other uses. Its mild reaction conditions and excellent stereoselectivity make it an excellent reaction that serves its purpose well. It will no doubt continue to be an important synthetic tool for the practicing organic chemist.(source: http://www.chem.wisc.edu/areas/organic/studsemin/jantzi/jantzi-abs.pdf)

CARBOXYLATE-N=N-CARBOXYLATE Products

Products	CAS RN.
Di-tert-butyl azodicarboxylate	870-50-8
Diethyl azodicarboxylate	1972-28-7
Diisopropyl azodicarboxylate	2446-83-5
Dimethyl Azodicarboxylate	2446-84-6
Diphenyl azodicarboxylate	2449-14-1
Dibenzyl azodicarboxylate	2449-05-0
Diethyl hydrazodicarboxylate	4114-28-7
1,1'-Azobis(N,N-dimethylformamide)	10465-78-8
1,1'-(Azodicarbonyl)dipiperidine	10465-81-3
Bis(2,2,2-trichloroethyl)azodicarboxylate	38857-88-4

SALES SPECIFICATION

APPEARANCE

97.0% min

BOILING POINT