DIISOPROPYL AZODICARBOXYLATE

DIAD; Propan-2-yl (NE)-N-propan-2-yloxycarbonyliminocarbamate; Diazenedicarboxylic acid bis(1-methylethyl) ester;

DIISOPROPYL AZODICARBOXYLATE

 

PRODUCT IDENTIFICATION

CAS RN

2446-83-5

EINECS RN

219-502-8

FORMULA

(CH3)2CHOOCN=NCOOCH(CH3)2

MOLE WEIGHT

202.21

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE

clear to orange liquid

MELTING POINT

 

BOILING POINT

75 C at 25 mmHg

DENSITY

1.027

SOLUBILITY IN WATER

Insoluble (soluble in most common organic solvents)

pH

 

VAPOR DENSITY

 

REFRACTIVE INDEX

1.418 - 1.422

FLASH POINT

106 C

 

STABILITY AND REACTIVITY
STABILITY Stable under normal conditions

INCOMPATIBLE MATERIALS

Alcohols, oxidizing agents, strong bases. light, excess heat, temperatures above 100 C.
DECOMPOSITION PRODUCTS

Carbon oxides, Nitrogen oxides.

POLYMERIZATION Has not been reported

NFPA RATINGS

 

 

SAFETY

HAZARD NOTES

Irritating to eyes, respiratory system and skin. Light sensitive.

EYE

Causes eye irritation. May cause chemical conjunctivitis.

SKIN

Causes skin irritation.

INGESTION

May cause gastrointestinal irritation with nausea, vomiting and diarrhea.

INHALATION

Dust is irritating to the respiratory tract. Can produce delayed pulmonary edema

CHRONIC

Prolonged or repeated skin contact may cause dermatitis. Effects may be delayed.

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

3082
HAZARD CLASS

9

PACKING GROUP

III

HAZARD SYMBOL

XN

RISK PHRASES

36/37/38-40-48/20/22

SAFETY PHRASES

36

 

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 Azodicarboxylate2446-84-6
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

clear to orange liquid
ASSAY

98.0% min

DICHLOROMETHANE

2.0% max

 

PACKING

200kgs/drum

 

PRICE