Diisopropyl azodicarboxylate Chemical Properties

Melting point:

3-5 °C

Boiling point:

75 °C/0.25 mmHg (lit.)

Density 

1.027 g/mL at 25 °C (lit.)

vapor pressure 

1.04 hPa (20 °C)

refractive index 

n20/D 1.420(lit.)

Flash point:

223 °F

storage temp. 

Store below +30°C.

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Liquid

color 

Clear to slightly turbid yellow-orange to red

Water Solubility 

insoluble

Sensitive 

Light Sensitive

BRN 

1912326

InChI

InChI=1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3

InChIKey

VVWRJUBEIPHGQF-UHFFFAOYSA-N

SMILES

N(C(OC(C)C)=O)=NC(OC(C)C)=O

CAS DataBase Reference

2446-83-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi,N,F

Risk Statements 

36/38-51/53-5-43-36/37/38-11-48/20/22-40

Safety Statements 

36-61-47A-36/37/39-29-26-16-60-36/37

RIDADR 

UN 3082 9/PG 3

WGK Germany 

1

F 

4.10-8

Hazard Note 

Harmful/Irritant

HazardClass 

9

PackingGroup 

III

HS Code 

29270000

MSDS

• Language:English Provider:DIAD
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Diisopropyl azodicarboxylate Usage And Synthesis

Product description

Isopropyl azodicarboxylate (Acronym DIAD; foaming agent DIPA) belongs to diisopropyl azo-hydroxy acid salt. At room temperature, it is an orange-red transparent oily liquid with special smell and is soluble in almost all organic solvents and plasticizers. It is also insoluble in water but soluble in common plasticizer. It can be well miscible with plastic with good thermal stability. Storage stability: the decomposition substance is colorless, non-toxic, non-pollution, non-blooming and odorless. In the range of 40~120 °C, it can obtain high gas evolution. It is also the liquid blowing agent of vinyl resin and can be used to make light-colored vinyl foam. It has a uniform pore structure, with different formulations and processing conditions obtaining the foam of either closed pore or open pore. It can also be used as pharmaceutical intermediates and organic synthesis reagents.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Uses

It can be used as dye intermediates, pharmaceutical intermediates, organic synthesis reagents, and the foaming agent of the rubber plastics liquid.
Isopropyl azodicarboxylate can be used for the liquid foaming agent of vinyl resin. It can be used to make light-colored vinyl foam. It has a uniform pore structure with different formulations and processing conditions giving foam of either closed pore or open pore. It can also be used as pharmaceutical intermediates, and organic synthesis reagents.

Chemical Properties

CLEAR ORANGE LIQUID

Uses

Diisopropyl Azodicarboxylate is an azodicarboxylic acid derivative used as a reagent in the production of many organic compounds. Diisopropyl Azodicarboxylate is commonly used as an oxidizer in Mitsun obu reactions and can also serve as a selective deprotectant of N-benzyl groups in the presence of other protecting groups.

Uses

Diisopropyl azodicarboxylate is used as an important reagent in the production of many organic compounds. It is used in association with triphenyl phosphine in Mitsunobu reaction of alcohols, acids and amides. It acts as reactant in the preparation of chromenes resembling classical cannabinoids, norbornene-based guanidine-rich polymers and acceptor-donor-acceptor organic dyes.

General Description

Reacted with dioxaphosphorinanes and iron catalyst to generate rearranged phosphonium ylide products.

Synthesis

General procedure for the synthesis of diisopropyl azodicarboxylate from diisopropyl hydrazine-1,2-dicarboxylate: Hydrazine hydrate (200 mg, 4.0 mmol), tetrahydrofuran (10 mL), and sodium carbonate (551 mg, 5.2 mmol) were added to a 30 mL round-bottomed flask, and isopropyl chlorocarbonate (980 mg, 8.0 mmol) was added dropwise, slowly, and under ice bath cooling. After the dropwise addition, the reaction was continued for 1 hour. Upon completion of the reaction, the solid insoluble material was removed by filtration and the filtrate was concentrated to about 90% of the original volume to give a tetrahydrofuran solution of diisopropyl 1,2-hydrazinedicarboxylate. Toluene (10 mL) was added to this solution, and the remaining tetrahydrofuran was removed by concentration to obtain a toluene solution of diisopropyl 1,2-hydrazinedicarboxylate. Subsequently, pyridine (316.4 mg, 4.0 mmol) and additional toluene (10 mL) were added to this toluene solution, and the reaction was carried out by slowly adding N-bromosuccinimide (711.9 mg, 4.0 mmol) at 20 °C for 2 hours. At the end of the reaction, the reaction solution was washed with water (3 mL x 2), dried over anhydrous magnesium sulfate and concentrated to dryness. The residue was purified by distillation to give diisopropyl azodicarboxylate as a clarified liquid (628.5 mg, 77.8% yield).

Purification Methods

Purify the azo compound by distillation at as high a vacuum as possible. Since it is likely to explode, use an oil bath for heating the still, and all operations should be carried out behind an adequate shield. [Kauer Org Synth Coll Vol IV 412 1963, Beilstein 3 III 233]. This reagent is useful in the Mitsunobu reaction [Mitsunobu Synthesis 1 1981, Gennari et al. J Am Chem Soc 108 6394 1986, Evans et al. J Am Chem Soc 108 6394 1986, Hughes Org React 42 335 1992, Dodge et al. Org Synth 73 110 1996, Hughes Org Prep Proc Int 28 127 1996, Ferguson & Marcelle J Am Chem Soc 128 4576 2006; see also di-tert-butyl azodicarboxylate and DEAD above].

References

[1] Organic Letters, 2016, vol. 18, # 24, p. 6300 - 6303
[2] Patent: JP5920622, 2016, B2. Location in patent: Paragraph 0029-0031
[3] Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, # 11, p. 2361 - 2364
[4] Zhurnal Organicheskoi Khimii, 1971, vol. 7, # 11, p. 2271 - 2274
[5] Organic and Biomolecular Chemistry, 2017, vol. 15, # 9, p. 1970 - 1975

Diisopropyl azodicarboxylate(2446-83-5)Related Product Information

• Diisopropyl malonate
• Propyl chloroformate
• Diethyl azodicarboxylate
• Di-tert-Butyl azodicarboxylate
• Diallyl phthalate
• 2'-Hydroxy-3-phenylpropiophenone
• Isopropyl chloroformate
• Diisopropyl phosphite
• Isopropylparaben
• DIISOPROPYL METHYLPHOSPHONATE
• Triisopropyl orthoformate
• Dimethyl 2,2'-azobis(2-methylpropionate)
• 2,2′-Azobis(2-methylpropionamidine) dihydrochloride
• 2,2'-AZOBIS[2-METHYL-N-(2-HYDROXYETHYL)PROPIONAMIDE]
• Bis(4-chlorobenzyl) azodicarboxylate
• 1,1'-(Azodicarbonyl)-dipiperidine
• N,N,N',N'-Tetramethylazodicarboxamide
• 2,2'-Azobis(2-methylpropionitrile)