Diisopropylazodicarboxylat

Bezeichnung:Diisopropylazodicarboxylat

CAS-Nr2446-83-5

Englisch Name:Diisopropyl azodicarboxylate

CBNumberCB8764409

SummenformelC8H14N2O4

Molgewicht202.21

MOL-Datei2446-83-5.mol

Synonyma

Diisopropylazodicarboxylat

Diisopropylazodicarboxylat physikalisch-chemischer Eigenschaften

Schmelzpunkt	3-5 °C
Siedepunkt	75 °C/0.25 mmHg (lit.)
Dichte	1.027 g/mL at 25 °C (lit.)
Dampfdruck	1.04 hPa (20 °C)
Brechungsindex	n20/D 1.420(lit.)
Flammpunkt	223 °F
storage temp.	Store below +30°C.
Löslichkeit	Chloroform (Slightly), Ethyl Acetate (Slightly)
Aggregatzustand	Liquid
Farbe	Clear to slightly turbid yellow-orange to red
Wasserlöslichkeit	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 Datenbank	2446-83-5(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi,N,F
R-Sätze:	36/38-51/53-5-43-36/37/38-11-48/20/22-40
S-Sätze:	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
Speicherklasse	10 - Combustible liquids
Hazard Classifications	Aquatic Chronic 2 Carc. 2 Eye Irrit. 2 Skin Irrit. 2 STOT RE 2 STOT SE 3

Gefahreninformationscode (GHS)

Diisopropyl azodicarboxylate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/38:Reizt die Augen und die Haut.
R51/53:Giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R5:Beim Erwärmen explosionsfähig.
R43:Sensibilisierung durch Hautkontakt möglich.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R11:Leichtentzündlich.
R48/20/22:Gesundheitsschädlich: Gefahr ernster Gesundheitsschäden bei längerer Exposition durch Einatmen und durch Verschlucken.
R40:Verdacht auf krebserzeugende Wirkung.
S-Sätze Betriebsanweisung:
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S29:Nicht in die Kanalisation gelangen lassen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S16:Von Zündquellen fernhalten - Nicht rauchen.
S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
Chemische Eigenschaften
CLEAR ORANGE LIQUID
Verwenden
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.
Verwenden
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.
Allgemeine Beschreibung
Reacted with dioxaphosphorinanes and iron catalyst to generate rearranged phosphonium ylide products.
Synthese

19740-72-8

2446-83-5

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).
läuterung methode
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].
Einzelnachweise
[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

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