Dibenzyl azodicarboxylate

CAS NO.：2449-05-0
Empirical Formula: C16H14N2O4
Molecular Weight: 298.29
MDL number: MFCD00016737
EINECS: 219-508-0
SAFETY DATA SHEET (SDS)
Update Date: 2024-10-31 13:32:20

What is Dibenzyl azodicarboxylate?

Chemical properties

yellow to orange crystalline powder

The Uses of Dibenzyl azodicarboxylate

Dibenzyl azodicarboxylate is a reagent used in the synthesis of Minocycline-d6 (M344797). Minocycline-d6 is a labeled second generation tetracycline antibiotic. Antibacterial.

The Uses of Dibenzyl azodicarboxylate

Dibenzyl azodicarboxylate was used as electrophilic reagent in the synthesis of C-glycosyl α-amino acids via proline-catalyzed α-amination of C-glycosylalkyl aldehydes. It was used in enantioselective synthesis of optically active pyrazolidine derivatives.

General Description

Dibenzyl azodicarboxylate undergoes[4+2] cycloaddition reaction with glycal to yield 2-aminoglycosides.

Synthesis

PIDA (phenyliodine diacetate) and DCM (dichloromethane) were added to compound dibenzyl hydrazine-1,2-dicarboxylate, and the mixture was reacted with stirring at room temperature for 30 minutes to obtain DBAD (dibenzyl azodicarboxylate) in a yield of 97%.

Properties of Dibenzyl azodicarboxylate

Melting point:	43-47 °C (lit.)
Boiling point:	439.72°C (rough estimate)
Density	1.2028 (rough estimate)
refractive index	1.6240 (estimate)
Flash point:	>230 °F
storage temp.	2-8°C
form	Crystalline Powder
color	Yellow to orange
Sensitive	Light Sensitive
BRN	2298734
InChI	InChI=1S/C16H14N2O4/c19-15(21-11-13-7-3-1-4-8-13)17-18-16(20)22-12-14-9-5-2-6-10-14/h1-10H,11-12H2
CAS DataBase Reference	2449-05-0(CAS DataBase Reference)
EPA Substance Registry System	Diazenedicarboxylic acid, bis(phenylmethyl) ester (2449-05-0)

Safety information for Dibenzyl azodicarboxylate

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.