Basic information
- CAS
2449-05-0- Standard SMILES
O=C(/N=N/C(=O)OCc1ccccc1)OCc1ccccc1- InChIKey
IRJKSAIGIYODAN-ISLYRVAYSA-N- Molecular formula
- C16H14N2O4
- Average molar mass
- 298.29 g/mol
Overview
See also: 1,2-Bis(phenylmethyl) 1,2-diazenedicarboxylate (annotation moved to).
Names & identifiers
- Preferred name
- Dibenzyl azodicarboxylate
- IUPAC
- benzyl (NE)-N-phenylmethoxycarbonyliminocarbamate
- English name
- Dibenzyl azodicarboxylate
- Molecular formula
- C16H14N2O4
- Molecular weight
- 298.29
Names & synonyms
Dibenzyl azodicarboxylateO9NGE39Q8ODiazenedicarboxylic acid, bis(phenylmethyl) ester1,2-Diazenedicarboxylic acid, 1,2-bis(phenylmethyl) esterNSC-620564(E)-dibenzyl diazene-1,2-dicarboxylateNSC620564UNII-O9NGE39Q8OEINECS 219-508-0phenylmethyl {[benzyloxycarbonyl]diazenyl}formateN-{[(benzyloxy)carbonyl]imino}(benzyloxy)formamideDibenzyl azodicarboxylate, 96%
Show more names
DBADDibenzyl diazene-1,2-dicarboxylateDZADDibenzyl azodicarboxMinocycline Impurity 49Dibenzy| azodicarbo×ylateDibenzylazodicarboxylate,98%Bis(benzyloxycarbonyl)diazene
CHEMBL1964960DTXCID1024887Tox21_301610SBB058571AKOS015889670(E)-dibenzyldiazene-1,2-dicarboxylateCS-W009965NCGC00256225-01
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 3.9
- Topological polar surface area
- 77.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 6
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 350
Physicochemical properties
- Melting point
- 43 · 43-47 °C (lit.)
- Boiling point
- 439.72 °C · 439.72°C (rough estimate)
- Density
- 1.2028 · 1.2028 (rough estimate)
- refractive index
- 1.624 · 1.6240 (estimate)
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
- form
- Crystalline Powder
- color
- Yellow to orange
- Sensitive
- Light Sensitive
- BRN
- 2298734 · 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
- InChIKey
- IRJKSAIGIYODAN-ISLYRVAYSA-N
- SMILES
- N(C(OCC1=CC=CC=C1)=O)=NC(OCC1=CC=CC=C1)=O
- CAS DataBase Reference
- 2449 · 2449-05-0(CAS DataBase Reference)
- FDA UNII
- 9 NGE39Q8O · O9NGE39Q8O
Safety & regulation
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- 3224
- hs_code
- 29270000
- risk_code
- 36/37/38-11
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,F
- safety_code
- 26-37/39-16
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
UsesDibenzyl azodicarboxylate is a reagent used in the synthesis of Minocycline-d6 (M344797). Minocycline-d6 is a labeled second generation tetracycline antibiotic. Antibacterial.
UsesDibenzyl 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 DescriptionDibenzyl azodicarboxylate undergoes[4+2] cycloaddition reaction with glycal to yield 2-aminoglycosides.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
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Related reactions
73 records
Compound notes
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