1,2-Bis(phenylmethyl) 1,2-diazenedicarboxylate
Basic information
- CAS
2449-05-0- Standard SMILES
O=C(N=NC(=O)OCc1ccccc1)OCc1ccccc1- InChIKey
IRJKSAIGIYODAN-UHFFFAOYSA-N- Molecular formula
- C16H14N2O4
- Average molar mass
- 298.29 g/mol
- Monoisotopic mass
- 298.09535693
Names & identifiers
- Preferred name
- 1,2-Bis(phenylmethyl) 1,2-diazenedicarboxylate
- IUPAC
- benzyl N-phenylmethoxycarbonyliminocarbamate
- English name
- Dibenzyl azodicarboxylate
- Molecular formula
- C16H14N2O4
- Molecular weight
- 298.29
Names & synonyms
2449-05-0RefChem:4114061,2-Bis(phenylmethyl) 1,2-diazenedicarboxylateDibenzyl azodicarboxylatedibenzyl diazene-1,2-dicarboxylateDBADMFCD00016737Azodicarboxylic Acid Dibenzyl EsterDTXSID3044887952229-16-21,2-Diazenedicarboxylic acid, 1,2-bis(phenylmethyl) esterDibenzylazodicarboxylate
Show more names
DZAD(E)-dibenzyl diazene-1,2-dicarboxylateDibenzyl azodicarboxMinocycline Impurity 49Dibenzy| azodicarbo×ylateBis(benzyloxycarbonyl)diazene
Diazenedicarboxylic Acid Bis(phenylmethyl) Ester; Azodi-Formic Acid Dibenzyl Ester ; Dibenzyl Azodicarboxylate; NSC 620564benzyl N-benzyloxycarbonyliminocarbamatephenylmethyl {[benzyloxycarbonyl]diazenyl}formatebenzyl N-phenylmethoxycarbonyliminocarbamatedibenzylazodicarboxylate,98%SCHEMBL602246SCHEMBL602247CHEMBL3182293
Database identifiers
- CAS
2449-05-0- PubChem CID
- 75557
- DTXSID
DTXSID3044887- ChEMBL
CHEMBL3182293- EC Number
- 219-508-0
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
- EPA Substance Registry System
- Diazenedicarboxylic acid, bis(phenylmethyl) ester (2449-05-0)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,F
- Risk Statements
- 36 · 36/37/38-11
- Safety Statements
- 26 · 26-37/39-16
- RIDADR
- 3224 · 3224
- WGK Germany
- 3 · 3
- TSCA
- TSCA listed
- HS Code
- 29270000 · 29270000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
- REACH Registrations
- Active
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 51 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
1,2-Diazenedicarboxylic acid, 1,2-bis(phenylmethyl) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Diazenedicarboxylic acid, 1,2-bis(phenylmethyl) ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 01-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21848
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
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
Uses & manufacturing
U.S. Production2020: 15,517 lb
Consumer UsesIntermediate
Industry UsesIntermediate
General Manufacturing Information
Pharmaceutical and Medicine Manufacturing
1,2-Diazenedicarboxylic acid, 1,2-bis(phenylmethyl) ester: ACTIVE
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
Related reactions
20 records
Compound notes
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