tert-butyl 2-diazoacetate

• ChemBase ID: 151010
• Molecular Formular: C6H10N2O2
• Molecular Mass: 142.1558
• Monoisotopic Mass: 142.07422757
• SMILES: CC(C)(C)OC(=O)C=[N+]=[N-]
• Canonical SMILES: O=C(C=[N+]=[N-])OC(C)(C)C
• InChI: InChI=1S/C6H10N2O2/c1-6(2,3)10-5(9)4-8-7/h4H,1-3H3
• InChIKey: JBVSBLLOZVDAAZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl 2-diazoacetate
• IUPAC Traditional name: tert-butyl 2-diazoacetate
• Synonyms: tert-Butyl diazoacetate; 2-Diazo-acetic Acid 1,1-Dimethylethyl Ester; (tert-Butoxycarbonyl)diazomethane; tert-Butyl Diazoacetate, 85%; 重氮基乙酸叔丁酯

Database IDs

• CAS Number: 35059-50-8
• MDL Number: MFCD01318409
• PubChem SID: 24871716; 162245169
• PubChem CID: 6269672

CALCULATED PROPERTIES

• Acid pKa: 8.766363
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.20888293
• LogD (pH = 7.4): -0.21298511
• Log P: -0.20882863
• Molar Refractivity: 34.7747 cm^3
• Polarizability: 13.887765 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Yellow Oil
• Boiling Point: 51-53 °C/12 mmHg(lit.)
• Flash Point: 109.4 °F; 43 °C
• Density: 1.026 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.453(lit.)

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Toxic (T)
• UN Number: 1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 45-63-10-22-36/37/38
• Safety Statements: 53-26-36/37-45
• GHS Pictograms: GHS02; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H302-H315-H319-H335-H350-H361
• GHS Precautionary statements: P201-P261-P281-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Impurities: ≤15% dichloromethane
• Linear Formula: N2CHCO2C(CH3)3

DETAILS

Sigma Aldrich - 480754

Packaging
1 g in glass bottle
Application
New Diazoacetate Formulations

Toronto Research Chemicals - B691035

An intermediate in the production of Zolpidem metabolites

REFERENCES

• Klupsch, F., et al.: Chem. Pharm. Bull., 54, 1318 (2006)
• Epple, R., et al.: Bioorg. Med. Chem. Lett., 16, 5488 (2006)