480754

tert-Butyl diazoacetate

• Synonym(s): (tert-Butoxycarbonyl)diazomethane, 1,1-Dimethylethyl diazoacetate, 2-Diazoacetic acid tert-butyl ester, 2-Diazonio-1-[(2-methylpropan-2-yl)oxy]ethenolate, Diazoacetic acid 1,1-dimethylethyl ester, tert-Butyl α-diazoacetate
• Linear Formula: N₂CHCO₂C(CH₃)₃
• CAS Number: 35059-50-8
• Molecular Weight: 142.16
• MDL number: MFCD01318409
• UNSPSC Code: 12352108
• PubChem Substance ID: 24871716
• NACRES: NA.22

Properties

• impurities: ≤15% dichloromethane
• refractive index: n20/D 1.453 (lit.)
• bp: 51-53 °C/12 mmHg (lit.)
• density: 1.026 g/mL at 25 °C (lit.)
• storage temp.: 2-8°C
• SMILES string: CC(C)(C)OC(=O)C=[N+]=[N-]
• InChI: 1S/C6H10N2O2/c1-6(2,3)10-5(9)4-8-7/h4H,1-3H3
• InChI key: JBVSBLLOZVDAAZ-UHFFFAOYSA-N

Description

General description

tert-Butyl diazoacetate can be used for numerous organic transformations, including cyclopropanation, insertion, and aziridine-forming reactions. 

Application

New Diazoacetate Formulations

tert-Butyl diazoacetate may be used for the preparation of tert-butyl 2-(4-chlorophenyl)cyclopropane-1-carboxylate with high enantioselectivity and trans-cis selectivity via cyclopropanation with 4-chlorostyrene in the presence of a chiral (salen)cobalt(III) bromide complex as a catalyst.

It is a key starting material in the total synthesis of manzacidin A. It can also be used in the synthesis of diastero- and enantioselective synthesis of 2-vinylcyclopropa[b]indolines from 2-vinylindoles.

Safety Information

• Pictograms: GHS02,GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H226,H302,H315,H319,H335,H350,H361
• Precautionary Statements: P202 - P210 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Flam. Liq. 3 - Repr. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): 109.4 °F - closed cup
• Flash Point(C): 43 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves