tert-Butyl diazoacetate

Base Information

• Chemical Name: tert-Butyl diazoacetate
• CAS No.: 35059-50-8
• Molecular Formula: C6H10 N2 O2
• Molecular Weight: 142.158
• Hs Code.: 2927000090
• European Community (EC) Number: 628-315-4
• DSSTox Substance ID: DTXSID20408281
• Nikkaji Number: J645.201I
• Mol file: 35059-50-8.mol

Synonyms:tert-Butyl diazoacetate;35059-50-8;tert-Butyl 2-diazoacetate;t-butyl diazoacetate;tert-Butyl Diazoacetate, 85%;tert-Butyl Diazoacetate, 85per cent;tert-butyl-diazoacetate;DTXSID20408281;JBVSBLLOZVDAAZ-UHFFFAOYSA-N;Diazo-acetic acid tert-butyl ester;AMY15513;BCP32485;AKOS022185108;AS-81749;CS-0368614;FT-0664027;D87815;EN300-100815;t-Butyl diazoacetate;J-019846

Chemical Property of tert-Butyl diazoacetate

Chemical Property:

• Refractive Index: n20/D 1.453(lit.)
• Boiling Point: 51-53 °C12 mm Hg(lit.)
• Flash Point: 110 °F
• PSA: 63.69000
• Density: 1.026 g/mL at 25 °C(lit.)
• LogP: 0.70976
• Storage Temp.: Refrigerator
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 142.074227566
• Heavy Atom Count: 10
• Complexity: 175

Purity/Quality:

98%,99%, ^*data from raw suppliers

tert-ButylDiazoacetate,85% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,F
• Statements: 45-10-22-36/37/38-63-67-65-48/20-38-11
• Safety Statements: 53-16-23-36/37/39-45-36/37-26-62

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C=[N+]=[N-]
• General Description: **TERT-BUTYL DIAZOACETATE** is a reagent used in catalytic asymmetric cyclopropanation reactions, particularly for synthesizing conformationally restricted homotryptamine derivatives. In the presence of pybox-Ru(II) catalysts, it reacts with 1-tosyl-3-vinylindoles to yield trans-2-(indol-3-yl)-1-cyclopropanecarboxylic esters with high enantioselectivity (81–88% ee). This method provides a scalable and efficient alternative to diazomethane-based syntheses and has been applied to produce potent SSRIs like BMS-505130, demonstrating enhanced binding affinity to serotonin transporters. Its utility lies in enabling the construction of rigidified bioactive scaffolds for drug discovery.

Technology Process of tert-Butyl diazoacetate

There total 15 articles about tert-Butyl diazoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

tert-butyl acetoacetate (1694-31-1) → t-butyl diazoacetate (35059-50-8)

Guidance literature:

With 4-toluenesulfonyl azide; tetrabutylammomium bromide; sodium hydroxide; In water; pentane; at 0 ℃; for 12.3333h;

DOI:10.1021/acs.orglett.0c02138

Reference yield: 90.0%

tert-butyl 2-diazo-3-oxobutanoate (13298-76-5) → t-butyl diazoacetate (35059-50-8)

Guidance literature:

With potassium hydroxide; In diethyl ether; water; at 20 ℃; for 16h;

DOI:10.1021/jacs.1c11503

Reference yield: 70.0%

→ t-butylazidoacetoacetate + t-butyl diazoacetate (35059-50-8)

Guidance literature:

upstream raw materials:

tert-butyl 2-formamidoacetate

Glycine tert-butyl ester

glycine t-butyl ester acetate salt

(tert-Butoxycarbonylmethylene)triphenylphosphorane

Downstream raw materials:

cyclohexyl-acetic acid tert-butyl ester

Phenylhydrazon des Glyoxylsaeure-tert.-butylesters

tert-butyl glycolate

tert-butyl nitrodiazoacetate

Refernces

Catalytic asymmetric diazoacetate cyclopropanation of 1-tosyl-3- vinylindoles. A route to conformationally restricted homotryptamines

10.1021/ol050790n

The research explores a method for synthesizing conformationally restricted homotryptamine-like compounds, which are of interest in drug discovery for their potential as selective serotonin reuptake inhibitors (SSRIs). The study focuses on the catalytic asymmetric cyclopropanation of 1-tosyl-3-vinylindoles using ethyl- and tert-butyldiazoacetate, catalyzed by pybox-Ru(II) complexes. The aim is to develop a scalable and efficient synthesis that avoids the use of diazomethane and offers greater catalytic efficiency than existing methods. The researchers found that 1-tosyl-3-vinylindoles are excellent substrates for this reaction, yielding N-protected trans-2-(indol-3-yl)-1-cyclopropanecarboxylic esters with good yields and high enantiomeric excess (81?88% ee). The study demonstrates the utility of this method by converting one of the cycloadducts into the potent SSRI BMS-505130, which showed a 10-fold improvement in binding potency to the serotonin transporter compared to a more flexible analogue. The findings suggest that this catalytic asymmetric cyclopropanation method is a valuable approach for synthesizing conformationally restricted homotryptamines with potential therapeutic applications.