38427-91-7

Basic information

• Product Name: tert-butyl (2-phenylethenyl)carbamate
• CAS NO: 38427-91-7
• Molecular Formula: C₁₃H₁₇NO₂
• Molecular Weight: 219.2796
• Mol File: 38427-91-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 314.2°C at 760 mmHg
• Flash Point: 143.8°C
• Density: 1.05g/cm³
• Vapor Pressure: 0.000474mmHg at 25°C
• Refractive Index: 1.544
• CAS DataBase Reference: tert-butyl (2-phenylethenyl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (2-phenylethenyl)carbamate(38427-91-7)
• EPA Substance Registry System: tert-butyl (2-phenylethenyl)carbamate(38427-91-7)

Safety Data

• Hazardous Substances Data: 38427-91-7(Hazardous Substances Data)

Usage

General Description

Tert-butyl (2-phenylethenyl)carbamate, also known as tBPC, is a chemical compound with a molecular formula of C14H21NO2. It is commonly used as a protecting group for amino acids and peptides in organic synthesis. tBPC is stable and easy to handle, making it a popular choice for protecting the amino group during peptide synthesis. It can be easily removed under mild conditions, allowing for the isolation of the desired peptide sequences. tBPC is also used as a reagent in the preparation of various organic compounds and as a building block in the synthesis of pharmaceuticals and agrochemicals.

Upstream product

• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4248-19-5 tert-butyl carbazate 
• 774225-32-0 tert-butyl 2-phenyl-1-(phenylsulfonyl)ethylcarbamate 
• 621-82-9 Cinnamic acid 
• 75-65-0 tert-butyl alcohol 
• 122-78-1 phenylacetaldehyde 

Downstream Products

• 1204391-10-5 C₂₅H₃₂N₂O₄ 
• 122-78-1 phenylacetaldehyde 
• 38427-90-6 N-(t-butoxycarbonyl)phenethylamine 
• 1323967-15-2 4-phenyl-6,6-dimethyl-1,3-oxazinan-2-one 
• 1323967-31-2 5,5-dideutero-6,6-dimethyl-4-phenyl-1,3-oxazinan-2-one 

Relevant articles and documents

Direct Catalytic Asymmetric Mannich Reaction with Dithiomalonates as Excellent Mannich Donors: Organocatalytic Synthesis of (R)-Sitagliptin

In this study, dithiomalonates (DTMs) were demonstrated to be exceptionally efficient Mannich donors in terms of reactivity and stereoselectivity in cinchona-based-squaramide-catalyzed enantioselective Mannich reactions of diverse imines or α-amidosulfones as imine surrogates. Owing to the superior reactivity of DTMs as compared to conventional malonates, the catalyst loading could be reduced to 0.1 mol % without the erosion of enantioselectivity (up to 99 % ee). Furthermore, by the use of a DTM, even some highly challenging primary alkyl α-amidosulfones were smoothly converted into the desired adducts with excellent enantioselectivity (up to 97 % ee), whereas the use of a malonate or monothiomalonate resulted in no reaction under identical conditions. The synthetic utility of the chiral Mannich adducts obtained from primary alkyl substrates was highlighted by the organocatalytic, coupling-reagent-free synthesis of the antidiabetic drug (?)-(R)-sitagliptin.

Base-Mediated Intramolecular Decarboxylative Synthesis of Alkylamines from Alkanoyloxycarbamates

A general and effective method for the synthesis of alkylamine via intramolecular decarboxylation of alkanoyloxycarbamates is described. The alkanoyloxycarbamates are readily prepared with alkyl carboxylic acids and hydroxylamine. The reaction shows a broad range of substrates (primary and secondary alkyl) with functional tolerance, and the corresponding products were obtained in good yields under mild conditions.

Diastereoselective preparation of novel tetrahydrooxazinones via heterocycloaddition of N-Boc, O-Me-acetals

Under Lewis acid conditions, reaction of N-Boc, O-Me acetals with the (R)-(+)-O-vinyl-pantolactone does not lead to the expected dihydrooxazine, but to the corresponding tetrahydrooxazinone, as a result of the loss of the t-Bu group. A diastereoselective