169324-82-7

Basic information

• Product Name: 2-(BOC-AMINO)-3-BUTEN-1-OL
• Synonyms: 2-(BOC-AMINO)-3-BUTEN-1-OL;Carbamic acid, [1-(hydroxymethyl)-2-propenyl]-, 1,1-dimethylethyl ester (9CI);tert-butyl 1-hydroxybut-3-en-2-ylcarbaMate;1,1-Dimethylethyl N-[1-(hydroxymethyl)-2-propen-1-yl]-carbamate
• CAS NO: 169324-82-7
• Molecular Formula: C₉H₁₇NO₃
• Molecular Weight: 187.24
• Product Categories: N-BOC
• Mol File: 169324-82-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(BOC-AMINO)-3-BUTEN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(BOC-AMINO)-3-BUTEN-1-OL(169324-82-7)
• EPA Substance Registry System: 2-(BOC-AMINO)-3-BUTEN-1-OL(169324-82-7)

Safety Data

• Hazardous Substances Data: 169324-82-7(Hazardous Substances Data)

Usage

General Description

2-(BOC-AMINO)-3-BUTEN-1-OL is a chemical compound containing a Boc (tert-butoxycarbonyl) protected amino group attached to a butenol moiety. It is commonly used in organic synthesis as a building block for the creation of various complex molecules. The Boc group serves as a protective group for the amino functionality, allowing for selective reactions with other functional groups without affecting the amino group. The butenol moiety provides a handle for further modifications or coupling reactions. This chemical is utilized in the pharmaceutical, agrochemical, and materials science industries for the synthesis of various bioactive compounds, polymers, and other useful molecules.

Upstream product

• 115148-32-8 3-(4-methoxyphenyl)-4-vinyloxazolidin-2-one 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 144634-45-7 4-vinyloxazolidin-2-one 
• 451502-79-7 tert-butyl 2-oxo-4-vinyloxazolidinone-3-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 99726-03-1 2-aminobut-3-en-1-ol hydrochloride 
• 267668-24-6 N-tert-butyloxycarbonyl-N-(1-hydroxymethyl-2-propenyl)benzenesulfenamide 
• 451502-80-0 ethyl (2Z)-4-[(p-methoxyanilino)carbonyloxy]-2-butenyl carbonate 

Downstream Products

• 271260-96-9 (R)-3-(tert-butoxycarbonyl)-4-[2-(2,4,6-trimethylphenyl)ethyl]-2,2-dimethyloxazolidine 

Relevant articles and documents

In situ enzymatic screening (ISES): A tool for catalyst discovery and reaction development

Can enzymes help organic chemists identify new transition-metal catalysts? The first example of the in situ enzymatic monitoring of an organic transformation is described. Thus, a transition-metal-mediated allylic-amination reaction in the organic layer (

Fe(II)-catalyzed imidation of allyl sulfides and subsequent [2,3]- sigmatropic rearrangement. Preparation of α-branched N-tert-butyloxycarbonyl (Boc)-protected N-allylamines

Allyl aryl sulfides 1 and 5 were shown to undergo an imidation/[2,3]- sigmatropic rearrangement reaction upon treatment with N-tert- butyloxycarbonyl azide (BocN3) and catalytic amounts of FeCl2 in CH2Cl2. The N-Boc-protected N-allyl sulfenamides 3 and 21 were obtained in yields between 48 and 75% (12 examples). Whereas the reaction is well suited for the transformation of α-unbranched sulfides to α-branched sulfenamides, the enantiomerically pure α-branched sulfides 10 and 13 reacted sluggishly. The corresponding sulfenamides 22 and 23 were obtained in only moderate enantiomeric excess (36-39% ee). A reaction mechanism is proposed that postulates the intermediacy of an N-Boc-substituted Fe(IV)-nitrene complex 14 acting as the imidation reagent in the catalytic cycle. Possible side reactions are discussed. The benzenesulfenamides 3 were further converted into N-Boc-N-allylamines 4 by removal of the phenylsulfanyl group. Bu3SnH in benzene was found to be the reagent of choice for the deprotection of α- branched amines that bear a secondary allyl substituent (five examples, 71- 93% yield). This method failed for the α-branched amines 3i-k with a tertiary allyl substituent. The phenylsulfanyl group was finally removed with P(OEt)3/NEt3 in CH2Cl2 (three examples, 43-62% yield).