tert-Butyl 2-bromoacrylate

Base Information

• Chemical Name: tert-Butyl 2-bromoacrylate
• CAS No.: 79762-78-0
• Molecular Formula: C7H11 Br O2
• Molecular Weight: 207.07
• Hs Code.: 2916190090
• European Community (EC) Number: 623-031-7
• DSSTox Substance ID: DTXSID90404038
• Nikkaji Number: J1.164.923H
• Wikidata: Q82207997
• Mol file: 79762-78-0.mol

Synonyms:tert-Butyl 2-bromoacrylate;79762-78-0;Tert-butyl 2-bromoprop-2-enoate;Alpha-bromo-tert-butyl acrylate,95%;starbld0043874;SCHEMBL1811888;DTXSID90404038;tert-Butyl 2-bromoacrylate, 95%;AKOS040768683;CS-0258501;FT-0769341;EN300-7032402

Chemical Property of tert-Butyl 2-bromoacrylate

Chemical Property:

• Vapor Pressure: 0.482mmHg at 25°C
• Refractive Index: n20/D 1.458(lit.)
• Boiling Point: 80-85 °C/35 mmHg(lit.)
• Flash Point: 88 °C
• PSA: 26.30000
• Density: 1.277 g/mL at 25 °C(lit.)
• LogP: 2.23670
• Storage Temp.: ?20°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 205.99424
• Heavy Atom Count: 10
• Complexity: 156

Purity/Quality:

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

tert-Butyl 2-bromoacrylate 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(=C)Br

Technology Process of tert-Butyl 2-bromoacrylate

There total 2 articles about tert-Butyl 2-bromoacrylate 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: 95.0%

tert-butyl 2,3-dibromopropionate (138034-79-4,49855-41-6) → tert-butyl 2-bromoprop-2-enoate (79762-78-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/acs.joc.8b02012

Reference yield:

tert-Butyl acrylate (1663-39-4,25232-27-3) → tert-butyl 2-bromoprop-2-enoate (79762-78-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Br₂ / CH₂Cl₂ / 2 h / 5 °C

2: 80 percent / Et₃N / diethyl ether / 20 °C

With bromine; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1002/ejic.200600405

Reference yield: 91.0%

benzaldehyde (100-52-7) + tert-butyl 2-bromoprop-2-enoate (79762-78-0) → tert-butyl 4-hydroxy-4-phenylbut-2-ynoate

Guidance literature:

With 2,2,6,6-tetramethylpiperidinyl-lithium; In 2-methyltetrahydrofuran; at -40 ℃; for 2.5h; Inert atmosphere;

DOI:10.1039/c2gc35305a

upstream raw materials:

tert-butyl 2,3-dibromopropionate

tert-Butyl acrylate

Downstream raw materials:

C₄₀H₅₉NO₃Si

C₃₈H₅₅NO₃Si

Refernces

• 1、 Pace, Vittorio,Castoldi, Laura,Alcantara, Andres R.,Holzer, Wolfgang. "Robust eco-friendly protocol for the preparation of γ-hydroxy- α,β-acetylenic esters by sequential one-pot elimination-addition of 2-bromoacrylates to aldehydes promoted by LTMP in 2-MeTHF". supporting information; experimental part. p. 1859 - 1863. Retrieved 2012/08/14.
• 2、 Boucher, Jean-Luc,Stella, Lucien. "DIENOPHILIE DES OLEFINES CAPTODATIVES - VI SYNTHESES ET CYCLOADDITIONS DE DIELS-ALDER DES α-ALKYLTHIO-ACRYLATES D'ALKYLE AVEC LE CYCLOPENTADIENE: INFLUENCE DES FACTEURS STERIQUES SUR LA REACTIVITE ET SUR LA STEREOSELECTIVITE". . p. 3595 - 3606. Retrieved 2007/10/02.