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407097

Sigma-Aldrich

1-Bromo-2,4,6-tri-tert-butylbenzene

97%

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About This Item

Fórmula lineal:
[(CH3)3C]3C6H2Br
Número de CAS:
3975-77-7
Peso molecular:
325.33
Beilstein/REAXYS Number:
1913257
MDL number:
MFCD00191861
UNSPSC Code:
12352100
PubChem Substance ID:
24865424
NACRES:
NA.22

assay

97%

mp

168-173 °C (lit.)

SMILES string

CC(C)(C)c1cc(c(Br)c(c1)C(C)(C)C)C(C)(C)C

InChI

1S/C18H29Br/c1-16(2,3)12-10-13(17(4,5)6)15(19)14(11-12)18(7,8)9/h10-11H,1-9H3

InChI key

JOKZWHPYNRDCOA-UHFFFAOYSA-N

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General description

1-Bromo-2,4,6-tri-tert-butylbenzene (2,4,6-tri-tert-butylbromobenzene) is a hindered aryl bromide. 1-Bromo-2,4,6-tri-tert-butylbenzene on reaction with phenylboronic acid yields α,α-dimethyl-β-phenyl hydrostyrene.

Application

1-Bromo-2,4,6-tri-tert-butylbenzene was used in the synthesis of bulky biarylphosphine ligand. This ligand was reported to participate in the Pd-catalyzed C-O cross-coupling of a wide range of aryl halides and phenols under milder conditions. It was used to investigate the effect on oligomerization of increased steric bulk in dimethylindium(III) chalcogenolates. It may be used to form α,α-dimethyl-β-phenyl hydrostyrene by reacting with phenylboronic acid.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

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The first Cu-and amine-free Sonogashira-type cross-coupling in the C-6-alkynylation of protected 2'-deoxyadenosine.
Ngassa FN, et al.
Tetrahedron, 65(21), 4085-4091 (2009)
Palladium(0)-catalyzed intermolecular amination of unactivated C(sp³)-H bonds.
Jun Pan et al.
Angewandte Chemie (International ed. in English), 50(37), 8647-8651 (2011-08-04)
Glen G Briand et al.
Dalton transactions (Cambridge, England : 2003), 39(16), 3833-3841 (2010-04-08)
The effect on oligomerization of increased steric bulk in dimethylindium(III) chalcogenolates (Me(2)InER') (E = O, S, Se) has been examined. The facile reaction of Me(3)In with a series of phenols, thiophenols and selenophenols afforded the compounds [Me(2)InO(C(6)H(5))](2) (1), [Me(2)InO(2,6-Me(2)C(6)H(3))](2) (2)
Luca Salvi et al.
Organic letters, 14(1), 170-173 (2011-12-21)
A new bulky biarylphosphine ligand (L8) has been developed that allows the Pd-catalyzed C-O cross-coupling of a wide range of aryl halides and phenols under milder conditions than previously possible. A direct correlation between the size of the ligand substituents

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