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Key Documents

568155

Sigma-Aldrich

4,4,5,5,-Tetramethyl-2-phenylsulfanylmethyl-1,3,2-dioxaborolane

97%

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About This Item

Linear Formula:
C6H5SCH2BC2O2(CH3)4
CAS Number:
Molecular Weight:
250.16
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

refractive index

n20/D 1.5280 (lit.)

bp

105-108 °C/0.1 mmHg (lit.)

density

1.059 g/mL at 25 °C (lit.)

SMILES string

CC1(C)OB(CSc2ccccc2)OC1(C)C

InChI

1S/C13H19BO2S/c1-12(2)13(3,4)16-14(15-12)10-17-11-8-6-5-7-9-11/h5-9H,10H2,1-4H3

InChI key

DGPGLPBMZOKGON-UHFFFAOYSA-N

Application

4,4,5,5,-Tetramethyl-2-phenylsulfanylmethyl-1,3,2-dioxaborolane is used to prepare aryl/heteroaryl derivatives via the formation of C-C and C-hetero bonds.
It can also be used as:
  • A starting material in the synthesis of α-aminoboronic acids as serine proteases inhibitors.
  • A substrate in the coupling reactions with carbonyl compounds under Ir-catalyzed photoredox conditions.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of boronic acid analogues of α-amino acids by introducing side chains as electrophiles
Jagannathan S, et al.
The Journal of Organic Chemistry, 66(19), 6375-6380 (2001)
A Photoredox Coupling Reaction of Benzylboronic Esters and Carbonyl Compounds in Batch and Flow
Chen Y, et al.
Organic Letters, 21(15), 6140-6144 (2019)

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