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Sigma-Aldrich

Tri-tert-butyl borate

98%

Synonym(s):

Boron tert-butoxide, Tri-tert-butoxyborane

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About This Item

Linear Formula:
[(CH3)3CO]3B
CAS Number:
7397-43-5
Molecular Weight:
230.15
MDL number:
MFCD00009652
UNSPSC Code:
12352103
PubChem Substance ID:
24854180
NACRES:
NA.22

assay

98%

form

liquid

refractive index

n20/D 1.389 (lit.)

bp

101 °C/74 mmHg (lit.)

mp

18-19 °C (lit.)

density

0.811 g/mL at 25 °C (lit.)

SMILES string

CC(C)(C)OB(OC(C)(C)C)OC(C)(C)C

InChI

1S/C12H27BO3/c1-10(2,3)14-13(15-11(4,5)6)16-12(7,8)9/h1-9H3

InChI key

ZMCWFMOZBTXGKI-UHFFFAOYSA-N

General description

Tri-tert-butyl borate is an organoborate commonly used to prepare other borate esters. It is also used as a substrate in Rh-catalyzed carbonylation reactions.

Application

Tri-tert-butyl borate can be used as:
  • An additive in the synthesis of chiral α-hydroxy esters by reacting dimethylzinc with α-ketoesters using (−)-2-exo-morpholinoisobornane-10-thiol.
  • A starting material in the synthesis of boronate of (+)-pinane-2,3-diol.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

84.2 °F - closed cup

flash_point_c

29 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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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Tri?tert ?butylborate
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2012)
Asymmetric addition of dimethylzinc to α-ketoesters catalyzed by (−)-MITH
Wu H, et al.
The Journal of Organic Chemistry, 73(16), 6445-6447 (2008)
Tri?tert ?butylborate
e-EROS Encyclopedia of Reagents for Organic Synthesis (2012)
Chiral carbanions, part 4: Borylation of (trimethylsilyl) methyl N, N-dialkylcarbamates-Diastereoselectivity and structural studies
Simov BP, et al.
Synthesis, 2004(16), 2704-2710 (2004)

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