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236608

Sigma-Aldrich

Tri-tert-butyl borate

98%

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Synonym(s):
Boron tert-butoxide, Tri-tert-butoxyborane
Linear Formula:
[(CH3)3CO]3B
CAS Number:
Molecular Weight:
230.15
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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124230419885270776
Tri-tert-butyl borate 98%

236608

Tri-tert-butyl borate

tert-Butyl bromoacetate 98%

124230

tert-Butyl bromoacetate

tert-Butyl propiolate 98%

419885

tert-Butyl propiolate

tert-Butyl formate 99%

270776

tert-Butyl formate

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

density

0.811 g/mL at 25 °C (lit.)

density

1.321 g/mL at 25 °C (lit.)

density

0.919 g/mL at 25 °C (lit.)

density

0.872 g/mL at 25 °C (lit.)

bp

101 °C/74 mmHg (lit.)

bp

50 °C/10 mmHg (lit.)

bp

52-53 °C/27 mmHg (lit.)

bp

82-83 °C (lit.)

form

liquid

form

liquid

form

liquid

form

liquid

mp

18-19 °C (lit.)

mp

-

mp

18-20 °C (lit.)

mp

-

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

signalword

Warning

hcodes

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


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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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