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417149

Sigma-Aldrich

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

97%

Synonym(s):

4,4,5,5-Tetramethyl-2-[(propan-2-yl)oxy]-1,3,2-dioxaborolane, Isopropoxy 4,4,5,5-tetramethyl-1,3,2-dioxaborolane, Isopropoxyboronic acid pinacol ester, Isopropyl pinacol borate, Isopropylpinacolylborate

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5 ML
CN¥336.71
25 ML
CN¥694.81
100 ML
CN¥1,586.59
500 ML
CN¥4,631.61

About This Item

Empirical Formula (Hill Notation):
C9H19BO3
CAS Number:
61676-62-8
Molecular Weight:
186.06
MDL number:
MFCD00192241
UNSPSC Code:
12352103
PubChem Substance ID:
24866125
NACRES:
NA.22

CN¥336.71

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Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.409 (lit.)

bp

73 °C/15 mmHg (lit.)

density

0.912 g/mL at 25 °C (lit.)

SMILES string

CC(C)OB1OC(C)(C)C(C)(C)O1

InChI

1S/C9H19BO3/c1-7(2)11-10-12-8(3,4)9(5,6)13-10/h7H,1-6H3

InChI key

MRWWWZLJWNIEEJ-UHFFFAOYSA-N

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1 of 4

This Item
663212659851324647
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 97%

417149

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Isopropenylboronic acid pinacol ester contains BHT as stabilizer, 94.5%

663212

Isopropenylboronic acid pinacol ester

Cyclopropylboronic acid pinacol ester 96%

659851

Cyclopropylboronic acid pinacol ester

Allylboronic acid pinacol ester 97%

324647

Allylboronic acid pinacol ester

assay

97%

assay

95%

assay

96%

assay

97%

bp

73 °C/15 mmHg (lit.)

bp

47-49 °C/9 mbar

bp

146 °C

bp

50-53 °C/5 mmHg (lit.)

density

0.912 g/mL at 25 °C (lit.)

density

0.894 g/mL at 25 °C

density

0.922 g/mL at 25 °C

density

0.896 g/mL at 25 °C (lit.)

refractive index

n20/D 1.409 (lit.)

refractive index

n20/D 1.4320

refractive index

n20/D 1.433

refractive index

n20/D 1.4268 (lit.)

form

liquid

form

-

form

-

form

-

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

Application

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane can be used as a reagent to borylate arenes[1][2] and to prepare fluorenylborolane.[3]

It can also be used in the synthesis of following intermediates for generating conjugated copolymers:
  • 9,9-Dioctyl-2,7-bis(4,4,5,5-tetramethyl1,3,2-dioxaborolane-2-yl)dibenzosilole.[4]
  • 3,9-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,11-di(1-decylundecyl)indolo[3,2-b]carbazole.[5]
  • 2,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene.[6]
  • 2,7-Bis(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2′-yl)-N-9′′-heptadecanylcarbazole.[7]

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

109.4 °F - closed cup

Flash Point(C)

43 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves
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    Lot/Batch Number
    SHBM8873
    SHBM9091
    SHBM5972
    SHBM2092
    SHBL2187

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    Novel red-emitting fluorene-based copolymers.
    Hou Q, et al.
    Journal of Materials Chemistry, 12(10), 2887-2892 (2002)
    Regioselective halogen-metal exchange reaction of 3-substituted 1, 2-dibromo arenes: The synthesis of 2-substituted 5-bromobenzoic acids
    Menzel K, et al.
    Synlett, 2006(12), 1948-1952 (2006)
    A low?bandgap poly (2, 7?carbazole) derivative for use in high?performance solar cells.
    Blouin N, et al.
    Advanced Materials, 19(17), 2295-2300 (2007)
    Albertus J Sandee et al.
    Journal of the American Chemical Society, 126(22), 7041-7048 (2004-06-04)
    We report the synthesis and photophysical study of a series of solution-processible phosphorescent iridium complexes. These comprise bis-cyclometalated iridium units [Ir(ppy)(2)(acac)] or [Ir(btp)(2)(acac)] where ppy is 2-phenylpyridinato, btp is 2-(2'-benzo[b]thienyl)pyridinato, and acac is acetylacetonate. The iridium units are covalently attached
    A New Poly (2, 7?Dibenzosilole) Derivative in Polymer Solar Cells.
    Boudreault P, et al.
    Macromolecular Rapid Communications, 28(22), 2176-2179 (2007)
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