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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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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

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

Application

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

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.
  • 3,9-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,11-di(1-decylundecyl)indolo[3,2-b]carbazole.
  • 2,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene.
  • 2,7-Bis(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2′-yl)-N-9′′-heptadecanylcarbazole.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

417149-100ML:
417149-25ML:
417149-BULK:
417149-500ML:
417149-VAR:
417149-5ML:

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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A New Poly (2, 7?Dibenzosilole) Derivative in Polymer Solar Cells.
Boudreault P, et al.
Macromolecular Rapid Communications, 28(22), 2176-2179 (2007)
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)
Ken-Tsung Wong et al.
Organic letters, 8(22), 5029-5032 (2006-10-20)
p-Tolyl-substituted ladder-type oligo(p-phenylene)s containing three, four, and five phenylene rings were readily synthesized. The uniform aryl substitution of these systems allowed us to determine the coplanarity of the pi-conjugated backbones crystallographically. The intramolecular annulations eliminate almost all of the conformational
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