ChemicalBook > CAS DataBase List > 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole

Product Name
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole
CAS No.
365564-11-0
Chemical Name
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole
Synonyms
1-(Triisopropylsilyl)-1H-...;N-TIPS pyrrole-3-boronic acid pinacol ester;1-(Triisopropylsilyl)pyrrole-3-boronic Acid Pinacol Ester;1-(Triisopropylsilyl)-1H-pyrrole-3-boronic acid pinacol ester;1-(triisopropylsilyl)-1H-pyrrol-3-ylboronic acid pinacol ester;3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tripropan...;1-(Triisopropylsilyl)-1H-pyrrole-3-boronic acid pinacol ester - [T7679];3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(propan-2-yl)silyl]-1H-pyrrole;3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole;tri(propan-2-yl)-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrol-1-yl]silane
CBNumber
CB42520180
Molecular Formula
C19H36BNO2Si
Formula Weight
349.39
MOL File
365564-11-0.mol
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3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole Property

Melting point:
59 °C
Boiling point:
383.6±15.0 °C(Predicted)
Density 
0.94±0.1 g/cm3(Predicted)
storage temp. 
Storage temp. 2-8°C
pka
-2.53±0.70(Predicted)
form 
Powder or Solid
color 
White to yellow
InChI
InChI=1S/C19H36BNO2Si/c1-14(2)24(15(3)4,16(5)6)21-12-11-17(13-21)20-22-18(7,8)19(9,10)23-20/h11-16H,1-10H3
InChIKey
GWFIZBYDIHGZRJ-UHFFFAOYSA-N
SMILES
N1([Si](C(C)C)(C(C)C)C(C)C)C=CC(B2OC(C)(C)C(C)(C)O2)=C1
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Safety

HS Code 
2933998090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC
Product number
T302793
Product name
3-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(propan-2-yl)silyl]-1H-pyrrole
Packaging
50mg
Price
$45
Updated
2021/12/16
TRC
Product number
T302793
Product name
3-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(propan-2-yl)silyl]-1H-pyrrole
Packaging
500mg
Price
$90
Updated
2021/12/16
Matrix Scientific
Product number
096383
Product name
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-methylethyl)silyl]-1H-pyrrole
Purity
95+%
Packaging
1g
Price
$152
Updated
2021/12/16
ChemScene
Product number
CS-0051659
Product name
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-methylethyl)silyl]-1H-pyrrole
Packaging
1g
Price
$75
Updated
2021/12/16
SynQuest Laboratories
Product number
8H87-1-06
Product name
1-(Triisopropylsilyl)-1H-pyrrole-3-boronic acid, pinacol ester
Packaging
1g
Price
$88
Updated
2021/12/16
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3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole Chemical Properties,Usage,Production

Synthesis

87630-36-2

25015-63-8

365564-11-0

To a stirred solution of 3-bromo-1-(triisopropylmethylsilyl)pyrrole (6.50 g, 21.50 mmol) and pinacolborane (4.13 g, 32.25 mmol) in toluene (120 mL) was sequentially added PdCl2(ACN)2 (0.45 g, 1.72 mmol), dicyclohexyl (2',6'-dimethoxybiphenyl-2-yl)phosphine (2.65 g, 6.45 mmol) and triethylamine (6.53 g, 64.50 mmol). The reaction mixture was degassed twice with nitrogen and subsequently heated to 90 °C and kept for 16 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming complete consumption of the raw materials the reaction was stopped and cooled to room temperature. The reaction mixture was diluted with ethyl acetate (200 mL), filtered through a pad of diatomaceous earth and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (eluent ratio: ethyl acetate/hexane from 1/200 to 1/50) to afford the target product 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-methylethyl)methanesilyl]-1H-pyrrole (3.50 g, 46% yield) as a white solid.

References

[1] Angewandte Chemie - International Edition, 2006, vol. 45, # 21, p. 3484 - 3488
[2] Journal of the American Chemical Society, 2007, vol. 129, # 11, p. 3358 - 3366
[3] Angewandte Chemie - International Edition, 2006, vol. 45, # 21, p. 3484 - 3488
[4] Journal of Organic Chemistry, 2008, vol. 73, # 14, p. 5589 - 5591
[5] Organic Letters, 2010, vol. 12, # 19, p. 4224 - 4227

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole Preparation Products And Raw materials

Raw materials

Preparation Products

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3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole Suppliers

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View Lastest Price from 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole manufacturers

ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD
Product
3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(propan-2-yl)silyl]-1H-pyrrole 365564-11-0
Price
US $3.00-9.00/KG
Min. Order
0.1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2025-07-05

365564-11-0, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrroleRelated Search:

3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-5-(piperidin-4-yl)pyridine 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2,4,5-d3 3-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoroMethyl)benzonitrile dimethylsilanediol 2-Methylbenzo[d]oxazol-6-ylboronic acid pinacol ester 4-METHYLPYRIDINE-2-BORONIC ACID PINACOL ESTER 2-(2,5-Dihydrofuran-3-yl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane 2-(TRIFLUOROMETHYL)PYRIDINE-4-BORONIC ACID PINACOL ESTER 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole

  • 1-(Triisopropylsilyl)-1H-...
  • 1-(Triisopropylsilyl)-1H-pyrrole-3-boronic acid pinacol ester
  • 1H-Pyrrole, 3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-Methylethyl)silyl]-
  • 3-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-Methylethyl)silyl]-1H-pyrrole
  • N-TIPS pyrrole-3-boronic acid pinacol ester
  • 1-(triisopropylsilyl)-1H-pyrrol-3-ylboronic acid pinacol ester
  • 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(propan-2-yl)silyl]-1H-pyrrole
  • 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole
  • 1-(Triisopropylsilyl)pyrrole-3-boronic Acid Pinacol Ester
  • tri(propan-2-yl)-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrol-1-yl]silane
  • 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tripropan...
  • 1-(Triisopropylsilyl)-1H-pyrrole-3-boronic acid pinacol ester - [T7679]
  • 365564-11-0