Cas no 87630-36-2 (3-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole)

3-Bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole is a brominated pyrrole derivative featuring a tris(isopropyl)silyl (TIPS) protecting group. The TIPS moiety enhances steric hindrance, improving stability and selectivity in synthetic applications. This compound serves as a versatile intermediate in organic synthesis, particularly in the functionalization of pyrrole rings for pharmaceuticals, agrochemicals, and materials science. The bromine atom provides a reactive site for further cross-coupling reactions, such as Suzuki or Stille couplings, enabling precise structural modifications. Its robust shelf stability and compatibility with various reaction conditions make it a reliable reagent for complex heterocyclic frameworks. The compound is typically handled under inert conditions to preserve reactivity.
3-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole structure
87630-36-2 structure
Product Name:3-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole
CAS No:87630-36-2
MF:C13H24BrNSi
MW:302.325863838196
MDL:MFCD01321136
CID:654362
PubChem ID:2763302
Update Time:2025-06-06

3-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole Chemical and Physical Properties

Names and Identifiers

    • 3-Bromo-1-(triisopropylsilyl)pyrrole
    • (3-bromopyrrol-1-yl)-tri(propan-2-yl)silane
    • 1H-Pyrrole, 3-bromo-1-[tris(1-methylethyl)silyl]-
    • 3-Bromo-1-(triisopropylsilyl)-1H -pyrrole
    • 3-bromo-1-[tris(1-methylethyl)silyl]-1H-Pyrrole
    • 3-Bromo-1-[triisopropylsilyl]-1H-pyrrole
    • 3-Bromo-1-(triisopropylsilyl)-1H-pyrrole
    • 3-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole
    • 3-bromo-N-triisopropylsilylpyrrole
    • (3-Bromopyrrol-1-yl)-triisopropyl-silane
    • C13H24BrNSi
    • CNAUTMPRKBSDLH-UHFFFAOYSA-N
    • 3-bromo-1-triisopropylsilylpyrrole
    • 3-bromo-1-triisopropylsilyl-pyrrole
    • STL557817
    • BBL104006
    • 3-Bromo-1-[tris(1-methylethyl)silyl]-1H-pyrrole (ACI)
    • 3-Bromo-1-(triisopropylsilanyl)-1H-pyrrole
    • 3-Bromo-1-(tripropan-2-ylsilyl)-1H-pyrrole
    • 3-Bromo-N-(triisopropylsilyl)pyrrole
    • SCHEMBL369247
    • 3-Bromo-1-triisopropylsilyl pyrrole
    • MFCD01321136
    • B1899
    • SY031245
    • DB-057011
    • 3-Bromo-1(triisopropysilyl)pyrrole, 97%
    • PB12917
    • 3-BROMO-1(TRIISOPROPYSILYL)PYRROLE
    • EN300-109530
    • J-511784
    • DTXSID90376882
    • DS-13290
    • CS-0038939
    • 87630-36-2
    • 3-Bromo-1(triisopropysilyl)pyrrole;3-Bromo-1-[tris(1-methylethyl)silyl]-1h-pyrrole;
    • S03129
    • AKOS015835928
    • 3-BROMO-1-TRIISOPROPYLSILANYL-1H-PYRROLE
    • MDL： MFCD01321136
    • Inchi： 1S/C13H24BrNSi/c1-10(2)16(11(3)4,12(5)6)15-8-7-13(14)9-15/h7-12H,1-6H3
    • InChI Key： CNAUTMPRKBSDLH-UHFFFAOYSA-N
    • SMILES： BrC1=CN([Si](C(C)C)(C(C)C)C(C)C)C=C1

Computed Properties

  • Exact Mass: 301.08600
  • Monoisotopic Mass: 301.08614g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 4
  • Complexity: 206
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 4.9
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing

Experimental Properties

  • Color/Form: Not determined
  • Density: 1.147?g/mL?at 25?°C
  • Boiling Point: 100 oC (0.1 Torr)
  • Flash Point: Degrees Fahrenheit:>230°F
    Degrees Celsius:>110°C
  • Refractive Index: n20/D 1.519
  • Solubility: Insuluble (9.4E-3 g/L) (25 oC),
  • PSA: 4.93000
  • LogP: 5.27420
  • Solubility: Not determined
  • Sensitiveness: Sensitive to humidity

3-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole Security Information

3-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole Customs Data

  • HS CODE：2933990090
  • Customs Data：

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

3-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole Pricemore >>

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TRC
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3-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: N-Bromosuccinimide Solvents: Tetrahydrofuran ;  -78 °C; 2 h, -78 °C
Reference
Synthesis of the Ring C Pyrrole of Native Chlorophylls and Bacteriochlorophylls
Wang, Pengzhi ; et al, Journal of Organic Chemistry, 2019, 84(17), 11286-11293

Production Method 2

Reaction Conditions
1.1 Reagents: Hydroquinone ,  N-Bromosuccinimide Solvents: Acetone
Reference
The synthesis of new 3-substituted pyrroles
Stefan, Klaus Peter; et al, Chemische Berichte, 1989, 122(1), 169-74

Production Method 3

Reaction Conditions
1.1 Solvents: Tetrahydrofuran
Reference
A synthesis of 3-substituted pyrroles through the halogen-metal exchange reaction of 3-bromo-1-(triisopropylsilyl)pyrrole
Kozikowski, Alan P.; et al, Journal of Organic Chemistry, 1984, 49(17), 3239-40

Production Method 4

Reaction Conditions
1.1 Reagents: Sodium hydride
1.2 Reagents: N-Bromosuccinimide
Reference
Poly(carboxypyrrole)s That Depolymerize from Head to Tail in the Solid State in Response to Specific Applied Signals
Kim, Hyungwoo ; et al, Journal of the American Chemical Society, 2020, 142(20), 9447-9452

Production Method 5

Reaction Conditions
1.1 Reagents: N-Bromosuccinimide Solvents: Tetrahydrofuran
Reference
High-pressure Diels-Alder reactions of 1-methoxycarbonyl-3-methylthio- and -3-phenylthiopyrrole. An efficient entry to 7-azabicyclo[2.2.1] heptanes
Keijsers, Jan; et al, Heterocycles, 1989, 29(1), 79-86

Production Method 6

Reaction Conditions
1.1 Solvents: Tetrahydrofuran
Reference
Pyrrole, Imidazolone and Imidazolidinone Chemistry for the Synthesis of Heterocyclic Natural Products
Cantos-Llopart, Carme, 2003, , ,

Production Method 7

Reaction Conditions
1.1 Solvents: Tetrahydrofuran
Reference
β-Substituted pyrroles via electrophilic substitution of N-triisopropylsilylpyrrole
Muchowski, Joseph M.; et al, Tetrahedron Letters, 1983, 24(33), 3455-6

Production Method 8

Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran
1.2 Reagents: N-Bromosuccinimide Solvents: Tetrahydrofuran
Reference
Highly Efficient Monophosphine-Based Catalyst for the Palladium-Catalyzed Suzuki-Miyaura Reaction of Heteroaryl Halides and Heteroaryl Boronic Acids and Esters
Billingsley, Kelvin; et al, Journal of the American Chemical Society, 2007, 129(11), 3358-3366

Production Method 9

Reaction Conditions
1.1 Solvents: Tetrahydrofuran
1.2 Reagents: N-Bromosuccinimide Solvents: Acetonitrile
Reference
A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds
Billingsley, Kelvin L.; et al, Angewandte Chemie, 2006, 45(21), 3484-3488

Production Method 10

Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Dimethylformamide
2.1 Solvents: Tetrahydrofuran
Reference
Pyrrole, Imidazolone and Imidazolidinone Chemistry for the Synthesis of Heterocyclic Natural Products
Cantos-Llopart, Carme, 2003, , ,

3-bromo-1-[tris(propan-2-yl)silyl]-1H-pyrrole Raw materials

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