Tri-N-Propylsilane

• CAS: 998-29-8
• Catalog Number: ACM998298-3
• Category: Main Products
• Molecular Weight: 158.36 g/mol
• Molecular Formula: C9H22Si
• Synonyms: 1-(Dipropylsilyl)propane
• SMILES: CCC[Si](CCC)CCC
• InChI: InChI=1S/C9H21Si/c1-4-7-10(8-5-2)9-6-3/h4-9H2,1-3H3
• InChI Key: MMYRBBZVCDXGHG-UHFFFAOYSA-N
• Boiling Point: 171 °C
• Flash Point: 110 °C
• Density: 0.758 g/mLat25°C(lit.
• Appearance: Colorless Liquid
• Complexity: 47.5
• Covalently-Bonded Unit Count: 1
• EC Number: 213-649-1
• Exact Mass: 157.141252g/mol
• Formal Charge: 0
• H-Bond Acceptor: 0
• H-Bond Donor: 0
• Heavy Atom Count: 10
• Monoisotopic Mass: 157.141252g/mol
• NSC Number: 96837
• Packaging: 10 g; 100 g
• Rotatable Bond Count: 6

Case Study

Tri-N-Propylsilane as a Substrate for Iridium-Catalyzed Borylation to Form Silylboranes

Boebel, Timothy A.,et al. Organometallics 27.22 (2008): 6013-6019.

Silylboranes are versatile reagents for transition metal-catalyzed functionalization of unsaturated organic molecules, yet their synthesis traditionally requires silyllithium reagents and boron electrophiles. This study introduces a direct, catalytic approach: iridium-catalyzed borylation of silane Si-H bonds using bis(pinacolato)diboron (B2pin2). Tri-n-propylsilane (n-Pr3SiH) was investigated as a representative trialkylhydrosilane substrate.
Synthesis: The reaction employs [Ir(cod)OMe]2 (0.5 mol%) and 4,4'-di-tert-butylbipyridine (dtbpy, 1 mol%) in cyclohexane at 80 °C for 6 h with excess silane (4 equiv relative to B2pin2). The product, tri-n-propylsilylboronic acid pinacol ester (n-Pr3SiBpin), was isolated by silica gel chromatography.
Key Results: Tri-n-propylsilane underwent efficient borylation, affording n-Pr3SiBpin in 66% isolated yield (71% by GC), demonstrating the method's applicability to alkyl-substituted hydrosilanes. Longer alkyl chains generally improved conversion and yield, while sterically hindered silanes (e.g., i-Pr3SiH) failed to react. Alkoxy- and amino-substituted silanes were unreactive. The resulting silylborane serves as an effective boron source for iridium-catalyzed arene C-H borylation, forming arylboronic esters and regenerating the silane.

Tri-N-Propylsilane as a Side-Chain Component for Conjugated Polymer Donors in High-Efficiency Polymer Solar Cells

Bin, Haijun, et al. Advanced Energy Materials 8.8 (2018): 1702324.

Side-chain engineering is a powerful strategy for optimizing the photovoltaic properties of conjugated polymer donors in polymer solar cells (PSCs). In this work, tri-n-propylsilane was incorporated as the alkylsilyl side chain in a series of medium-bandgap conjugated polymers (J71) based on a bithienyl-benzodithiophene (BDTT) donor unit and a fluorobenzotriazole (FBTA) acceptor unit. The polymer J71 was synthesized via Stille-coupling polycondensation, with tri-n-propylsilyl groups attached to the BDTT unit.
J71 (tri-n-propylsilyl) exhibited a high absorption coefficient with a vibronic shoulder at 580 nm, indicating strong π-π stacking and ordered molecular packing. The HOMO energy level of J71 (-5.40 eV) was optimally positioned-lower than J70 (triethyl, -5.37 eV) but higher than polymers with bulkier side chains-balancing open-circuit voltage (Voc) and charge transfer efficiency.
PSCs based on J71:m-ITIC achieved a power conversion efficiency (PCE) of 12.05%, with Voc = 0.944 V, Jsc = 18.09 mA/cm2, and FF = 70.59%-among the highest reported values at the time. J71 exhibited high and balanced charge carrier mobilities, contributing to excellent Jsc and FF. Photoluminescence quenching efficiencies exceeded 99% for J71 blends, confirming efficient charge transfer despite a small ΔEHOMO (0.12 eV) with the m-ITIC acceptor.
Tri-n-propylsilane thus serves as an alkylsilyl side-chain component for conjugated polymer donors, balancing molecular ordering, energy level tuning, and charge transport to achieve high-performance PSCs.

Custom Reviews

August 24, 2023

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Custom Q&A

What is the molecular formula of Tri-N-propylsilane?

The molecular formula of Tri-N-propylsilane is C9H21Si.

What is the molecular weight of Tri-N-propylsilane?

The molecular weight of Tri-N-propylsilane is 157.35 g/mol.

What is the InChI of Tri-N-propylsilane?

The InChI of Tri-N-propylsilane is InChI=1S/C9H21Si/c1-4-7-10(8-5-2)9-6-3/h4-9H2,1-3H3.

What is the InChIKey of Tri-N-propylsilane?

The InChIKey of Tri-N-propylsilane is MMYRBBZVCDXGHG-UHFFFAOYSA-N.

What is the CAS number of Tri-N-propylsilane?

The CAS number of Tri-N-propylsilane is 998-29-8.

What is the UNII of Tri-N-propylsilane?

The UNII of Tri-N-propylsilane is NNJ2F2HV9X.

How many hydrogen bond donor count does Tri-N-propylsilane have?

Tri-N-propylsilane has 0 hydrogen bond donor count.

How many hydrogen bond acceptor count does Tri-N-propylsilane have?

Tri-N-propylsilane has 0 hydrogen bond acceptor count.

How many rotatable bond count does Tri-N-propylsilane have?

Tri-N-propylsilane has 6 rotatable bond count.

Is Tri-N-propylsilane a canonicalized compound?

Yes, Tri-N-propylsilane is a canonicalized compound.