3-Isocyanatopropyltrimethoxysilane

Catalog Number	ACM15396006-9
CAS	15396-00-6
Structure
Description	Liquid
Synonyms	3-(Trimethoxysilyl)propyl isocyanate
IUPAC Name	3-isocyanatopropyl(trimethoxy)silane
Molecular Weight	205.28
Molecular Formula	C7H15NO4Si
Canonical SMILES	CO[Si](CCCN=C=O)(OC)OC
InChI	InChI=1S/C7H15NO4Si/c1-10-13(11-2,12-3)6-4-5-8-7-9/h4-6H2,1-3H3
InChI Key	FMGBDYLOANULLW-UHFFFAOYSA-N
Melting Point	<0 °C
Purity	95%+
Density	1 g/cm³
Appearance	Clear, colorless liquid
Complexity	169
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	0
EC Number	239-415-9
Exact Mass	205.07703449
Heavy Atom Count	13
Hydrogen Bond Acceptor Count	5
Hydrogen Bond Donor Count	0
Monoisotopic Mass	205.07703449
Rotatable Bond Count	7
Topological Polar Surface Area	57.1 Ų

Knowledge & Learning Case Study Q&A

3-Isocyanatopropyltrimethoxysilane Used in Cellulose Modification

Liu M, et al. Carbohydrate Polymers, 2022, 288, 119367.

3-Isocyanatopropyltrimethoxysilane (ISPTMOS) can be used as a modifier for cellulose modification to introduce permanent hydrophobicity. The hydrophobic Cellulose nonwoven (CNW) fabric was prepared as follows:
ISPTMOS was used as a surface chemical modifier with n-hexane (35 g) and dibutyl tin dilaurate (DBTDL) (0.25 wt% n-hexane) as solvent and catalyst, respectively.
Pure CNW (~1.6 g) was immersed in TBIS solution, heated at 70 °C for 10 min, washed with hexane (30 mL × 3 times) to remove the residual modifier and catalyst, and dried under vacuum at 80 °C for 2 h to remove the solvent.

3-Isocyanatopropyltrimethoxysilane for the Preparation of Transparent Flame Retardant Coatings for PMMA

Zhang K, et al. Composites Part A: Applied Science and Manufacturing, 2022, 159, 107004.

3-Isocyanatopropyltrimethoxysilane can be used in conjunction with a novel phosphorus/nitrogen-containing hyperbranched polyphenylphosphate (PHP) to prepare transparent flame-retardant coatings for poly(methyl methacrylate) (PMMA). First, PHP is reacted with 3-Isocyanatopropyltrimethoxysilane to obtain PHP with a siloxane at the end, and then its siloxane groups are hydrolysed to form a sol-gel solution, which is then coated onto a PMMA substrate to form a transparent PMMA coating.
The specific preparation method is as follows:
PHP and 3-Isocyanatopropyltrimethoxysilane were dissolved in 5 mL of DMF and dibutyltin dilaurate (DBTDL) was added as a catalyst.
After 12 hours of stirring, 0.5 mL of H₂O was added to the solution and DBTDL was added as a catalyst for hydrolysis of the siloxane moiety at the same time.
The solution was heat-treated in a constant temperature oil bath at 80°C for 8 hours to remove some of the DMF to obtain a viscous sol-gel solution.
Finally, the sol-gel solution was uniformly coated on the PMMA substrate and the PMMA substrate was dried in an air convection oven at 80°C for 24 hours.

3-Isocyanatopropyltrimethoxysilane Used in Modification of Cellulose Nanocrystals

Yang X, et al. Carbohydrate Polymers, 2020, 229, 115509.

Modification of cellulose nanocrystals (CNC) with 3-Isocyanatopropyltrimethoxysilane (IPMS) improves their dispersion in RTV silicone rubber matrix. The modified CNC (ICNC) can be used as cross-linkers and nanofillers.
CNC was chemically modified as follows:
The CNC surface was modified by the reaction between the hydroxyl group of CNC and the isocyanate group of IPMS. A suspension of CNC was added to a three-necked flask equipped with a magnetic stirrer, and then IPMS was added drop by drop to the suspension at a molar ratio of 8:1 to react the isocyanate groups of IPMS with the hydroxyl groups of CNC.
The reaction was carried out at 60 °C for 5 h under nitrogen protection. After the reaction, unreacted IPMS and solvent DMSO were removed by centrifugation to obtain ICNCs.
The ICNCs were dispersed in toluene to form a suspension and the solvent was removed by centrifugation and dispersed again into toluene. This process was repeated 3-4 times.
The amount of IPMS grafted was determined by measuring the amount of reactive hydroxyl groups on the ICNCs.

3-Isocyanatopropyltrimethoxysilane for the Preparation of Silylated Moisture-curable Prepolymer Variant Crosslinkers (PUXL)

Efstathiou S, et al. Materials Advances, 2024, 5(8), 3396-3410.

The polymer is synthesized by reacting polyetheramine Jeffamine D-4000 with isophorone diisocyanate (IPDI) to form a bis(primary amino)-terminated polymer. This polymer is then post-functionalized with 3-isocyanatopropyltrimethoxysilane (IPTMS) to produce a silanized, moisture-curing prepolymer variant crosslinker (PUXL).
The specific synthesis procedure for the PUXL prepolymer crosslinker is detailed below:
Jeffamine D-4000 (4700 g, 1.18 mol, 1 eq., amine content: 0.49) was placed in a gas-tight, oil-jacketed reaction vessel equipped with stainless steel distillation impellers. The mixture was heated to 85 °C under nitrogen with stirring at 120 rpm, monitored by an online temperature probe. Once the desired temperature was achieved, the stirring rate was increased, and IPDI (121.58 g, 0.55 mol, 0.47 eq.) was added. The mixture reacted for 15 minutes before adding IPTMS (235.79 g, 1.19 mol, 0.99 eq.). After an additional 20 minutes of reaction, the final product was collected, analyzed by FT-IR to confirm the absence of residual isocyanate groups, and stored under a layer of nitrogen.

3-Isocyanatopropyltrimethoxysilane for the Preparation of a Novel Composite Coating of Functionalized Graphene Stitched Silicon Carbide/Fluoropolymer

Yuan S, et al. Chemical Engineering Journal, 2023, 472, 144881.

3-Isocyanatopropyltrimethoxysilane (IPTMS) is used to prepare FEVE/Gr@PDA-IPTMS-SiC composite coatings, which offer excellent long-term corrosion protection and enhanced hydrogen barrier properties.
Method:
1. Preparation of Polydopamine-Coated Graphene (Gr@PDA)
Disperse 0.2 g of graphene powder into 200 mL of an aqueous solution containing 0.2 g of dopamine and 0.24 g of Tris-HCl (pH 8.5). Stir the mixture continuously at room temperature for 24 hours. Filter and wash the solution repeatedly with deionized water until no unreacted dopamine remains. Freeze-dry the Gr@PDA powder for about 12 hours.
2. Preparation of Composite Filler Gr@PDA-IPTMS-SiC
Disperse 0.2 g of Gr@PDA powder into 100 mL of DMF solution with mechanical stirring for about 2 minutes. Add 2 g of IPTMS to the dispersion and place it in a 75 °C water bath with continuous stirring for 2 hours. Filter and wash the mixture repeatedly with anhydrous ethanol until no IPTMS remains. Dry the Gr@PDA-IPTMS powder at 80 °C for 1 hour. Mix the Gr@PDA-IPTMS powders with SiC in a 1:10 mass ratio in anhydrous ethanol and deionized water (10:1 mass ratio). Sonicate the mixture for 10 minutes to ensure homogeneous dispersion. Place the mixture in a 60 °C water bath with continuous stirring for 2 hours. Use an ultrasonic cell crusher for about 2 hours with 5-second sonication and 3-second pauses to ensure complete dispersion and reaction. Filter and dry the mixture in an oven at 80 °C to evaporate the solvent, synthesizing the Gr@PDA-IPTMS-SiC composite filler.
3. Preparation of FEVE/Gr@PDA-IPTMS-SiC Composite Coating
Polish a Q235 steel plate with 80-mesh sandpaper, clean with anhydrous ethanol, and dry in an oven at 80 °C. Add 5 g of FEVE resin, 1 g of curing agent N3390, and varying concentrations of Gr@PDA-IPTMS-SiC into a rotating cup equipped with a mixer. Mix and then place in an automatic rotary gravity vacuum mixer to disperse the filler fully in the FEVE and curing agent, and remove air bubbles. Spin-coat the dispersion on the polished steel plate at 1650 rpm for 10 seconds. Initially cure the coated plates at room temperature for 12-15 hours. Finally, heat the coatings in an oven at 120 °C for 1 to 2 hours to complete the curing process.

Our products and services are for research use only and cannot be used for any clinical purposes.

Online Inquiry

3-Isocyanatopropyltrimethoxysilane (15396-00-6)

Send A Message