58698-89-8

Basic information

• Product Name: 3-isothiocyanatopropyltriethoxysilane
• Synonyms: 3-isothiocyanatopropyltriethoxysilane;3-TriethoxylsilylpropylIsothiocyanate
• CAS NO: 58698-89-8
• Molecular Formula: C₁₀H₂₁NO₃SSi
• Molecular Weight: 263.43
• Mol File: 58698-89-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 290.8°Cat760mmHg
• Flash Point: 129.7°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 0.00353mmHg at 25°C
• Refractive Index: 1.457
• Storage Temp.: Refrigerator, Under inert atmosphere
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• CAS DataBase Reference: 3-isothiocyanatopropyltriethoxysilane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-isothiocyanatopropyltriethoxysilane(58698-89-8)
• EPA Substance Registry System: 3-isothiocyanatopropyltriethoxysilane(58698-89-8)

Safety Data

• Hazardous Substances Data: 58698-89-8(Hazardous Substances Data)

Usage

Description

3-isothiocyanatopropyltriethoxysilane is an organosilane compound characterized by its ability to form covalent bonds with inorganic surfaces and organic polymers. It is known for its versatility in chemical reactions and its potential applications in various industries due to its unique properties.

Uses

Used in Photopolymerization Industry:
3-isothiocyanatopropyltriethoxysilane is used as a key component in the synthesis of photopolymerization initiators containing -Si(OR)3 groups. These initiators play a crucial role in the process of photopolymerization, which is a technique used to create polymers from monomers through the action of light. The presence of the isothiocyanatopropyl group in the molecule enhances the reactivity and performance of the initiator, making it a valuable addition to the field of photopolymerization.

InChI:InChI=1/C10H21NO3SSi/c1-4-12-16(13-5-2,14-6-3)9-7-8-11-10-15/h4-9H2,1-3H3

Synthetic route

carbon disulfide (75-15-0) + 3-aminopropyltriethoxysilane (919-30-2) → triethoxy (3‑isothiocyanatopropyl)silane (58698-89-8)

Conditions	Yield
Stage #1: carbon disulfide; 3-aminopropyltriethoxysilane In tetrahydrofuran at 0 - 5℃; for 3h; Addition; Stage #2: With CYANAMID; triethylamine In tetrahydrofuran at 40℃; for 3h; Elimination;	95%
With sodium In ethanol for 5h; Heating;	75%
Stage #1: carbon disulfide; 3-aminopropyltriethoxysilane In tetrahydrofuran at 0℃; for 3.33333h; Stage #2: With triethylamine; N-Cyanoguanidine In tetrahydrofuran at 40℃; for 3h;	49%
Stage #1: carbon disulfide; 3-aminopropyltriethoxysilane In tetrahydrofuran at 0℃; for 3h; Stage #2: With triethylamine; N-Cyanoguanidine In tetrahydrofuran at 40℃; for 3h;	49%

thiophosgene (463-71-8) + 3-aminopropyltriethoxysilane (919-30-2) → triethoxy (3‑isothiocyanatopropyl)silane (58698-89-8)

Conditions	Yield
Stage #1: 3-aminopropyltriethoxysilane With triethylamine In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: thiophosgene In tetrahydrofuran at 0℃; for 3h; Inert atmosphere;	57%

C10H23NO3S2Si → triethoxy (3‑isothiocyanatopropyl)silane (58698-89-8)

Conditions	Yield
With 1,4-diamino-2,3-dichloroanthraquinone; triethylamine In tetrahydrofuran at 40℃; for 3h; Yield given;

3-aminopropyltriethoxysilane (919-30-2) + ammonium thiocyanate (1147550-11-5) → triethoxy (3‑isothiocyanatopropyl)silane (58698-89-8)

Conditions	Yield
In toluene for 5h; Addition; Heating;

3-aminopropyltriethoxysilane (919-30-2) → triethoxy (3‑isothiocyanatopropyl)silane (58698-89-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 3 h / 0 - 5 °C 2: DCDA, Et3N / tetrahydrofuran / 3 h / 40 °C View Scheme

N-{3-[diethoxy-iodosilyl]propyl}-N'-[3-(triethoxysilyl)propyl]thiourea → 3-triethoxysilylpropyl thiocyanate (34708-08-2) + triethoxy (3‑isothiocyanatopropyl)silane (58698-89-8)

Conditions	Yield
Heating;	A n/a B 1.3 g

triethoxy (3‑isothiocyanatopropyl)silane (58698-89-8) + 1,4-phenylenediamine (106-50-3) → C6H4(NHC(S)NHCH2CH2CH2Si(OC2H5)3)2 (198645-55-5)

Conditions	Yield
In ethanol for 2h; Heating;	95%

triethoxy (3‑isothiocyanatopropyl)silane (58698-89-8) + N-<2-(acetylamino)-2-deoxy-3,4,6-triacetyl-β-D-glucopyranosyl>-N2-<(1,1-dimethylethoxy)carbonyl>-L-asparagine (76521-35-2) → N4-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N2-(tert-butoxycarbonyl)-L-asparagine 3-(triethoxysilyl)propylamide (128174-40-3)

Conditions	Yield
In chloroform for 48h; Ambient temperature;	88%

(R,R)-1,2-diphenylethylenediamine (35132-20-8) + triethoxy (3‑isothiocyanatopropyl)silane (58698-89-8) → 1‑((1R,2R)‑2‑amino‑1,2‑diphenylethyl)‑3‑(3‑(triethoxysilyl)propyl)thiourea

Conditions	Yield
In dichloromethane at 25℃; for 24h; Inert atmosphere;	62%

(S,S)-1,2-diphenyl-1,2-diaminoethane (29841-69-8) + triethoxy (3‑isothiocyanatopropyl)silane (58698-89-8) → 1‑((1S,2S)‑2‑amino‑1,2‑diphenylethyl)‑3‑(3‑(triethoxysilyl)propyl)thiourea

Conditions	Yield
In dichloromethane at 25℃; for 24h; Inert atmosphere;	59%

C8H10N4S (1307310-23-1) + triethoxy (3‑isothiocyanatopropyl)silane (58698-89-8) → C18H31N5O3S2Si (1345722-64-6)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	48%

triethoxy (3‑isothiocyanatopropyl)silane (58698-89-8) + (2-aminoethyl)diphenylphosphane (4848-43-5) → C24H37N2O3PSSi

Conditions	Yield
In ethanol for 1h; Addition; Heating;

triethoxy (3‑isothiocyanatopropyl)silane (58698-89-8) + 1,4-phenylenediamine (106-50-3) → 1-(4-aminophenyl)-3-[3-(triethoxysilyl)propyl]thiourea

Conditions	Yield
In tetrahydrofuran at 20℃; for 24h; Schlenk technique;

Upstream product

• 75-15-0 carbon disulfide 
• 919-30-2 3-aminopropyltriethoxysilane 
• 1147550-11-5 ammonium thiocyanate 
• 463-71-8 thiophosgene 

Downstream Products

• 198645-55-5 C₆H₄(NHC(S)NHCH₂CH₂CH₂Si(OC₂H₅)3)2 

Relevant articles and documents

TRIETHOXY(3-ISOTHIOCYANATOPROPYL)SILANE

The reaction of triethoxy(3-aminopropyl)silane with carbon disulfide and ortho-chloroethyl formate in absolute ethanol gave triethoxy(3-isothiocyanatopropyl)silane for the first time.The presence of SCN and (C2H5O)3Si groups in this compound enabled us to use it for the preparation of adsorbents and polymer coatings with biocidal activity. Keywords: triethoxy(3-isothiocyanatopropyl)silane, triethoxy(3-aminopropyl)silane, carbon disulfide, orthochloroethyl formate.

Water soluble homogeneous catalysts that are recoverable by phase selectivity and host-guest interactions

A chemical reaction is catalyzed in an organic solvent using a water soluble N-heterocyclic carbene homogeneous catalyst to form a reaction mixture. An aqueous phase in the reaction mixture. A solvent in which the catalyst is insoluble is added to the reaction mixture, causing the catalyst to migrate to the aqueous phase to form a catalyst-laden aqueous phase. The catalyst is extracted from the catalyst-laden aqueous phase.

Acyl iodides in organic synthesis. Reactions of acetyl iodide with urea, thiourea, and their N,N′-disubstituted derivatives

Acetyl iodide reacted with urea and its derivatives to give the corresponding N-substituted products. The reactions of acetyl iodide with thiourea, N,N′-dimethylthiourea, imidazolidine-2-thione, and hexahydropyrimidine-2-thione resulted in the formation o