24801-88-5

Basic information

• Product Name: 3-Isocyanatopropyltriethoxysilane
• Synonyms: gamma-isocyanatopropyltriethoxysilane;i7840;Isocyanatopropyltriethoxysilane;Silane,triethoxy(3-isocyanatopropyl)-;triethoxy(3-isocyanatopropyl)-silan;y9030;yh9030;ZERENEX ZX007474
• CAS NO: 24801-88-5
• Molecular Formula: C₁₀H₂₁NO₄Si
• Molecular Weight: 247.36
• EINECS: 246-467-6
• Product Categories: Adhesion Promoters;Coupling Agents;Isocyanate Silanes;Surface Modifiers;silane
• Mol File: 24801-88-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 283 °C(lit.)
• Flash Point: 171 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.999 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0106mmHg at 25°C
• Refractive Index: n20/D 1.42(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Hydrolyzes in water.
• Sensitive: Moisture Sensitive
• BRN: 4404652
• CAS DataBase Reference: 3-Isocyanatopropyltriethoxysilane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Isocyanatopropyltriethoxysilane(24801-88-5)
• EPA Substance Registry System: 3-Isocyanatopropyltriethoxysilane(24801-88-5)

Safety Data

• Hazard Codes: T+
• Statements: 21/22-26-34-42
• Safety Statements: 23-26-28-36/37/39-45
• RIDADR: UN 3390 6.1/PG 1
• WGK Germany: 3
• RTECS: VV6691000
• F: 10-19-21
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 24801-88-5(Hazardous Substances Data)

Usage

Description

3-isocyanatepropyltriethoxysilane is an isocyanate functional silane. It is used for the functionalization of numerous compounds with active hydrogen atoms. It hydrolyzes in the presence of moisture to form silanols, which can react with themselves to produce siloxanes. 3-isocyanatepropyltriethoxysilane is mainly applied in these aspects: As crosslinkers for one part moisture curable urethane adhesives, sealants and coatings. As adhesion promoters for one part moisture curable and two part reactive urethane systems. As adhesion promoters for silicone sealants or coatings, to enhance adhesion to organic substrates with active hydrogen atoms. It can provide good wet adhesion to glass, metal and other inorganic substrates, and can provide good thermal, chemical and UV stable performance. It hydrolyzes slower than SiSiB? PC2710, SiSiB? PC2720 is better for applications requring greater open time or enhanced shelf stability.

Chemical Properties

Colorless clear liquid

Uses

3-Isocyanatopropyltriethoxysilane is used in preparation of antistatic adhesive and liquid crystal display device.

Hazard

A poison by skin contact. Moderately toxic by inhalation. A mild skin and severe eye irritant.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H21NO4Si/c1-4-13-16(14-5-2,15-6-3)9-7-8-11-10-12/h4-9H2,1-3H3

Synthetic route

potassium cyanate (590-28-3) + (3-chloropropyl)triethoxysilane (5089-70-3) → 3-(triethoxypropyl) isocyanate (24801-88-5)

Conditions	Yield
at 100℃; for 12h; Temperature; Inert atmosphere; Ionic liquid;	99.5%

Triethoxysilane (998-30-1) + allylisocyanate (1476-23-9) → 3-(triethoxypropyl) isocyanate (24801-88-5)

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex at 40 - 85℃; for 4.5h;	95.7%

N-(3-triethoxysilylpropyl)-O-ethylcarbamate (17945-05-0) → 3-(triethoxypropyl) isocyanate (24801-88-5)

Conditions	Yield
at 220℃; under 37.5038 Torr;	92%
With di(n-butyl)tin oxide at 150℃; for 6h; Kinetics; Catalytic behavior; Reagent/catalyst; Temperature;	60%
With dibutyltin dilaurate In ethanol at 200℃;

(3-chloropropyl)triethoxysilane (5089-70-3) + urea (57-13-6) → 3-(triethoxypropyl) isocyanate (24801-88-5)

Conditions	Yield
Stage #1: (3-chloropropyl)triethoxysilane; urea With ammonium chloride at 130℃; for 3h; Inert atmosphere; Stage #2: With manganese octanoate at 200℃; for 2h; Reagent/catalyst; Temperature; Inert atmosphere;	71%

3-aminopropyltriethoxysilane (919-30-2) → 3-(triethoxypropyl) isocyanate (24801-88-5)

Conditions	Yield
In N,N-dimethyl-aniline; toluene
With pyridine In diethyl ether
Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol / 6 h / 80 °C / Inert atmosphere 2: dibutyltin dilaurate / ethanol / 200 °C View Scheme

(2S)-2-[(diphenylphosphino)methyl]pyrrolidine (60261-46-3) + 3-(triethoxypropyl) isocyanate (24801-88-5) → (S)-1-(3-triethoxysilylpropyl)aminocarbonyl-2-diphenylphosphinomethylpyrrolidine (163809-05-0)

Conditions	Yield
In dichloromethane for 8h; Ambient temperature;	100%

3-(triethoxypropyl) isocyanate (24801-88-5) + L-proline tert-butylamide (128018-18-8) → (S)-1-(3-triethoxysilylpropyl)aminocarbonyl-2-t-butylaminocarbonylpyrrolidine (163809-03-8)

Conditions	Yield
In dichloromethane Ambient temperature;	100%

3-(triethoxypropyl) isocyanate (24801-88-5) + (2S,4S)-4-amino-1-benzyloxycarbonyl-2-tert-butylaminocarbonylpyrrolidine (197911-06-1) → (2S,4S)-1-benzyloxycarbonyl-2-tert-butylaminocarbonyl-4-(3-triethoxysilylpropylaminocarbonylamino)pyrrolidine

Conditions	Yield
In dichloromethane at 20℃; for 18h;	100%

3-(triethoxypropyl) isocyanate (24801-88-5) + 1-amino-4,5-bis(dimethylamino)naphthalene (199342-45-5) → 4-[(triethoxysilyl)propylaminocarbonylamino]-1,8-bis(dimethylamino)naphthalene

Conditions	Yield
In dichloromethane for 2h;	100%

9-hydroxymethylanthracene (1468-95-7) + 3-(triethoxypropyl) isocyanate (24801-88-5) → C25H33NO5Si

Conditions	Yield
With dicyclohexyl-carbodiimide	100%
at 100℃; for 5h; Schlenk technique; Inert atmosphere;	57%
With triethylamine In tetrahydrofuran for 24h; Heating;

4'-aminobenzo-15-crown-5-ether (60835-71-4) + 3-(triethoxypropyl) isocyanate (24801-88-5) → 4-[3-(triethoxysilyl)propyl]ureidobenzo-15-crown-5

Conditions	Yield
In chloroform at 20℃; for 48h;	100%
In acetonitrile for 5h; Heating;	90%

6-nitroveratryl alcohol (1016-58-6) + 3-(triethoxypropyl) isocyanate (24801-88-5) → 3-triethoxysilylpropyl-N-(4,5-dimethoxy-2-nitrobenzyloxycarbonyl)amine

Conditions	Yield
With di-n-butyltin dilaulate In tetrahydrofuran Heating;	100%
With dibutyltin dilaurate In benzene at 70℃; for 2h;	78%
With dibutyltin dilaurate In tetrahydrofuran at 20℃; for 24h;	64%

3-(triethoxypropyl) isocyanate (24801-88-5) + 3,5-bis(phenylthiomethyl)aniline (251912-40-0) → C30H40N2O4S2Si

Conditions	Yield
In dichloromethane at 20℃; for 8h;	100%

3-(triethoxypropyl) isocyanate (24801-88-5) + (2S,4S)-Nα-Cbz-4-aminoproline benzyl ester (329191-57-3) → (2S,4S)-1,2-dibenzyloxycarbonyl-4-(3-triethoxysilylpropylaminocarbonylamino)pyrrolidine

Conditions	Yield
In dichloromethane at 20℃; for 18h;	100%

3-(diethoxy-methyl-silanyl)-propylamine (3179-76-8) + 3-(triethoxypropyl) isocyanate (24801-88-5) → N-[3-(triethoxysilyl)propyl]-N'-[3-(diethoxysilylmethyl)propyl]urea

Conditions	Yield
In ethanol for 2h;	100%
In acetone at 65℃; for 12h;

3-(triethoxypropyl) isocyanate (24801-88-5) + di-n-propylamine (142-84-7) → N-di-n-propyl-N'-[3-(triethoxysilyl)propyl]urea

Conditions	Yield
In hexane at 20℃; for 3h;	100%

tetrakis(4-aminophenyl)porphyrin (22112-84-1) + 3-(triethoxypropyl) isocyanate (24801-88-5) → 5,10,15,20-tetrakis[4-((3-triethoxysilyl)propylureido)phenyl]porphyrin

Conditions	Yield
With triethylamine In tetrahydrofuran; acetonitrile	100%

3-(triethoxypropyl) isocyanate (24801-88-5) + 4-aminobenzo-18-crown-6 (68941-06-0) → 4-[3-(triethoxysilyl)propyl]ureidobenzo-18-crown-6

Conditions	Yield
In dichloromethane at 20℃; for 48h;	100%
In toluene at 85℃; for 12h;	92%

3-(triethoxypropyl) isocyanate (24801-88-5) + hexan-1-ol (111-27-3) → C16H35NO5Si

Conditions	Yield
at 85℃; for 24h;	100%

5-(dibromomethylene)-3-(1-hydroxydodecyl)furan-2(5H)-one + 3-(triethoxypropyl) isocyanate (24801-88-5) → 1-(5,5-dibromomethylene-3-dodecyl-2(5H)furanone)triethoxysilylpropylcarbamate

Conditions	Yield
at 85℃; for 24h;	100%

4-amino-phenol (123-30-8) + 3-(triethoxypropyl) isocyanate (24801-88-5) → 1-(3-(triethoxysilyl)propyl)-3-(4-hydroxyphenyl)urea (1028843-30-2)

Conditions	Yield
In chloroform at 80℃; for 5h;	100%
In chloroform at 80℃; for 5h;	95%

8-methyl-11,12-dihydroindolo[2,3-a]carbazol-3-ol (1045860-38-5) + 3-(triethoxypropyl) isocyanate (24801-88-5) → 8-methyl-11,12-dihydroindolo[2,3-a]carbazol-3-yl 3-(triethoxysilyl)propylcarbamate (1157854-31-3)

Conditions	Yield
With triethylamine In tetrahydrofuran for 48h; Inert atmosphere; Reflux;	100%

3,3,5,5,7,7,8,8,8-nonafluorooctanol (56281-06-2) + 3-(triethoxypropyl) isocyanate (24801-88-5) → 3-(4,4,4-triethoxysilyl-propyl)-carbamic acid-3,3,5,5,6,6,7,7,8,8,8-undecafluoro-octyl ester (1159854-12-2)

Conditions	Yield
iron(III) chloride In 4-methyl-2-pentanone at 60 - 110℃; for 3h;	100%

2-(3,3,5,5,6,6,7,7,8,8,8-undecafluoro-octylsulfanyl)-ethyl-ammonium chloride (1158091-31-6) + 3-(triethoxypropyl) isocyanate (24801-88-5) → C20H33F11N2O4SSi (1159854-02-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20 - 60℃; for 1h;	100%

2-(3,3,4,4-tetrafluoro-4-heptafluoropropyloxy-butylsulfanyl)-ethylamine (1158091-30-5) + 3-(triethoxypropyl) isocyanate (24801-88-5) → 1-[2-(3,3,4,4-tetrafluoro-4-heptafluoropropyloxy-butylsulfanyl)-ethyl]-3-(triethoxysilyl-propyl)-urea (1159854-03-1)

Conditions	Yield
at 65℃; for 1h;	100%

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octane-1-sulfonic acid (3-amino-propyl)-N-methyl-amide (1159854-04-2) + 3-(triethoxypropyl) isocyanate (24801-88-5) → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octane-1-sulfonic acid-N-methyl-{3-[3-(triethoxysilyl-propyl)-ureido]-propyl}-amide (1159854-06-4)

Conditions	Yield
In tetrahydrofuran at 0 - 50℃; for 1h;	100%

3,3,5,5,6,6,7,7,8,8,8-undecafluoro-octane-1-thiol (1158091-20-3) + 3-(triethoxypropyl) isocyanate (24801-88-5) → [3-(triethoxysilyl-propyl)-thiocarbamic acid S-(3,3,5,5,6,6,7,7,8,8,8-undecafluoro-octyl)ester] (1159854-14-4)

Conditions	Yield
dibutyltin(II) dilaurate at 70℃; for 12h;	100%

(1-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-1H-1,2,3-triazol-4-yl)methanol (929200-08-8) + 3-(triethoxypropyl) isocyanate (24801-88-5) → [2-(triethoxysilyl)-propyl]-carbamic acid [1-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-1H-[1,2,3]triazol-4-yl]-methyl ester (1159854-09-7)

Conditions	Yield
dibutyltin(II) dilaurate In tetrahydrofuran at 50℃; for 5h;	100%

1,1,2,2,5,5,6,6,9,9,10,10-dodecahydroperfluoro-1-dodecanol (1159854-10-0) + 3-(triethoxypropyl) isocyanate (24801-88-5) → poly(α-fluoro-ω-2-hydroxyethyl terminated ethylene-co-tetrafluoroethylene )

Conditions	Yield
iron(III) chloride In 4-methyl-2-pentanone for 3h; Heating / reflux;	100%

3-(triethoxypropyl) isocyanate (24801-88-5) + histamine (51-45-6) → 1-(2-(1H-imidazol-4-yl)ethyl)-3-(3-(triethoxysilyl)propyl)urea

Conditions	Yield
In methanol at 40 - 60℃; for 13h; Kinetics; Temperature;	100%

3-(triethoxypropyl) isocyanate (24801-88-5) + ethanolamine (141-43-5) → 1-(2-hydroxyethyl)-3-(3-(triethoxysilyl)propyl)urea

Conditions	Yield
In chloroform at 20℃;	100%

C77H179N9S8Si7 (1426827-73-7) + 3-(triethoxypropyl) isocyanate (24801-88-5) → C87H200N10O4S8Si8

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;	100%

2-chloroethanamine hydrochloride (870-24-6) + 3-(triethoxypropyl) isocyanate (24801-88-5) + potassium thioacetate (10387-40-3) → C14H30N2O5SSi

Conditions	Yield
Stage #1: 2-chloroethanamine hydrochloride; 3-(triethoxypropyl) isocyanate With sodium ethanolate In ethanol at -78 - -65℃; for 3h; Stage #2: potassium thioacetate In ethanol at 50℃; for 4h; Reflux;	100%

2,2'-dithiodi(1H-imidazole) (89418-44-0) + 3-(triethoxypropyl) isocyanate (24801-88-5) → 2,2'-dithiobis{1-[3-(triethoxysilyl)propylcarbamoyl]-1H-imidazole}

Conditions	Yield
In N,N-dimethyl-formamide at 20 - 40℃; for 6h;	100%

bis-benzimidazole disulfide (1155-37-9) + 3-(triethoxypropyl) isocyanate (24801-88-5) → 2,2'-dithiobis{1-[3-(triethoxysilyl)propylcarbamoyl]-1H-benzimidazole}

Conditions	Yield
In N,N-dimethyl-formamide at 20 - 40℃; for 4h;	100%

Upstream product

• 590-28-3 potassium cyanate 
• 5089-70-3 (3-chloropropyl)triethoxysilane 
• 998-30-1 Triethoxysilane 
• 1476-23-9 allylisocyanate 
• 919-30-2 3-aminopropyltriethoxysilane 
• 57-13-6 urea 
• 17945-05-0 N-(3-triethoxysilylpropyl)-O-ethylcarbamate 

Downstream Products

• 188541-09-5 3-triethoxysilylpropyl-N-(4,5-dimethoxy-2-nitrobenzyloxycarbonyl)amine 
• 813468-12-1 C₃₂H₄₈F₁₂N₂O₁₀Si₂ 
• 952525-54-1 C₂₁H₃₅NO₆Si 
• 952525-53-0 C₂₂H₃₇NO₆Si 
• 1002921-46-1 4-[(E)-2-{4-nitro-2-[({[3-(triethoxysilyl)propyl]carbamoyl}oxy)methyl]phenyl}vinyl]phenyl 3-(triethoxysilyl)propylcarbamate 
• 1002921-48-3 3-{4-[(E)-2-{4-nitro-2-[({[3-(triethoxysilyl)propyl]carbamoyl}oxy)methyl]phenyl}vinyl]phenoxy}propyl acrylate 
• 1002921-49-4 4-[(E)-2-(4-nitrophenyl)vinyl]phenyl [3-(triethoxysilyl)propyl]carbamate 
• 1028843-32-4 1-(3-(triethoxysilyl)propyl)-3-((4-hydroxymethyl)phenyl)urea 
• 1028843-30-2 1-(3-(triethoxysilyl)propyl)-3-(4-hydroxyphenyl)urea 
• 1028843-31-3 1-(3-(triethoxysilyl)propyl)-3-(4-methoxyphenyl)urea 
• 3451-83-0 1-(3-(triethoxysilyl)propyl)-3-phenyl urea 
• 1051924-68-5 C₃₇H₆₂N₁₀O₁₁Si 
• 1012872-50-2 5-[3-(triethoxysilanyl)-propylcarbamoyloxy]-2-iodo-benzoic acid 

Relevant articles and documents

Formation and Depolymerization of Oligomers during Thermal Cracking of Silicon-Containing Carbamates

Polymerization reactions in the thermal cracking of N-substituted carbamates to produce the corresponding isocyanates significantly reduce the yield of isocyanates and thus vastly hinder the industrial application of such non-phosgene routes. Herein, we tried to recycle the oligomers generated during the thermal cracking of 3-ethylcarbamatopropyltriethoxysilane (CPTS) to produce 3-isocyanatopropyltriethoxysilane (IPTS). Firstly, the polymerized substrates of the pyrolysis reaction were analyzed by NMR, IR, MALDI-TOF-MS and TG, indicating the pyrolysis substrates were mixtures of CPTS (25 wt%), polyureas (74 wt%), imines, and other compounds (a carbonyl group source, but also forms hydrogen bonds with polyureas. In addition, NH3 co-produced can also modify the reaction system microenvironment, which might be favorable for the dissociation of polyureas. With optimized conditions, more than 96 % of polymerized substrates could be reverted to CPTS for secondary cracking.

Preparation method of 3-isocyanate propyltriethoxysilane

The invention relates to a preparation method of 3-isocyanate propyltriethoxysilane, belonging to the field of fine chemical synthesis. The method comprises synthesizing the 3-isocyanate propyltriethoxysilane from chloropropyltriethoxysilane and potassium cyanate through one-step synthesis in an ionic liquid adopted as a solvent under a catalysis function. An isocyanate process is adopted, and aiming at disadvantages, of the process, that reaction raw materials are difficult to dissolve and yields are low, the preparation method of the 3-isocyanate propyltriethoxysilane based on the ionic liquid is provided.

Method for preparing isocyanate-based silane by hydrosilylation reaction

The invention relates to a synthetic method of an isocyanate-based silane coupling agent and belongs to the field of synthesis of silane coupling agents. The preparation method comprises the followingsteps: taking allyl urea and sodium nitrite as main raw materials, taking toluene as a solvent, and taking tetra-n-butyl ammonium bromide as a catalyst to synthesize allyl isocyanate; then, under theaction of a noble metal catalyst such as platinum or rhodium, carrying out hydrosilylation with silicon-hydrogen bond containing hydrogenalkoxysilanes such as trimethoxy silane, triethoxy silane andthe like for carrying out a reaction to generate an isocyanate-based silane coupling agent crude product; and then carrying out reduced pressure distillation treatment to obtain the isocyanate-based silane coupling agent product. The method has the advantages of simple operation, high reaction conversion rate, high yield, stable quality, safe environment-friendly energy-saving efficient productionprocess, and the like, and industrial production is easy to realize.