15396-00-6

Basic information

• Product Name: 3-Isocyanatopropyltrimethoxysilane
• Synonyms: GAMMA-ISOCYANOPROPYLTRIMETHOXYSILANE;3-ISOCYANATOPROPYLTRIMETHOXYSILANE;3-(trimethoxysilyl)propyl isocyanate;Trimethoxy(3-isocyanotopropyl)silane;(3-isocyanatopropyl)trimethoxy-silan;3-Isocyanatopropyltrimethyoxysilane;Silane,(3-isocyanatopropyl)trimethoxy-;3-isocyanatepropyltrimethoxysilane
• CAS NO: 15396-00-6
• Molecular Formula: C₇H₁₅NO₄Si
• Molecular Weight: 205.28
• EINECS: 239-415-9
• Product Categories: Isocyanate Silanes;SILANE
• Mol File: 15396-00-6.mol
• Article Data: 23

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 95-98°C 10mm
• Flash Point: 108°C
• Appearance: Colorless clear liquid
• Density: 1,084 g/cm3
• Vapor Pressure: 0.272mmHg at 25°C
• Refractive Index: 1.421
• Water Solubility: 1000g/L at 20℃
• CAS DataBase Reference: 3-Isocyanatopropyltrimethoxysilane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Isocyanatopropyltrimethoxysilane(15396-00-6)
• EPA Substance Registry System: 3-Isocyanatopropyltrimethoxysilane(15396-00-6)

Safety Data

• Statements: 21/22-26-34-42
• Safety Statements: 23-26-36/37/39-24/25
• RIDADR: 2927
• HazardClass: 6.1/8
• PackingGroup: II
• Hazardous Substances Data: 15396-00-6(Hazardous Substances Data)

Usage

Chemical Properties

Colorless clear liquid

Flammability and Explosibility

Notclassified

InChI:InChI=1/C7H15NO4Si/c1-10-13(11-2,12-3)6-4-5-8-7-9/h4-6H2,1-3H3

Synthetic route

3-(trimethoxysilyl)propan-1-amine (13822-56-5) + urea (57-13-6) → 3-(trimethoxysilyl)propyl isocyanate (15396-00-6)

Conditions	Yield
Stage #1: 3-(trimethoxysilyl)propan-1-amine; urea With Trimethyl orthoacetate In dimethyl sulfoxide at 90 - 95℃; for 9h; Stage #2: With sulfuric acid; copper(II) oxide In dimethyl sulfoxide at 75 - 80℃; for 4.5h; pH=6.5; Concentration; Temperature; pH-value;	98.2%
Stage #1: 3-(trimethoxysilyl)propan-1-amine; urea In methanol at 180℃; under 8250.83 - 10501.1 Torr; for 12.5h; Stage #2: With tin(ll) chloride at 195℃; under 56.2556 Torr;	92%

N-(3-trimethoxysilylpropyl) O-methyl carbamate (23432-62-4) → 3-(trimethoxysilyl)propyl isocyanate (15396-00-6)

Conditions	Yield
With Methyltrichlorosilane; triethylamine In toluene at 40 - 100℃; for 1h; Inert atmosphere;	96%
With tin(ll) chloride at 195℃; under 45.0045 Torr;	89%
Stage #1: N-(3-trimethoxysilylpropyl) O-methyl carbamate; iron(III) oxide at 250℃; under 750.075 Torr; Gas phase; Microwave irradiation; Stage #2: Fe2O3-coated, straight-channeled cordierite at 440℃; under 750.075 Torr; Product distribution / selectivity; Gas phase;	73%

trimethoxysilane (2487-90-3) + allylisocyanate (1476-23-9) → 3-(trimethoxysilyl)propyl isocyanate (15396-00-6)

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex at 50 - 80℃; for 3h;	95%
With di(rhodium)tetracarbonyl dichloride at 80℃; for 2.5h; Reagent/catalyst; Schlenk technique;	68.8%

isocyanatopropyltrichlorosilane (26169-38-0) + trimethyl orthoformate (149-73-5) → 3-(trimethoxysilyl)propyl isocyanate (15396-00-6)

Conditions	Yield
at 85 - 95℃; for 7h; Industrial scale;	84%

urea (57-13-6) + 3-Chloropropyltrimethoxysilan (2530-87-2) → 3-(trimethoxysilyl)propyl isocyanate (15396-00-6)

Conditions	Yield
Stage #1: urea; 3-Chloropropyltrimethoxysilan With ammonium chloride at 120℃; for 3h; Inert atmosphere; Stage #2: With cobalt(II) naphthenate at 160℃; for 3h; Reagent/catalyst; Temperature; Inert atmosphere;	70%

N-(3-trimethoxysilylpropyl) O-methyl carbamate (23432-62-4) → 3-(trimethoxysilyl)propyl isocyanate (15396-00-6) + tris-[3-(trimethoxysilyl)propyl]isocyanurate (26115-70-8)

Conditions	Yield
at 210℃; under 100 - 300 Torr; for 1.65 - 5.65h; Product distribution / selectivity;

phosgene (75-44-5) + 3-(trimethoxysilyl)propan-1-amine (13822-56-5) → 3-(trimethoxysilyl)propyl isocyanate (15396-00-6)

Conditions	Yield
With 2,2'-dimorpholinodiethyl ether In ethyl acetate at 0 - 10℃;

methyl carbamate (598-55-0) + 3-Chloropropyltrimethoxysilan (2530-87-2) → 3-(trimethoxysilyl)propyl isocyanate (15396-00-6)

Conditions	Yield
at 60 - 120℃; for 5h;	155 g

Upstream product

• 57-13-6 urea 
• 2530-87-2 3-Chloropropyltrimethoxysilan 
• 2487-90-3 trimethoxysilane 
• 1476-23-9 allylisocyanate 
• 598-55-0 methyl carbamate 
• 26169-38-0 isocyanatopropyltrichlorosilane 
• 149-73-5 trimethyl orthoformate 
• 13822-56-5 3-(trimethoxysilyl)propan-1-amine 
• 75-44-5 phosgene 
• 23432-62-4 N-(3-trimethoxysilylpropyl) O-methyl carbamate 

Downstream Products

• 26115-70-8 tris-[3-(trimethoxysilyl)propyl]isocyanurate 
• 1191100-31-8 C₄₉H₆₈N₆O₉Si₂ 
• 1447729-07-8 C₄₇H₂₉F₁₅GaN₇O₄Si 

Relevant articles and documents

PREPARATION OF ISOCYANATOSILANES

There is provided herein a method and an apparatus for producing an isocyanatoorganosilane which method includes feeding a carbamatoorganosilane to a cracking device where it is thermally dissociated into a reaction product mixture comprising isocyanatoorganosilane, alcohol, and heavies, followed by separating the mixture in a distillation column of two parts and collecting the isocyanatoorganosilane from the distillation column via a side stream having a predetermined location between the top and bottom parts of the column; and wherein the distillation column is configured to have a ratio of the length of the bottom part of the distillation column to the length of the top part of the distillation column which is effective to provide a side stream having a high purity and high weight percent of isocyanatoorganosilane.

Preparation method of 3-isocyanatopropyltrialkoxysilane

A preparation method of 3-isocyanatopropyltrialkoxysilane comprises the steps of (1) mixing 3-chloropropyltrialkoxysilane, urea and ammonium salt, heating to 120-130 DEG C, stirring to allow reactingfor 2-3 hours, cooling, and removing solid by centrifuging or filtering; (2) adding the separated liquid into a manganese or cobalt carboxylate catalyst, heating to 150-200 DEG C under nitrogen protection, and stirring to allow reacting for 1-2 hours; (3) sampling the reaction product, rectifying under reduced pressure after qualification is confirmed by detection, and separating the target product. The preparation method has the advantage of evidently reduced production cost.

Method for preparing 3-isocyanatopropyltrimethoxysilane

The invention relates to a method for preparing 3-isocyanatopropyltrimethoxysilane. The method is characterized in that [3-(trimethoxysilane)propyl]methyl carbamate is used as a raw material to reactwith methyl trichlorosilane, and thus 3-isocyanatopropyltrimethoxysilane is synthesized by one step. The preparation method provided by the invention is simple, the production process is safe, the reaction temperature is easy to control, production equipment is simple, and thus the method is suitable for industrial production.