Reaction #3875718
Related Literature (1)
openreactiondata ↗doi:10.1039/C8SC04228D
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9d4f2526c5a645c488cdccca749c1a9eNo renderable structure data available
CO[Si](C)(CCCN)OCChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-[dimethoxy(methyl)silyl]propan-1-amine |
|---|---|
| IUPAC Name | — |
| CAS Number | 3663-44-3 |
| Database ID | 77233 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-[dimethoxy(methyl)silyl]propan-1-amine (CAS 3663-44-3) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 77233
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
7 reactions · 7 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9d4f2526c5a645c488cdccca749c1a9eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: German Patent No. 2408480 describes the reaction of a silazane derivative from allylamine and an organohydrochlorosilane, in the presence of a proton acceptor to form an intermediate silazane which then undergoes a hydrosilylation reaction catalyzed by a platinum catalyst. Upon alcoholysis, the intermediate hydrosilylation product forms 3-aminopropylmethyldiethoxysilane in 70% overall yield. A molar excess of at least 50% of allylamine is used in this process. Identification of the beta-isomer in the product was not made. Japanese Patent No. 10017578 describes another method of synthesis by hydrosilylation of N,N-bis(tri-methylsilyl)allylamine by methyldimethoxysilane. The product of that reaction is then heated with methanol to form 3-aminopropylmethyldimethoxysilane in at least 85% overall yield. The presence of the beta-isomer in the product was not identified. Japanese Patent No. 11209384 describes the use of a rhodium:cyclooctadiene complex as a hydrosilylation catalyst for the addition of methyldiethoxysilane to allylamine to form 3-aminopropylmethyldiethoxy-silane in 78% yield. 2-Aminopropylmethyldiethoxysilane is formed in very low levels in this process not exceeding 0.5%. a hydrosilylation reaction
Source ID: ord-525c10f50d2f4b8ab86217af38d16d3dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: German Patent No. 2408480 describes the reaction of a silazane derivative from allylamine and an organohydrochlorosilane, in the presence of a proton acceptor to form an intermediate silazane which then undergoes a hydrosilylation reaction catalyzed by a platinum catalyst. Upon alcoholysis, the intermediate hydrosilylation product forms 3-aminopropylmethyldiethoxysilane in 70% overall yield. A molar excess of at least 50% of allylamine is used in this process. Identification of the beta-isomer in the product was not made. Japanese Patent No. 10017578 describes another method of synthesis by hydrosilylation of N,N-bis(tri-methylsilyl)allylamine by methyldimethoxysilane. The product of that reaction is then heated with methanol to form 3-aminopropylmethyldimethoxysilane in at least 85% overall yield. The presence of the beta-isomer in the product was not identified. Japanese Patent No. 11209384 describes the use of a rhodium:cyclooctadiene complex as a hydrosilylation catalyst for the addition of methyldiethoxysilane to allylamine to form 3-aminopropylmethyldiethoxy-silane in 78% yield. 2-Aminopropylmethyldiethoxysilane is formed in very low levels in this process not exceeding 0.5%. a hydrosilylation reaction
Source ID: ord-525c10f50d2f4b8ab86217af38d16d3dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: German Patent No. 2408480 describes the reaction of a silazane derivative from allylamine and an organohydrochlorosilane, in the presence of a proton acceptor to form an intermediate silazane which then undergoes a hydrosilylation reaction catalyzed by a platinum catalyst. Upon alcoholysis, the intermediate hydrosilylation product forms 3-aminopropylmethyldiethoxysilane in 70% overall yield. A molar excess of at least 50% of allylamine is used in this process. Identification of the beta-isomer in the product was not made. Japanese Patent No. 10017578 describes another method of synthesis by hydrosilylation of N,N-bis(tri-methylsilyl)allylamine by methyldimethoxysilane. The product of that reaction is then heated with methanol to form 3-aminopropylmethyldimethoxysilane in at least 85% overall yield. The presence of the beta-isomer in the product was not identified. Japanese Patent No. 11209384 describes the use of a rhodium:cyclooctadiene complex as a hydrosilylation catalyst for the addition of methyldiethoxysilane to allylamine to form 3-aminopropylmethyldiethoxy-silane in 78% yield. 2-Aminopropylmethyldiethoxysilane is formed in very low levels in this process not exceeding 0.5%. a hydrosilylation reaction
Source ID: ord-525c10f50d2f4b8ab86217af38d16d3dConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Into the same reactor as used in Example 1, 17.1 parts of allylamine, 0.3 part of carbazole, 0.00005 part as platinum atom of the same platinum complex as in Example 1 were charged, 31.8 parts of methyldimethoxysilane were added dropwise at 40° C. over 5 minutes, followed further by continuing stirring for 4 hours while maintaining the liquid temperature at 60° C. After cooling, 1.7 parts of ethanol were added and distillation was carried out to give 36.2 parts of γ-aminopropylmethyldimethoxysilane boiling at 105° to 109° C./50 Torr. This corresponded to 74% yield based on the theoretical amount. were charged After cooling distillation
Source ID: ord-46a696554a9c4062962a984843635509Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: There is considerable prior art relating to the synthesis of poly(aminoalkylmethylsiloxanes). Generally, poly(aminoalkylmethylsiloxanes) have been produced by first preparing aminoalkylmethyldialkoxysilanes, followed by hydrolysis with or without an endblocking agent, such as a trimethylsilyl derivative, to form cyclic and linear poly(3-aminoalkylmethylsiloxanes). The isomeric purity of the poly(aminoalkylmethylsiloxane) fluids, prepared in the manner of the prior art, is dependent upon the isomeric purity of the aminoalkylmethyldialkoxysilane prepared in the first step of the synthesis. German Patent No. 2408480 describes the reaction of a silazane derivative from allylamine and an organohydrochlorosilane, in the presence of a proton acceptor to form an intermediate silazane which then undergoes a hydrosilylation reaction catalyzed by a platinum catalyst. Upon alcoholysis, the intermediate hydrosilylation product forms 3-aminopropylmethyldiethoxysilane in 70% overall yield. A molar excess of at least 50% of allylamine is used in this process. Identification of the beta-isomer in the product was not made. Japanese Patent No. 10017578 describes another method of synthesis by hydrosilylation of N,N-bis(trimethylsilyl)allylamine by methyldimethoxysilane. The product of that reaction is then heated with methanol to form 3-aminopropylmethyldimethoxysilane in at least 85% overall yield. The presence of the beta-isomer in the product was not made. Japanese Patent No. 11209384 describes the use of a rhodium:cyclooctadiene complex as a hydrosilylation catalyst for the addition of methyldiethoxysilane to allylamine to form 3-aminopropylmethyldiethoxysilane in 78% yield. 2-Aminopropylmethyldiethoxysilane is formed at very low levels in this process not exceeding 0.5%. U.S. Pat. No. 5,391,675 describes the formation of an aminopropylmethylsiloxy-containing polydimethylsiloxane by barium or strontium hydroxide catalyzed condensation of a silanol terminated polydimethylsiloxane with a 3-aminopropylalkoxysilane with elimination of an alcohol. a hydrosilylation reaction
Source ID: ord-96cb857d0b8f45029f567cccfd76a83eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: German Patent No. 2408480 describes the reaction of a silazane derivative from allylamine and an organohydrochlorosilane, in the presence of a proton acceptor to form an intermediate silazane which then undergoes a hydrosilylation reaction catalyzed by a platinum catalyst. Upon alcoholysis, the intermediate hydrosilylation product forms 3-aminopropylmethyldiethoxysilane in 70% overall yield. A molar excess of at least 50% of allylamine is used in this process. Identification of the beta-isomer in the product was not made. Japanese Patent No. 10017578 describes another method of synthesis by hydrosilylation of N,N-bis(tri-methylsilyl)allylamine by methyldimethoxysilane. The product of that reaction is then heated with methanol to form 3-aminopropylmethyldimethoxysilane in at least 85% overall yield. The presence of the beta-isomer in the product was not identified. Japanese Patent No. 11209384 describes the use of a rhodium:cyclooctadiene complex as a hydrosilylation catalyst for the addition of methyldiethoxysilane to allylamine to form 3-aminopropylmethyldiethoxy-silane in 78% yield. 2-Aminopropylmethyldiethoxysilane is formed in very low levels in this process not exceeding 0.5%. a hydrosilylation reaction
Source ID: ord-525c10f50d2f4b8ab86217af38d16d3dPubChem References
These sources are listed in the compound's public database record.
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