31469-22-4

Basic information

• Product Name: 1,1-BIS(TRIMETHYLSILYLOXY)-1-PROPENE
• Synonyms: 1,1-BIS(TRIMETHYLSILYLOXY)-1-PROPENE;Methylketene Bis(trimethylsilyl) Acetal
• CAS NO: 31469-22-4
• Molecular Formula: C₉H₂₂O₂Si₂
• Molecular Weight: 218.44
• Mol File: 31469-22-4.mol

Chemical Properties

• Boiling Point: 60 °C (11 mmHg)
• Flash Point: 25 °C
• Appearance: /
• Storage Temp.: 0-6°C
• CAS DataBase Reference: 1,1-BIS(TRIMETHYLSILYLOXY)-1-PROPENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-BIS(TRIMETHYLSILYLOXY)-1-PROPENE(31469-22-4)
• EPA Substance Registry System: 1,1-BIS(TRIMETHYLSILYLOXY)-1-PROPENE(31469-22-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-10
• Safety Statements: 37/39-26-16
• Hazardous Substances Data: 31469-22-4(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 16844-98-7 trimethylsilyl propionate 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 802294-64-0 propionic acid 

Downstream Products

• 492-37-5 hydratropic acid 
• 29679-58-1 Fenoprofen 
• 256663-37-3 2-methyl-3-phenyl-pent-4-enoic acid 
• 351207-68-6 trans-2-methyl-5-phenyl-pent-4-enoic acid 
• 22071-15-4 ketoprofen 
• 5104-49-4 fluorobiprofen 
• 23981-80-8 naproxen 
• 15687-27-1 ibuprofen 
• 1782417-51-9 C₁₀H₉NO₂ 
• 1249725-52-7 2-(3-cyanophenyl)propanoic acid 
• 21762-10-7 (RS)-2-(3-nitrophenyl)propionic acid 
• 22410-97-5 (RS)-2-(4-benzoylphenyl)propanoic acid 
• 1226149-97-8 α-(3,5-dimethylphenyl)propionic acid 

Relevant articles and documents

Catalytic Asymmetric Synthesis of Unprotected β2-Amino Acids

We report here a scalable, catalytic one-pot approach to enantiopure and unmodified β2-amino acids. A newly developed confined imidodiphosphorimidate (IDPi) catalyzes a broadly applicable reaction of diverse bis-silyl ketene acetals with a silylated aminomethyl ether, followed by hydrolytic workup, to give free β2-amino acids in high yields, purity, and enantioselectivity. Importantly, both aromatic and aliphatic β2-amino acids can be obtained using this method. Mechanistic studies are consistent with the aminomethylation to proceed via silylium-based asymmetric counteranion-directed catalysis (Si-ACDC) and a transition state to explain the enantioselectivity is suggested on the basis of density functional theory calculation.

Palladium-Catalyzed α-Arylation of Carboxylic Acids and Secondary Amides via a Traceless Protecting Strategy

A novel traceless protecting strategy is presented for the long-standing challenge of conducting the palladium-catalyzed α-arylation of carboxylic aids and secondary amides with aryl halides. Both of the presented coupling processes occur with a variety of carboxylic acids and amides and with a variety of aryl bromides containing a broad range of functional groups, including base-sensitive functionality like acyl, alkoxycarbonyl, nitro, cyano, and even hydroxyl groups. Five commercial drugs were prepared through this method in one step in 81-96% yield. Gram-scale synthesis of medication Naproxen and Flurbiprofen with low palladium loading further highlights the practical value of this method.

One-pot synthesis of 3-hydroxymaleic anhydrides by cyclization of 1,1-bis(trimethylsilyloxy)ketene acetals with oxalyl chloride

Functionalized 3-hydroxymaleic anhydrides were prepared by cyclization of 1,1-bis(trimethylsilyloxy)ketene acetals with oxalyl chloride.

Synthesis of 7,8-benzo-9-aza-4-oxabicyclo[3.3.1]nonan-3-ones by sequential 'condensation-iodolactonization' reactions of 1,1-bis(trimethylsilyloxy)ketene acetals with isoquinolines

Functionalized 7,8-benzo-9-aza-4-oxabicyclo[3.3.1]nonan-3-ones were prepared by regio- and diastereoselective condensation of 1,1-bis(silyloxy) ketene acetals with isoquinolinium salts and subsequent regioselective and stereospecific iodolactonization.

One-pot synthesis of 3-hydroxymaleic anhydrides by cyclization of 1,1-bis(trimethylsilyloxy)ketene acetals with oxalyl chloride

Functionalized 3-hydroxymaleic anhydrides were prepared by cyclization of 1,1-bis(trimethylsilyloxy)ketene acetals with oxalyl chloride.

α-SILYL TRIMETHYLSILYLESTERS FROM ALIPHATIC CARBOXYLIC ACID DIANIONS

The synthesis of α-silyl trimethylsilyl esters from aliphatic carboxylic acid dianions is reported.The results indicate kinetic and thermodynamic control of silylation of acid dianions.

Reactions of Trialkylsilyl Trifluoromethanesulfonates, II. - Synthesis of O-Alkyl-O-(trialkylsilyl)ketene Acetals and 2-(Trialkylsilyl)carboxylates

Alkyl carboxylates 2 are silylated by trialkylsilyl triflates 1 in the presence of triethylamine (3) to yield ketene acetals 4.In reactions of the esters 6 mixtures of ketene acetals 7 and at the α-carbon silylated esters 8 are obtained.Ethanoic acid esters and lactones are doubly silylated to give the products 11, 12, and 15, respectively.Under suitable conditions silylation of the esters 10 gives rise to the 2-trimethylsilylethanoic acid esters 13.The thermodynamically more stable products are obtained.Product distributions depend on the structure of the esters and the silylating agents 1.