85287-67-8

Basic information

• Product Name: 1,1-BIS(TRIMETHYLSILYLOXY)-1-BUTENE
• Synonyms: 1,1-BIS(TRIMETHYLSILYLOXY)-1-BUTENE
• CAS NO: 85287-67-8
• Molecular Formula: C₁₀H₂₄O₂Si₂
• Molecular Weight: 232.47
• Mol File: 85287-67-8.mol

Chemical Properties

• Boiling Point: 70 °C (11 mmHg)
• Flash Point: 25 °C
• Appearance: /
• Storage Temp.: 0-6°C
• CAS DataBase Reference: 1,1-BIS(TRIMETHYLSILYLOXY)-1-BUTENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-BIS(TRIMETHYLSILYLOXY)-1-BUTENE(85287-67-8)
• EPA Substance Registry System: 1,1-BIS(TRIMETHYLSILYLOXY)-1-BUTENE(85287-67-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-10
• Safety Statements: 37/39-26-16
• Hazardous Substances Data: 85287-67-8(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Upstream product

• 16844-99-8 trimethylsilyl butyrate 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 75-77-4 chloro-trimethyl-silane 
• 107-92-6 butyric acid 

Downstream Products

• 85287-80-5 3-Ethyl-4-phenylsulfanyl-dihydro-furan-2-one 
• 85287-82-7 3-Ethyl-5-methyl-4-phenylsulfanyl-dihydro-furan-2-one 
• 85287-73-6 3-Ethyl-4-phenylsulfanyl-tetrahydro-pyran-2-one 
• 85287-75-8 3-Ethyl-6-methyl-4-phenylsulfanyl-tetrahydro-pyran-2-one 
• 85287-90-7 (4aR,8aR)-3-Ethyl-4-phenylsulfanyl-octahydro-chromen-2-one 
• 99940-43-9 C₁₆H₂₉NO₃Si₂ 
• 1575-73-1 2-ethyl-pent-4-enoic acid 
• 15410-83-0 2-(naphthalen-2-yl)butanoic acid 
• 137245-80-8 trans-2-ethyl-5-phenyl-pent-4-enoic acid 
• 90-27-7 2-Phenylbutyric acid 
• 32949-81-8 2-(3-Phenoxy-phenyl)-butyric acid 
• 345220-92-0 2-(α-anilino-benzyl)-butyric acid 
• 14367-04-5 erythro-2-Ethyl-3-hydroxy-3-phenylpropionsaeure 
• 14367-04-5 threo-2-Ethyl-3-hydroxy-3-phenylpropionsaeure 

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.