786-03-8

Usage

Physical state

Colorless, volatile liquid

Primary uses

a. Solvent
b. Starting material for the synthesis of various organic compounds

Applications

a. Production of perfumes
b. Production of dyes
c. Production of pharmaceuticals

Hazardous properties

a. Potential to cause skin and eye irritation
b. Harmful if inhaled or ingested

Safety precautions

Handle with caution and follow proper safety procedures when working with it.

Upstream product

• 119-61-9 benzophenone 
• 504-63-2 trimethyleneglycol 
• 908093-98-1 diazodiphenylmethane 
• 17887-80-8 1,3-bis(trimethylsiloxy)propane 
• 10359-08-7 2,2-diphenyl-1,3-dithiane 
• 33735-40-9 2,2-diphenyl-1,3-oxathiolane 

Downstream Products

• 119-61-9 benzophenone 
• 10359-08-7 2,2-diphenyl-1,3-dithiane 
• 101-81-5 Diphenylmethane 

Relevant academic research and scientific papers

Substituent Effects in the Acid-Catalyzed Hydrolysis of Cyclic Acetals of Benzophenones

Eight 2,2-diaryl-1,3-dioxanes were prepared and the kinetic substituent effects regarding acid-catalyzed hydrolysis were studied in 80percent dioxane-water(v/v) at 30 deg C.The log k were well correlated with the Yukawa-Tsuno equation: log k/ko

Indium(III) triflate catalysed transacetalisation reactions of diols and triols under solvent-free conditions

Acyclic acetals and ketals undergo transacetalisation in the presence of catalytic quantities of indium(III) triflate (In(OTf)3) and diols or triols under solvent-free conditions to generate the corresponding cyclic acetals and ketals in excellent yield. The methodology has been further developed to encompass a tandem acetalisation-acetal exchange protocol, which provides a facile and high yielding route to cyclic ketals from unreactive ketones under very mild reaction conditions.

Acetalization of carbonyl compounds catalyzed by bismuth triflate under solvent-free conditions

Carbonyl compounds were converted to the corresponding 1,3-dioxolanes and 1,3-dioxanes with ethylene glycol and 1,3-propandiol in the presence of bismuth triflate under solvent-free conditions. In addition, high chemoselective protection of aldehydes in the presence of ketones has been achieved.

N-bromosuccinimide (NBS) catalyzed highly chemoselective acetalization of carbonyl compounds using silylated diols and pentaerythritol under neutral aprotic conditions

Various types of carbonyl compounds are efficiently converted to their 1,3-dioxanes and pentaerythritol diacetals by the use of either 1,3-bistrimethylsiloxy propane (A) or 1,3-bistrimethylsilanyloxy-2,2- bistrimethylsilanyloxymethyl propane (D) and a catalytic amount of N-bromosuccinimide (3-10 mol%) under essentially neutral aprotic condition, respectively. A variety of functionalities such as both aliphatic and phenolic -OTBDMS, -OMe, -OBz, furan ring, double bonds and more significantly phenolic -OTHP survived under the present reaction condition. The efficient conversion of two α-tertiary ketones to their cyclic acetals was also achieved using the present protocol.

Highly efficient and chemoselective interchange of 1,3-oxathioacetals and dithioacetals to acetals promoted by N-halosuccinimide

Highly efficient interconversion of a range of 1,3-oxathiolanes, 1,3-dithiolanes and 1,3-dithianes to their acetals at ambient temperature using N-bromosuccinimide or N-chlorosuccinimide and different types of alcohols and diols was investigated.

Iodine-catalyzed, efficient and mild procedure for highly chemoselective acetalization of carbonyl compounds under neutral aprotic conditions

Various types of carbonyl compounds are efficiently converted to their 1,3-dioxanes by the use of 1,3-bis(trimethylsiloxy)propane (BTSP) and a catalytic amount of iodine (3-7 mol%) under essentially neutral aprotic condition.

Tetrabutylammonium tribromide (TBATB) as an efficient generator of HBr for an efficient chemoselective reagent for acetalization of carbonyl compounds

Acyclic and cyclic acetals of various carbonyl compounds were obtained in excellent yields under a mild reaction condition in the presence of trialkyl orthoformate and a catalytic amount of tetrabutylammonium tribromide (TBATB) in absolute alcohol. Chemoselective acetalization of an aldehyde in the presence of ketone, unsymmetrical acetal formation, shorter reaction times, mild reaction conditions, the stability of acid-sensitive protecting groups, high efficiencies, facile isolation of the desired products, and the catalytic nature of the reagent make the present methodology a practical alternative.

2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO) as a versatile, efficient, and chemoselective catalyst for the acetalization and transacetalization of carbonyl compounds, the preparation of acetonides from epoxides and acylals (1,1-diacetates) from aldehydes

The efficient and chemoselective preparation of acetals and ketals from carbonyl compounds, transacetalization reactions, the conversion of epoxides to acetonides, and the preparation of acylals from aldehydes in the presence of catalytic amounts of 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TABCO) are described.

The effect of a para substituent on the conformational preference of 2,2-diphenyl-1,3-dioxanes: Evidence for the anomeric effect from X-ray crystal structure analysis

The molecular structures of 2,2-di(para-substituted phenyl)-1,3-dioxanes were elucidated for the first time by X-ray crystallographic analysis, which revealed two important structural features: (1) These compounds have the chair conformation in which electron-withdrawing aryl groups [viz. p-nitro-or p-(trifluormethyl)phenyl] are always axial and electron-donating aryl groups (viz. p-methoxyphenyl) are always equatorial. (2) In these compounds as well as in symmetrically substituted 2,2-diphenyl-1,3-dioxane the axial C2-aryl bond is longer than the equatorial C2-aryl bond. The axial preference of the electron-withdrawing aryl group was also demonstrated in solution by 1H and 13C NMR spectroscopy. The anomeric carbon substituted with an electron-withdrawing aryl group resonates at an unusually high field, as does the aromatic carbon bearing the electron-withdrawing substituent. The observed 13C NMR data clearly indicate enhanced electron density at these carbons due to the anomeric effect. Semiempirical molecular orbital calculations by the MOPAK PM3 method reproduced the bond lengthening for axial C2-aryl, while the heat of formation derived from this calculation failed to support the axial preference of electron-withdrawing aryl groups. The X-ray crystallographic data on the conformational preference and bond lengths at the anomeric carbon, as well as the solution NMR spectroscopic data, clearly indicate the anomeric effect that is best rationalized in terms of stabilizing interaction between the lone-pair electrons on the ring oxygens and the antibonding orbital of the axial C2-aryl bond.

Efficient and chemoselective conversion of carbonyl compounds to 1,3-dioxanes catalyzed with N-bromosuccinimide under almost neutral reaction conditions

(formula presented) Various types of carbonyl compounds were converted to the corresponding 1,3-dioxanes in the presence of ethyl orthoformate, 1,3-propanediol, and a catalytic amount of NBS via an in situ acetal exchange process. In contrast to conventional acid-catalyzed acetalization reactions, acid-sensitive substrates such as THP ethers and TBDMS ethers remain intact under described reaction conditions.