85157-47-7

Usage

Physical State

Colorless, viscous liquid

Odor

Slightly floral

Uses

a. Production of pharmaceuticals
b. Production of resins
c. Production of plasticizers

Antimicrobial

Exhibits antimicrobial properties

Antiseptic

Used as an antiseptic in various products

Preservative

Acts as a preservative in different applications

Synthesis

Used as an intermediate in the synthesis of other organic compounds

Safety Precautions

a. Harmful if ingested
b. Harmful if inhaled
c. Harmful if it comes into contact with the skin
d. Harmful if it comes into contact with the eyes

Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 925-90-6 ethylmagnesium bromide 
• 557-20-0 diethylzinc 
• 357427-68-0 rac-1,2-bis(1-hydroxypropyl)benzene 
• 403656-44-0 (S)-2-[1-(4-methoxybenzyloxy)propyl]benzaldehyde 
• 403656-45-1 C₁₇H₁₉BrO₂ 
• 170379-92-7 (1S)-1-(2-bromophenyl)propan-1-ol 
• 6630-33-7 ortho-bromobenzaldehyde 
• 679420-05-4 (R)-3-ethyl-2-oxaindan-1-ol 
• 75-03-6 ethyl iodide 

Downstream Products

• 357427-66-8 (S,S)-1,2-bis(1-hydroxypropyl)benzene 
• 62708-40-1 (E)-1-formyl-2-(2-methylethenyl)benzene 
• 33996-35-9 1,2-dipropenyl-benzene 
• 33996-36-0 1,2-bis-(1,2-dibromo-propyl)-benzene 

Relevant academic research and scientific papers

Optical resolution of C2-symmetric racemic 1,4-diols with o-xylylene structure by chiral resolving agent (S)-ALBO-V

Optical resolution of C2-symmetric racemic 1,4-diols, 1,2-bis(1-hydroxyalkyl)benzene, was examined using (S)-5-allyl-2-oxabicyclo[3.3.0]octene ((S)-ALBO-V) as chiral resolving agent. Diastereomeric acetals obtained from the 1,4-diols with (S)-A

Synthesis of α,β-unsaturated dioxanes, dioxolanes and dioxepanes by trans-acetalisation of dimethylacetals with meso or C 2-symmetrical 1,2-, 1,3- and 1,4-diols

Several o-dibenzylic diols were prepared reacting organometallics with o-phthalaldehyde at room temperature in ether. The identity of the meso and C2-symmetrical (D,L) isomers as well as their ratio were determined by chiral gas chromatography. The meso and C2 (racemic) stereoisomeric diols were easily separated by flash chromatography on silica gel. A set of 18 α,β-unsaturated acetals were then prepared reacting those, as well as commercially available 1,2, 1,3 and 1,4 diols, with the corresponding methylacetals in acidic medium. A trans-acetalisation procedure adapted to the cases of fragile allylic alcohols or unfavorable 1,6 diols-derived dioxonanes based on a Dean-Stark trapping of methanol was also employed.

NEW CHIRAL DIOLS, THEIR MANUFACTURE AND LIGANDS AND CATALYSTS DERIVED THEREFROM

The present invention relates to a method for the preparation of C2-symmetric 1,4-diols of the formula IVA or IVB, wherein ring A, R1 and R2 have the meanings given in the specification, that makes use of the metallation of pure enantiomers of α-(aryl or heteroaryl)-α-substituted alkanol compounds or the use of said alkanol compounds in the preparation of said mmetric 1,4-diols; novel C2--symmetric 1,4-diols in enantiomerically pure form; and methods of use or their use in the synthesis of chiral ligands which find use to produce catalysts for a variety of asymmetric transformations such as hydrogenations.

An efficient enantioselective preparation of (S,S)-1,2-bis(1-hydroxyalkyl)benzene

(S,S)-1,2-Bis(1-hydroxyalkyl)benzenes were obtained in >99% ee's with high diastereoselectivity by the enantioselective addition of dialkylzinc to (S)-2-[1-(4-methoxybenzyloxy)alkyl]-benzaldehyde (86% ee) in the presence of a catalytic amount of (S)-2-(4-

Enantioselective dialkylation of 1,2-phthalicdicarboxaldehyde

A new two-step, one-pot procedure is reported for the enantioselective synthesis of C2-symmetric diols derived from 1,2-phthalicdicarboxaldehyde. The first step involves the enantioselective addition of a dialkylzinc compound to one of the aldehyde groups, affording a lactol organozinc derivative. In the second step this lactol derivative is converted to the appropriate diol with the aid of a Grignard reagent and subsequent hydrolysis. This methodology also allows the synthesis of unsymmetric diols.

Regioselective bromomethylation of 1,2-dialkylbenzenes

This paper describes a systematic exploration of the regioselective bromomethylation of 1,2-dialkylbenzenes as a function of the reaction temperature and the chain length of the alkyl groups. At both 80 and 110 °C, bromomethyl groups can be introduced into the 4 and 5 positions of 1,2-dialkylbenzenes with high selectivity when the alkyl chains consist of two or more carbon atoms.

Conformational Studies by Dynamic NMR. 62.1 Stereomutations of Rotamers and of Conformational Enantiomers in 1,2-Diacylbenzenes

A number of 1,2-diacylbenzenes have been investigated by dynamic NMR spectroscopy. The 1,2-formyl derivative 1 was found to exist (at -162 °C) in the nearly coplanar ZE and EE conformations (70percent and 30percent, respectively) that interconvert with a free energy of activation of 4.9 kcal mol-1. On the contrary, the more hindered 1,2-diisobutanoylbenzene (4) adopts a twisted conformation (as indicated by the 13C spectrum at -157 °C) which, in principle, might correspond either to a meso or to a racemic stereolabile structure. Only the racemic conformer is, however, believed to be populated, and the interconversion barrier between the RR and SS conformational enantiomers has been determined (5.6 kcal mol-1). Although the 1,2-diacetyl- and 1,2-dipropanoylbenzenes did not exhibit dynamic NMR effects in solution, they were assigned a twisted (racemic) conformation on the basis of the corresponding solid state 13C CP-MAS spectra, in that they display a 1:1 doublet signal for each pair of enantiotopic carbons. All these conclusions agree with the predictions of molecular mechanics calculations.

Asymmetric synthesis of chiral diols by the catalytic enantioselective dialkylation of tere-, iso-, and phthalaldehydes and by a catalytic enantioselective autoinductive reaction

Optically pure aromatic diols were synthesized by the highly enantioselective dialkylation of aromatic dialdehydes with dialkylzincs in the presence of a catalytic amount of chiral aminoalcohol 1 or chiral thiophosphoramide alcohol 2 with Ti(0-i-Pr)4. The chiral titanium(IV) alkoxide of 4b, a diisopropylated product of isophthalaldehyde, catalyzed the addition of diisopropylzinc to isophthalaldehyde to gave a chiral zinc alkoxide of 4b with the same configuration by an enantioselective autoinductive reaction (up to 44% e.e.).

A Novel Cyclization of 1,2-Bis(2,2-dibromocyclopropyl)benzenes with Methyllithium

The CBr2 bis adducts 7, 8, and 10 react with MeLi at - 78 deg C to give the dicyclopropanaphthalenes 17 - 19.Thus, from meso-7 syn-17, and from d,l-7 anti-17 are formed stereoselectively.The reaction may proceed via the intermediates A or B.The carbenoid