67528-24-9

Usage

Uses

Used in Pharmaceutical Industry:
(1S,2S)-2-bromo-2,3-dihydro-1H-inden-1-ol is used as a building block for the production of pharmaceuticals and other organic compounds. Its chiral nature makes it a valuable component in the synthesis of various drugs and medicinal compounds.
Used in Asymmetric Synthesis:
(1S,2S)-2-bromo-2,3-dihydro-1H-inden-1-ol is used as a key intermediate in asymmetric synthesis, a technique that allows for the selective formation of one enantiomer over another. This is crucial in the production of enantiomerically pure compounds, which are often necessary for biological activity and pharmaceutical applications.
Used in Synthesis of Natural Products:
(1S,2S)-2-bromo-2,3-dihydro-1H-inden-1-ol is used in the synthesis of natural products, which are complex organic compounds found in nature. Its unique structure and reactivity make it a useful component in the creation of these natural products.
Used in Chiral Ligand Synthesis:
(1S,2S)-2-bromo-2,3-dihydro-1H-inden-1-ol is used as a chiral ligand in catalytic reactions. Chiral ligands are essential for enantioselective catalysis, a process that allows for the selective formation of one enantiomer over another in a chemical reaction.
Used in Medicinal Chemistry Research:
(1S,2S)-2-bromo-2,3-dihydro-1H-inden-1-ol has applications in the field of medicinal chemistry and is being explored for its potential biological activity. Its unique properties and reactivity make it a promising candidate for the development of new drugs and therapeutic agents.

Upstream product

• 5837-70-7 (±)-trans-2-bromo-2,3-dihydro-1H-inden-1-yl acetate 
• 85354-33-2 (+)-(1S,2S)-trans-2-bromo-1-(methyloxyacetoxy)indan 
• 10368-44-2 trans-2-bromo-1-indanol 
• 95-13-6 1-indene 
• 108-22-5 Isopropenyl acetate 
• 214603-19-7 2,3-dihydro-1-oxo-1H-inden-2-yl-4-methylbenzenesulfonate 

Downstream Products

• 768-22-9 (1S,2R)-epoxyindane 
• 142678-92-0 (1R,2S)-amino indanol 
• 163061-74-3 (1S,2S)-1-amino-2,3-dihydro-1H-inden-2-ol 

Relevant academic research and scientific papers

A convenient synthesis of (1S,2R)-1,2-indene oxide and trans-(1S,2S)-2-bromo-1-indanol via oxazaborolidine-catalyzed borane reduction

A facile synthesis of (1S,2R)-indene oxide with >99% e.e. and (1S,2S)-trans-2-bromo-1-indanol with 87% e.e. has been established by employing CBS-oxazaborolidine-catalyzed asymmetric borane reduction of 2-p-toluenesulfonyloxy-1-indanone using N-ethyl-N-isopropylaniline-borane complex as the borane carrier.

Enzymatic resolution of indene bromohydrin acetate using immobilized lipase

Enzymatic resolution of indene bromohydrin acetate by hydrolysis or alcoholysis in the presence of immobilized lipase from Candida antarctica (Novozym 435) has been investigated. Enantiomerically enriched (1S,2S)-(+)-2-bromoindan-1-ol and (1R,2R)-(-)-1-acetoxy-2-bromoindan were obtained when indene bromohydrin acetate was treated with Novozym 435 and cyclohexanol in dibutyl ether for 30 hours at 40°C.

Synthesis of enantiomerically pure (1S, 2R)-epoxy indane and cis-(1R, 2S)-2-amino-1-indanol

Enantiomerically pure (1S, 2R)-epoxy indane and cis-(1R, 2S)-2-amino-1-indanol were synthesized via highly enantioselective lipase catalyzed transesterification of racemic trans-2-bromo-1-indanol.

The absolute configuration of 2-bromo-2,3-dihydro-1H-inden-1-ols

All four possible stereoisomers of cis- and trans-2-bromo-2,3-dihydro-1H-inden-1-ols, which are important intermediates in the synthesis of biologically active compounds, were synthesized and their configurations were studied by enzymatic kinetic resoluti

Halohydrin and its derivatives low priced high-efficient synthetic method (by machine translation)

The invention discloses a halohydrin low priced high-efficient synthetic method, the organic solvent of formula I shown in the olefin compound with a halide, sulfoxide and additive mixing, by the olefin of hydroxy halogenate reaction, can be a high selectivity of the halohydrin the system results in the type II shown, wherein R1 , R2 , R3 , R4 , R5 And R6 Are selected from hydrogen, halogen, alkyl, hydroxyalkyl, alkoxy, ester, acyl, amido, dialkyl amino, aryl, substituted aromatic, heterocyclic aromatic group or substituted heterocyclic aromatic, R1 , R2 , R3 , R4 , R5 And R6 The presence of the respective independent may be identical or different; or R1 And R2 , R1 And R3 , R2 And R4 , R3 And R4 , R5 And R6 Combining to form a cycloalkyl or substituted cycloalkyl, benzo ring alkyl or substituted cycloalkyl, heterocycle or substituted heterocycle; M selected from hydrogen, lithium, sodium, potassium, cesium, beryllium, magnesium, calcium, strontium, barium, zinc, copper, iron, ammonium or tetraalkyl ammonium; X chlorine, bromine or iodine. (by machine translation)

Chemical Synthesis and Optical Purity Determination of Optically Active 1,2-Epoxyindan and Alcohol Products which are also derived from Mammalian or Microbial Metabolism of Indene or Indanones

(+)-trans-2-Bromo-1-hydroxyindan (5) has been resolved into its enantiomers by preparative h.p.l.c. or fractional crystallization of the bromo-menthyloxy-acetoxydiastereoisomers (6a) and (6b).The bromohydrin (5) or bromo-esters (6a, 6b and 7) have in turn been converted into (-)-(1R,2S)-1,2-epoxyindan (2), (-)-(1R,2R)-trans-1-acetoxy-2-bromoindan (7), (+)-(1S)-indanol (8), (-)-(1R,2R)-trans-indan-1,2-diol (3), and (-)-(1S,2R)-cis-indan-1,2-diol (4).The optical purity of the alcohol products (3), (4), and (8) was determined by n.m.r. and h.p.l.c. analysis of their 2-methoxy-2-phenyl-2-trifluoromethylacetates.The previously unknown optical purity of the chiral alcohols (3), (4), (5), and (8), which had been isolated in earlier mammalian and microbial metabolism studies, has also been deduced.

MICROBIALLY MEDIATED ENANTIOSELECTIVE HYDROLYSIS OF RACEMIC ACETATES

The enantioselective hydrolyses of a series of racemic hydroaromatic acetates by Rhizopus nigricans to produce optically active alcohols are described.A rule predicting the absolute stereochemistry of the resulting alcohols is proposed.