636601-27-9

Usage

Uses

Used in Organic Synthesis:
4,4'-Dibromo-1,1'-spirobiindane-7,7'-diol is used as a building block in organic synthesis for the preparation of various complex organic molecules. Its unique structure and reactivity make it a valuable intermediate in the synthesis of pharmaceuticals and agrochemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4,4'-Dibromo-1,1'-spirobiindane-7,7'-diol is used as a key component in the development of new drugs. Its potential pharmacological properties are being studied for the treatment of various diseases, making it a promising candidate for drug discovery and development.
Used in Agrochemical Industry:
4,4'-Dibromo-1,1'-spirobiindane-7,7'-diol is also utilized in the agrochemical industry for the synthesis of pesticides and other agrochemical products. Its unique chemical properties contribute to the development of effective and environmentally friendly solutions for agricultural applications.
Used as a Stabilizer in Polymers and Plastics:
In the polymer and plastics industry, 4,4'-Dibromo-1,1'-spirobiindane-7,7'-diol is used as a stabilizer to enhance the durability and performance of various materials. Its presence helps to improve the stability and resistance of polymers and plastics against environmental factors, such as heat, light, and oxidation.
It is important to handle 4,4'-Dibromo-1,1'-spirobiindane-7,7'-diol with caution and follow proper safety protocols due to its potential hazards.

Upstream product

• 223137-76-6 (S)-4,4'-dibromo-7,7'-dimethoxy-1,1'-spirobiindane 
• 223137-76-6 4,4'-dibromo-7,7'-dimethoxy-1,1'-spirobiindane 
• 636601-27-9 4,4'-dibromo-2,2',3,3'-tetrahydro-1,1'-spirobi[1H-indene]-7,7'-diol 
• 223137-81-3 (S)-7,7'-dimethoxy-2,2',3,3'-tetrahydro-1,1'-spirobi[indene] 
• 881915-97-5 (1E,4E)-1,5-bis(3-hydroxyphenyl)penta-1,4-dien-3-one 
• 1427054-10-1 1,5-bis(2-bromo-5-hydroxyphenyl)pentan-3-one 
• 100-83-4 meta-hydroxybenzaldehyde 

Downstream Products

• 223137-87-9 2,2′,3,3′-tetrahydro-1,1′-spirobi[indene]-7,7′-diol 
• 636601-27-9 (S)-4,4'-dibromo-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-7,7'-diol 
• 636601-30-4 (S)-4,4'-dimethoxy-7,7'-dihydroxy-1,1'-spirobiindane 

Relevant academic research and scientific papers

SPHENOL, A New Chiral Framework for Asymmetric Synthesis

Privileged chiral catalysts have found tremendous applications and thus immensely advanced asymmetric synthesis in the past few decades. However, truly privileged chiral frameworks are still extremely limited. Thus, the search for and development of new v

Erratum: SPHENOL, a new chiral framework for asymmetric synthesis (Journal of the American Chemical Society (2021) 143:32 (12445-12449) DOI: 10.1021/jacs.1c05709)

Page 12447. The description of the synthesis of 3,3'-diiodide 9 in the paragraph related to Scheme 4a is incorrect. The enantiopure compound 9 was obtained from SPHENOL with a methoxymethyl group as the protecting group, instead of a methyl group. The detailed procedures are provided in the updated Supporting Information. The third sentence of that paragraph, "A three-step sequence involving protection of the diol into methyl ether.", should be replaced by "A three-step sequence involving protection of the diol into methoxymethyl ether.". In footnote a of Scheme 4, "aReaction conditions: (i) NaH, MeI; (ii) nBuLi, TMEDA; I2; (iii) BBr3, DCM.", should be replaced by "aReaction conditions: (i) NaH, MOMBr; (ii) nBuLi, TMEDA, I2; (iii) HCl (6.0 M), 1,4-dioxane.".

COMPOUND AND METHOD FOR PREPARING CHIRAL COMPOUND

A compound and a method for preparing achiral compound using the compound are provided. The compound has a structure of Formula (I) , wherein R1 are independently C1-4 alkyl group or a monovalent group derived from a chiral alcohol a

Phosphoric Acid-Catalyzed Asymmetric Synthesis of SPINOL Derivatives

Axially chiral 1,1′-spirobiindane-7,7′-diol (SPINOL) is the most fundamental and important privileged structure from which other chiral ligands containing a 1,1′-spirobiindane backbone are synthesized. Driven by the development of enantioselective syntheses of axially chiral SPINOL derivatives, we have successfully developed the first phosphoric acid-catalyzed asymmetric approach. This approach is highly convergent and functional group tolerant, efficiently providing SPINOLs in good yield with excellent enantioselectivity, thus delivering a practical and straightforward access to this privileged structure. It should be emphasized that the catalyst loading could be decreased to only 0.1 mol% for the preparative-scale synthesis. Furthermore, 4,4′-dimethyl-SPINOL-phosphoric acid was synthesized and applied to catalyze the model reaction for synthesis of enantioenriched SPINOL derivatives.

A convenient resolution method for 1,1′-bi-2-naphthol and 4,4′-dibromo-1,1′-spirobiindane-7,7′-diol with menthyl chloroformate in the presence of TBAB

A convenient resolution method for 1,1′-bi-2-naphthol and 4,4′-dibromo-1,1′-spirobiindane-7,7′-diol has been developed with crude (-)-menthyl chloroformate as the resolution reagent in the presence of tetrabutylammonium bromide acting as a phase transfer catalyst in an aqueous NaOH/CH2Cl2 two phase solution. The deprotection of the hydroxy group was carried out via an aqueous KOH/EtOH solution. Both enantiomers of 1,1′-bi-2-naphthol and 4,4′-dibromo-1,1′- spirobiindane-7,7′-diol were obtained in high yields. Both ee's of (S)-(+) and (R)-(-)-4,4′-dibromo-1,1′-spirobiindane-7,7′-diol were above 99%. Most of the (-)-menthol could be easily recovered in a deprotection procedure and thus be reused for the formation of (-)-menthyl chloroformate without further purification.

Synthesis of chiral 4,4′-disubstituted 1,1′-spirobiindane-7, 7′-diols and related phosphoramidites: The substituent effect of SIPHOS ligands in Rh-catalyzed asymmetric hydrogenation

Three chiral 4,4′-substituted 1,1′-spirobiindane-7,7′- diols and related monodentate spiro phosphoramidite ligands have been readily synthesized from enantiomerically pure 1,1′-spirobiindane-7,7′-diol. Excellent enantioselectivities were obtained with the