87161-57-7

Basic information

• Product Name: (1S, 2S, 5R)-NEOMENTHYL BROMIDE
• Synonyms: (1S, 2S, 5R)-NEOMENTHYL BROMIDE
• CAS NO: 87161-57-7
• Molecular Formula: C₁₀H₁₉Br
• Molecular Weight: 219.164
• Mol File: 87161-57-7.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S, 2S, 5R)-NEOMENTHYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S, 2S, 5R)-NEOMENTHYL BROMIDE(87161-57-7)
• EPA Substance Registry System: (1S, 2S, 5R)-NEOMENTHYL BROMIDE(87161-57-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 87161-57-7(Hazardous Substances Data)

Usage

Description

(1S, 2S, 5R)-NEOMENTHYL BROMIDE is a chiral compound belonging to the neomenthyl group, characterized by its high stereoselectivity and a characteristic minty odor. It is a colorless liquid that is soluble in organic solvents such as ether and ethanol, playing a significant role in the field of organic chemistry for producing enantiomerically pure compounds.

Uses

Used in Pharmaceutical Industry:
(1S, 2S, 5R)-NEOMENTHYL BROMIDE is used as a reagent in organic synthesis for the preparation of chiral pharmaceuticals. Its high stereoselectivity makes it valuable in creating enantiomerically pure compounds, which are essential for the development of effective and safe medications.
Used in Agrochemical Industry:
(1S, 2S, 5R)-NEOMENTHYL BROMIDE is also used as a reagent in the synthesis of chiral agrochemicals, contributing to the development of targeted and efficient pest control solutions.
Used as a Chiral Resolving Agent:
(1S, 2S, 5R)-NEOMENTHYL BROMIDE is utilized as a chiral resolving agent in various chemical processes, enabling the separation and production of specific enantiomers for use in different applications, including the synthesis of enantiomerically pure compounds for research and development purposes.

Upstream product

• 2216-51-5 (-)-menthol 
• 51788-61-5 bromo-cyano-triphenyl-phosphorane 
• 2230-82-2 menthyl tosylate 
• 72020-06-5 2-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)tetrahydro-2H-pyran 
• 2216-52-6 Neomenthol 
• 89-78-1 1R,2RS,4S-(-)-menthol 
• 134052-28-1 2-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran 

Downstream Products

• 16052-42-9 (1R,2S,5R)-menthyl chloride 
• 13371-12-5 neomenthyl chloride 
• 1678-82-6 trans-1,4-menthane 
• 1357000-40-8 2-((1R,2R,5R)-2-isopropyl-5-methylcyclohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

Regioselective Hydroalkylation of Vinylarenes by Cooperative Cu and Ni Catalysis

Disclosed here is a dual copper and nickel catalytic system with a silyl hydride source for promoting the linear selective hydroalkylation of vinylarenes. This carbon–carbon bond-forming protocol is applied to couple a variety of functionalized vinylarenes with alkyl halides applying a nickel(II) NNN pincer complex in the presence of an NHC-ligated copper catalyst. This combination allows for a 1 mol % loading of the nickel catalyst leading to turnover numbers of up to 72. Over 40 examples are presented, including applications for pharmaceutical diversification. Labeling experiments demonstrated the regioselectivity of the reaction and revealed that the copper catalyst plays a crucial role in enhancing the rate for formation of the reactive linear alkyl nickel complex. Overall, the presented work provides a complimentary approach for hydroalkylation reactions, whilst providing a preliminary mechanistic understanding of the cooperativity between the copper and nickel complexes.

1,2-Dibromotetrachloroethane: An efficient reagent for many transformations by modified Appel reaction

An efficient and facile method has been developed for the synthesis of alkyl bromides from various alcohols under mild conditions using a triphenylphosphine (PPh 3) /1,2-dibromotetrachloroethane (DBTCE) complex in excellent yields and very short time (5 min). This method can also be applied for the transformation of chiral alcohols to their corresponding bromides in very high enantiomeric excess. The PPh 3 /DBTCE complex is also successfully applied to ring-opening reactions of cyclic ethers in mild conditions. Esterification, amidation, and formation of acid anhydrides under very mild experimental conditions are also successfully accomplished by following a modification of the Appel reaction protocol in this work.

Halogenation of primary alcohols using a tetraethylammonium halide/[Et 2NSF2]BF4 combination

The halogenation of primary alcohols is presented. The use of a combination of tetraethylammonium halide and [Et2NSF2]BF4 (XtalFluor-E) allows for chlorination and bromination reactions to proceed efficiently (up to 92% yield) with a wide range of alcohols. Iodination reactions are also possible albeit in lower yields.