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

General Description

(1S, 2S, 5R)-neomenthyl bromide is a chiral compound that belongs to the neomenthyl group. It is commonly used as a reagent in organic synthesis, particularly in the preparation of chiral pharmaceuticals and agrochemicals. (1S, 2S, 5R)-NEOMENTHYL BROMIDE is known for its high stereoselectivity and is widely used as a chiral resolving agent. (1S, 2S, 5R)-neomenthyl bromide is a colorless liquid with a characteristic minty odor, and it is soluble in organic solvents such as ether and ethanol. It is important in the field of organic chemistry for its role in producing enantiomerically pure compounds for various applications.

Upstream product

• 2216-51-5 (-)-menthol 
• 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 
• 51788-61-5 bromo-cyano-triphenyl-phosphorane 

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.