10340-84-8

Basic information

• Product Name: (R)-(-)-CITRONELLYL BROMIDE
• Synonyms: (R)-(-)-CITRONELLYL BROMIDE;8-BROMO-2,6-DIMETHYL-2-OCTENE;citronellyl bromide;(6R)-2,6-Dimethyl-2-octene;[R,(-)]-2,6-Dimethyl-2-octene;(R)-(-)-Citronellyl bromide 97%;(6R)-8-bromo-2,6-dimethyloct-2-ene
• CAS NO: 10340-84-8
• Molecular Formula: C₁₀H₁₉Br
• Molecular Weight: 219.16
• Mol File: 10340-84-8.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 111 °C12 mm Hg(lit.)
• Flash Point: 203 °F
• Appearance: /
• Density: 1.11 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.076mmHg at 25°C
• Refractive Index: n20/D 1.474(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-(-)-CITRONELLYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-CITRONELLYL BROMIDE(10340-84-8)
• EPA Substance Registry System: (R)-(-)-CITRONELLYL BROMIDE(10340-84-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 10340-84-8(Hazardous Substances Data)

Usage

General Description

(R)-(-)-Citronellyl Bromide is a chemical compound primarily used in the fragrance and flavor industries. It belongs to the family of Monocarboxylic Acids and Derivatives, characterized by an aliphatic monocarboxylic acid functionality. It is a halide derivative of citronellol, a natural compound found in roses and geraniums. The presence of bromine in the compound increases its stability and reactivity, making it more manageable in various organic synthesis applications. As its name suggests, it has a unique lemon fragrance, making it popular in the creation of citrusy perfumes and flavorings.

InChI:InChI=1/C10H19Br/c1-9(2)5-4-6-10(3)7-8-11/h5,10H,4,6-8H2,1-3H3/t10-/m1/s1

Upstream product

• 5949-05-3 (S)-Citronellal 
• 106-22-9 Citronellol 
• 41144-01-8 (S)-3,7-dimethyl-6-octenyl tosylate 
• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 84560-01-0 (6R)-8-hydroxy-2,6-dimethyloctan-3-one 
• 71841-73-1 citronellol-tetrahydropyranyl ether 
• 18951-85-4 (R)-citronellic acid 
• 20425-54-1 (R)-1-citronellyl acetate 
• 7789-60-8 phosphorus tribromide 
• 67214-54-4 (R)-citronellyl tosylate 
• 35026-81-4 (2S)-methylbuthyl-1-magnesium bromide 
• 1117-61-9 (3R)-citronellol 
• 20425-48-3 methyl (R)-(+)-citronellate 

Downstream Products

• 20425-54-1 (R)-1-citronellyl acetate 
• 3383-83-3 (S)-1-bromo-3,7-dimethyloctane 
• 1166400-04-9 tetrakis-{4-[(3'R)-3',7'-dimethyloct-6'enyloxy]phenyl}ethene 
• 1029433-87-1 4-[(3S)-3,7-dimethyl-6-octenyl]aniline 
• 222984-22-7 C₅₉H₁₀₂O₆ 
• 222984-13-6 3-O-trityl-2-O-(R)-3,7-dimethyloctyl-1-O-benzyl-sn-glycerol 
• 222984-14-7 1-O-benzyl-2-O-(R)-3,7-dimethyloctyl-sn-glycerol 
• 212781-57-2 3,3'-O-(1,16-hexadecamethylene)-2,2'-di-O-<(R)-3,7-dimethyloctyl>-1-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-1'-O-(dibenzylphosphono)-sn-diglycerol 
• 222984-11-4 3,3'-O-(1,16-hexadecamethylene)bis<1-O-p-methoxyphenyldiphenylmethyl-2-O-<(R)-3,7-dimethyloctyl>-sn-glycerol> 
• 222984-24-9 3,3'-O-(1,16-hexadecamethylene)-2,2'-di-O-<(R)-3,7-dimethyloctyl>-1-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-1'-O-benzyl-sn-diglycerol 
• 222984-15-8 3,3'-O-(1,16-hexadecamethylene)bis<1-O-benzyl-2-O-<(R)-3,7-dimethyloctyl>-sn-glycerol> 

Relevant articles and documents

Novel tdp1 inhibitors based on adamantane connected with monoterpene moieties via heterocyclic fragments

Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is a promising target for anticancer therapy due to its ability to counter the effects topoisomerase 1 (Top1) poison, such as topotecan, thus, decreasing their efficacy. Compounds containing adamantane and monoterpenoid residues connected via 1,2,4-triazole or 1,3,4-thiadiazole linkers were synthesized and tested against Tdp1. All the derivatives exhibited inhibition at low micromolar or nanomolar concentrations with the most potent inhibitors having IC50 values in the 0.35–0.57 μM range. The cytotoxicity was determined in the HeLa, HCT-116 and SW837 cancer cell lines; moderate CC50 (μM) values were seen from the mid-teens to no effect at 100 μM. Furthermore, citral derivative 20c, α-pinene-derived compounds 20f, 20g and 25c, and the citronellic acid derivative 25b were found to have a sensitizing effect in conjunction with topotecan in the HeLa cervical cancer and colon adenocarcinoma HCT-116 cell lines. The ligands are predicted to bind in the catalytic pocket of Tdp1 and have favorable physicochemical properties for further development as a potential adjunct therapy with Top1 poisons.

Stereoselective Synthesis of the Antileukemic Sesquiterpene (+)-Caparratriene from L-menthol and Tiglic Aldehyde

A stereoselective synthesis of natural (+)-caparratriene was developed starting from commercially available L-menthol and tiglic aldehyde. The key step was a Wittig reaction of the latter with the triphenylphosphorane generated from (R)-(–)-citronellyl bromide. (+)-Caparratriene as a mixture (4:1) of 2E,4E- and 2E,4Z-stereoisomers is a known anticancer agent.

Total synthesis of four stereoisomers of methyl 4,8,12-trimethylpentadecanoate, a major component of the sex pheromone of the stink bug: Edessa meditabunda

The male-produced sex pheromone of the stink bug Edessa meditabunda was previously identified as a mixture of the esters methyl 4,8,12-trimethylpentadecanoate (1) and methyl 4,8,12-trimethyltetradecanoate (2), produced in a ratio of 92 : 8, respectively.

Synthesis of the 1,5-dimethylic chiron enantiomers, 3,7,11-trimethyldodec-10-en-1-ol: Application to enantiomeric syntheses of tribolure and a marine fatty acid

A convenient synthesis of the title chiron antipodes has been developed starting from (±)-citronellol via a sequential acetylation protocol using two lipases. The different stereoisomers of the chiron were then functionalized by simple routes to (4R,8R)-dimethyldecanal, an insect pheromone and (5R,9R)-5,9,13-trimethyltetradecanoic acid, a marine phospholipid fatty acid.

Enantiospecific synthesis of 6-methylheptadec-(9E)-enoic acid enantiomers, the antimicrobial principles of Sporothrix species

An efficient synthesis of the title compound I in both its enantiomeric forms has been developed starting from (R)-citronellol. This involved the introduction of the required alkyl chain and the acidic component at the termini of the starting chiron via judicious derivatization of its bifunctionality to provide the enantiomers of I. The other key features of the synthesis were: (i) use of easily accessible and inexpensive materials/reagents; (ii) operational simplicity; and (iii) brevity.

Custom-Made Pyrene Photocatalyst-Promoted Desulfonylation of Arylethenyl Sulfones Using Green-Light-Emitting Diodes

The Sonogashira coupling of 1,3,6,8-tetrabromopyrene with 4-[(-)-β-citronellyloxy]phenylethyne was employed to synthesize 1,3,6,8-tetra[4-(citronellyloxy)phenylethynyl]pyrene. The pyrene derivative catalyzed the reductive desulfonylation of ethenyl sulfones via visible-light irradiation (514 nm green light-emitting diodes) in the presence of i -Pr 2NEt. The β-citronellyloxy groups provided the sufficient solubility to the highly π-expanded pyrene catalyst, and their polar oxygen functionalities enabled the easy separation of the catalyst from the products via column chromatography.