5389-87-7

Basic information

• Product Name: GERANYL CHLORIDE
• Synonyms: (e)-1-chloro-3,7-dimethyl-2,6-octadiene;7-dimethyl-6-octadien(e)-1-chloro-3;alpha,omega-octadiene;GERANYL CHLORIDE;(E)-1-CHLORO-3,7-DIMETHYL-OCTA-2,6-DIENE;1-CHLORO-3,7-DIMETHYL-2,6-OCTADIENE;(E)-8-Chloro-2,6-dimethyl-2,6-octadiene;Geranyl chloride,trans-1-Chloro-3,7-dimethyl-2,6-octadiene
• CAS NO: 5389-87-7
• Molecular Formula: C₁₀H₁₇Cl
• Molecular Weight: 172.69
• EINECS: 224-783-5
• Mol File: 5389-87-7.mol
• Article Data: 65

Chemical Properties

• Boiling Point: 102-104 °C12 mm Hg(lit.)
• Flash Point: 194 °F
• Appearance: /
• Density: 0.931 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.118mmHg at 25°C
• Refractive Index: n20/D 1.4808(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: GERANYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: GERANYL CHLORIDE(5389-87-7)
• EPA Substance Registry System: GERANYL CHLORIDE(5389-87-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2810
• WGK Germany: 3
• RTECS: RG5275000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 5389-87-7(Hazardous Substances Data)

Usage

Description

GERANYL CHLORIDE, also known as 3,7-dimethylocta-2,6-dienyl dihydrochloride, is an organic compound that serves as a versatile building block in the synthesis of various natural products and pharmaceuticals. It is a colorless to pale yellow liquid with a strong, pungent odor. GERANYL CHLORIDE is known for its reactivity in palladium-catalyzed cross-coupling reactions, making it a valuable intermediate in organic synthesis.

Uses

Used in Pharmaceutical Industry:
GERANYL CHLORIDE is used as a starting reagent for the synthesis of various compounds with potential pharmaceutical applications. Its ability to undergo α-substitution in palladium-catalyzed cross-coupling reactions allows for the creation of complex molecular structures with potential therapeutic properties.
Used in Synthesis of Moenocinol:
GERANYL CHLORIDE is used as a starting reagent for the synthesis of moenocinol, a C25 compound with potential applications in the pharmaceutical industry. GERANYL CHLORIDE's unique structure may offer novel therapeutic benefits.
Used in Synthesis of 2-Methyl-6-Geranylphenol:
GERANYL CHLORIDE is utilized as a starting material in the synthesis of 2-methyl-6-geranylphenol, a compound with potential applications in the pharmaceutical and chemical industries. Its unique structure and properties may contribute to the development of new drugs or materials.
Used in Synthesis of Manoalide and Seco-Manoalide Analogs:
GERANYL CHLORIDE serves as a key intermediate in the synthesis of manoalide and seco-manoalide analogs, which are complex natural products with potential pharmaceutical applications. The synthesis of these compounds using GERANYL CHLORIDE highlights its importance in the development of novel therapeutic agents.

InChI:InChI=1/C10H17Cl/c1-9(2)5-4-6-10(3)7-8-11/h5,7H,4,6,8H2,1-3H3/b10-7+

Upstream product

• 106-25-2 Nerol 
• 108-75-8 2,4,6-trimethyl-pyridine 
• 106-24-1 Geraniol 
• 124-63-0 methanesulfonyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 106-24-1 Nerol 
• 98-88-4 benzoyl chloride 
• 75-36-5 acetyl chloride 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 56-23-5 tetrachloromethane 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 35189-96-9 3-methyl-2-butenylmagnesium chloride 
• 59830-37-4 1-phenylsulfonyl-2-methyl-4-hydroxy-but-2-ene 
• 503-60-6 3,3-dimethyl-allyl chloride 

Downstream Products

• 64708-41-4 (E)-3-isopropenyl-6,10-dimethyl-undeca-5,9-dien-2-one 
• 56051-73-1 Methyl (E)-4,8-dimethyl-3,7-nonadienoate 
• 133984-36-8 3,7-dimethyl-2,6-octadien-1-yl 2,2,2-trifluoroethyl ether 
• 133984-37-9 3,7-dimethyl-1,6-octadien-3-yl 2,2,2-trifluoroethyl ether 
• 133984-38-0 α-terpinyl 2,2,2-trifluoroethyl ether 
• 110450-99-2 (E)-S-t-butyl 7,11-dimethyl-3-oxododeca-6,10-dienethioate 
• 94853-48-2 4-((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-1-isopropenyl-2-methyl-benzene 
• 94853-36-8 2-[4-((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-2-methyl-phenyl]-propan-2-ol 
• 459-85-8 (E)-4,8-dimethylnona-3,7-dienoic acid 
• 91425-06-8 ((E)-4,8-Dimethyl-1-phenyl-nona-3,7-dienyl)-trimethyl-silane 
• 107390-73-8 1,3-dioxo-1-(2-hydroxy-4-methoxyphenyl)-2-geranyl-3-(2,4-dimethoxyphenyl)propane 
• 64997-56-4 (2'E)-1-hydroxy-2-(3',7'-dimethylocta-2',6'-dienyl)-4-methoxy-6-methylbenzene 
• 74016-21-0 (E)-4,7,11-Trimethyl-dodeca-6,10-dien-3-one 
• 77012-37-4 (E)-4-(4,8-dimethylnona-3,7-dien-1-yl)-2-isopropyl-1-methoxybenzene 

Relevant articles and documents

New Polyaminoisoprenyl Antibiotics Enhancers against Two Multidrug-Resistant Gram-Negative Bacteria from Enterobacter and Salmonella Species

A series consisting of new polyaminoisoprenyl derivatives were prepared in moderate to good chemical yields varying from 32 to 64% according to two synthetic pathways: (1) using a titanium-reductive amination reaction affording a 50/50 mixture of cis and trans isomers and (2) a direct nucleophilic substitution leading to a stereoselective synthesis of the compounds of interest. These compounds were then successfully evaluated for their in vitro antibiotic enhancer properties against resistant Gram-negative bacteria of four antibiotics belonging to four different families. The mechanism of action against Enterobacter aerogenes of one of the most efficient of these chemosensitizing agents was precisely evaluated by using fluorescent dyes to measure outer-membrane permeability and to determine membrane depolarization. The weak cytotoxicity encountered led us to perform an in vivo experiment dealing with the treatment of mice infected with Salmonella typhimurium and affording preliminary promising results in terms of tolerance and efficiency of the polyaminoisoprenyl derivative 5r/doxycycline combination.

Asymmetric Total Synthesis of (-)-Spirochensilide A, Part 1: Diastereoselective Synthesis of the ABCD Ring and Stereoselective Total Synthesis of 13(R)-Demethyl Spirochensilide A

A concise and diastereoselective construction of the ABCD ring system of spirochensilide A is described. The key steps of this synthesis are a semipinacol rearrangement reaction to stereoselectively construct the AB ring system bearing two vicinal quaternary chiral centers and a Co-mediated Pauson-Khand reaction to form the spiro-based bicyclic CD ring system. This chemistry leads to the stereoselective synthesis of 13(R)-demethyl spirochensilide A, paving the way for the first asymmetric total synthesis of (-)-spirochensilide A.

Construction of Pentacyclic Limonoid Skeletons via Radical Cascade Reactions

Limonoids 1 and 2 share a 6/6/6/5-membered ABCD-ring system and a six-membered oxacycle and differ in their C9-stereochemistries. A new radical-based strategy was devised to construct the pentacyclic skeletons of 1 and 2. An oxacycle-fused A-ring and enyne fragments were coupled to produce radical precursors 4a-4c with different C7-oxygen functionalities. The bridgehead tertiary bromide of 4a-4c participated in a radical cascade reaction with the three unsaturated bonds to cyclize the C9-diastereomeric BCD-rings.