Geranyl bromide

Base Information

• Chemical Name: Geranyl bromide
• CAS No.: 6138-90-5
• Molecular Formula: C10H17Br
• Molecular Weight: 217.149
• Hs Code.: 2903399090
• European Community (EC) Number: 228-123-7
• UNII: FG8US6W9BB
• DSSTox Substance ID: DTXSID80884229
• Nikkaji Number: J29.188I,J798.254B
• Mol file: 6138-90-5.mol

Synonyms:Geranyl bromide;6138-90-5;(E)-1-Bromo-3,7-dimethylocta-2,6-diene;2,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-;(2E)-1-bromo-3,7-dimethylocta-2,6-diene;trans-geranyl bromide;2,6-Octadiene, 1-bromo-3,7-dimethyl-, (E)-;EINECS 228-123-7;(2E)-1-Bromo-3,7-dimethyl-2,6-octadiene;Geranylbromide;1-bromo-3,7-dimethyl-2,6-octadiene;1-bromo-3,7-dimethylocta-2,6-diene;trans-Geranyl bromide;(2E)-Geranyl bromide;(E)-geranyl bromide;Geranyl bromide, 95%;trans-1-Bromo-3,7-dimethyl-2,6-octadiene;FG8US6W9BB;SCHEMBL492564;SCHEMBL492565;Geranyl Bromide (90per cent);DTXSID80884229;AMY42104;BCP05145;MFCD00000243;AKOS015950707;8-Bromo-2,6-dimethyl-2,6-octadiene;BCP9000723;2,6-Octadiene, 1-bromo-3,7-dimethyl-;MS-20560;(E)-1-Bromo-3,7-dimethyl-2,6-octadiene;Geranyl bromide, technical, >=95.0% (T);D94747;J-521412

Chemical Property of Geranyl bromide

Chemical Property:

• Appearance/Colour: grey yellow liquid
• Vapor Pressure: 0.115mmHg at 25°C
• Refractive Index: n20/D 1.504(lit.)
• Boiling Point: 227.7 °C at 760 mmHg
• Flash Point: 95 °C
• PSA: 0.00000
• Density: 1.121 g/cm³
• LogP: 4.07400
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Water Solubility.: Immiscible with water.
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 216.05136
• Heavy Atom Count: 11
• Complexity: 150

Purity/Quality:

97% ^*data from raw suppliers

GeranylBromide(>80%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CCCC(=CCBr)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CBr)/C)C
• General Description: Geranyl bromide, also known as (2E)-1-bromo-3,7-dimethylocta-2,6-diene or trans-geranyl bromide, is a brominated derivative of geraniol and serves as a key reagent in organic synthesis, particularly in the formation of polyenic intermediates for terpenoid cyclization. In the context of the study, it was utilized as a precursor in the cyclization of polyenic β-keto sulphoxides to produce optically active cyclic terpenoids, demonstrating its utility in stereoselective synthetic routes. The compound's reactivity under Lewis acid conditions (e.g., SnCl4) highlights its role in facilitating biogenetic-like cyclizations, contributing to the efficient preparation of chiral terpenoid frameworks such as dihydropyran derivatives and lactones.

Technology Process of Geranyl bromide

There total 34 articles about Geranyl bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Geraniol (106-24-1) → trans-geranyl bromide (6138-90-5)

Guidance literature:

With phosphorus tribromide; In diethyl ether; at 0 ℃; for 2h;

DOI:10.1021/ja00169a041

Reference yield: 97.0%

1,3-bis{2-[2-(tert-butoxycarbonylamino)ethoxy]ethyl}thiourea (497962-48-8) → trans-geranyl bromide (6138-90-5)

Guidance literature:

With pyridine; phosphorus tribromide; In diethyl ether; hexane; at 0 ℃; for 0.25h;

DOI:10.1002/1099-0690(200209)2002:17<3015::AID-EJOC3015>3.0.CO;2-G

Reference yield: 96.0%

→ trans-geranyl bromide (6138-90-5)

Guidance literature:

upstream raw materials:

Geraniol

1-chloro-3,7-dimethylocta-2,6-diene

3,7-dimethyl-octa-2,6-dienyl diphenyl phosphate

1,3-bis{2-[2-(tert-butoxycarbonylamino)ethoxy]ethyl}thiourea

Downstream raw materials:

methyl (6E)-farnesoate

methyl (E,E)-farnesoate

2-Geranyl-2-(phenylthio)hexansaeure

(1E,3E)-4,8-dimethyl-1-phenyl-1,3,7-nonatriene

Refernces

Cyclisation of Polyenic β-Keto Sulphoxides. A Novel Route to Optically Active Intermediates for Cyclic Terpenoid Synthesis

10.1039/c39910001173

The research focuses on the cyclisation of polyenic β-keto sulphoxides as a novel route to optically active intermediates for cyclic terpenoid synthesis. The purpose of this study was to explore the potential of using polyenic β-keto sulphoxides as precursors for the biogenetic-like cyclisation of polyenes, which could lead to the synthesis of optically pure cyclic terpenoids. The researchers successfully demonstrated that optically active polyenic β-keto sulphoxides 4 and 5, when mediated by SnCl4, undergo cyclisation to yield diastereoisomeric dihydropyran derivatives 6a,b and 10a,b, respectively. These derivatives could be further converted into (+)-dihydroactinidiolide 7 and (-)-norambreinolide 11. The study concluded that this method provides an efficient route to optically active intermediates for the synthesis of cyclic terpenoids, using chemicals such as SnCl4, geranyl bromide, farnesyl bromide, and RuO2-NaIO4 in the process.