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:

98%,99%, ^*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
• Uses: Geranyl bromide is used for the preparation of 3,7-dihydroxyflavone derivatives and baicalein. It is also involved in the synthesis of potential flavonoidic modulators of P-glycoprotein activity. Further, it reacts with benzenesulfinic acid to prepare geranyl phenyl sulfone. In addition to this, it takes part in the palladium catalyzed cross coupling with aryl and alkenylgold(I) phosphanes.

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:

3,7-dimethylocta-1,6-dien-3-ol

3,7-dimethyl-(2E)-2,6-octadienyl ethyl ether

geraniol methyl ether

3,7-dimethyl-2E,6-octadien-1-yl acetate

Refernces

• 1、 Komatsu, Yuzo,Kitazume, Tomoya. "Preparation of 2,6-difluoromanoalogues derivatives". . p. 61 - 67. Retrieved 2000.
• 2、 Cormier, Morgan,de la Torre, Aurélien,Marek, Ilan. "Total Synthesis of C30 Botryococcene and epi-Botryococcene by a Diastereoselective Ring Opening of Alkenylcyclopropanes". . p. 13237 - 13241. Retrieved 2018.
• 3、 Montero,Clavel,Imbach. "Synthesis of allylic phosphonates of biological interest". . p. 1163 - 1164. Retrieved 1987.
• 4、 Fuse, Shinichiro,Nakamura, Kentarou,Mifune, Yuto,Marubayashi, Hironori,Hijikuro, Ichiro,Nojima, Shuichi,Tanaka, Hiroshi,Takahashi, Takashi. "Rapid library synthesis of amphiphiles based on a dioxinone scaffold and identification of nonlamellar liquid crystals". . p. 2806 - 2813. Retrieved 2014.
• 5、 Chepanova, Arina A.,Dyrkheeva, Nadezhda S.,Ilina, Ekaterina S.,Korchagina, Dina V.,Lavrik, Olga I.,Mozhaitsev, Evgenii S.,Munkuev, Aldar A.,Reynisson, Jóhannes,Salakhutdinov, Nariman F.,Suslov, Evgeniy V.,Volcho, Konstantin P.,Zakharenko, Alexandra L.,Zakharova, Olga D.. "Novel tdp1 inhibitors based on adamantane connected with monoterpene moieties via heterocyclic fragments". . . Retrieved 2021/06/12.
• 6、 Mupparapu, Nagaraju,Lin, Yu-Hsin Cindy,Kim, Tae Ho,Elshahawi, Sherif I.. "Regiospecific Synthesis of Calcium-Independent Daptomycin Antibiotics using a Chemoenzymatic Method". supporting information. p. 4176 - 4182. Retrieved 2021/02/01.