(S)-(+)-Citronellyl bromide

Base Information

• Chemical Name: (S)-(+)-Citronellyl bromide
• CAS No.: 143615-81-0
• Molecular Formula: C₁₀H₁₉Br
• Molecular Weight: 219.165
• European Community (EC) Number: 629-109-7
• DSSTox Substance ID: DTXSID30447702
• Nikkaji Number: J1.310.776I
• Mol file: 143615-81-0.mol

Synonyms:(S)-(+)-Citronellyl bromide;143615-81-0;(6S)-8-BROMO-2,6-DIMETHYLOCT-2-ENE;(S)-citronellyl bromide;2-Octene,8-bromo-2,6-dimethyl-, (6S)-;(S)(-)Citronellyl bromide;SCHEMBL1513157;DTXSID30447702;QPKCDMXLSDFCQD-JTQLQIEISA-N;(S)-(+)-Citronellyl bromide, 95%;AKOS025294503;(S)-8-bromo-2,6-dimethyloct-2-ene;AS-82004;(S)-(+)-8-Bromo-2,6-dimethyl-2-octene;J-007846

Chemical Property of (S)-(+)-Citronellyl bromide

Chemical Property:

• Vapor Pressure: 0.0756mmHg at 25°C
• Refractive Index: n20/D 1.474(lit.)
• Boiling Point: 235.7°Cat760mmHg
• Flash Point: 95°C
• PSA: 0.00000
• Density: 1.092g/cm³
• LogP: 4.15390
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 5
• Exact Mass: 218.06701
• Heavy Atom Count: 11
• Complexity: 112

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-(+)-Citronellyl bromide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CCC=C(C)C)CCBr
• Isomeric SMILES: C[C@@H](CCC=C(C)C)CCBr

Technology Process of (S)-(+)-Citronellyl bromide

There total 5 articles about (S)-(+)-Citronellyl 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: 98.0%

(S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) → (S)-citronellyl bromide (10340-84-8,4895-14-1,58800-75-2,143615-81-0)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20 ℃; for 20h;

DOI:10.1055/s-0040-1706025

Reference yield:

(S)-3,7-dimethyl-6-octenyl tosylate (41144-01-8,67214-54-4,93303-23-2,116661-43-9) → (S)-citronellyl bromide (10340-84-8,4895-14-1,58800-75-2,143615-81-0)

Guidance literature:

With sodium bromide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)00371-3

Reference yield:

(S)-Citronellal (5949-05-3) → (S)-citronellyl bromide (10340-84-8,4895-14-1,58800-75-2,143615-81-0)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / methanol

2: Et₃N

3: NaBr / dimethylformamide

With sodium tetrahydroborate; triethylamine; sodium bromide; In methanol; N,N-dimethyl-formamide; 1: Reduction / 2: Tosylation / 3: Substitution;

DOI:10.1016/S0040-4039(00)00371-3

upstream raw materials:

(S)-3,7-dimethyl-6-octen-1-ol

Citronellol

(S)-3,7-dimethyl-6-octenyl tosylate

(S)-Citronellal

Downstream raw materials:

(R)-1-citronellyl acetate

(S)-1-bromo-3,7-dimethyloctane

1,2-bis((S)-3,7-dimethyloct-6-enyloxy)-3-(octyloxy)benzene

1,2-bis((S)-3,7-dimethyloct-6-enyloxy)benzene

Refernces

• 1、 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.
• 2、 Schulz, Stefan,Szczerbowski, Daiane,Zarbin, Paulo Henrique Gorgatti. "Total synthesis of four stereoisomers of methyl 4,8,12-trimethylpentadecanoate, a major component of the sex pheromone of the stink bug: Edessa meditabunda". . p. 5034 - 5044. Retrieved 2020/07/30.