111-24-0 Usage
Chemical Properties
clear colorless to yellow-brownish liquid and has an aromatic odor.. soluble in benzene and chloroform, insoluble in water.
Uses
Different sources of media describe the Uses of 111-24-0 differently. You can refer to the following data:
1. 1,5-Dibromopentane is used in the preparation of 1,5-di-Grignard reagent and novel spirocyclic pyrrolidones. It acts as a growth supplement for Yarrowia lipolytica 3589, a tropical marine yeast. It is involved in the synthesis of N-alkylated piperidine as well as tetrydrothiopyran (thiane) by reaction with primary amine and sodium sulfide respectively.
2. 1,5-Dibromopentane can be used to prepare:Derivatives of 5-pyrazolones.O-alkylated phloroglucinol derivatives, which forms the core of poly(alkyl aryl ether) dendrimers.Intermediate for dezocine viz, (R)-(+)-1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone using 1-methyl-7-methoxy-2-tetralone.
Preparation
1,5-Dibromopentane was obtained by ring-opening bromination of tetrahydropyran. In a 500ml flask, add 250g of 48% hydrobromic acid, 75g of concentrated sulfuric acid, 21.5g of redistilled tetrahydropyran (86.5-87.5°C fraction) in turn to a reflux condenser and heat the brown mixture gently to reflux for 3h. After cooling to room temperature, partition the lower layer of dibromide and wash each with saturated sodium carbonate solution and water once. Dried with anhydrous calcium chloride. Distill under reduced pressure and collect the 104-106°C (2.53 kPa) fraction as 1,5-dibromopentane in 46-47 g yield and 80-82% yield.1,5-Dibromopentane synthesis route
Synthesis Reference(s)
Organic Syntheses, Coll. Vol. 3, p. 692, 1955The Journal of Organic Chemistry, 48, p. 1678, 1983 DOI: 10.1021/jo00158a018
General Description
1,5-Dibromopentane is a growth supplement for Yarrowia lipolytica 3589, a tropical marine yeast.
Check Digit Verification of cas no
The CAS Registry Mumber 111-24-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 1 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 111-24:
(5*1)+(4*1)+(3*1)+(2*2)+(1*4)=20
20 % 10 = 0
So 111-24-0 is a valid CAS Registry Number.
InChI:InChI=1/C5H10Br2/c6-4-2-1-3-5-7/h1-5H2
111-24-0Relevant articles and documents
Finch, Karol P.,Gafoor, Mansoor A.,Mapolie, Selwyn F.,Moss, John R.
, p. 963 - 972 (1991)
Scalable anti-Markovnikov hydrobromination of aliphatic and aromatic olefins
Galli, Marzia,Fletcher, Catherine J.,Del Pozo, Marc,Goldup, Stephen M.
supporting information, p. 5622 - 5626 (2016/07/06)
To improve access to a key synthetic intermediate we targeted a direct hydrobromination-Negishi route. Unsurprisingly, the anti-Markovnikov addition of HBr to estragole in the presence of AIBN proved successful. However, even in the absence of an added initiator, anti-Markovnikov addition was observed. Re-examination of early reports revealed that selective Markovnikov addition, often simply termed "normal" addition, is not always observed with HBr unless air is excluded, leading to the rediscovery of a reproducible and scalable initiator-free protocol.
Light-mediated deoxygenation of alcohols with a dimeric gold catalyst
McCallum, Terry,Slavko, Ekaterina,Morin, Mathieu,Barriault, Louis
supporting information, p. 81 - 85 (2015/02/18)
A new protocol for the reductive deoxygenation of primary alcohols was explored. This photo-mediated method combines a novel approach to bromination of alcohols merged with the powerful reducing capability of [Au2(dppm)2]Cl2 [dppm = 1,1-bis(diphenylphosphino)methane] as a photoredox catalyst. The highly efficient methods discussed are marked by the use of UVA light-emitting diodes, which have significantly reduced reaction times and lowered setup cost.
