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2114-39-8 Usage

Chemical Properties

clear colorless to light brown liquid

Check Digit Verification of cas no

The CAS Registry Mumber 2114-39-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,1 and 4 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 2114-39:
(6*2)+(5*1)+(4*1)+(3*4)+(2*3)+(1*9)=48
48 % 10 = 8
So 2114-39-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H11Br/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7H2,1H3

2114-39-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-BROMO-1-PHENYLPROPANE

1.2 Other means of identification

Product number -
Other names Benzene, (2-bromopropyl)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2114-39-8 SDS

2114-39-8Synthetic route

1-phenyl-2-propyl 2-(methoxyethoxyethylcarboxy)-1-benzosulfonate
866942-23-6

1-phenyl-2-propyl 2-(methoxyethoxyethylcarboxy)-1-benzosulfonate

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Conditions
ConditionsYield
With lithium bromide In acetone for 2h;96%
With lithium bromide In acetone for 2h; Product distribution / selectivity; Heating / reflux;96%
With sodium bromide In acetone for 30h; Product distribution / selectivity; Heating / reflux;11%
(±)-1-phenylpropanyl-2-yl methansulfonate
61380-47-0

(±)-1-phenylpropanyl-2-yl methansulfonate

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 60℃; for 8h; Concentration; Temperature; Time; Inert atmosphere; Green chemistry;95%
(±)-1-phenylpropanyl-2-yl methansulfonate
61380-47-0

(±)-1-phenylpropanyl-2-yl methansulfonate

A

1-phenylpropene
637-50-3

1-phenylpropene

B

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 90℃; for 1h; Concentration; Temperature; Time; Inert atmosphere; Green chemistry;A 34%
B 95%
3-phenyl-2-propanol
698-87-3

3-phenyl-2-propanol

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Conditions
ConditionsYield
With carbon tetrabromide; N,N-dimethyl-formamide; sodium bromide; 4,7-diphenyl-2,1,3-benzothiadiazole In N,N-dimethyl-formamide at 20℃; for 24h; Schlenk technique; Irradiation; Green chemistry;88%
With hydrogen bromide at 100℃; im Rohr;
With 3-ethyl-2-fluoro-benzothiazolium; tetrafluoroborate; lithium bromide In acetone
With pyridine; thionyl chloride; diethyl ether Erwaermen des Reaktionsprodukts mit Thionylbromid und wenig Pyridin-hydrobromid;
Multi-step reaction with 2 steps
1: pyridine / 20 °C
2: 1-n-butyl-3-methylimidazolim bromide / 8 h / 60 °C / Inert atmosphere; Green chemistry
View Scheme
allylbenzene
300-57-2

allylbenzene

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Conditions
ConditionsYield
With C6H12N2O*BrH at 20℃; for 10h;82%
With hydrogen bromide; acetic acid
1-phenyl-2-propyl-4-toluenesulfonate
14135-71-8

1-phenyl-2-propyl-4-toluenesulfonate

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Conditions
ConditionsYield
With lithium bromide In acetone for 11h;81%
With lithium bromide In acetone for 11h; Product distribution / selectivity; Heating / reflux;81%
With sodium bromide In acetone for 30h; Product distribution / selectivity; Heating / reflux;16%
With lithium bromide In acetone
allyl bromide
106-95-6

allyl bromide

benzene
71-43-2

benzene

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Conditions
ConditionsYield
With aluminum oxide; zinc dibromide for 3h; Ambient temperature;77%
With aluminum oxide; zinc dibromide at 15℃; for 1.5h; further catalysts and temperatures;68.3%
allylbenzene
300-57-2

allylbenzene

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

acetic acid
64-19-7

acetic acid

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

sulfuric acid
7664-93-9

sulfuric acid

NaBr

NaBr

A

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

B

1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

1-phenyl-2-propyl-4-toluenesulfonate
14135-71-8

1-phenyl-2-propyl-4-toluenesulfonate

lithium bromide

lithium bromide

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Conditions
ConditionsYield
With acetone
N-(1-methyl-2-phenylethyl)benzamide
70631-05-9

N-(1-methyl-2-phenylethyl)benzamide

phosphorus pentabromide
7789-69-7

phosphorus pentabromide

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Conditions
ConditionsYield
verminderter Druck;
(+-)-<2-benzamino-propyl>-benzene

(+-)-<2-benzamino-propyl>-benzene

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Conditions
ConditionsYield
With phosphorus pentabromide at 55 - 110℃; under 25 Torr;
(+-)-<2-hydroxy-propyl>-benzene

(+-)-<2-hydroxy-propyl>-benzene

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Conditions
ConditionsYield
With phosphorus tribromide; benzene
With hydrogen bromide
N-[COCH2O[4-C6H4(C3HS2N-OCOCH(Me)CH2Ph)]]-Gly-Wang resin

N-[COCH2O[4-C6H4(C3HS2N-OCOCH(Me)CH2Ph)]]-Gly-Wang resin

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Conditions
ConditionsYield
With Bromotrichloromethane In benzene for 2h; Hunsdiecker reaction; Irradiation;
1-phenyl-2-phenyltelluropropane

1-phenyl-2-phenyltelluropropane

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Conditions
ConditionsYield
With bromine; sodium bromide at 20℃; for 2.5h; Kinetics; Activation energy; Further Variations:; Temperatures;
3-phenyl-2-propanol
698-87-3

3-phenyl-2-propanol

A

1-phenylpropene
637-50-3

1-phenylpropene

B

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 20 °C
2: 1-n-butyl-3-methylimidazolim bromide / 1 h / 90 °C / Inert atmosphere; Green chemistry
View Scheme
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); polystyrene-supported organotin catalyst In N,N-dimethyl acetamide at 80℃; for 6.5h;93%
With indium(III) chloride; sodium tetrahydroborate In acetonitrile at 20℃; for 2h;90%
With triethylsilane; indium(III) chloride; triethyl borane In hexane; dichloromethane at 20℃; for 2h;83%
Multi-step reaction with 2 steps
1: tetrahydrofuran / 0.5 h / 20 °C / Glovebox; Sealed tube; Irradiation
2: sodium methylate / 12 h / 20 °C / Glovebox; Sealed tube; Irradiation
View Scheme
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

3-((E)-but-2-enoyl)oxazolidin-2-one
109299-92-5

3-((E)-but-2-enoyl)oxazolidin-2-one

3-(3,4-dimethyl-5-phenyl-pentanoyl)-oxazolidin-2-one

3-(3,4-dimethyl-5-phenyl-pentanoyl)-oxazolidin-2-one

Conditions
ConditionsYield
With triethyl borane; oxygen; tri-n-butyl-tin hydride; ytterbium(III) triflate In tetrahydrofuran; hexane; dichloromethane at -78℃; for 4h;93%
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

S-pent-4-yn-1-yl ethanethioate
524689-75-6

S-pent-4-yn-1-yl ethanethioate

pent-4-ynyl(1-phenylpropan-2-yl)sulfane
1010447-21-8

pent-4-ynyl(1-phenylpropan-2-yl)sulfane

Conditions
ConditionsYield
Stage #1: S-pent-4-yn-1-yl ethanethioate With potassium hydroxide In methanol at 0℃; for 0.25h; Inert atmosphere;
Stage #2: (2-bromopropyl)-benzene In methanol at 50℃; for 2h;
93%
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

1-propenylbenzene
873-66-5

1-propenylbenzene

Conditions
ConditionsYield
With sodium hydride; 2,8,9-trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane hydro-chloride In [D3]acetonitrile for 2h;91%
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-(1-phenylpropan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
916658-74-7

2-(1-phenylpropan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; copper(l) chloride In tetrahydrofuran at 20℃; for 5h; Inert atmosphere;90%
With lithium tert-butoxide In N,N-dimethyl-formamide at 25℃; for 0.5h; Reagent/catalyst; Inert atmosphere; Schlenk technique;90%
With copper; lithium methanolate In N,N-dimethyl-formamide at 25℃; for 3h;82%
bromobenzene
108-86-1

bromobenzene

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

1,1-diphenylpropane
1530-03-6

1,1-diphenylpropane

Conditions
ConditionsYield
With nickel(II) bromide dimethoxyethane; [Ir(dF(CF3)ppy)2(phen)]PF6; Bathocuproine; diisopropylamine; magnesium bromide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; Irradiation; regioselective reaction;87%
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

2-methyl-N-phenylacrylamide
1611-83-2

2-methyl-N-phenylacrylamide

C19H23NO

C19H23NO

Conditions
ConditionsYield
With methanol; tris-(trimethylsilyl)silane; [Ir[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine]2(4,4′-di-t-Bu-2,2′-bipyridine)]PF6; sodium carbonate at 25℃; for 1h; Giese Free Radical Synthesis; Irradiation;86%
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

sodium 2-methoxy-5-methylbenzene sulphinate
82635-16-3

sodium 2-methoxy-5-methylbenzene sulphinate

buta-1,3-diene
106-99-0

buta-1,3-diene

(E)-1-methoxy-4-methyl-2-((5-methyl-6-phenylhex-2-en-1-yl)sulfonyl)benzene

(E)-1-methoxy-4-methyl-2-((5-methyl-6-phenylhex-2-en-1-yl)sulfonyl)benzene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In tetrahydrofuran; N,N-dimethyl acetamide at 20℃; for 48h; Heck Reaction; Schlenk technique; Inert atmosphere; Irradiation;86%
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

((4-(tert-butyl)phenyl)ethynyl)magnesium bromide
1237541-27-3

((4-(tert-butyl)phenyl)ethynyl)magnesium bromide

1-(tert-butyl)-4-(3-methyl-4-phenylbut-1-yn-1-yl)benzene
1604039-75-9

1-(tert-butyl)-4-(3-methyl-4-phenylbut-1-yn-1-yl)benzene

Conditions
ConditionsYield
With Bis<2-(N,N-dimethylamino)aethyl>aether; iron(II) bromide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 16h; Inert atmosphere; Glovebox;83%
bromobenzene
108-86-1

bromobenzene

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

1,2-diphenylpropane
5814-85-7

1,2-diphenylpropane

Conditions
ConditionsYield
With nickel(II) bromide dimethoxyethane; [Ir(dF(CF3)ppy)2(phen)]PF6; diisopropylamine; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium bromide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; Irradiation; regioselective reaction;80%
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

C17H25BF3O2(1-)*Li(1+)

C17H25BF3O2(1-)*Li(1+)

1,2-diphenylpropane
5814-85-7

1,2-diphenylpropane

Conditions
ConditionsYield
With iron(III)-acetylacetonate; magnesium bromide ethyl etherate In tetrahydrofuran at 40℃; for 1h;77%
mercaptoundecahydro-closo-dodecaborate bis-tetramethylammonium salt

mercaptoundecahydro-closo-dodecaborate bis-tetramethylammonium salt

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

tetramethylammonium S,S-bis(1-phenypropan-2-yl)sulfonio-undecahydro-closo-dodecaborate

tetramethylammonium S,S-bis(1-phenypropan-2-yl)sulfonio-undecahydro-closo-dodecaborate

Conditions
ConditionsYield
In water; acetonitrile soln. of bromide in MeCN was added dropwise over 20 min to stirred soln.of B compd. in MeCN/H2O (4/1); stirred at room temp. for 48 h; evapd. (vac.); redissolved in MeCN; filtered; ether added; filtered; recrystd. (H2O); elem. anal.;75%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

1-methoxy-4-(1-phenylbutyl)benzene
1438827-73-6

1-methoxy-4-(1-phenylbutyl)benzene

Conditions
ConditionsYield
With (6,6’-dimethyl-2,2'-bipyridine)nickel(II) dibromide; potassium bromide In N,N-dimethyl acetamide at 20℃; for 24h; Electrochemical reaction; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;75%
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

benzoic acid
65-85-0

benzoic acid

2-methyl-1,3-diphenylpropan-1-one
4842-43-7

2-methyl-1,3-diphenylpropan-1-one

Conditions
ConditionsYield
With bis(acetylacetonate)nickel(II); di-tert-butyl dicarbonate; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc In N,N-dimethyl-formamide; acetonitrile at 25℃; for 12h; Inert atmosphere;74%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

(E)-(3-methylbut-1-ene-1,4-diyl)dibenzene
1309466-74-7

(E)-(3-methylbut-1-ene-1,4-diyl)dibenzene

Conditions
ConditionsYield
With palladium diacetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine In dimethyl sulfoxide at 28℃; for 24h; Inert atmosphere; Irradiation; Sealed tube; stereoselective reaction;74%
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

2,2'-bis(1,3,2-benzodioxaborole)
13826-27-2

2,2'-bis(1,3,2-benzodioxaborole)

2-(1-phenylpropan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
916658-74-7

2-(1-phenylpropan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
Stage #1: (2-bromopropyl)-benzene; 2,2'-bis(1,3,2-benzodioxaborole) With p-phenylpyridine; sodium methylate In acetonitrile for 12h; Glovebox; Irradiation; Sealed tube; Inert atmosphere;
Stage #2: 2,3-dimethyl-2,3-butane diol With triethylamine In acetonitrile for 1h; Catalytic behavior; Reagent/catalyst; Solvent; Glovebox; Sealed tube; Inert atmosphere;
71%
Stage #1: (2-bromopropyl)-benzene; 2,2'-bis(1,3,2-benzodioxaborole) With tetrakis(triphenylphosphine) palladium(0); potassium methanolate In acetonitrile at 25℃; for 8h; Irradiation; Inert atmosphere;
Stage #2: 2,3-dimethyl-2,3-butane diol With triethylamine In acetonitrile for 1h;
31%
C6H4NCH2CHCCH2
491-35-0

C6H4NCH2CHCCH2

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

4-methyl-2-(1-phenylpropan-2-yl)quinoline

4-methyl-2-(1-phenylpropan-2-yl)quinoline

Conditions
ConditionsYield
With carbon tetrabromide; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In water at 40℃; for 42h; Minisci Aromatic Substitution; Sealed tube; Inert atmosphere; Irradiation;67%
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

trifluoro(2-tolyl)silane
363-86-0

trifluoro(2-tolyl)silane

1-phenyl-2-(2-tolyl)propane

1-phenyl-2-(2-tolyl)propane

Conditions
ConditionsYield
With (1,2-dimethoxyethane)dichloronickel(II); (1S,2R)-(+)-norphedrine; lithium hexamethyldisilazane; water; cesium fluoride In N,N-dimethyl acetamide at 60℃; for 16h; Hiyama cross-coupling;65%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

1-methoxy-4-(1-phenylpropyl)benzene
27238-93-3

1-methoxy-4-(1-phenylpropyl)benzene

Conditions
ConditionsYield
With 2.9-dimethyl-1,10-phenanthroline; nickel(II) perchlorate hexahydrate; tetrabutylammomium bromide In N,N-dimethyl acetamide at 20℃; for 10h; Glovebox; Sealed tube; Electrochemical reaction; Inert atmosphere; regioselective reaction;60%
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

6-<(4-methylbenzenesulfonyl)oxy>hexanoic acid, ethyl ester
122822-50-8

6-<(4-methylbenzenesulfonyl)oxy>hexanoic acid, ethyl ester

ethyl 7-methyl-8-phenyloctanoate

ethyl 7-methyl-8-phenyloctanoate

Conditions
ConditionsYield
With copper(l) iodide; lithium methanolate; magnesium; bis-diphenylphosphinomethane In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Schlenk technique;58%
1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

(3-methylbutane-1,1,4-triyl)tribenzene

(3-methylbutane-1,1,4-triyl)tribenzene

Conditions
ConditionsYield
With p-phenylpyridine; cyclohexa-1,4-diene; sodium methylate; bis(pinacol)diborane In tetrahydrofuran for 24h; Glovebox; Sealed tube; Irradiation; Inert atmosphere;58%
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

2-fluoro-1-phenylpropane
40888-89-9

2-fluoro-1-phenylpropane

Conditions
ConditionsYield
With potassium phosphate; benzophenone; 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)-2-trisilanol; N-fluorobis(benzenesulfon)imide In water; acetonitrile at 20℃; for 4h; Irradiation; Inert atmosphere;56%
(2-bromopropyl)-benzene
2114-39-8

(2-bromopropyl)-benzene

sodium 1-phenyl-2-propanesulfonate
76653-17-3

sodium 1-phenyl-2-propanesulfonate

Conditions
ConditionsYield
With sodium sulfite In ethanol; water for 35h; Heating;54%

2114-39-8Relevant articles and documents

Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes

Cruz, Daniel A.,Sinka, Victoria,De Armas, Pedro,Steingruber, Hugo Sebastian,Fernández, Israel,Martín, Víctor S.,Miranda, Pedro O.,Padrón, Juan I.

supporting information, p. 6105 - 6109 (2021/08/18)

A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence of parts per million amounts of the Cu(I) species and the formation of the Markovnikov product occurs in the presence of 30 mol % iron(II) bromide. Density functional theory calculations combined with Fukui's radical susceptibilities support the obtained results.

HBr–DMPU: The First Aprotic Organic Solution of Hydrogen Bromide

Li, Zhou,Ebule, Rene,Kostyo, Jessica,Hammond, Gerald B.,Xu, Bo

supporting information, p. 12739 - 12743 (2017/09/25)

HBr and DMPU (1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone) form a room-temperature-stable complex that provides a mild, effective, and selective hydrobrominating reagent toward alkynes, alkenes, and allenes. HBr–DMPU could also replace other halogenating reagents in the halo-Prins reaction, ether cleavage, and deoxy-bromination reactions.

A facile and green protocol for nucleophilic substitution reactions of sulfonate esters by recyclable ionic liquids [bmim][X]

Liu, Yajun,Xu, Yongnan,Jung, Sun Ho,Chae, Junghyun

, p. 2692 - 2698,7 (2012/12/12)

Ionic liquids [bmim][X] (X = Cl, Br, I, OAc, SCN) are highly efficient reagents for nucleophilic substitution reactions of sulfonate esters derived from primary and secondary alcohols. The counter anions (X-) of the ionic liquids, [bmim][X], effectively replace the sufonates affording the corresponding substitution products such as alkyl halides, acetates, and thiocyanides in excellent yields. The newly developed protocol is very environmentally attractive because the reactions use stoichiometric amounts of ionic liquids as sole reagents in most cases and do not require additional solvents, any other activating reagents, non-conventional equipment, or special precautions. Moreover, these ionic liquids can be readily recycled without loss of reactivity, making the whole process greener.

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