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637-59-2

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637-59-2 Usage

Chemical Properties

Colorless to light yellow liqui

Uses

1-Bromo-3-phenylpropane is used in the synthesis of MraY natural inhibitors as antibacterial agents. Also used in the preparation of quinolinone derivatives as potent and selective MAO-B inhibitors.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 31, p. 4189, 1983 DOI: 10.1248/cpb.31.4189

Purification Methods

Wash the bromide successively with conc H2SO4, water, 10% aqueous Na2CO3 and again with water, then dry it with CaCl2 and fractionally distil it just before use. [Beilstein 5 IV 982.]

Check Digit Verification of cas no

The CAS Registry Mumber 637-59-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 7 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 637-59:
(5*6)+(4*3)+(3*7)+(2*5)+(1*9)=82
82 % 10 = 2
So 637-59-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H11Br/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2

637-59-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Bromo-3-phenylpropane

1.2 Other means of identification

Product number -
Other names Benzene, (3-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:637-59-2 SDS

637-59-2Synthetic route

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

3-Phenyl-1-propanol

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With polystyrene-supported triphenylphosphine dibromide In chloroform at 61℃; for 3h;100%
Stage #1: 3-Phenyl-1-propanol With diisopropyl-carbodiimide; copper(II) bis(trifluoromethanesulfonate) In tetrahydrofuran at 100℃; for 0.0833333h; microwave irradiation;
Stage #2: With Acetyl bromide In tetrahydrofuran at 150℃; for 0.0833333h; microwave irradiation; Further stages.;
98%
With allyl bromide; 1,1'-carbonyldiimidazole In acetonitrile for 1.5h; Heating;97%
3-phenylpropyl 4-methylbenzenesulfonate
3742-75-4

3-phenylpropyl 4-methylbenzenesulfonate

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 50℃; for 1h; Concentration; Temperature; Time; Inert atmosphere; Green chemistry;100%
With lithium bromide In [(2)H6]acetone at 20℃; for 32h; Inert atmosphere;95%
With potassium bromide In N,N-dimethyl-formamide at 20℃; for 12h; Product distribution / selectivity;94%
3-phenylpropanol methanesulfonate
69804-99-5

3-phenylpropanol methanesulfonate

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 50℃; for 1h; Concentration; Temperature; Time; Inert atmosphere; Green chemistry;100%
With sodium bromide In N,N-dimethyl-formamide at 25 - 30℃;80%
With sodium tetrahydroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h;
2-(3-Phenyl-propoxysulfonyl)-benzoic acid 1,4,7,10-tetraoxa-cyclododec-2-ylmethyl ester
866942-21-4

2-(3-Phenyl-propoxysulfonyl)-benzoic acid 1,4,7,10-tetraoxa-cyclododec-2-ylmethyl ester

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In acetone at 20℃; for 1.3h; Product distribution; Further Variations:; Reagents; Temperatures; reaction time;98%
With lithium bromide In [(2)H6]acetone at 20℃; for 1.3h; Inert atmosphere;95%
2-(3-phenyl-propoxysulfonyl)-benzoic acid 2-methoxy-ethyl ester
866942-17-8

2-(3-phenyl-propoxysulfonyl)-benzoic acid 2-methoxy-ethyl ester

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In acetone for 0.3h; Product distribution; Further Variations:; Reagents; Temperatures; reaction time; Heating;97%
With lithium bromide In [(2)H6]acetone at 20℃; for 12h; Inert atmosphere;95%
3-phenylpropyl 2-(methoxyethoxyethylcarboxy)-1-benzosulfonate
866942-18-9

3-phenylpropyl 2-(methoxyethoxyethylcarboxy)-1-benzosulfonate

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In acetone for 0.1h; Product distribution; Further Variations:; Reagents; Temperatures; reaction time; Heating;97%
With lithium bromide In acetone for 0.1h; Product distribution / selectivity; Heating / reflux;97%
With lithium bromide In [(2)H6]acetone at 20℃; for 5h; Inert atmosphere;95%
3-phenylpropyl 2-(methylcarboxy)-1-benzenesulfonate
866942-16-7

3-phenylpropyl 2-(methylcarboxy)-1-benzenesulfonate

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In acetone for 0.75h; Product distribution; Further Variations:; Reagents; reaction time; Heating;96%
With lithium bromide In acetone for 0.75h; Product distribution / selectivity; Heating / reflux;96%
With sodium bromide In acetone for 3h; Product distribution / selectivity; Heating / reflux;94%
With potassium bromide In acetone for 15h; Product distribution / selectivity; Heating / reflux;92%
3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With indium(III) bromide; trimethylsilyl bromide; 1,1,3,3-Tetramethyldisiloxane In chloroform at 20 - 60℃; for 1.08333h; Reagent/catalyst; Solvent; Sealed tube; Inert atmosphere;96%
With trimethylsilyl bromide; 1,1,3,3-Tetramethyldisiloxane; indium tribromide In chloroform at 60℃; for 1h; Reagent/catalyst; Sealed tube; Inert atmosphere;96%
With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane; trimethylsilyl cyanide In chloroform at 60℃; Inert atmosphere;
2-(3-phenyl-propoxysulfonyl)-benzoic acid 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl ester
866942-19-0

2-(3-phenyl-propoxysulfonyl)-benzoic acid 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl ester

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In [(2)H6]acetone at 20℃; for 3.3h; Inert atmosphere;95%
With sodium bromide In acetone for 3.6h; Product distribution; Further Variations:; Reagents; Temperatures; reaction time; Heating;94%
2-(3-phenyl-propoxysulfonyl)-benzoic acid 2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethyl ester
866942-20-3

2-(3-phenyl-propoxysulfonyl)-benzoic acid 2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethyl ester

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With sodium bromide In acetone for 2.5h; Product distribution; Further Variations:; Reagents; Temperatures; reaction time; Heating;95%
With lithium bromide In [(2)H6]acetone at 20℃; for 2.3h; Inert atmosphere;95%
trimethyl(3-phenylpropoxy)silane
14629-60-8

trimethyl(3-phenylpropoxy)silane

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With 4-aminophenyl diphenylphosphinite; N-Bromosuccinimide In dichloromethane for 1.5h; Heating;95%
2-(3-phenylpropoxy)tetrahydro-2H-pyran
112471-51-9

2-(3-phenylpropoxy)tetrahydro-2H-pyran

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With 4-aminophenyl diphenylphosphinite; N-Bromosuccinimide In dichloromethane for 3h; Heating;95%
C22H30O5S

C22H30O5S

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In [(2)H6]acetone at 20℃; for 25h; Inert atmosphere;95%
With lithium bromide In acetone at 20℃; for 4.5h;
C18H21FO5S

C18H21FO5S

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In [(2)H6]acetone at 20℃; for 10h; Inert atmosphere;95%
With lithium bromide In acetone at 20℃; for 3.5h;
C20H25FO6S

C20H25FO6S

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In [(2)H6]acetone at 20℃; for 4h; Inert atmosphere;95%
With lithium bromide In acetone at 20℃; for 1h;
3-phenylpropyl 2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-5-fluorobenzene-1-sulfonate

3-phenylpropyl 2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-5-fluorobenzene-1-sulfonate

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In [(2)H6]acetone at 20℃; for 2.5h; Inert atmosphere;95%
With lithium bromide In acetone at 20℃; for 0.5h;
3-phenylpropyl quinoline-8-sulfonate
1082742-89-9

3-phenylpropyl quinoline-8-sulfonate

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In [(2)H6]acetone at 20℃; for 4.5h; Inert atmosphere;95%
With titanium(IV) bromide In dichloromethane at 20℃; for 5.5h; Inert atmosphere;89%
C20H24F2O6S
1174295-53-4

C20H24F2O6S

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In [(2)H6]acetone at 20℃; for 2.5h; Inert atmosphere;95%
C22H28F2O7S
1174295-54-5

C22H28F2O7S

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In [(2)H6]acetone at 20℃; for 1.8h; Inert atmosphere;95%
C24H34O6S
1174295-48-7

C24H34O6S

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In [(2)H6]acetone at 20℃; for 8.8h; Inert atmosphere;95%
C26H38O7S
1174295-49-8

C26H38O7S

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In [(2)H6]acetone at 20℃; for 6.8h; Inert atmosphere;95%
3-phenylpropyl 1-trifluoromethanesulfonate
66950-73-0

3-phenylpropyl 1-trifluoromethanesulfonate

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With lithium bromide In [(2)H6]acetone at 20℃; for 2h; Inert atmosphere;95%
3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

4-(diphenylphosphino)-benzyltrimethylammonium bromide
1229444-43-2

4-(diphenylphosphino)-benzyltrimethylammonium bromide

A

Br(1-)*C22H25NOP(1+)
1268610-56-5

Br(1-)*C22H25NOP(1+)

B

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With carbon tetrabromide In 1,2-dichloro-ethane at 60℃; for 2h;A n/a
B 95%
3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

N-methyl-N-[4-(diphenylphosphino)benzyl]pyrrolidinium bromide
1229444-44-3

N-methyl-N-[4-(diphenylphosphino)benzyl]pyrrolidinium bromide

A

Br(1-)*C24H27NOP(1+)
1229444-42-1

Br(1-)*C24H27NOP(1+)

B

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With carbon tetrabromide In 1,2-dichloro-ethane at 40℃; for 2h; Inert atmosphere;A 93%
B 95%
2-(3-Phenyl-propoxysulfonyl)-benzoic acid 1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethyl ester
866942-22-5

2-(3-Phenyl-propoxysulfonyl)-benzoic acid 1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethyl ester

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With sodium bromide In acetone for 0.37h; Product distribution; Further Variations:; Reagents; Temperatures; reaction time; Heating;93%
1,3-diisopropyl-2-(3-phenyl-propyl)-isourea

1,3-diisopropyl-2-(3-phenyl-propyl)-isourea

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With N-Bromosuccinimide In tetrahydrofuran at 80℃; for 4.5h;92%
1-(3-phenylpropyl)-5-aza-1-stanna-bicyclo[3.3.3]undecane

1-(3-phenylpropyl)-5-aza-1-stanna-bicyclo[3.3.3]undecane

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile at 20℃; Inert atmosphere; Sealed tube;82%
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

A

biphenyl
92-52-4

biphenyl

B

1,3-diphenylpropane
1081-75-0

1,3-diphenylpropane

C

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With copper(I) bromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 4h; Product distribution; Heating; Grignard reagent added dropwise to the other reaction partners;A 3%
B 16%
C 81%
3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

A

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

1-Bromo-3-phenylpropane

B

phenylpropyl chloride
104-52-9

phenylpropyl chloride

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine; N,N-dimethyl-formamide; sodium bromide In dichloromethane at 25℃; for 0.25h;A 80%
B n/a
cyclopropylbenzene
873-49-4

cyclopropylbenzene

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

1-Bromo-3-phenylpropane

Conditions
ConditionsYield
With boron tribromide; tert-butyl alcohol In dichloromethane at 23℃; for 1h; regioselective reaction;77%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

(3-azidopropyl)benzene
27126-20-1

(3-azidopropyl)benzene

Conditions
ConditionsYield
With sodium azide In water; acetone at 20℃;100%
With sodium azide In N,N-dimethyl-formamide at 80℃;100%
With sodium azide In dimethyl sulfoxide at 20℃;100%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

para-thiocresol
106-45-6

para-thiocresol

(3-phenylpropyl)(p-tolyl)sulfane
38644-97-2

(3-phenylpropyl)(p-tolyl)sulfane

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 12h;100%
With potassium hydroxide
With potassium carbonate In acetone at 45℃;
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

1-iodo-3-phenylpropan
4119-41-9

1-iodo-3-phenylpropan

Conditions
ConditionsYield
With sodium iodide In acetone for 6h; Reflux;100%
With sodium iodide In acetone Reflux;97%
With potassium iodide In acetone for 2h; Reflux;95%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

5-azido-5-deoxy-1,2-O-isopropylidene-3-O-methoxymethyl-β-L-idofuranose
845778-49-6

5-azido-5-deoxy-1,2-O-isopropylidene-3-O-methoxymethyl-β-L-idofuranose

5-azido-5-deoxy-6-O-(3-phenylpropyl)-1,2-O-isopropylidene-3-O-methoxymethyl-β-L-idofuranose
763122-34-5

5-azido-5-deoxy-6-O-(3-phenylpropyl)-1,2-O-isopropylidene-3-O-methoxymethyl-β-L-idofuranose

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃;100%
N-methyl-N-methoxy-2-benzyloxy-4-hexenamide
863642-50-6

N-methyl-N-methoxy-2-benzyloxy-4-hexenamide

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

1-Bromo-3-phenylpropane

1-phenyl-5-benzyloxy-7-nonen-4-one
863642-51-7

1-phenyl-5-benzyloxy-7-nonen-4-one

Conditions
ConditionsYield
Stage #1: 1-Bromo-3-phenylpropane With magnesium In tetrahydrofuran Heating;
Stage #2: N-methyl-N-methoxy-2-benzyloxy-4-hexenamide In tetrahydrofuran at 0℃; for 1.5h;
100%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

(R)-quinuclidin-3-ol
25333-42-0

(R)-quinuclidin-3-ol

(3R)-3-hydroxy-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octane bromide

(3R)-3-hydroxy-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octane bromide

Conditions
ConditionsYield
In tetrahydrofuran for 7h; Heating / reflux;100%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

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

1-Bromo-3-phenylpropane

1-methyl-3-(3-phenylpropyl)imidazolium bromide

1-methyl-3-(3-phenylpropyl)imidazolium bromide

Conditions
ConditionsYield
at 140℃; Continuous flow; neat (no solvent);100%
In acetonitrile for 8h; Reflux;
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

methyl 2-cyanoacetate
105-34-0

methyl 2-cyanoacetate

cyano-di(3-phenyl-prop-1-yl)acetic acid methyl ester
1202778-95-7

cyano-di(3-phenyl-prop-1-yl)acetic acid methyl ester

Conditions
ConditionsYield
Stage #1: methyl 2-cyanoacetate With sodium methylate In methanol at 20℃;
Stage #2: 1-Bromo-3-phenylpropane In methanol Reflux;
100%
pyridine
110-86-1

pyridine

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

1-Bromo-3-phenylpropane

1-(3-phenylpropyl)pyridinium bromide
53394-58-4

1-(3-phenylpropyl)pyridinium bromide

Conditions
ConditionsYield
for 24h; Reflux;100%
In acetonitrile at 70℃; for 31.5h;84%
at 140℃; Neat (no solvent);
In N,N-dimethyl-formamide at 100℃; for 4h; Sealed tube;
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

propionic acid
802294-64-0

propionic acid

(±)-2-methyl-5-phenylpentanoic acid
143097-60-3

(±)-2-methyl-5-phenylpentanoic acid

Conditions
ConditionsYield
Stage #1: propionic acid With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -20 - 20℃; for 0.5h;
Stage #2: 1-Bromo-3-phenylpropane In tetrahydrofuran; hexane at 0 - 20℃; for 2h;
100%
Stage #1: propionic acid With n-butyllithium; diisopropylamine In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -20 - 20℃; for 0.5h;
Stage #2: 1-Bromo-3-phenylpropane In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at 0 - 20℃; for 2h;
100%
Stage #1: propionic acid With n-butyllithium; diisopropylamine In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at 20℃; for 0.5h;
Stage #2: 1-Bromo-3-phenylpropane In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at 0 - 20℃; for 2h;
100%
Stage #1: propionic acid With n-butyllithium; diisopropylamine In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -20 - 20℃; for 0.5h;
Stage #2: 1-Bromo-3-phenylpropane In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at 0 - 20℃; for 2h;
100%
Stage #1: propionic acid With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;
Stage #2: 1-Bromo-3-phenylpropane In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;
62%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

N-(1-(3-(4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl)ethyl)acetamide

N-(1-(3-(4-hydroxyphenyl)-1,2,4-oxadiazol-5-yl)ethyl)acetamide

N-(1-(3-(4-(3-phenylpropoxy)phenyl)-1,2,4-oxadiazol-5-yl)ethyl)acetamide

N-(1-(3-(4-(3-phenylpropoxy)phenyl)-1,2,4-oxadiazol-5-yl)ethyl)acetamide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide at 80℃; for 3h;100%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

triphenylphosphine
603-35-0

triphenylphosphine

(3-phenylpropyl)triphenylphosphonium bromide
7484-37-9

(3-phenylpropyl)triphenylphosphonium bromide

Conditions
ConditionsYield
at 80℃; for 3h;99%
In toluene for 50h; Reflux;92%
In toluene for 62h; Heating;92%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

Bis(trimethylsilyl)methyl-methylether
120703-53-9

Bis(trimethylsilyl)methyl-methylether

(4-Methoxy-4,4-bis-trimethylsilanyl-butyl)-benzene
120703-47-1

(4-Methoxy-4,4-bis-trimethylsilanyl-butyl)-benzene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane99%
With n-butyllithium 1) hexane, THF, 0 deg C, 20 min, 2a) -78 deg C, 5 min, 2b) 0 deg C, 1 h; Yield given. Multistep reaction;
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

Propylbenzene
103-65-1

Propylbenzene

Conditions
ConditionsYield
With LiCrH4*2LiCl*2THF In tetrahydrofuran at 25℃; for 12h;99%
With indium(III) chloride; sodium tetrahydroborate In acetonitrile at 20℃; for 2h;95%
With sodium tetrahydroborate; water In methanol at 20℃; for 0.5h;87%
2-Iodophenol
533-58-4

2-Iodophenol

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

1-Bromo-3-phenylpropane

1-iodo-2-(3-phenylpropoxy)benzene
939990-21-3

1-iodo-2-(3-phenylpropoxy)benzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide99%
1-(3-hydroxy-2,4-dimethoxy-6-methyl-5-nitrophenyl)ethanone
1201582-46-8

1-(3-hydroxy-2,4-dimethoxy-6-methyl-5-nitrophenyl)ethanone

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

1-Bromo-3-phenylpropane

1-(2,4-dimethoxy-6-methyl-5-nitro-3-(3-phenylpropoxy)phenyl)ethanone
1201582-47-9

1-(2,4-dimethoxy-6-methyl-5-nitro-3-(3-phenylpropoxy)phenyl)ethanone

Conditions
ConditionsYield
Stage #1: 1-(3-hydroxy-2,4-dimethoxy-6-methyl-5-nitrophenyl)ethanone With sodium hydride In N,N-dimethyl-formamide; oil at 20℃; for 0.25h;
Stage #2: 1-Bromo-3-phenylpropane In N,N-dimethyl-formamide; oil at 20℃;
99%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

4-chloro-phenol
106-48-9

4-chloro-phenol

1-chloro-4-(3-phenylpropoxy)benzene
1044066-84-3

1-chloro-4-(3-phenylpropoxy)benzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;99%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

meta-hydroxyacetanilide
621-42-1

meta-hydroxyacetanilide

N-(3-(3-phenylpropoxy)phenyl)acetamide

N-(3-(3-phenylpropoxy)phenyl)acetamide

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 40℃;99%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

N-(4-methoxybenzyl)-2-nitro-N-(prop-2-yn-1-yl)benzenesulfonamide
171414-16-7

N-(4-methoxybenzyl)-2-nitro-N-(prop-2-yn-1-yl)benzenesulfonamide

N-(4-methoxybenzyl)-N-(3-phenylpropyl)-2-nitrobenzenesulfonamide
704892-79-5

N-(4-methoxybenzyl)-N-(3-phenylpropyl)-2-nitrobenzenesulfonamide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1.25h;99%
4-carbethoxypiperidine
1126-09-6

4-carbethoxypiperidine

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

1-Bromo-3-phenylpropane

ethyl 1-(3-phenylpropyl)piperidine-4-carboxylate
21327-50-4

ethyl 1-(3-phenylpropyl)piperidine-4-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 2h;98.6%
With potassium carbonate In N,N-dimethyl-formamide at 70℃;87%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

1,2-bis(3-phenylpropyl)disulfane
89987-96-2

1,2-bis(3-phenylpropyl)disulfane

Conditions
ConditionsYield
With potassium sulfide; nickel(II) chloride hexahydrate; acetylacetone; potassium hydroxide In water; N,N-dimethyl-formamide at 110℃; for 6h;98%
With potassium 5-methyl-1,3,4-oxadiazole-2-thiolate In water at 40℃; for 1h;98%
With potassium fluoride on basic alumina; thioacetamide; copper(l) chloride In N,N-dimethyl-formamide at 110℃; for 5h;95%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

2-acetylaminomalonic acid diethyl ester
1068-90-2

2-acetylaminomalonic acid diethyl ester

2-acetylamino-2-(3-phenyl-propyl)malonic acid diethyl ester
52161-73-6

2-acetylamino-2-(3-phenyl-propyl)malonic acid diethyl ester

Conditions
ConditionsYield
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium ethanolate In ethanol at 20℃; for 1.5h;
Stage #2: 1-Bromo-3-phenylpropane In ethanol for 16h; Heating;
98%
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium ethanolate In ethanol at 20℃; for 1.5h;
Stage #2: 1-Bromo-3-phenylpropane In ethanol for 16.25h; Heating / reflux;
98%
(i) Na, EtOH, (ii) /BRN= 2205527/; Multistep reaction;
With sodium ethanolate; sodium In ethanol; nitrogen
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium ethanolate In ethanol at 20℃; for 2h;
Stage #2: 1-Bromo-3-phenylpropane In ethanol at 20 - 73℃; for 28.25h;
methanol
67-56-1

methanol

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

1-Bromo-3-phenylpropane

3-methoxypropylbenzene
2046-33-5

3-methoxypropylbenzene

Conditions
ConditionsYield
With silver tetrafluoroborate; 1-(2-bromo-1,1-dimethoxyethyl)benzene at 25℃; for 4h;98%
With sodium for 2h; Heating;51 g
With sodium
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

1-(3-chloro-1-oxopropyl)-4-(3-bromopropyl)benzene
253308-01-9

1-(3-chloro-1-oxopropyl)-4-(3-bromopropyl)benzene

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane at 20℃; for 6h; Friedel-Crafts acylation;98%
1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

diethyl methyl(3-phenylpropyl)malonate
98468-72-5

diethyl methyl(3-phenylpropyl)malonate

Conditions
ConditionsYield
Stage #1: Diethyl methylmalonate With lithium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: 1-Bromo-3-phenylpropane In N,N-dimethyl-formamide at 80℃; for 3h;
98%
1H-imidazole
288-32-4

1H-imidazole

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

1-Bromo-3-phenylpropane

1-(3-phenylpropyl)-1H-imidazole
56643-92-6

1-(3-phenylpropyl)-1H-imidazole

Conditions
ConditionsYield
Stage #1: 1H-imidazole With sodium hydroxide In dimethyl sulfoxide at 70 - 80℃; for 1.5h;
Stage #2: 1-Bromo-3-phenylpropane In dimethyl sulfoxide at 70 - 80℃; for 13h;
98%
Stage #1: 1H-imidazole With potassium carbonate In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: 1-Bromo-3-phenylpropane In tetrahydrofuran Heating;
In N,N-dimethyl-formamide16.1 g (86%)

637-59-2Relevant articles and documents

Recent advances in heterolytic nucleofugal leaving groups

Lepore, Salvatore D.,Mondal, Deboprosad

, p. 5103 - 5122 (2007)

-

Ni-Catalyzed Formal Cross-Electrophile Coupling of Alcohols with Aryl Halides

Lin, Quan,Ma, Guobin,Gong, Hegui

, p. 14102 - 14109 (2021/11/20)

Direct coupling of unactivated alcohols remains a challenge in current synthetic chemistry. We herein demonstrate a strategy building upon in situ halogenation/reductive coupling of alcohols with aryl halides to forge Csp2-Csp3 bonds. The combination of 2-chloro-3-ethylbenzo[d]oxazol-3-ium salt (CEBO) and TBAB as the mild bromination reagents enables rapid transformation of a wide range of alcohols to their bromide counterparts within one to 5 min in CH3CN and DMF, which is compatible with the Ni-catalyzed cross-electrophile coupling conditions in the presence of a chemical reductant. The present method is suitable for arylation of a myriad of structurally complex alcohols with no need for prepreparation of alkyl halides. More importantly, the mild and kinetically rapid bromination process has shown good selectivity in the bromination/arylation of symmetric diols and less sterically hindered hydroxyl groups in polyols, thus offering promise for selective functionalization of diols and polyols without laborious protecting/deprotecting operations. The practicality of this work is also evident in the arylation of a number of carbohydrates, drug compounds, and naturally occurring alcohols.

Boron tribromide as a reagent for anti-Markovnikov addition of HBr to cyclopropanes

Chen, Shuming,Gieuw, Matthew H.,Houk, K. N.,Ke, Zhihai,Yeung, Ying-Yeung

, p. 9426 - 9433 (2020/10/02)

Although radical formation from a trialkylborane is well documented, the analogous reaction mode is unknown for trihaloboranes. We have discovered the generation of bromine radicals from boron tribromide and simple proton sources, such as water ortert-butanol, under open-flask conditions. Cyclopropanes bearing a variety of substituents were hydro- and deuterio-brominated to furnish anti-Markovnikov products in a highly regioselective fashion. NMR mechanistic studies and DFT calculations point to a radical pathway instead of the conventional ionic mechanism expected for BBr3

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