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627-18-9 Usage

Chemical Properties

colourless liquid

Uses

Different sources of media describe the Uses of 627-18-9 differently. You can refer to the following data:
1. Structure-mutagenic activity relationships in the Salmonella typhimurium TA100 strain in a series of short-chain halogenated hydrocarbons and alcohols.
2. A reagent used in the synthesis of quaternary chiral prolines
3. 3-Bromo-1-propanol is used in the synthesis of fluorescent halide-sensitive quinolinium dyes, chiral, quaternary prolines through cyclization of quaternary amino acids and molten salt-polymers. It is utilized for the study of micellar media and in microemulsions based on cationic or a nonionic surfactant by reacting with phenols. It acts as a grafting agent in the synthesis of recyclable reagents and an intermediate in the synthesis of organic molecules.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 2544, 1955 DOI: 10.1021/ja01614a053Synthesis, p. 1161, 1985 DOI: 10.1055/s-1985-31464Tetrahedron Letters, 32, p. 3243, 1991 DOI: 10.1016/S0040-4039(00)79734-6

General Description

Clear colorless liquid.

Air & Water Reactions

Highly flammable. Water soluble.

Reactivity Profile

3-Bromo-1-propanol may be sensitive to prolonged exposure to light.

Fire Hazard

3-Bromo-1-propanol is combustible.

Check Digit Verification of cas no

The CAS Registry Mumber 627-18-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 7 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 627-18:
(5*6)+(4*2)+(3*7)+(2*1)+(1*8)=69
69 % 10 = 9
So 627-18-9 is a valid CAS Registry Number.
InChI:InChI=1/C3H7BrO/c4-2-1-3-5/h5H,1-3H2

627-18-9 Well-known Company Product Price

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  • Alfa Aesar

  • (B22857)  3-Bromo-1-propanol, 97%   

  • 627-18-9

  • 5g

  • 260.0CNY

  • Detail
  • Alfa Aesar

  • (B22857)  3-Bromo-1-propanol, 97%   

  • 627-18-9

  • 25g

  • 601.0CNY

  • Detail
  • Alfa Aesar

  • (B22857)  3-Bromo-1-propanol, 97%   

  • 627-18-9

  • 100g

  • 2094.0CNY

  • Detail

627-18-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Bromo-1-propanol

1.2 Other means of identification

Product number -
Other names 2-Propanone,1-bromo-3-hydroxy

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:627-18-9 SDS

627-18-9Synthetic route

potassium (3-bromopropyl)trifluoroborate

potassium (3-bromopropyl)trifluoroborate

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With Oxone; water In acetone at 20℃; for 0.0333333h;98%
3-(tetrahydro-2H-pyran-2-yloxy)propyl bromide
33821-94-2

3-(tetrahydro-2H-pyran-2-yloxy)propyl bromide

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With silica-supported NaHSO4 In methanol at 20℃; for 0.25h;93%
trimethyleneglycol
504-63-2

trimethyleneglycol

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With hydrogen bromide In benzene for 20h; Heating;90%
With hydrogen bromide In water; benzene for 28h; Heating;79%
With tetrabutylammomium bromide; hydrogen bromide In water for 0.0833333h; Microwave irradiation;75%
3-(tert-butyldimethylsilyloxy)propyl bromide
89031-84-5

3-(tert-butyldimethylsilyloxy)propyl bromide

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With Selectfluor In acetonitrile at 150℃; for 0.0833333h; Microwave irradiation;83%
With methanol; trimethylsilyl bromide at 20℃; for 0.0833333h; chemoselective reaction;83%
Methyl 3-bromopropionate
3395-91-3

Methyl 3-bromopropionate

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With zinc(II) tetrahydroborate In tetrahydrofuran at 67℃; for 2h;79%
trimethylene oxide
503-30-0

trimethylene oxide

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With dimethylboron bromide; triethylamine In dichloromethane at 0℃; for 2h;78%
With sodium bromide at 50℃; for 18h; Green chemistry;29%
With diethyl ether; magnesium bromide zuletzt in Benzol bei Siedetemperatur;
3-Bromopropionic acid
590-92-1

3-Bromopropionic acid

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With zinc(II) tetrahydroborate In tetrahydrofuran for 6h; Heating;75%
trimethylene oxide
503-30-0

trimethylene oxide

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

A

pentan-1-ol
71-41-0

pentan-1-ol

B

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With diethyl ether
trimethylene oxide
503-30-0

trimethylene oxide

ethylmagnesium bromide

ethylmagnesium bromide

A

pentan-1-ol
71-41-0

pentan-1-ol

B

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

2-oxo-1,3,2-dioxathiane
4176-55-0

2-oxo-1,3,2-dioxathiane

diethyl ether
60-29-7

diethyl ether

phenylmagnesium bromide

phenylmagnesium bromide

A

biphenyl
92-52-4

biphenyl

B

1,1'-sulfinylbisbenzene
945-51-7

1,1'-sulfinylbisbenzene

C

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-Bromopropionyl chloride
15486-96-1

3-Bromopropionyl chloride

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether at -75℃;
3-bromopropyl acetate
592-33-6

3-bromopropyl acetate

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With methanol
Ethyl 3-bromopropionate
539-74-2

Ethyl 3-bromopropionate

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With zinc(II) tetrahydroborate In 1,2-dimethoxyethane for 18h; sonication; or with N,N-dimethylaniline, 12 h;
allyl alcohol
107-18-6

allyl alcohol

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; bromine; zirconium(IV) chloride 1.) THF, 30 deg C, 3 h; 2.) THF/benzene, r.t., 1 h; Yield given. Multistep reaction;
diethyl ether
60-29-7

diethyl ether

3-Bromopropionyl chloride
15486-96-1

3-Bromopropionyl chloride

lithium alanate

lithium alanate

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
at -75℃;
at -15℃;
at 35℃;
aluminium trichloride
7446-70-0

aluminium trichloride

diethyl ether
60-29-7

diethyl ether

3-Bromopropionyl chloride
15486-96-1

3-Bromopropionyl chloride

lithium alanate

lithium alanate

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
at -75℃;
at -15℃;
at 35℃;
Methyl 3-bromopropionate
3395-91-3

Methyl 3-bromopropionate

lithium alanate aluminium chloride

lithium alanate aluminium chloride

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With diethyl ether at -75℃;
3-Bromopropionyl chloride
15486-96-1

3-Bromopropionyl chloride

lithium alanate aluminium chloride

lithium alanate aluminium chloride

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With diethyl ether at -75℃;
hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

trimethyleneglycol
504-63-2

trimethyleneglycol

A

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

1,3-dibromo-propane

B

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
unter verschiedenen Bedingungen;
sulfuric acid
7664-93-9

sulfuric acid

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

hydrogen bromide

trimethyleneglycol
504-63-2

trimethyleneglycol

A

bis(3-bromopropyl) ether
58929-72-9

bis(3-bromopropyl) ether

B

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

1,3-dibromo-propane

C

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
bei der Destillation;
1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

A

1,2-dioxacyclohexane
5703-46-8

1,2-dioxacyclohexane

B

allyl bromide
106-95-6

allyl bromide

C

trimethyleneglycol
504-63-2

trimethyleneglycol

D

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

Conditions
ConditionsYield
With metal oxide; water at 150℃; under 5931.67 Torr; for 1h;
1-(4-methoxybenzyl)piperazine
21867-69-6

1-(4-methoxybenzyl)piperazine

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-[4-(4-Methoxy-benzyl)-piperazin-1-yl]-propan-1-ol
79837-50-6

3-[4-(4-Methoxy-benzyl)-piperazin-1-yl]-propan-1-ol

Conditions
ConditionsYield
With potassium carbonate In butanone Heating;100%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-(tert-butyldimethylsilyloxy)propyl bromide
89031-84-5

3-(tert-butyldimethylsilyloxy)propyl bromide

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1.5h;100%
With 1H-imidazole In tetrahydrofuran at 20℃; for 24h;100%
With dmap; triethylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;100%
1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-(nitrooxy)propan-1-ol
100502-66-7

3-(nitrooxy)propan-1-ol

Conditions
ConditionsYield
With silver nitrate In acetonitrile for 24h; Ambient temperature;100%
With silver nitrate In acetonitrile at 20℃; for 24h;86%
With silver nitrate In acetonitrile Heating;78.3%
4-methyl-1-naphthol
10240-08-1

4-methyl-1-naphthol

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

1-(3-hydroxypropoxy)-4-methylnaphthalene
222161-54-8

1-(3-hydroxypropoxy)-4-methylnaphthalene

Conditions
ConditionsYield
With potassium carbonate In acetone for 4h; Heating;100%
4-bromo-phenol
106-41-2

4-bromo-phenol

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-(4-Bromophenoxy)-1-propanol
67900-64-5

3-(4-Bromophenoxy)-1-propanol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;93%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 12h;83%
tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-(tert-butyldiphenylsilyloxy)propyl bromide
177338-13-5

3-(tert-butyldiphenylsilyloxy)propyl bromide

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane for 21h; Inert atmosphere;100%
In dichloromethane at 0℃;99%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 9h;97%
triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

(3-bromopropoxy)triisopropylsilane
215650-24-1

(3-bromopropoxy)triisopropylsilane

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane for 18h;100%
With 1H-imidazole In dichloromethane for 20h;100%
With 1H-imidazole In dichloromethane at 20℃; for 60h;100%
meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-(3-hydroxy-propoxy)-benzaldehyde
245510-06-9

3-(3-hydroxy-propoxy)-benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 3h; Reflux;100%
Stage #1: meta-hydroxybenzaldehyde With potassium carbonate In DMF (N,N-dimethyl-formamide) for 0.166667h;
Stage #2: 1-bromo-3-propanol In DMF (N,N-dimethyl-formamide) for 2h; Heating / reflux;
95%
With potassium carbonate In acetonitrile for 48h; Heating;90%
With potassium carbonate In acetonitrile for 48h; Heating / reflux;90%
With potassium carbonate In acetonitrile for 5h; Heating / reflux;
C21H23BrN4O2
890532-75-9

C21H23BrN4O2

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

C24H28Br2N4O2
890532-85-1

C24H28Br2N4O2

Conditions
ConditionsYield
With bis(1-methylethyl) ester diazenedicarboxylic acid; triphenylphosphine In tetrahydrofuran at 20℃; for 1h;100%
tert-butyl (2S)-2-(4-hydroxyphenyl)morpholine-4-carboxylate
879205-96-6

tert-butyl (2S)-2-(4-hydroxyphenyl)morpholine-4-carboxylate

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

tert-butyl (2S)-2-(4-(3-bromopropyloxy)phenyl)morpholine-4-carboxylate
879205-97-7

tert-butyl (2S)-2-(4-(3-bromopropyloxy)phenyl)morpholine-4-carboxylate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at 20℃; for 10h;100%
5-(5-chloro-2-hydroxylphenyl)isoxazole
86176-56-9

5-(5-chloro-2-hydroxylphenyl)isoxazole

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

5-[2-(3-Bromo-propoxy)-5-chloro-phenyl]-isoxazole
1233227-88-7

5-[2-(3-Bromo-propoxy)-5-chloro-phenyl]-isoxazole

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;100%
2-oxo-2,3-dihydro-1,3-benzothiazole-6-carbaldehyde
438634-98-1

2-oxo-2,3-dihydro-1,3-benzothiazole-6-carbaldehyde

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-(3-hydroxypropyl)-2-oxo-2,3-dihydro-1,3-benzothiazole-6-carbaldehyde
1435516-79-2

3-(3-hydroxypropyl)-2-oxo-2,3-dihydro-1,3-benzothiazole-6-carbaldehyde

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 3h;100%
With potassium carbonate; potassium iodide In acetonitrile at 65℃; for 48h;
With potassium carbonate; potassium iodide In acetonitrile at 65℃; for 48h;
[(1S,3aR,5aS,6R,11bR,11cS)-10-[(t-butyldimethylsilyl)oxy]-1,2,3a,4,5,6,7,11c-octahydro-3H-6,11b-(epiminoethano)-1,5a-methanonaphtho[1,2-e]indol-3-yl] (phenyl)methanone

[(1S,3aR,5aS,6R,11bR,11cS)-10-[(t-butyldimethylsilyl)oxy]-1,2,3a,4,5,6,7,11c-octahydro-3H-6,11b-(epiminoethano)-1,5a-methanonaphtho[1,2-e]indol-3-yl] (phenyl)methanone

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

[(1S,3aR,5aS,6R,11bR,11cS)-10-[(t-butyldimethylsilyl)oxy]-14-(3-hydroxypropyl)-1,2,3a,4,5,6,7,11c-octahydro-3H-6,11b-(epiminoethano)-1,5a-methanonaphtho[1,2-e]indol-3-yl](phenyl)methanone

[(1S,3aR,5aS,6R,11bR,11cS)-10-[(t-butyldimethylsilyl)oxy]-14-(3-hydroxypropyl)-1,2,3a,4,5,6,7,11c-octahydro-3H-6,11b-(epiminoethano)-1,5a-methanonaphtho[1,2-e]indol-3-yl](phenyl)methanone

Conditions
ConditionsYield
Stage #1: [(1S,3aR,5aS,6R,11bR,11cS)-10-[(t-butyldimethylsilyl)oxy]-1,2,3a,4,5,6,7,11c-octahydro-3H-6,11b-(epiminoethano)-1,5a-methanonaphtho[1,2-e]indol-3-yl] (phenyl)methanone; 1-bromo-3-propanol With potassium carbonate; potassium iodide In acetonitrile for 20h; Inert atmosphere; Reflux;
Stage #2: With hydrogenchloride
100%
2-bromo-3-chloro-4-(4-ethoxybenzyl)-6-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenol

2-bromo-3-chloro-4-(4-ethoxybenzyl)-6-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenol

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-(2-bromo-3-chloro-4-(4-ethoxybenzyl)-6-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenoxy)propan-1-ol

3-(2-bromo-3-chloro-4-(4-ethoxybenzyl)-6-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenoxy)propan-1-ol

Conditions
ConditionsYield
With potassium carbonate In acetone at 55℃; for 15h;100%
4-(benzyloxy)-2-bromo-3,5-dimethoxyphenol

4-(benzyloxy)-2-bromo-3,5-dimethoxyphenol

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-(4-(benzyloxy)-2-bromo-3,5-dimethoxyphenoxy)propan-1-ol

3-(4-(benzyloxy)-2-bromo-3,5-dimethoxyphenoxy)propan-1-ol

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 21h; Inert atmosphere;100%
8-mercapto-1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione
1790-74-5

8-mercapto-1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

C11H16N4O3S

C11H16N4O3S

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;100%
3-benzyl-6-bromo-2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)phenol

3-benzyl-6-bromo-2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)phenol

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

C49H48BrClO7

C49H48BrClO7

Conditions
ConditionsYield
With potassium carbonate In acetone at 20 - 50℃; for 12h;100%
6-bromo-3-(1-hydroxy-2-methylpropan-2-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

6-bromo-3-(1-hydroxy-2-methylpropan-2-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

6-bromo-3-(1-hydroxy-2-methylpropan-2-yl)-1-(3 -hydroxypropyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

6-bromo-3-(1-hydroxy-2-methylpropan-2-yl)-1-(3 -hydroxypropyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 18h;100%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-(tetrahydro-2H-pyran-2-yloxy)propyl bromide
33821-94-2

3-(tetrahydro-2H-pyran-2-yloxy)propyl bromide

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane for 5h;99%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 5h;98%
With toluene-4-sulfonic acid In dichloromethane at 20℃; Inert atmosphere;97.4%
1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-azidopropan-1-ol
72320-38-8

3-azidopropan-1-ol

Conditions
ConditionsYield
With sodium azide In water at 60℃;99%
With sodium azide In water at 80℃; for 72h; Inert atmosphere; Schlenk technique;98%
With sodium azide In N,N-dimethyl-formamide at 90℃;97%
triphenylphosphine
603-35-0

triphenylphosphine

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-hydroxypropyltriphenylphosphonium bromide
51860-45-8

3-hydroxypropyltriphenylphosphonium bromide

Conditions
ConditionsYield
In toluene for 16h; Reflux;99%
In toluene at 110℃; for 16h;99%
In toluene at 110℃; for 16h;99%
D-glucal triacetate
2873-29-2

D-glucal triacetate

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3'-bromopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
142631-67-2

3'-bromopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane for 0.0833333h; Ambient temperature;99%
With boron trifluoride diethyl etherate In dichloromethane at 20℃; Ferrrier rearrangement;85%
With erbium(III) triflate In nitromethane at 20℃; for 0.166667h; Ferrier rearrangement;75%
bromo-triphenyl-methane
596-43-0

bromo-triphenyl-methane

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

((3-bromopropoxy)methanetrityl)tribenzene
76504-33-1

((3-bromopropoxy)methanetrityl)tribenzene

Conditions
ConditionsYield
With dmap; triethylamine In N,N-dimethyl-formamide for 24h; Ambient temperature;99%
With dmap; triethylamine In dichloromethane for 4h; Ambient temperature;95%
With dmap; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;85%
t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-(tert-butyldimethylsilyloxy)propyl bromide
89031-84-5

3-(tert-butyldimethylsilyloxy)propyl bromide

Conditions
ConditionsYield
Stage #1: 1-bromo-3-propanol With 2,6-dimethylpyridine; calcium hydride In dichloromethane at 0℃; Inert atmosphere;
Stage #2: t-butyldimethylsiyl triflate In dichloromethane at 20℃; for 2h; Inert atmosphere;
99%
In dichloromethane at 0℃; for 4h;85%
sodium thiophenolate
930-69-8

sodium thiophenolate

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-phenylthiopropanol
24536-40-1

3-phenylthiopropanol

Conditions
ConditionsYield
In methanol for 0.75h; Ambient temperature;99%
N,N'-ditoluenesulfonyl-1,3-diaminopropane
53364-99-1

N,N'-ditoluenesulfonyl-1,3-diaminopropane

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

N4,N8-ditosyl-4,8-diaza-1,11-undecanediol
124615-98-1

N4,N8-ditosyl-4,8-diaza-1,11-undecanediol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 24h; Alkylation;99%
4-Iodophenol
540-38-5

4-Iodophenol

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-(4-iodophenoxy)propan-1-ol
145073-42-3

3-(4-iodophenoxy)propan-1-ol

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide for 6h; Reflux;99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;84%
With potassium carbonate In N,N-dimethyl-formamide at 180℃; for 0.5h; Irradiation; microwave irradiation;75%
Stage #1: p-Iodophenol With potassium hydroxide In ethanol at 20℃; for 1h; deprotonation;
Stage #2: 1-bromo-3-propanol In ethanol at 50℃; for 16h; Alkylation;
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide
3-Bromophenol
591-20-8

3-Bromophenol

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-(3-bromophenoxy)propan-1-ol
92584-63-9

3-(3-bromophenoxy)propan-1-ol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;99%
Stage #1: 3-Bromophenol With sodium hydride In N,N-dimethyl-formamide
Stage #2: 1-bromo-3-propanol In N,N-dimethyl-formamide
With potassium carbonate In acetonitrile Reflux;
benzoyl chloride
98-88-4

benzoyl chloride

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

3-bromopropyl benzoate
6065-69-6

3-bromopropyl benzoate

Conditions
ConditionsYield
With triethylamine In diethyl ether at 0 - 20℃; for 9.5h;99%
With triethylamine In diethyl ether at 0 - 20℃; for 14.5h;99%
With pyridine In tetrahydrofuran at 20℃;63%
With pyridine; dmap In 1,2-dichloro-ethane at 60℃; for 2h;
6-hydroxy-1-(3-isopropoxy-benzoyl)-7-methoxy-isoquinoline-4-carboxylic acid ethyl ester

6-hydroxy-1-(3-isopropoxy-benzoyl)-7-methoxy-isoquinoline-4-carboxylic acid ethyl ester

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

6-(3-hydroxy-propoxy)-hydroxy-1-(3-isopropoxy-benzoyl)-7-methoxy-isoquinoline-4-carboxylic acid ethyl ester

6-(3-hydroxy-propoxy)-hydroxy-1-(3-isopropoxy-benzoyl)-7-methoxy-isoquinoline-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20 - 85℃; for 2h;99%

627-18-9Relevant articles and documents

-

Nystrom

, p. 610 (1959)

-

Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides

Lambert, Tristan H.,Steiniger, Keri A.

supporting information, p. 8013 - 8017 (2021/10/25)

The efficient and regioselective hydrosilylation of epoxides co-catalyzed by a pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is reported. This method allows for the reductive opening of terminal, monosubstituted epoxides to form unbranched, primary alcohols. A range of substrates including both terminal and nonterminal epoxides are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP derivative as a ligand for transition-metal catalysis.

Acid-Catalyzed Intramolecular Ring-Opening Reactions of Cyclopropanated Oxabenzonorbornadienes with Carboxylic Acid Nucleophiles

Carlson, Emily,Ho, Angel,Koh, Samuel,Macleod, Matthew P.,Pounder, Austin,Tam, William

, (2021/12/02)

The present work demonstrates the ability of carboxylic acid tethered cyclopropanated oxabenzonorbornadienes (CPOBDs) to undergo ring-opening reactions in mild acidic conditions. The optimized reaction conditions involve the use of pTsOH in DCE at 90 °C. Two regioisomers are formed but the reactions are highly regioselective towards type 3 ring-opened products. It was observed that substitution at the C5 and aryl positions of CPOBD significantly hinders the ring-opening reactions leading to decreased yields of ring-opened products, although high regioselectivity for the Type 3 ring-opened products is still maintained. Herein, the first examples of acid-catalyzed intramolecular ring-opening reactions of CPOBD with carboxylic acid nucleophiles are reported.

Preparation of useful building blocks, α-iodo- and bromoalkanols from cyclic ethers using the Dowex H+/NaX (X = I, Br) approach

Turhanen, Petri A.,Veps?l?inen, Jouko J.

, p. 15937 - 15940 (2016/02/19)

Our recently reported novel green chemistry tool was effectively used for opening cyclic ethers to produce α-iodo- and bromoalkanols. The synthesis of 4-iodobutanoic acid from γ-butyrolactone has also been described. The method is based on the use of a dried Dowex H+/NaX (X = Br, I)-system, which is effective at producing α-iodoalkanols and some α-bromoalkanols from commercially available cyclic ethers. Additionally, opening of three different crown ethers to form α-iodo(polyethylene)glycols with various chain lengths is demonstrated. Haloalkanols are important building blocks in synthetic chemistry e.g. for medicinal chemistry purposes.

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