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627-27-0 Usage

Description

3-Buten-1-ol, also known as homoallyl alcohol, is an aliphatic primary alcohol that can be synthesized by the dehydration of 1,4-butanediol using a cerium catalyst. It is a liquid with unique chemical properties, including intramolecular hydrogen bonding, which has been studied using FT-IR and 1H NMR spectroscopic data. Its microwave spectrum has been recorded and analyzed, and its gas-phase enthalpy of formation is reported to be -147.3 ± 1.8kJ mol-1.

Uses

Used in Organic Synthesis:
3-Buten-1-ol is used as a reagent in organic synthesis, serving as a key component in various chemical reactions and the production of different compounds.
Used in Chemical Research:
3-Buten-1-ol is employed in the study of the Mn-catalyzed hydrohydrazination of olefins, a process that involves the conversion of olefins to hydrazines. It is also used in the study of the conversion of propargylic acetates to ethers catalyzed by ferric chloride, which is an important reaction in the synthesis of various organic compounds.
Used in Asymmetric Total Synthesis:
3-Buten-1-ol serves as a starting reagent in the asymmetric total synthesis of natural seimatopolide B, a complex organic molecule with potential applications in various fields.
Used in the Synthesis of Bimetallic Nanoparticles:
It is also used in the synthesis of catalytic bimetallic nanoparticles, which have applications in catalysis and other areas of materials science.

Synthesis

The synthesis of?3-Buten-1-ol is as follows:After adding 24.3 g (1 mol) of magnesium turnings, 50 g of diethyl ether and 1 ml of dibromoethane in a 500 mL four-necked flask,A solution of 62.5 g of vinyl chloride (1 mol) dissolved in 200 g of diethyl ether was added dropwise to magnesium and diethyl ether, and the micro reflux was controlled, and the dropwise addition was completed, and the mixture was kept under a micro reflux for 2 hours, and the temperature was lowered to -5 °C;Then 44 g (1 mol) of ethylene oxide was dissolved in 60 g of diethyl ether. Ethylene oxide is added dropwise to the vinylmagnesium chloride solution prepared above, control the temperature -5-5 degrees, and stir at this temperature for 1 hour. Sampling gas phase analysis until the reaction is complete; pour the reaction solution into a 1000 mL beaker, Add 200mL of ice water and add ammonium chloride until the residual magnesium disappears. Control the temperature 0-10 ° C, stir for 1 hour after the addition, add salt to saturation, static layering. The organic layer was separated and washed twice with 100 ml of saturated brine, and a polymerization inhibitor was added. The product is subjected to rectification to obtain 53 g of 3-buten-1-ol, and the content is 99.2%. The yield was 73.6%.

Check Digit Verification of cas no

The CAS Registry Mumber 627-27-0 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, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 627-27:
(5*6)+(4*2)+(3*7)+(2*2)+(1*7)=70
70 % 10 = 0
So 627-27-0 is a valid CAS Registry Number.
InChI:InChI=1/C4H8O/c1-2-3-4-5/h2,5H,1,3-4H2

627-27-0 Well-known Company Product Price

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  • Alfa Aesar

  • (L00767)  3-Buten-1-ol, 98+%   

  • 627-27-0

  • 5g

  • 539.0CNY

  • Detail
  • Alfa Aesar

  • (L00767)  3-Buten-1-ol, 98+%   

  • 627-27-0

  • 25g

  • 1627.0CNY

  • Detail

627-27-0SDS

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-Buten-1-ol

1.2 Other means of identification

Product number -
Other names Homatropin

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:627-27-0 SDS

627-27-0Synthetic route

1-butyn-4-ol
927-74-2

1-butyn-4-ol

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With 2,6-bis[1-(2,6-diisopropylphenylimino)ethyl]pyridine cobalt(II) dichloride; diethoxymethylane; sodium triethylborohydride In neat (no solvent) at -78 - 40℃; for 1h;97%
With hydrogen In methanol at 20℃; under 760.051 Torr; for 4.5h; Green chemistry;92%
With hydrogen In methanol under 760.051 Torr; for 5h;87%
formaldehyd
50-00-0

formaldehyd

allyldibutyltin chloride
64549-05-9

allyldibutyltin chloride

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
In water at 20℃; for 0.0833333h;97%
1-(4-methoxybenzyloxy)-3-butene
142860-83-1

1-(4-methoxybenzyloxy)-3-butene

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With t-butyl bromide In acetonitrile for 1h; Reflux; chemoselective reaction;93%
Cyclopropylmethanol
2516-33-8

Cyclopropylmethanol

A

homoalylic alcohol
627-27-0

homoalylic alcohol

B

cyclobutanol
2919-23-5

cyclobutanol

Conditions
ConditionsYield
With hydrogenchloride In water for 3h; Heating;A 3%
B 92%
With hydrogenchloride In water at 100℃; for 3h;A n/a
B 57%
With hydrogenchloride In water at 100℃; for 0.00166667h;
formaldehyd
50-00-0

formaldehyd

allyl bromide
106-95-6

allyl bromide

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
Stage #1: formaldehyd; allyl bromide With zinc In ethyl acetate at 75℃; for 5h; Large scale;
Stage #2: With ammonium chloride for 2h; Large scale;
87%
With magnesium In diethyl ether for 6h; Heating;72%
With magnesium In diethyl ether39%
Stage #1: allyl bromide With tin In water at 20℃; for 0.166667h; Green chemistry;
Stage #2: formaldehyd In water at 20℃; for 3h; Green chemistry;
75 %Chromat.
With ammonium chloride; zinc In tetrahydrofuran at 20℃; for 2.5h; Inert atmosphere;
Butane-1,4-diol
110-63-4

Butane-1,4-diol

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With hydrogen at 350℃; Reagent/catalyst;85.9%
With 1-hexadecylcarboxylic acid at 330 - 345℃; under 760 Torr; for 32h;50%
With Er2O3 nanoparticles HT-150-24 at 350℃; for 5h;
Heating;
With yttria-stabilized zirconia at 325℃; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;
Butane-1,4-diol
110-63-4

Butane-1,4-diol

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With hydrogen at 350℃; for 0.6h; Reagent/catalyst; Temperature; Flow reactor;A n/a
B 85.9%
With Mg and Yb-containing organic foam into the binaryoxides at 350℃; Reagent/catalyst; Temperature; Inert atmosphere;A n/a
B 71.1%
With Er2O3 nanoparticles CM-1000 at 350℃; for 5h;
at 350℃; Reagent/catalyst; Flow reactor; Inert atmosphere;
epoxybutene
930-22-3

epoxybutene

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With formic acid; tributyl-amine; tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In water at 50 - 120℃; for 4.5 - 26h; Product distribution / selectivity;85.8%
With formic acid; tributyl-amine; tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In tetrahydrofuran; water at 62℃; for 1.21667 - 2.56667h; Product distribution / selectivity;78.5%
With ammonium formate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tributylphosphine In 1,4-dioxane for 2h; Heating;100 % Chromat.
3-chlorotetrahydrofuran
19311-38-7

3-chlorotetrahydrofuran

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With sodium In diethyl ether84%
With diethyl ether; sodium
(2R,3R)-2-But-3-enyloxy-3-heptadecafluorooctyl-tetrahydro-pyran

(2R,3R)-2-But-3-enyloxy-3-heptadecafluorooctyl-tetrahydro-pyran

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With methanol; toluene-4-sulfonic acid In tetrahydrofuran at 70℃; for 24h; deprotection of alcoholic OH;78%
D,L-1,2,4-butanetriol
3068-00-6

D,L-1,2,4-butanetriol

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With rhenium(VII) oxide; triphenylphosphine at 165℃; for 1h;77%
With rac-3-octanol at 170℃; for 1h;28%
2-But-3-enyl-benzo[1,3,2]dioxaborole

2-But-3-enyl-benzo[1,3,2]dioxaborole

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With hydroxide; dihydrogen peroxide76%
oxirane
75-21-8

oxirane

chloroethylene
75-01-4

chloroethylene

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
Stage #1: chloroethylene With magnesium In diethyl ether; ethylene dibromide for 2h; Reflux;
Stage #2: oxirane In diethyl ether; ethylene dibromide at -5 - 5℃; for 1h; Temperature; Solvent;
73.6%
vinylmagnesium chloride
3536-96-7

vinylmagnesium chloride

2-bromoethanol
540-51-2

2-bromoethanol

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
copper(I) bromide In tetrahydrofuran at -40 - 3℃; for 2.5h;72%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

homoalylic alcohol
627-27-0

homoalylic alcohol

C

(E/Z)-2-buten-1-ol
6117-91-5

(E/Z)-2-buten-1-ol

Conditions
ConditionsYield
With hydrogen at 350℃; for 0.6h; Reagent/catalyst; Flow reactor;A n/a
B 69.9%
C n/a
but-3-enoic acid
625-38-7

but-3-enoic acid

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride50%
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride
formaldehyd
50-00-0

formaldehyd

allylmagnesium bromide
2622-05-1

allylmagnesium bromide

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
Grignar reaction;46%
With diethyl ether
cyclobutanecarbonyl m-chlorobenzoyl peroxide
70458-21-8

cyclobutanecarbonyl m-chlorobenzoyl peroxide

A

homoalylic alcohol
627-27-0

homoalylic alcohol

B

Cyclopropylmethanol
2516-33-8

Cyclopropylmethanol

C

3-butenyl m-chlorobenzoate
70458-29-6

3-butenyl m-chlorobenzoate

D

cyclobutyl m-chlorobenzoate
70458-27-4

cyclobutyl m-chlorobenzoate

E

cyclopropylmethyl m-chlorobenzoate
70458-28-5

cyclopropylmethyl m-chlorobenzoate

F

cyclobutanol
2919-23-5

cyclobutanol

Conditions
ConditionsYield
With acetic acid; potassium iodide In tetrachloromethane at 26℃; Rate constant; on silica;A 4.3%
B 9.6%
C 19.5%
D 11.8%
E 45.5%
F 6.5%
With acetic acid; potassium iodide In neat (no solvent) at 26℃; Rate constant; on silica;
With acetic acid; potassium iodide In chloroform at 55℃; Rate constant;
With acetic acid; potassium iodide In tetrachloromethane at 55℃; Rate constant;
cyclobutanecarbonyl m-chlorobenzoyl peroxide
70458-21-8

cyclobutanecarbonyl m-chlorobenzoyl peroxide

A

homoalylic alcohol
627-27-0

homoalylic alcohol

B

3-butenyl m-chlorobenzoate
70458-29-6

3-butenyl m-chlorobenzoate

C

cyclobutyl m-chlorobenzoate
70458-27-4

cyclobutyl m-chlorobenzoate

D

cyclopropylmethyl m-chlorobenzoate
70458-28-5

cyclopropylmethyl m-chlorobenzoate

Conditions
ConditionsYield
With acetic acid; potassium iodide In tetrachloromethane at 26℃; Further byproducts given;A 4.3%
B 19.5%
C 11.8%
D 45.5%
1-bromo-4-butene
5162-44-7

1-bromo-4-butene

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With sodium carbonate for 15h; Heating;45%
formaldehyd
50-00-0

formaldehyd

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With magnesium In diethyl ether for 2h; Heating;45%
(E)-N-benzylidenebenzenesulfonamide
130552-90-8

(E)-N-benzylidenebenzenesulfonamide

allyl-trimethyl-silane
762-72-1

allyl-trimethyl-silane

A

homoalylic alcohol
627-27-0

homoalylic alcohol

B

N-(1-phenylbut-3-en-1-yl)benzenesulfonamide
217947-24-5

N-(1-phenylbut-3-en-1-yl)benzenesulfonamide

Conditions
ConditionsYield
With indium(III) chloride; chloro-trimethyl-silane In nitromethane at 20℃; for 6h; Sakurai-Hosomi reaction;A 8 % Spectr.
B 40%
Ti(OCH2CH(CH2)2)4

Ti(OCH2CH(CH2)2)4

A

homoalylic alcohol
627-27-0

homoalylic alcohol

B

Cyclopropylmethanol
2516-33-8

Cyclopropylmethanol

C

Di-(1-butenyl)ether (trans/trans)
22597-56-4

Di-(1-butenyl)ether (trans/trans)

D

bis(cyclopropylmethyl) ether
74976-40-2

bis(cyclopropylmethyl) ether

E

allylcarbinyl cyclopropylcarbinyl ether
74976-38-8

allylcarbinyl cyclopropylcarbinyl ether

Conditions
ConditionsYield
In gas byproducts: CH2CH(CH2)2, CH2(CH)2CH2; decomposition at a pressure of 0.01 mm Hg at 550°C; further compounds: (CH2)2CHCHO (trace), TiO2, H2 (<0.5%), C (4%); NMR; GC; mass spectra;A 37%
B 23%
C 12%
D 10%
E 18%
formaldehyd
50-00-0

formaldehyd

propene
187737-37-7

propene

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
In water at 220℃; under 6000.6 Torr; for 10h; Reagent/catalyst; Autoclave;2.47%
at 246℃;
In 1,4-dioxane at 149.84℃; for 4h;
oxirane
75-21-8

oxirane

tetrahydrofuran
109-99-9

tetrahydrofuran

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

homoalylic alcohol
627-27-0

homoalylic alcohol

oxirane
75-21-8

oxirane

vinylmagnesium chloride
3536-96-7

vinylmagnesium chloride

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With tetrahydrofuran
oxirane
75-21-8

oxirane

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With tetrahydrofuran
(RS)-3-bromotetrahydrofuran
19311-37-6

(RS)-3-bromotetrahydrofuran

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With diethyl ether; magnesium und Zersetzen mit Wasser;
With diethyl ether; sodium und Zersetzen mit Wasser;
4-methyl-1,3-dioxane
1120-97-4

4-methyl-1,3-dioxane

homoalylic alcohol
627-27-0

homoalylic alcohol

Conditions
ConditionsYield
With tricalcium diphosphate; water at 350℃;
homoalylic alcohol
627-27-0

homoalylic alcohol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

but-3-enyl 4-methylbenzenesulfonate
778-29-0

but-3-enyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃;100%
With potassium hydroxide In diethyl ether at 20℃; for 3h;99%
With dmap; triethylamine In dichloromethane at 20℃; for 3h; Inert atmosphere;99%
homoalylic alcohol
627-27-0

homoalylic alcohol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

4-methanesulfonyloxy-1-butene
40671-34-9

4-methanesulfonyloxy-1-butene

Conditions
ConditionsYield
With triethylamine In dichloromethane at -15℃; for 1h; Green chemistry;100%
With triethylamine In dichloromethane at -15℃; for 1.5h;100%
With triethylamine In dichloromethane at 0℃; for 5h;98%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

homoalylic alcohol
627-27-0

homoalylic alcohol

2-(3-butenyloxy)tetrahydropyran
59574-65-1

2-(3-butenyloxy)tetrahydropyran

Conditions
ConditionsYield
With toluene-4-sulfonic acid In diethyl ether for 5h; Ambient temperature;100%
In dichloromethane at 0℃; for 2h;95%
With hydrogenchloride at 20℃; Addition;91%
homoalylic alcohol
627-27-0

homoalylic alcohol

benzoyl chloride
98-88-4

benzoyl chloride

3-butenyl benzoate
18203-32-2

3-butenyl benzoate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
With triethylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;91%
With triethylamine In dichloromethane at 0 - 20℃; for 3h;91%
homoalylic alcohol
627-27-0

homoalylic alcohol

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

4-tert-butyldiphenylsilyloxy-1-butene
135006-32-5

4-tert-butyldiphenylsilyloxy-1-butene

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere;100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Inert atmosphere;100%
With 1H-imidazole In N,N-dimethyl-formamide for 17h; Ambient temperature;99%
homoalylic alcohol
627-27-0

homoalylic alcohol

acetylacetone
123-54-6

acetylacetone

(Z)-4-But-3-enyloxy-pent-3-en-2-one

(Z)-4-But-3-enyloxy-pent-3-en-2-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Heating;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

sodium 4-methylbenzenesulfinate
824-79-3

sodium 4-methylbenzenesulfinate

3-Iodo-4-(toluene-4-sulfonyl)-butan-1-ol

3-Iodo-4-(toluene-4-sulfonyl)-butan-1-ol

Conditions
ConditionsYield
With iodine In water; ethyl acetate at 20℃; for 2.5h; iodosulfonization;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

p-Methoxybenzyl bromide
2746-25-0

p-Methoxybenzyl bromide

1-(4-methoxybenzyloxy)-3-butene
142860-83-1

1-(4-methoxybenzyloxy)-3-butene

Conditions
ConditionsYield
Stage #1: homoalylic alcohol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.0833333h;
Stage #2: p-Methoxybenzyl bromide In tetrahydrofuran at 0℃; for 1h;
100%
Stage #1: homoalylic alcohol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: p-Methoxybenzyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 0 - 20℃; for 17h; Inert atmosphere;
100%
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 12h;96%
homoalylic alcohol
627-27-0

homoalylic alcohol

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

1-(4-methoxybenzyloxy)-3-butene
142860-83-1

1-(4-methoxybenzyloxy)-3-butene

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide100%
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 20h; Inert atmosphere; Schlenk technique;97%
Stage #1: homoalylic alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.333333h;
Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; mineral oil at 0 - 20℃; for 3h;
96%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

homoalylic alcohol
627-27-0

homoalylic alcohol

2-(but-3-en-1-yloxy)isoindoline-1,3-dione
80042-17-7

2-(but-3-en-1-yloxy)isoindoline-1,3-dione

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 2.5h; Inert atmosphere;100%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 4.5h; Mitsunobu Displacement; Inert atmosphere;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 16.5h;
homoalylic alcohol
627-27-0

homoalylic alcohol

triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

1-triisopropylsiloxy-3-butene
169310-77-4

1-triisopropylsiloxy-3-butene

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere;100%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;98%
With 1H-imidazole In tetrahydrofuran at 20℃; for 5.5h;95%
homoalylic alcohol
627-27-0

homoalylic alcohol

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

but-3-enyl octanoate
1070316-20-9

but-3-enyl octanoate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

Octanal
124-13-0

Octanal

cis-2-heptyl-4-fluorotetrahydro-2H-pyran

cis-2-heptyl-4-fluorotetrahydro-2H-pyran

Conditions
ConditionsYield
With Et4NF*5HF at 20℃; for 0.166667h; Prins reaction; stereoselective reaction;100%
With Et4NF*5HF at 20℃; for 0.166667h; Prins cyclization; stereoselective reaction;
homoalylic alcohol
627-27-0

homoalylic alcohol

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

cis-4-fluoro-2-(4-nitrophenyl)tetrahydro-2H-pyran

cis-4-fluoro-2-(4-nitrophenyl)tetrahydro-2H-pyran

Conditions
ConditionsYield
With Et4NF*5HF at 20℃; for 0.333333h; Prins reaction; stereoselective reaction;100%
With HSO4- exchanged Amberlyst A26 resin-supported hydrogen fluoride In 1,2-dichloro-ethane at 20℃; for 5h; diastereoselective reaction;82%
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone complex with hydrogen fluoride In dichloromethane at 20℃; for 3h; diastereoselective reaction;81%
With Et4NF*5HF at 20℃; for 0.333333h; Prins cyclization; stereoselective reaction;
homoalylic alcohol
627-27-0

homoalylic alcohol

benzaldehyde
100-52-7

benzaldehyde

cis-4-fluoro-2-phenyltetrahydro-2H-pyran

cis-4-fluoro-2-phenyltetrahydro-2H-pyran

Conditions
ConditionsYield
With Et4NF*5HF at 20℃; for 0.333333h; Prins reaction; stereoselective reaction;100%
With HSO4- exchanged Amberlyst A26 resin-supported hydrogen fluoride In 1,2-dichloro-ethane at 20℃; for 5h; diastereoselective reaction;83%
With titanium(IV) fluoride In dichloromethane at 20℃; for 2.5h; Prins cyclization reaction;82%
With tetrafluoroboric acid diethyl ether In dichloromethane at 23℃; for 20h; diastereoselective reaction;76%
With Et4NF*5HF at 20℃; for 0.333333h; Prins cyclization; stereoselective reaction;
4-nitro-phenol
100-02-7

4-nitro-phenol

homoalylic alcohol
627-27-0

homoalylic alcohol

1‐(but‐3‐en‐1‐yloxy)‐4‐nitrobenzene
40742-21-0

1‐(but‐3‐en‐1‐yloxy)‐4‐nitrobenzene

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction; Reflux;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

meta-nitrophenol
554-84-7

meta-nitrophenol

1-but-3-enyloxy-3-nitrobenzene
374588-08-6

1-but-3-enyloxy-3-nitrobenzene

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran100%
homoalylic alcohol
627-27-0

homoalylic alcohol

O-(4-methoxybenzyl)-trichloroacetimidate
89238-99-3

O-(4-methoxybenzyl)-trichloroacetimidate

1-(4-methoxybenzyloxy)-3-butene
142860-83-1

1-(4-methoxybenzyloxy)-3-butene

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In toluene for 0.25h; Inert atmosphere;100%
With lanthanum triflate In toluene at 20℃; Inert atmosphere;
homoalylic alcohol
627-27-0

homoalylic alcohol

acrolein
107-02-8

acrolein

(E)-5-hydroxypent-2-enal
112596-89-1

(E)-5-hydroxypent-2-enal

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; for 24h;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

Bromoacetaldehyde diethyl acetal
2032-35-1

Bromoacetaldehyde diethyl acetal

4-(2,2-diethoxyethoxy)but-1-ene
1343915-25-2

4-(2,2-diethoxyethoxy)but-1-ene

Conditions
ConditionsYield
Stage #1: homoalylic alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere;
Stage #2: Bromoacetaldehyde diethyl acetal In tetrahydrofuran; mineral oil at 0 - 68℃; for 66h; Inert atmosphere;
100%
Stage #1: homoalylic alcohol With sodium hydride In water at 0℃; for 1h;
Stage #2: Bromoacetaldehyde diethyl acetal In water at 0 - 80℃; for 24h; Temperature;
100%
Stage #1: homoalylic alcohol In tetrahydrofuran at 0℃; for 1h;
Stage #2: Bromoacetaldehyde diethyl acetal In tetrahydrofuran at 70℃; for 48h; Temperature;
96.3%
Stage #1: homoalylic alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h;
Stage #2: Bromoacetaldehyde diethyl acetal In tetrahydrofuran; mineral oil at 0 - 68℃; for 66h;
77 g
homoalylic alcohol
627-27-0

homoalylic alcohol

2-bromo-N-(2-methoxyphenyl)benzenesulfonamide
924107-85-7

2-bromo-N-(2-methoxyphenyl)benzenesulfonamide

2-bromo-N-(but-3-en-1-yl)-N-(2-methoxyphenyl)benzenesulfonamide
1582316-68-4

2-bromo-N-(but-3-en-1-yl)-N-(2-methoxyphenyl)benzenesulfonamide

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 3.16667h; Mitsunobu Displacement;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

C16H17BrN2O3S
1286918-84-0

C16H17BrN2O3S

2-bromo-N-(but-3-en-1-yl)-N-(2-morpholinophenyl)benzenesulfonamide
1582316-69-5

2-bromo-N-(but-3-en-1-yl)-N-(2-morpholinophenyl)benzenesulfonamide

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 3.16667h; Mitsunobu Displacement;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

2-bromo-N-(2-nitrophenyl)benzenesulfonamide
1304050-40-5

2-bromo-N-(2-nitrophenyl)benzenesulfonamide

2-bromo-N-(but-3-en-1-yl)-N-(2-nitrophenyl)benzenesulfonamide
1582316-72-0

2-bromo-N-(but-3-en-1-yl)-N-(2-nitrophenyl)benzenesulfonamide

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 3.16667h; Mitsunobu Displacement;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

N-(3-butenyl)phthalimide
52898-32-5

N-(3-butenyl)phthalimide

Conditions
ConditionsYield
With phthalimide; di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 3.03333h;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

diethyl (1-((4-methylphenyl)sulfonamido)prop-1-en-1-yl)phosphonate

diethyl (1-((4-methylphenyl)sulfonamido)prop-1-en-1-yl)phosphonate

(E)-diethyl (1-((N-(but-3-en-1-yl)-4-methylphenyl)sulfonamido)prop-1-en-1-yl)phosphonate

(E)-diethyl (1-((N-(but-3-en-1-yl)-4-methylphenyl)sulfonamido)prop-1-en-1-yl)phosphonate

Conditions
ConditionsYield
With tributylphosphine; di-isopropyl azodicarboxylate In tetrahydrofuran; toluene at 20℃; for 1h; Mitsunobu Displacement; Inert atmosphere;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

L-valine
72-18-4

L-valine

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

(S)-1-(but-3-en-1-yloxy)-3-methyl-1-oxobutan-2-aminium 4-methylbenzenesulfonate

(S)-1-(but-3-en-1-yloxy)-3-methyl-1-oxobutan-2-aminium 4-methylbenzenesulfonate

Conditions
ConditionsYield
In water; toluene for 24h; Reflux; Dean-Stark;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

2-oxo-4-phenylbutyric acid
710-11-2

2-oxo-4-phenylbutyric acid

but-3-en-1-yl 3-phenylpropanoate
327620-61-1

but-3-en-1-yl 3-phenylpropanoate

Conditions
ConditionsYield
With 3-nitro(diacetoxyiodo)benzene In dichloromethane at 20℃; for 8h; Sealed tube; Darkness; chemoselective reaction;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

ethyl α-nitrocinnamate
18315-80-5, 18315-86-1, 16508-09-1

ethyl α-nitrocinnamate

ethyl 3-phenyl-2-nitropropionate
16782-23-3

ethyl 3-phenyl-2-nitropropionate

Conditions
ConditionsYield
With lithium hexamethyldisilazane at -78℃; Michael Addition;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-fluoro-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzenesulfonamide
1403480-28-3

N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-fluoro-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzenesulfonamide

2-(but-3-en-1-yloxy)-N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-Nmethylphenylsulfonamido)-2-methylbutyl)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzenesulfonamide
1403480-44-3

2-(but-3-en-1-yloxy)-N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-Nmethylphenylsulfonamido)-2-methylbutyl)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzenesulfonamide

Conditions
ConditionsYield
Stage #1: homoalylic alcohol With sodium hydride at 0℃; for 0.333333h;
Stage #2: N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-fluoro-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzenesulfonamide In tetrahydrofuran at 0℃;
99%
Stage #1: homoalylic alcohol With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h;
Stage #2: N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-fluoro-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzenesulfonamide In tetrahydrofuran at 0℃; for 2.75h;
99.5%
homoalylic alcohol
627-27-0

homoalylic alcohol

3,4-dichloro-butan-1-ol
38300-63-9

3,4-dichloro-butan-1-ol

Conditions
ConditionsYield
With Oxone; sodium chloride In dichloromethane; water at 0℃; for 0.5h; Darkness; diastereoselective reaction;99%
With chlorine
With tetrachloromethane; chlorine at -20℃;

627-27-0Relevant articles and documents

A recoverable Pd nanocatalyst for selective semi-hydrogenation of alkynes: Hydrogenation of benzyl-propargylamines as a challenging model

Uberman, Paula M.,Costa, Natalia J. S.,Philippot, Karine,C. Carmona, Rafaela,Dos Santos, Alcindo A.,Rossi, Liane M.

, p. 4566 - 4574 (2014)

We describe a recyclable heterogeneous palladium nanocatalyst for the selective hydrogenation of alkynes to alkenes. The catalyst was prepared through the decomposition of the organometallic precursor Pd2(dba)3 over a magnetic support, obtaining well-dispersed Pd nanoparticles that formed exclusively on the support surface, with average diameter of 3.5 ± 0.8 nm. The catalytic activity was investigated in the hydrogenation reactions of alkenes and alkynes, and the chemo- and stereoselectivity were evaluated in the hydrogenation of benzyl-propargylamines. The catalyst is highly selective in performing semi-hydrogenation reactions under mild conditions and short reaction times, with good overall yields. Furthermore, it can be easily recovered and recycled, with no leaching of palladium detected, and activities and selectivity retained over multiple reaction cycles. This journal is

Selective production of 1,3-butadiene from 1,3-butanediol over Y2Zr2O7 catalyst

Matsuda, Asami,Matsumura, Yoshitaka,Sato, Satoshi,Yamada, Yasuhiro

, p. 1651 - 1658 (2021/07/21)

The vapor-phase dehydration of 1,3-butanediol (1,3-BDO) to produce 1,3-butadiene (BD) was evaluated over yttrium zirconate, which was prepared through a hydrothermal aging process. 1,3-BDO was initially dehydrated to three unsaturated alcohols, namely 3-buten-2-ol, 3-buten-1-ol, and 2-buten-1-ol, followed by the further dehydration to BD. The catalytic activity of yttrium zirconate was greatly dependent on the calcination temperature. Also, the reaction temperature was one of the important factors to produce BD efficiently. The selectivity to BD was increased with increasing reaction temperature up to 375°C, while coke formation resulted in catalyst deactivation together with by-product formation at higher temperatures. Yttrium zirconate catalyst calcined at 900°C showed a high BD yield of 95% at 375°C and 10 hr on stream.

Palladium-Catalyzed Selective Reduction of Carbonyl Compounds

Sarkar, Nabin,Mahato, Mamata,Nembenna, Sharanappa

, p. 2295 - 2301 (2020/05/18)

Two new examples of structurally characterized β-diketiminate analogues i.e., conjugated bis-guanidinate (CBG) supported palladium(II) complexes, [LPdX]2; [L= {(ArHN)(ArN)–C=N–C=(NAr)(NHAr)}; Ar = 2,6-Et2-C6H3], X = Cl (1), Br (2) have been reported. The synthesis of complexes 1–2 was achieved by two methods. Method A involves deprotonation of LH by nBuLi followed by the treatment of LLi (insitu formed) with PdCl2 in THF, which afforded compound 1 in good yield (75 %). In Method B, the reaction between free LH and PdX2 (X = Cl or Br) in THF allowed the formation of complexes 1 (Yield 73 %) and 2 (Yield 52 %), respectively. Moreover, these complexes were characterized thoroughly by several spectroscopic techniques (1H, 13C NMR, UV/Vis, FT-IR, and HRMS), including single-crystal X-ray structural and elemental analyses. In addition, we tested the catalytic activity of these complexes 1–2 for the hydroboration of carbonyl compounds with pinacolborane (HBpin). We observed that compound 1 exhibits superior catalytic activity when compared to 2. Compound 1 efficiently catalyzes various aldehydes and ketones under solvent-free conditions. Furthermore, both inter- and intramolecular chemoselectivity hydroboration of aldehydes over other functionalities have been established.

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