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6261-22-9

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6261-22-9 Usage

Chemical Properties

clear light yellow liquid

Uses

2-Pentyn-1-ol was employed as starting reagent for the synthesis of (-)-muricatacin. It was also used in the preparation of (2Z)-3-tributylstannyl-2-penten-1-ol.

Check Digit Verification of cas no

The CAS Registry Mumber 6261-22-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,2,6 and 1 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 6261-22:
(6*6)+(5*2)+(4*6)+(3*1)+(2*2)+(1*2)=79
79 % 10 = 9
So 6261-22-9 is a valid CAS Registry Number.
InChI:InChI=1/C5H8O/c1-2-3-4-5-6/h6H,2,5H2,1H3

6261-22-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A12999)  2-Pentyn-1-ol, 98%   

  • 6261-22-9

  • 1g

  • 195.0CNY

  • Detail
  • Alfa Aesar

  • (A12999)  2-Pentyn-1-ol, 98%   

  • 6261-22-9

  • 5g

  • 634.0CNY

  • Detail
  • Alfa Aesar

  • (A12999)  2-Pentyn-1-ol, 98%   

  • 6261-22-9

  • 25g

  • 2524.0CNY

  • Detail
  • Aldrich

  • (335312)  2-Pentyn-1-ol  98%

  • 6261-22-9

  • 335312-5G

  • 668.07CNY

  • Detail

6261-22-9SDS

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 2-Pentyn-1-ol

1.2 Other means of identification

Product number -
Other names 2-Pentyn-1-ol

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:6261-22-9 SDS

6261-22-9Synthetic route

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

but-1-yne
107-00-6

but-1-yne

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With paraformaldehyde In tetrahydrofuran; hexane99%
2-pent-2-ynyloxy-tetrahydro-pyran
6261-21-8

2-pent-2-ynyloxy-tetrahydro-pyran

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With silica gel; iron(III) chloride for 96h; Ambient temperature;92%
With sulfuric acid In ethanol Heating;
With sulfuric acid In methanol
hydrogenchloride In methanol for 10h; Ambient temperature; Yield given;
With water; sulfuric acid In methanol at 65℃; for 2h;
formaldehyd
50-00-0

formaldehyd

but-1-yne
107-00-6

but-1-yne

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
Stage #1: but-1-yne With ethyl bromide; magnesium In tetrahydrofuran at 20 - 30℃; for 0.75h; Cooling with ice;
Stage #2: formaldehyd In tetrahydrofuran at 20℃; for 3h; Reflux;
Stage #3: With sulfuric acid In water Cooling with ice;
90%
With n-butyllithium In diethyl ether63%
Stage #1: but-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Inert atmosphere;
Stage #2: formaldehyd In tetrahydrofuran; hexane at 0 - 50℃; for 4h; Inert atmosphere;
Stage #1: but-1-yne With ethyl bromide; magnesium In tetrahydrofuran at 30℃; for 0.75h; Cooling with ice;
Stage #2: formaldehyd In tetrahydrofuran for 3h; Reflux;
Stage #1: but-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2.5h;
Stage #2: formaldehyd In tetrahydrofuran at 20℃; for 16h;
ethyl bromide
74-96-4

ethyl bromide

propargyl alcohol
107-19-7

propargyl alcohol

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With lithium amide; ammonia for 1h; Heating;85%
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran at -30℃; for 18h;70%
With lithium; ferric nitrate In tetrahydrofuran; ammonia for 2h;50%
ethyl bromide
74-96-4

ethyl bromide

lithium
7439-93-2

lithium

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
In ammonia85%
2-(2-pentynyloxy)tetrahydropyran

2-(2-pentynyloxy)tetrahydropyran

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With methanol; pyridinium p-toluenesulfonate at 50℃; for 3h;54%
ethyl bromide
74-96-4

ethyl bromide

3-(tetrahydropyran-2'-yloxy)propyne
6089-04-9

3-(tetrahydropyran-2'-yloxy)propyne

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With sodium amide Behandeln des Reaktionsprodukts mit wss.-methanol.Schwefelsaeure;
3-(tetrahydropyran-2'-yloxy)propyne
6089-04-9

3-(tetrahydropyran-2'-yloxy)propyne

ethyl iodide
75-03-6

ethyl iodide

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With sodium amide Behandeln des Reaktionsprodukts mit wss.-methanol.Schwefelsaeure;
4-chlorobut-2-yn-1-ol
13280-07-4

4-chlorobut-2-yn-1-ol

methylmagnesium bromide
75-16-1

methylmagnesium bromide

A

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

B

2-methyl-2,3-butadiene-1-ol
22742-89-8

2-methyl-2,3-butadiene-1-ol

Conditions
ConditionsYield
In diethyl ether at 5℃;
pent-2-ynyl acetate
10574-76-2

pent-2-ynyl acetate

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With sodium hydroxide In methanol; water Heating;
1-(1-ethoxy-ethoxy)-pent-2-yne
68480-09-1

1-(1-ethoxy-ethoxy)-pent-2-yne

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With sulfuric acid
1-vinyloxy-pent-2-yne
18450-62-9

1-vinyloxy-pent-2-yne

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride at 19.9 - 34.9℃; Kinetics;
4-chlorobut-2-yn-1-ol
13280-07-4

4-chlorobut-2-yn-1-ol

methyl magnesium iodide
917-64-6

methyl magnesium iodide

A

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

B

2-methyl-2,3-butadiene-1-ol
22742-89-8

2-methyl-2,3-butadiene-1-ol

Conditions
ConditionsYield
In diethyl ether at -30℃; for 0.5h; Yield given. Yields of byproduct given;
In diethyl ether at -30℃; for 0.5h; Yield given;
dimethylacetylene
503-17-3

dimethylacetylene

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

ethyl iodide
75-03-6

ethyl iodide

propargyl alcohol
107-19-7

propargyl alcohol

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With lithium amide; ammonia In tetrahydrofuran
Stage #1: propargyl alcohol With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78 - -65℃; for 1h; Cooling with acetone-dry icex; Inert atmosphere;
Stage #2: ethyl iodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -75 - 30℃; for 18h;
4-chlorobut-2-yn-1-ol
13280-07-4

4-chlorobut-2-yn-1-ol

methyl iodide
74-88-4

methyl iodide

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With magnesium 1.) Et2O, THF, 2.) Et2O, THF, 1 h, reflux; Yield given. Multistep reaction;
formaldehyd
50-00-0

formaldehyd

butyne-(1)-magnesium bromide

butyne-(1)-magnesium bromide

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

4-chlorobut-2-yn-1-ol
13280-07-4

4-chlorobut-2-yn-1-ol

methyl magnesium halide

methyl magnesium halide

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With diethyl ether
1-bromo-pent-2-yne
16400-32-1

1-bromo-pent-2-yne

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOAc / Heating
2: NaOH / methanol; H2O / Heating
View Scheme
ethyl bromide
74-96-4

ethyl bromide

propargyl alcohol
107-19-7

propargyl alcohol

ferric nitrate
7782-61-8

ferric nitrate

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With ammonia; lithium In water
1-(1-methoxy-1-methyl-ethoxy)-pent-2-yne
84282-45-1

1-(1-methoxy-1-methyl-ethoxy)-pent-2-yne

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With water; Amberlyst 15 at 22℃; for 1.5h; Product distribution / selectivity; Inert atmosphere;95.3 %Chromat.
1-(1-methoxy-1-methyl-propoxy)-pent-2-yne
1263216-89-2

1-(1-methoxy-1-methyl-propoxy)-pent-2-yne

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With water; sulfuric acid at 22℃; for 1.5h;
formaldehyd
50-00-0

formaldehyd

1-butynyl magnesium bromide
51207-09-1

1-butynyl magnesium bromide

butyne-(1)-magnesium bromide

butyne-(1)-magnesium bromide

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

ethyl pent-2-ynoate
55314-57-3

ethyl pent-2-ynoate

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Conditions
ConditionsYield
With diisobutylaluminium hydride In dichloromethane at -78℃; for 1h; Inert atmosphere;
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

methanesulfonic acid pent-2-ynyl ester
81159-43-5

methanesulfonic acid pent-2-ynyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at -5℃; for 0.416667h;100%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;69%
With triethylamine In dichloromethane at 20℃; for 0.5h;
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

cis-2-penten-1-ol
1576-95-0

cis-2-penten-1-ol

Conditions
ConditionsYield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760.051 Torr;99.5%
With hydrogen; Lindlar's catalyst98%
With hydrogen; ethylenediamine; P2-Nickel In ethanol for 8h;96%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

A

cis-2-penten-1-ol
1576-95-0

cis-2-penten-1-ol

B

pentan-1-ol
71-41-0

pentan-1-ol

Conditions
ConditionsYield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760 Torr; Kinetics;A 99.5%
B n/a
With hydrogen; ethylenediamine; Pd on pumice In tetrahydrofuran for 0.5h;A 98 % Chromat.
B 2 % Chromat.
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

toluene-4-sulfonic acid pent-2-ynyl ester
92666-05-2

toluene-4-sulfonic acid pent-2-ynyl ester

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane for 0.333333h; Ambient temperature;98%
With potassium hydroxide In diethyl ether at 0℃; for 4h;98%
With potassium hydroxide In diethyl ether at 20℃;89%
N-(tert-butoxycarbonyl)-4-nitrobenzenesulfonamide
895153-23-8

N-(tert-butoxycarbonyl)-4-nitrobenzenesulfonamide

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

4-nitro-N-(pent-2-yn-1-yl)benzene-1-sulfonamide
1489246-86-7

4-nitro-N-(pent-2-yn-1-yl)benzene-1-sulfonamide

Conditions
ConditionsYield
Stage #1: N-(tert-butoxycarbonyl)-4-nitrobenzenesulfonamide; pent-2-yn-1-ol With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
Stage #2: With trifluoroacetic acid In dichloromethane at 20℃; Inert atmosphere;
98%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

5-bromo-2-[(4-hydroxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester
287108-60-5

5-bromo-2-[(4-hydroxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester

5-bromo-3-methyl-2-[methyl-(4-pent-2-ynyloxy-benzenesulfonyl)-amino]-benzoic acid
287108-63-8

5-bromo-3-methyl-2-[methyl-(4-pent-2-ynyloxy-benzenesulfonyl)-amino]-benzoic acid

Conditions
ConditionsYield
97%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

C10H8N2O2S

C10H8N2O2S

pent-2-yn-1-yl 5-(p-tolyl)-1,2,3-thiadiazole-4-carboxylate

pent-2-yn-1-yl 5-(p-tolyl)-1,2,3-thiadiazole-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In 1,2-dichloro-ethane at 0 - 20℃; for 3.5h; Inert atmosphere;97%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

2,2,2-trichloroacetophenone
2902-69-4

2,2,2-trichloroacetophenone

pent-2-yn-1-yl benzoate

pent-2-yn-1-yl benzoate

Conditions
ConditionsYield
With N,N,N',N'',N'''-pentamethyldiethylenetriamine In neat (no solvent) at 20 - 25℃; for 6h;96%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

tris(2-pentyn-1-oxy)borane
1013654-71-1

tris(2-pentyn-1-oxy)borane

Conditions
ConditionsYield
With boric acid In toluene for 12h; Heating;95%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

C7H4N2O2S2

C7H4N2O2S2

pent-2-yn-1-yl 5-(thiophen-2-yl)-1,2,3-thiadiazole-4-carboxylate

pent-2-yn-1-yl 5-(thiophen-2-yl)-1,2,3-thiadiazole-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In 1,2-dichloro-ethane at 0 - 20℃; for 3.5h; Inert atmosphere;95%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1-<(tert-butyldimethylsilyl)-oxy>-2-pentyne
112373-26-9

1-<(tert-butyldimethylsilyl)-oxy>-2-pentyne

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 5h; Inert atmosphere;94%
With triethylamine In dichloromethane at 20℃;85%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; silylation;
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

4-methyl-N-(prop-1-yn-1-yl)benzenesulfonamide
286376-23-6

4-methyl-N-(prop-1-yn-1-yl)benzenesulfonamide

N-but-2-ynyl-4-methyl-N-pent-2-ynyl-benzenesulfonamide
615562-38-4

N-but-2-ynyl-4-methyl-N-pent-2-ynyl-benzenesulfonamide

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 15h; Mitsunobu reaction;94%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

tris-iso-propylsilyl acetylene
89343-06-6

tris-iso-propylsilyl acetylene

(E)-3-ethyl-5-(triisopropylsilyl)pent-2-en-4-yn-1-ol

(E)-3-ethyl-5-(triisopropylsilyl)pent-2-en-4-yn-1-ol

Conditions
ConditionsYield
With ammonium acetate; palladium diacetate; C28H29N2OP In toluene; acetonitrile at 60℃; for 20h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique; Sealed tube; stereoselective reaction;94%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

2-Nitrobenzenesulfonamide
5455-59-4

2-Nitrobenzenesulfonamide

2-nitro-N-(pent-2-yn-1-yl)benzene-1-sulfonamide

2-nitro-N-(pent-2-yn-1-yl)benzene-1-sulfonamide

Conditions
ConditionsYield
With 2-(diphenylphosphino)pyridine; di-tert-butyl-diazodicarboxylate In dichloromethane at 20℃; for 2h; Mitsunobu reaction;92%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

[[2,5-Ph2-3,4-Tol2(η5-C4CO)]Ru(CO)2]2

[[2,5-Ph2-3,4-Tol2(η5-C4CO)]Ru(CO)2]2

(E)-[2,5-Ph2-3,4-Tol2(η5-C4COH)]Ru(CO)2(C(Et)CHCHO)
1224466-20-9, 1224663-27-7

(E)-[2,5-Ph2-3,4-Tol2(η5-C4COH)]Ru(CO)2(C(Et)CHCHO)

Conditions
ConditionsYield
In (2)H8-toluene addn. of excess of EtCCCH2OH to soln. of Ru complex in C6D5CD3, shaking for 10-30 min until dissolving; addn. of pentane, filtration or concn., addn. of pentane, isolation of solid, crystn. by slow diffusion of pentane or hexane into THF soln.;90%
In dichloromethane-d2 addn. of excess of EtCCCH2OH to soln. of Ru complex in CD2Cl2, storage for 3-5 min; concn., addn. of pentane, isolation of solid;90%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

5-hydroxybicyclo[4.2.0]octa-1,3,5-trien-7-one

5-hydroxybicyclo[4.2.0]octa-1,3,5-trien-7-one

C13H12O2
1606590-17-3

C13H12O2

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 40℃;90%
5-Phenyl-1,2,3-thiadiazole-4-carboxylic acid
58792-15-7

5-Phenyl-1,2,3-thiadiazole-4-carboxylic acid

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

pent-2-yn-1-yl 5-phenyl-1,2,3-thiadiazole-4-carboxylate

pent-2-yn-1-yl 5-phenyl-1,2,3-thiadiazole-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In 1,2-dichloro-ethane at 0 - 20℃; for 3.5h; Inert atmosphere;90%
phenylacetic acid
103-82-2

phenylacetic acid

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

C13H14O2

C13H14O2

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;90%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

ethyl 3-ethyl-3,4-pentadienoate

ethyl 3-ethyl-3,4-pentadienoate

Conditions
ConditionsYield
With propionic acid at 140 - 145℃; for 5h;89%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

(2Z)-3-chloro-2-{[(1Z)-2-chloro-1-(hydroxymethyl)but-1-enyl]selanyl}pent-2-en-1-ol

(2Z)-3-chloro-2-{[(1Z)-2-chloro-1-(hydroxymethyl)but-1-enyl]selanyl}pent-2-en-1-ol

Conditions
ConditionsYield
With selenium dichloride In tetrahydrofuran at 20℃; for 0.75h;89%
With selenium(II) chloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; regiospecific reaction;89%
Multi-step reaction with 2 steps
1: selenium tetrachloride / chloroform / 0.5 h / 0 °C / Inert atmosphere
2: [(2)H6]acetone / 2.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: selenium tetrachloride / chloroform / 0.5 h / 0 °C
2: d6-acetone / 2.5 h / 20 °C
View Scheme
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

2-pent-2-ynyloxy-tetrahydro-pyran
6261-21-8

2-pent-2-ynyloxy-tetrahydro-pyran

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 0℃; for 3h;87%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

4-methyl-N-prop-2-ynylbenzenesulfonamide
55022-46-3

4-methyl-N-prop-2-ynylbenzenesulfonamide

4-methyl-N-(pent-2-yn-1-yl)-N-(prop-2-yn-1-yl)-benzenesulfonamide
222320-31-2

4-methyl-N-(pent-2-yn-1-yl)-N-(prop-2-yn-1-yl)-benzenesulfonamide

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 15h; Mitsunobu reaction;87%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

(E)-3-ethyl-6,6-dimethylhept-2-en-4-yn-1-ol

(E)-3-ethyl-6,6-dimethylhept-2-en-4-yn-1-ol

Conditions
ConditionsYield
With ammonium acetate; C40H37N2OP; bis(dibenzylideneacetone)-palladium(0) In toluene; acetonitrile at 60℃; for 16h; Inert atmosphere; stereoselective reaction;86%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

3-methylsalicylic acid methyl ester
23287-26-5

3-methylsalicylic acid methyl ester

methyl 3-methyl-2-(2-pentynyloxy)benzoate
488150-69-2

methyl 3-methyl-2-(2-pentynyloxy)benzoate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 5h; Mitsunobu reaction;85%
pent-2-yn-1-ol
6261-22-9

pent-2-yn-1-ol

allyl bromide
106-95-6

allyl bromide

allyl pent-2-ynyl ether
94513-13-0

allyl pent-2-ynyl ether

Conditions
ConditionsYield
Stage #1: pent-2-yn-1-ol With sodium hydride In tetrahydrofuran at 20℃; for 2h;
Stage #2: allyl bromide In tetrahydrofuran at 20℃; for 2h;
85%
Stage #1: pent-2-yn-1-ol With sodium hydride In tetrahydrofuran at 0 - 20℃;
Stage #2: allyl bromide In tetrahydrofuran at 20℃; for 2h;
85%
Stage #1: pent-2-yn-1-ol With sodium hydride In tetrahydrofuran at 0 - 20℃;
Stage #2: allyl bromide In tetrahydrofuran at 0 - 20℃;
85%
With sodium hydride In tetrahydrofuran at 20℃; for 2h;85%

6261-22-9Relevant articles and documents

Efficient and chemoselective hydrogenation of aldehydes catalyzed by well-defined PN3-pincer manganese(ii) catalyst precursors: An application in furfural conversion

Gholap, Sandeep Suryabhan,Dakhil, Abdullah Al,Chakraborty, Priyanka,Li, Huaifeng,Dutta, Indranil,Das, Pradip K.,Huang, Kuo-Wei

supporting information, p. 11815 - 11818 (2021/11/30)

Well-defined and air-stable PN3-pincer manganese(ii) complexes were synthesized and used for the hydrogenation of aldehydes into alcohols under mild conditions using MeOH as a solvent. This protocol is applicable for a wide range of aldehydes containing various functional groups. Importantly, α,β-unsaturated aldehydes, including ynals, are hydrogenated with the CC double bond/CC triple bond intact. Our methodology was demonstrated for the conversion of biomass derived feedstocks such as furfural and 5-formylfurfural to furfuryl alcohol and 5-(hydroxymethyl)furfuryl alcohol respectively.

Direct Access to Allenylphosphine Oxides via a Metal Free Coupling of Propargylic Substrates with P(O)H Compounds

Yang, Chun-Hua,Fan, Huihui,Li, Huimin,Hou, Shenyin,Sun, Xiangkun,Luo, Donghao,Zhang, Yinchao,Yang, Zhantao,Chang, Junbiao

supporting information, p. 9438 - 9441 (2019/11/20)

A direct and convenient approach for the coupling of propargylic substrates with diphenylphosphine oxide in the presence of Tf2O and 2,6-lutidine has been developed. The method provides a general approach for the construction of attractive allenylphosphoryl skeletons with high atom and step economy under metal free conditions.

A tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - triene synthetic method of eighteen carbon (by machine translation)

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Paragraph 0030; 0032, (2018/09/28)

The invention relates to a natural [...] pheromone component novel synthesis method, in particular relates to a tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - eighteen carbon triene synthetic method, it has [...], is non-toxic and harmless, which belongs to the field of drug synthesis. The invention uses inexpensive and easily obtained a halopropynyl alcohol as the reaction of the starting material, in order to iodo reagent catalytic coupling reaction as a key step, after six-step reaction, smooth synthetic tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - eighteen carbon triene, the operation is simple, low cost, easily obtained and cheap materials, mild reaction conditions, high yield, the large scale preparation. (by machine translation)

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