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917-92-0 Usage

Chemical Properties

colourless liquid

Uses

3,3-Dimethyl-1-butyne is used as an active pharmaceutical intermediate for terbinafine. It is also used in the preparation of 2,2,7,7-tetramethyl-octa-3,5-diyne. Further, it is used in the synthesis of erythro and threo isomers of B-(3,3-dimethyl-1,2-dideuterio-1-butyl)-9-BBN by hydroboration-deuteronolysis-hydroboration sequence.

Check Digit Verification of cas no

The CAS Registry Mumber 917-92-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,1 and 7 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 917-92:
(5*9)+(4*1)+(3*7)+(2*9)+(1*2)=90
90 % 10 = 0
So 917-92-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H10/c1-5-6(2,3)4/h1H,2-4H3

917-92-0 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • TCI America

  • (B1114)  3,3-Dimethyl-1-butyne  >96.0%(GC)

  • 917-92-0

  • 10mL

  • 390.00CNY

  • Detail
  • TCI America

  • (B1114)  3,3-Dimethyl-1-butyne  >96.0%(GC)

  • 917-92-0

  • 100mL

  • 1,980.00CNY

  • Detail
  • Alfa Aesar

  • (A14013)  3,3-Dimethyl-1-butyne, 98%   

  • 917-92-0

  • 5g

  • 423.0CNY

  • Detail
  • Alfa Aesar

  • (A14013)  3,3-Dimethyl-1-butyne, 98%   

  • 917-92-0

  • 25g

  • 1533.0CNY

  • Detail
  • Aldrich

  • (244392)  3,3-Dimethyl-1-butyne  98%

  • 917-92-0

  • 244392-5G

  • 580.32CNY

  • Detail
  • Aldrich

  • (244392)  3,3-Dimethyl-1-butyne  98%

  • 917-92-0

  • 244392-25G

  • 2,577.51CNY

  • Detail

917-92-0SDS

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 3,3-Dimethyl-1-butyne

1.2 Other means of identification

Product number -
Other names 1-Butyne, 3,3-dimethyl-

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:917-92-0 SDS

917-92-0Synthetic route

2,2-dichloro-3,3-dimethylbutane
594-84-3

2,2-dichloro-3,3-dimethylbutane

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 60℃; for 2h;99%
With potassium tert-butylate In dimethyl sulfoxide for 2h;90%
With 1,6,17-trioxa-(2',5')-diphenyl-1',3',4'-oxadiazolo[6]phane; 3,4-benz-1,6,17-(O)3-(2',5')-Ph2-1',3',4'-oxadiazolo[6]phane; sodium methylate In dimethyl sulfoxide; Petroleum ether at 30℃; for 4h;65%
1,2-dibromo-3,3-dimethylbutane
640-21-1

1,2-dibromo-3,3-dimethylbutane

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 60℃; for 2h;91%
With potassium hydroxide; tetraoctyl ammonium bromide In Petroleum ether at 90℃; for 6h;86%
With potassium tert-butylate; 18-crown-6 ether In Petroleum ether84%
With potassium hydroxide; 2,5-dimethyl-2,5-hexanediol at 100℃; for 0.75h;80%
With potassium tert-butylate Heating;
1,2-dibromo-3,3-dimethylbutane
640-21-1

1,2-dibromo-3,3-dimethylbutane

A

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

B

2-Bromo-3,3-dimethyl-1-butene
33693-77-5

2-Bromo-3,3-dimethyl-1-butene

C

1-bromo-3,3-dimethylbut-1-ene
13352-80-2

1-bromo-3,3-dimethylbut-1-ene

Conditions
ConditionsYield
With potassium hydroxide; Aliquat 336 In xylene Heating;A 91%
B n/a
C n/a
2-cyclohexylacetylene
931-48-6

2-cyclohexylacetylene

N-benzyl 4,4-dimethyl-pent-2-ynylamine
1610010-33-7

N-benzyl 4,4-dimethyl-pent-2-ynylamine

A

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

B

N-benzyl-3-cyclohexylprop-2-yn-1-amine

N-benzyl-3-cyclohexylprop-2-yn-1-amine

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A n/a
B 91%
acetylene
74-86-2

acetylene

tert-butyl alcohol
75-65-0

tert-butyl alcohol

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With palladium(II) sulfate; nickel(II) sulfate hexahydrate; methanesulfonic acid; sulfuric acid; sodium hydroxide In water at -5 - 5℃; under 3750.38 Torr; for 3h; Reagent/catalyst; Autoclave;90.2%
1-phenyl-4,4-dimethylpent-2-yn-1-one
17475-11-5

1-phenyl-4,4-dimethylpent-2-yn-1-one

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With potassium hydroxide; water In 1,3,5-trimethyl-benzene distillation;90%
1,1-dichloro-3,3-dimethyl-1-butene
32363-94-3

1,1-dichloro-3,3-dimethyl-1-butene

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran at -30 - 0℃; for 1h; Dehalogenation;90%
90%
4-Phenyl-1-butyne
16520-62-0

4-Phenyl-1-butyne

N-benzyl 4,4-dimethyl-pent-2-ynylamine
1610010-33-7

N-benzyl 4,4-dimethyl-pent-2-ynylamine

A

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

B

N-benzyl-5-phenylpent-2-yn-1-amine

N-benzyl-5-phenylpent-2-yn-1-amine

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A n/a
B 89%
N-benzyl 4,4-dimethyl-pent-2-ynylamine
1610010-33-7

N-benzyl 4,4-dimethyl-pent-2-ynylamine

hex-1-yne
693-02-7

hex-1-yne

A

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

B

N-benzylhept-2-yn-1-amine
1379038-80-8

N-benzylhept-2-yn-1-amine

Conditions
ConditionsYield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;A n/a
B 87%
3,3-dimethyl-1-(triphenylphosphanylidene)butan-2-one
288390-74-9

3,3-dimethyl-1-(triphenylphosphanylidene)butan-2-one

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
at 750℃; under 0.01 Torr; for 3h;82%
at 750℃; for 3h;82%
1,1-diamino-3,3-dimethylbutane

1,1-diamino-3,3-dimethylbutane

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
Stage #1: 1,1-diamino-3,3-dimethylbutane With potassium bisulfite In hexane at 95℃; for 5h;
Stage #2: With hypochlorous acid phenyl ester In hexane at 115℃; for 7h; Temperature;
79%
Ru3(CO)4{Ph2PC(H)C(Bu(t))}{(Ph2PCC(Bu(t))}(PPh2)

Ru3(CO)4{Ph2PC(H)C(Bu(t))}{(Ph2PCC(Bu(t))}(PPh2)

A

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

B

tert-butylethylene
558-37-2

tert-butylethylene

C

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

Conditions
ConditionsYield
In gas treatment in sealed vial under H2 for 45 min at 120 °C, partly decompd.;A 2.7%
B 19%
C 78%
3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
Stage #1: 3,3-dimethyl-butan-2-one With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: With diethyl chlorophosphate In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
Stage #3: With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
78%
With Nonafluorobutanesulfonyl fluoride; 1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2Λ5,4Λ5-catenadi(phosphazene) In 1-methyl-pyrrolidin-2-one at -10 - 20℃;60%
Multi-step reaction with 2 steps
1: phosphorus pentachloride / 12 h / 0 °C
2: potassium tert-butylate / dimethyl sulfoxide / 2 h
View Scheme
1,1-dichloro-3,3-dimethylbutane
6130-96-7

1,1-dichloro-3,3-dimethylbutane

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With potassium hydroxide; 2,3-dimethyl-2,3-butane diol; Aliquat 336 In Petroleum ether for 1.5h; Heating;62%
With sodium amide; mineral oil at 90 - 95℃;
1-Bromopinacolon
5469-26-1

1-Bromopinacolon

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With hydrogen bromide; toluene-4-sulfonic acid hydrazide In ethanol Ambient temperature;51%
(E)-3,3-dimethyl-1-butenyl(p-trifluoromethylphenyl)(tetrafluoroborato)-λ(3)-bromane

(E)-3,3-dimethyl-1-butenyl(p-trifluoromethylphenyl)(tetrafluoroborato)-λ(3)-bromane

potassium bis(triflyl)methanide
33249-12-6

potassium bis(triflyl)methanide

A

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

B

C9H12F6O4S2
1271169-55-1

C9H12F6O4S2

Conditions
ConditionsYield
In dichloromethane at -78 - 20℃; for 4h; Inert atmosphere;A 38%
B 43%
2,2-dichloro-3,3-dimethylbutane
594-84-3

2,2-dichloro-3,3-dimethylbutane

A

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

B

2-chloro-3,3-dimethyl-1-butene
27843-27-2

2-chloro-3,3-dimethyl-1-butene

Conditions
ConditionsYield
With potassium hydroxide; tetraoctyl ammonium bromide In Petroleum ether at 90℃; for 8h;A 38%
B n/a
(E)-3,3-dimethyl-1-butenyl(p-trifluoromethylphenyl)(tetrafluoroborato)-λ(3)-bromane

(E)-3,3-dimethyl-1-butenyl(p-trifluoromethylphenyl)(tetrafluoroborato)-λ(3)-bromane

potassium bis(trifluoromethylsulfonyl)imide
90076-67-8

potassium bis(trifluoromethylsulfonyl)imide

A

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

B

C8H11F6NO4S2
1271169-73-3

C8H11F6NO4S2

Conditions
ConditionsYield
In dichloromethane at -78 - 20℃; for 4h; Inert atmosphere;A 18%
B 32%
(E)-3,3-dimethyl-1-butenyl(p-trifluoromethylphenyl)(tetrafluoroborato)-λ(3)-bromane

(E)-3,3-dimethyl-1-butenyl(p-trifluoromethylphenyl)(tetrafluoroborato)-λ(3)-bromane

C9HF18O4S2(1-)*K(1+)
152192-85-3

C9HF18O4S2(1-)*K(1+)

A

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

B

C15H12F18O4S2
1271169-60-8

C15H12F18O4S2

Conditions
ConditionsYield
In dichloromethane at -78 - 20℃; for 4h; Inert atmosphere;A 15%
B 31%
pivalaldehyde
630-19-3

pivalaldehyde

C8H21N4PSi
145397-30-4

C8H21N4PSi

A

α-trimethylsilyloxy-α-tert-butylmethyl-N,N,N',N'-tetramethylphosphondiamide

α-trimethylsilyloxy-α-tert-butylmethyl-N,N,N',N'-tetramethylphosphondiamide

B

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
In pentane at 20℃;A 30%
B 14%
tert-butylethylene
558-37-2

tert-butylethylene

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With bromine; methyl cyclohexane at -60℃; und anschliessend mit Natriumamid in fluessigem Ammoniak bei -70grad;
2-chloro-3,3-dimethyl-1-butene
27843-27-2

2-chloro-3,3-dimethyl-1-butene

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With potassium hydroxide; ethanol; mineral oil at 200℃;
4,4-dimethyl-2-pentynoic acid
52418-50-5

4,4-dimethyl-2-pentynoic acid

A

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

B

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

3,3-dimethyl-[1-3H]but-1-yne
13139-80-5

3,3-dimethyl-[1-3H]but-1-yne

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With amine buffer; water at 25℃; Rate constant; μ = 0.10 M;
3,3-dimethylbut-1-en-2-yl diethyl phosphate
949091-15-0

3,3-dimethylbut-1-en-2-yl diethyl phosphate

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran
2-tert-butyl-4-methyl-1,3-oxazin-6-one
51779-49-8

2-tert-butyl-4-methyl-1,3-oxazin-6-one

A

tert-butyl isocyanide
630-18-2

tert-butyl isocyanide

B

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

C

1,2-propanediene
463-49-0

1,2-propanediene

D

acetonitrile
75-05-8

acetonitrile

E

prop-1-yne
74-99-7

prop-1-yne

Conditions
ConditionsYield
at -263.2℃; Mechanism; Irradiation;
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

3-(t-butyldimethylsilyloxy)prop-1-ynyllithium
91509-32-9

3-(t-butyldimethylsilyloxy)prop-1-ynyllithium

phenylcarbonochloridothioate
1005-56-7

phenylcarbonochloridothioate

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With pyridine; dmap 1.) THF, 75 min, from -70 deg C to r.t.; 2.) acetonitrile, 1.5 h; Yield given. Multistep reaction;
(E)-3,3-dimethyl-1-butenyl(phenyl)iodonium tetrafluoroborate

(E)-3,3-dimethyl-1-butenyl(phenyl)iodonium tetrafluoroborate

A

iodobenzene
591-50-4

iodobenzene

B

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With tetrabutyl-ammonium chloride; tetrabutylammonium perchlorate In acetonitrile at 25℃; Rate constant; var. solvents and var. concentration of reagents;
1,1-dichloro-3,3-dimethyl2-butanol methanesulfonate
246023-20-1

1,1-dichloro-3,3-dimethyl2-butanol methanesulfonate

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran at -30 - 0℃; for 1h; Elimination;78 % Chromat.
1,1,1-trichloro-3,3-dimethyl-2-butanol methanesulfonate
263904-19-4

1,1,1-trichloro-3,3-dimethyl-2-butanol methanesulfonate

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran; diethyl ether at -10 - 0℃; for 1h; Elimination;81 % Chromat.
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

2,2,7,7-tetramethyl-octa-3,5-diyne
6130-98-9

2,2,7,7-tetramethyl-octa-3,5-diyne

Conditions
ConditionsYield
With trimethylamine-N-oxide; sodium acetate; palladium dichloride; copper(l) iodide In acetonitrile at 20℃; for 9h;100%
With 1,4-diaza-bicyclo[2.2.2]octane; air; palladium diacetate; copper(l) iodide In acetonitrile at 20℃; for 2h;100%
With copper(l) iodide; ethyl 2,2-dibromoacetoacetate; triethylamine In dichloromethane at 20℃; for 24h;99%
formaldehyd
50-00-0

formaldehyd

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

4,4-dimethylpent-2-yn-1-ol
52323-98-5

4,4-dimethylpent-2-yn-1-ol

Conditions
ConditionsYield
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran at 0 - 20℃;
Stage #2: formaldehyd In tetrahydrofuran at 20 - 65℃; for 17h;
Stage #3: With water In ethyl acetate
100%
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: formaldehyd In tetrahydrofuran; hexane at -78 - 20℃; for 1h;
98%
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78 - 20℃; for 2h;97%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

(E)-5-trifluoromethanesulfonyloxymethylidene-1-cyclopenten-1-yl trifluoromethanesulfonate
134267-79-1

(E)-5-trifluoromethanesulfonyloxymethylidene-1-cyclopenten-1-yl trifluoromethanesulfonate

1-(3,3-Dimethyl-but-1-ynyl)-5-[4,4-dimethyl-pent-2-yn-(E)-ylidene]-cyclopentene
134251-51-7

1-(3,3-Dimethyl-but-1-ynyl)-5-[4,4-dimethyl-pent-2-yn-(E)-ylidene]-cyclopentene

Conditions
ConditionsYield
With diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran Ambient temperature;100%
With diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran Ambient temperature; other substrates;100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

1,3,5-Tri-tert-butylbenzene
1460-02-2

1,3,5-Tri-tert-butylbenzene

Conditions
ConditionsYield
With copper dichloride; palladium dichloride In butan-1-ol; benzene at 40℃; for 12h;100%
With copper dichloride; palladium dichloride In methanol; carbon dioxide at 40℃; under 120012 Torr; for 8h;97%
With palladium diacetate; methanesulfonic acid; molybdovanadophosphate (NPMoV); chloro-p-hydroquinone In 1,4-dioxane at 60℃; for 3h; under O2;63%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

4-oxobutyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
205068-09-3

4-oxobutyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

2,2,4,4-tetramethyl-oxazolidine-3-carboxylic acid 4-hydroxy-7,7-dimethyl-oct-5-ynyl ester
253882-22-3

2,2,4,4-tetramethyl-oxazolidine-3-carboxylic acid 4-hydroxy-7,7-dimethyl-oct-5-ynyl ester

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78 - -18℃; Addition;100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

hexan-1-amine
111-26-2

hexan-1-amine

carbon monoxide
201230-82-2

carbon monoxide

(E)-4,4-Dimethyl-pent-2-enoic acid hexylamide

(E)-4,4-Dimethyl-pent-2-enoic acid hexylamide

Conditions
ConditionsYield
Stage #1: 3,3-Dimethylbut-1-yne; carbon monoxide With quinoline; tri(2-furyl)germane; tris(2,4-di-tert-butylphenyl)phosphite; bis(η3-allyl-μ-chloropalladium(II)) In toluene at 20℃; under 760.051 Torr; for 5.5h;
Stage #2: hexan-1-amine; dmap In toluene at 70℃; for 6h; Further stages.;
100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

carbon monoxide
201230-82-2

carbon monoxide

dibenzylamine
103-49-1

dibenzylamine

(E)-4,4-dimethyl-N,N-bis(phenylmethyl)-2-pentenamide
252667-35-9

(E)-4,4-dimethyl-N,N-bis(phenylmethyl)-2-pentenamide

Conditions
ConditionsYield
Stage #1: 3,3-Dimethylbut-1-yne; carbon monoxide With quinoline; tri(2-furyl)germane; tris(2,4-di-tert-butylphenyl)phosphite; bis(η3-allyl-μ-chloropalladium(II)) In toluene at 20℃; under 760.051 Torr; for 5.5h;
Stage #2: dibenzylamine; dmap In toluene at 70℃; for 6h; Further stages.;
100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

bis-{(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-ylmethyl}disulfide
116195-09-6

bis-{(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-ylmethyl}disulfide

(1S,2R)-2-hydroxy-10-(3,3-dimethyl-1-butynylthio)bornane
649885-42-7

(1S,2R)-2-hydroxy-10-(3,3-dimethyl-1-butynylthio)bornane

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane at -78℃;100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

(Z,Z)-3,6-dichloro-2,2,7,7-tetramethyl-3,5-octadiene

(Z,Z)-3,6-dichloro-2,2,7,7-tetramethyl-3,5-octadiene

Conditions
ConditionsYield
With copper dichloride; palladium dichloride In acetonitrile at 20℃; for 8h;100%
With di(rhodium)tetracarbonyl dichloride; tris(2,4,6-trimethylphenyl)phosphine; trifluoroacetyl chloride In chlorobenzene at 130℃; for 3h; stereoselective reaction;75%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

(Z,Z)-3,6-dibromo-2,2,7,7-tetramethylocta-3,5-diene

(Z,Z)-3,6-dibromo-2,2,7,7-tetramethylocta-3,5-diene

Conditions
ConditionsYield
With copper(ll) bromide; palladium(II) bromide In acetonitrile; benzene at 20℃; for 4h;100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

benzyl azide
622-79-7

benzyl azide

1-(4′-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole
871689-96-2

1-(4′-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole

Conditions
ConditionsYield
With bis[1-(4-sodiumsulfonatepropyl)-3-(2,4,6-trimethylphenyl)-4,5-dihydroimidazolyl-3-ylidine]copper(I) hexafluorophosphate In neat (no solvent) at 20℃; for 1.5h;100%
With copper(l) iodide; 1-decylimidazole at 25℃; for 3h; neat (no solvent);99%
With Cu98Mn2 nanoporous catalyst In toluene at 65℃; for 22h; Huisgen cycloaddition; regioselective reaction;99%
acetaldehyde o-iodophenyl ethyl acetal
870011-18-0

acetaldehyde o-iodophenyl ethyl acetal

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

2-(3,3-dimethyl-1-butynyl)-1-(1-ethoxyethoxy)benzene
1072840-21-1

2-(3,3-dimethyl-1-butynyl)-1-(1-ethoxyethoxy)benzene

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; triphenylphosphine; palladium dichloride In acetonitrile at 20℃; Sonogashira coupling; Inert atmosphere;100%
With copper(l) iodide; triethylamine; triphenylphosphine; palladium dichloride In acetonitrile Sonogashira coupling;
4-iodobenzo[b]thiophene-2-carboxamidine hydrochloride
149732-36-5

4-iodobenzo[b]thiophene-2-carboxamidine hydrochloride

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

methyl 4-iodobenzo[b]thiophene-2-carboxylate
146137-85-1

methyl 4-iodobenzo[b]thiophene-2-carboxylate

methyl 4-(3,3-dimethylbut-1-ynyl)benzo[b]thiophene-2-carboxylate
154629-73-9

methyl 4-(3,3-dimethylbut-1-ynyl)benzo[b]thiophene-2-carboxylate

Conditions
ConditionsYield
With CuI; bis(triphenylphosphine)palladium(II)-chloride In triethylamine100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

[(η(5)-C5Me4Ph)2Ti(η(2)-bis(trimethylsilyl)ethyne)]
252006-99-8

[(η(5)-C5Me4Ph)2Ti(η(2)-bis(trimethylsilyl)ethyne)]

[(η(5)-C5Me4Ph)2Ti(η(1)-(E)-CH=CHCMe3)(η(1)-CCCMe3)]
252007-12-8

[(η(5)-C5Me4Ph)2Ti(η(1)-(E)-CH=CHCMe3)(η(1)-CCCMe3)]

Conditions
ConditionsYield
In hexane 60°C (in dark, 4 h), evapn. (vac.); hexane addn., crystn. (-18°C, overnight);100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

[(η(5)-C5Me4(benzyl))2Ti(η(2)-bis(trimethylsilyl)ethyne)]
252007-00-4

[(η(5)-C5Me4(benzyl))2Ti(η(2)-bis(trimethylsilyl)ethyne)]

[(η(5)-C5Me4(benzyl))2Ti(η(1)-(E)-CH=CHCMe3)(η(1)-CCCMe3)]
252007-15-1

[(η(5)-C5Me4(benzyl))2Ti(η(1)-(E)-CH=CHCMe3)(η(1)-CCCMe3)]

Conditions
ConditionsYield
In hexane 60°C (in dark, 7 h), evapn. (vac.); hexane addn., crystn. (-18°C, overnight);100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

RuCl2(NCCH3)2(P(CH(CH3)2)3)2
216525-24-5

RuCl2(NCCH3)2(P(CH(CH3)2)3)2

RuCl2{=C=CH(t-Bu)}(Pi-Pr3)2

RuCl2{=C=CH(t-Bu)}(Pi-Pr3)2

Conditions
ConditionsYield
In dichloromethane Ar-atmosphere; stirring (40°C, 20 h); evapn., detd. by (1)H and (31)P NMR spectroscopy;100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

[FeCl(μ3-NPEt3)]4

[FeCl(μ3-NPEt3)]4

[Fe(CCC(CH3)3)(NP(C2H5)3)]4

[Fe(CCC(CH3)3)(NP(C2H5)3)]4

Conditions
ConditionsYield
With n-BuLi In tetrahydrofuran; hexane byproducts: LiCl; Ar atm.; cooling (-78°C), heating (-10°C), stirring (0°C, 2 h); evapn. (vac., 0°C), extraction (n-hexane), filtn., evapn. (dryness); elem. anal.;100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

C7H5(NCH(CH3)2)2AlCH2CH(CH3)2(OC(CH3)2)(1+)*B(C6F5)4(1-)=[C7H5(NCH(CH3)2)2AlCH2CH(CH3)2(OC(CH3)2)][B(C6F5)4]

C7H5(NCH(CH3)2)2AlCH2CH(CH3)2(OC(CH3)2)(1+)*B(C6F5)4(1-)=[C7H5(NCH(CH3)2)2AlCH2CH(CH3)2(OC(CH3)2)][B(C6F5)4]

C7H5(NCH(CH3)2)2AlCHCH(C(CH3)3)(1+)*B(C6F5)4(1-)=[C7H5(NCH(CH3)2)2AlCHCH(C(CH3)3)][B(C6F5)4]

C7H5(NCH(CH3)2)2AlCHCH(C(CH3)3)(1+)*B(C6F5)4(1-)=[C7H5(NCH(CH3)2)2AlCHCH(C(CH3)3)][B(C6F5)4]

Conditions
ConditionsYield
In further solvent(s) byproducts: C2H4; C6D5Cl, 23°C;100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

[CoBr(NP(C2H5)3)]4

[CoBr(NP(C2H5)3)]4

[Co(CCC(CH3)3)(NP(CH3)3)]4

[Co(CCC(CH3)3)(NP(CH3)3)]4

Conditions
ConditionsYield
With n-BuLi In tetrahydrofuran; hexane byproducts: LiBr; Ar atm.; cooling (-78°C), warming (0°C), stirring (6 h); evapn. (vac., 0°C), extraction (PhMe), filtn., concn.; elem. anal.;100%
1-(benzyloxy)-4-bromo-2-iodobenzene
612833-66-6

1-(benzyloxy)-4-bromo-2-iodobenzene

2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

1-benzyloxy-4-bromo-2-(3,3-dimethyl-1-butynyl)benzene
1063712-62-8

1-benzyloxy-4-bromo-2-(3,3-dimethyl-1-butynyl)benzene

Conditions
ConditionsYield
With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine In tetrahydrofuran at 20℃; for 10h;100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

(C12H10B2)(S(CH3)2)2
1233793-92-4

(C12H10B2)(S(CH3)2)2

(C6H4)2B2(CHCHC(CH3)3)2
1174742-42-7

(C6H4)2B2(CHCHC(CH3)3)2

Conditions
ConditionsYield
In benzene react. with 5 equiv. of tBuCCH in C6H6 at room temp.; Me2S from intermediate removed under reduced pressure; NMR;100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

isovaleraldehyde
590-86-3

isovaleraldehyde

(±)-2,7,7-trimethyloct-5-yn-4-ol
1226968-85-9

(±)-2,7,7-trimethyloct-5-yn-4-ol

Conditions
ConditionsYield
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: isovaleraldehyde In tetrahydrofuran at -78 - 20℃; for 1.5h; Inert atmosphere;
100%
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 0.583333h; Inert atmosphere;
Stage #2: isovaleraldehyde In tetrahydrofuran at -78 - 0℃; Inert atmosphere;
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

tin(IV) chloride
7646-78-8

tin(IV) chloride

1-trichlorostannyl-2-chloro-2-tert-butyl-ethene
1322728-83-5

1-trichlorostannyl-2-chloro-2-tert-butyl-ethene

Conditions
ConditionsYield
In dichloromethane N2; DCM soln. of ligand and SnCl4 (1:1 molar ratio) stirred at room temp. for 24 h; evapd. (vac., room temp.), NMR;100%
In chloroform-d1 N2; 1:1 mixt. at 25°C; NMR;
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

1-benzyl-2-bromo-1H-indole-3-carboxyaldehyde
288848-92-0

1-benzyl-2-bromo-1H-indole-3-carboxyaldehyde

1-benzyl-2-(3,3-dimethyl-1-butynyl)-1H-indole-3-carbaldehyde
1350934-38-1

1-benzyl-2-(3,3-dimethyl-1-butynyl)-1H-indole-3-carbaldehyde

Conditions
ConditionsYield
With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine In tetrahydrofuran at 40℃; Sonogashira reaction; Inert atmosphere;100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

1-methoxy-4-[1-(2-propynyloxy)-3-(phenylsulfanyl)-2-propyn-1-yl]benzene
1242027-78-6

1-methoxy-4-[1-(2-propynyloxy)-3-(phenylsulfanyl)-2-propyn-1-yl]benzene

(3E,4Z)-1-methoxy-4-[4-(4,4-dimethyl-2-pentynlidene)-3-(phenylsulfanylmethylene)tetrahydrofuran-2-yl]benzene
1380676-41-4

(3E,4Z)-1-methoxy-4-[4-(4,4-dimethyl-2-pentynlidene)-3-(phenylsulfanylmethylene)tetrahydrofuran-2-yl]benzene

Conditions
ConditionsYield
With copper(I) trifluoromethanesulfonate toluene adduct (1/1); tributyl-amine In toluene at 20℃; for 0.333333h; stereoselective reaction;100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

3-(4-methoxyphenyl)propional
20401-88-1

3-(4-methoxyphenyl)propional

(±)-1-(4-methoxyphenyl)-6,6-dimethylhept-4-yn-3-ol
1437710-09-2

(±)-1-(4-methoxyphenyl)-6,6-dimethylhept-4-yn-3-ol

Conditions
ConditionsYield
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 3-(4-methoxyphenyl)propional In tetrahydrofuran at -78 - 20℃; for 1.5h; Inert atmosphere;
100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

2-iodo-2',4',6'-triisopropylbenzophenone
1597428-24-4

2-iodo-2',4',6'-triisopropylbenzophenone

2-(3,3-dimethylbut-1-ynyl)-2',4',6'-triisopropylbenzophenone
1597428-26-6

2-(3,3-dimethylbut-1-ynyl)-2',4',6'-triisopropylbenzophenone

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran for 12h; Sonogashira Cross-Coupling; Reflux; Inert atmosphere;100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

(2-iodophenyl)(4-methoxyphenyl)methanone
138504-32-2

(2-iodophenyl)(4-methoxyphenyl)methanone

2-(3,3-dimethylbut-1-ynyl)-4'-methoxybenzophenone
1597428-54-0

2-(3,3-dimethylbut-1-ynyl)-4'-methoxybenzophenone

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 90℃; for 16h; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 80℃; for 16h; Sonogashira Cross-Coupling; Inert atmosphere;93%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 80℃; for 16h; Inert atmosphere;93%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

N-methoxy-N,2,2-trimethylhex-5-enamide
1586781-56-7

N-methoxy-N,2,2-trimethylhex-5-enamide

2,2,6,6-tetramethyldec-9-en-3-yn-5-one
1586781-57-8

2,2,6,6-tetramethyldec-9-en-3-yn-5-one

Conditions
ConditionsYield
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78 - 25℃; for 0.5h;
Stage #2: N-methoxy-N,2,2-trimethylhex-5-enamide In tetrahydrofuran; hexane at -78 - 25℃; for 2h;
100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

C14H12BrNO2

C14H12BrNO2

C20H21NO2

C20H21NO2

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran for 22.5h; Inert atmosphere; Reflux;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran for 22.5h; Inert atmosphere; Reflux;100%

917-92-0Relevant articles and documents

Hargrove,R.J.,Stang,J.S.

, p. 581 - 582 (1974)

Kocienski

, p. 3285 (1974)

Preparation method of 3, 3-dimethyl-1-butyne

-

Paragraph 0028-0031; 0034-0043, (2021/04/17)

The invention discloses a preparation method of 3, 3-dimethyl-1-butyne, which comprises the following steps: by using tert-butyl alcohol and acetylene which are simple, readily available and cheap as initial raw materials and using transition metal salt which is readily available on the market as a catalyst, directly reacting in the presence of acid to obtain a product, and carrying out simple distillation separation to obtain a high-purity product. The method is simple and convenient to operate, less in environmental pollution, good in product quality, high in yield, low in cost and more suitable for industrial production.

Synthesis method of terbinafine medical intermediate tert-butyl acetylene

-

Paragraph 0015; 0016, (2017/03/14)

A synthesis method of terbinafine medical intermediate tert-butyl acetylene includes the following steps of adding 310 ml of potassium bisulfite solution and 300 ml of potassium bisulfite to a reaction vessel provided with a stirrer, a thermometer, a dropping funnel and a condenser, raising the temperature of the solution to 90-95 DEG C, controlling the stirring speed at 150-170 rpm, dropwise adding 0.73 mol of 1,1-diamido-3,3-dimethylbutane, controlling the dropwise adding time at 3-5 hours, adding 0.81-0.84 mol of hypochloric acid phenyl ester, conducting reaction for 90-120 min, raising the temperature of the solution to 110-115 DEG C, continuing to conduct reaction for 3-5 hours, lowering the temperature of the solution to 10-15 DEG C, separating out solid, conducting filtering, saline solution washing, acetonitrile washing and pressure reduction distillation, collecting fraction of 100-108 DEG C, and conducting recrystallization in cyclohexane to obtain crystal tert-butyl acetylene.

Substituent effects on the photorearrangements of unsymmetrically substituted diazinobarrelenes

Hsieh, Hsing-Pang,Chen, Ann-Cheng,Villarante, Nelson R.,Chuang, Gary J.,Liao, Chun-Chen

, p. 1165 - 1178 (2013/03/14)

A series of diazinobarrelenes 8-15 engendered with alkyl functionalities at the barrelene skeleton were irradiated with 350 nm light under direct and acetone-sensitized reaction conditions. Under these conditions, all the barrelenes except barrelene 14 afforded semibullvalenes with varying degrees of regioselectivity and product distribution. Dicyanopyrazinobarrelenes 8-10 which furnished semibullvalenes 32-41via the aryl-vinyl initial bridging route were strongly controlled by the nitrile functionalities installed at the aromatic sites. Benzoquinoxalinobarrelenes 11-13 which afforded semibullvalenes 42-49, preferentially underwent photorearrangement via vinyl-vinyl bridging even if the compounds were excited at a wavelength where the quinoxaline moiety absorbed most of the light. Zimmerman's bridging hypothesis and the possibility for quinoxalines to undergo intramolecular triplet energy transfer could reasonably account for the observed regioselectivity. Barrelene 14 was insensitive to photorearrangement whereas benzo[f,h]quinoxalinobarrelene 15 preferentially underwent ADPM rearrangement affording semibullvalenes 50-52. Electronic and steric factors of alkyl substituents overwhelmingly controlled the product forming steps whereas localization and minimization of triplet energies greatly influenced the initial bridging interaction. The Royal Society of Chemistry 2013.

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