3,3-Dimethyl-1-butyne supplier

Name
3,3-Dimethyl-1-butyne
EINECS 213-035-3
CAS No. 917-92-0
Article Data84
CAS DataBase
Density 0.668 g/cm³
Solubility Miscible with chloroform, benzene and toluene. Immiscible with water.
Melting Point -78 °C
Formula C₆H₁₀
Boiling Point 37.7 °C at 760 mmHg
Molecular Weight 82.1454
Flash Point -34 °C
Transport Information UN 3295 3/PG 2
Appearance colourless liquid
Safety 3-16-26-33-7/9
Risk Codes 12-36/37/38
Molecular Structure
Hazard Symbols F+, Xi
Synonyms 3,3,3-Trimethylpropyne;1-Butyne,3,3-dimethyl-;3,3-Dimethylbutyne;Neohexyne;tert-Butylacetylene;tert-Butylethyne;
PSA 0.00000
LogP 1.66570

Synthetic route

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

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

Conditions

Conditions	Yield
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%

: 640-21-1
1,2-dibromo-3,3-dimethylbutane

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

Conditions

Conditions	Yield
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 ether	84%
With potassium hydroxide; 2,5-dimethyl-2,5-hexanediol at 100℃; for 0.75h;	80%
With potassium tert-butylate Heating;

: 640-21-1
1,2-dibromo-3,3-dimethylbutane

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

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

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

Conditions

Conditions	Yield
With potassium hydroxide; Aliquat 336 In xylene Heating;	A 91% B n/a C n/a

...Expand

: 931-48-6
2-cyclohexylacetylene

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

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

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

Conditions

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

...Expand

: 74-86-2
acetylene

: 75-65-0
tert-butyl alcohol

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

Conditions

Conditions	Yield
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%

: 17475-11-5
1-phenyl-4,4-dimethylpent-2-yn-1-one

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

Conditions

Conditions	Yield
With potassium hydroxide; water In 1,3,5-trimethyl-benzene distillation;	90%

: 32363-94-3
1,1-dichloro-3,3-dimethyl-1-butene

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

Conditions

Conditions	Yield
With methyllithium In tetrahydrofuran at -30 - 0℃; for 1h; Dehalogenation;	90%
	90%

: 16520-62-0
4-Phenyl-1-butyne

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

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

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

Conditions

Conditions	Yield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;	A n/a B 89%

...Expand

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

: 693-02-7
hex-1-yne

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

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

Conditions

Conditions	Yield
With Lu(N(SiMe3)2)3 In toluene at 130℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;	A n/a B 87%

...Expand

: 288390-74-9
3,3-dimethyl-1-(triphenylphosphanylidene)butan-2-one

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

Conditions

Conditions	Yield
at 750℃; under 0.01 Torr; for 3h;	82%
at 750℃; for 3h;	82%

: 1,1-diamino-3,3-dimethylbutane

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

Conditions

Conditions	Yield
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)

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

B: 558-37-2
tert-butylethylene

C: 75-83-2
2,2-Dimethylbutane

Conditions

Conditions	Yield
In gas treatment in sealed vial under H2 for 45 min at 120 °C, partly decompd.;	A 2.7% B 19% C 78%

...Expand

: 75-97-8
3,3-dimethyl-butan-2-one

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

Conditions

Conditions	Yield
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

: 6130-96-7
1,1-dichloro-3,3-dimethylbutane

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

Conditions

Conditions	Yield
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℃;

: 5469-26-1
1-Bromopinacolon

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

Conditions

Conditions	Yield
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

: 33249-12-6
potassium bis(triflyl)methanide

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

B: 1271169-55-1
C9H12F6O4S2

Conditions

Conditions	Yield
In dichloromethane at -78 - 20℃; for 4h; Inert atmosphere;	A 38% B 43%

...Expand

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

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

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

Conditions

Conditions	Yield
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

: 90076-67-8
potassium bis(trifluoromethylsulfonyl)imide

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

B: 1271169-73-3
C8H11F6NO4S2

Conditions

Conditions	Yield
In dichloromethane at -78 - 20℃; for 4h; Inert atmosphere;	A 18% B 32%

...Expand

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

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

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

B: 1271169-60-8
C15H12F18O4S2

Conditions

Conditions	Yield
In dichloromethane at -78 - 20℃; for 4h; Inert atmosphere;	A 15% B 31%

...Expand

: 630-19-3
pivalaldehyde

: 145397-30-4
C8H21N4PSi

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

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

Conditions

Conditions	Yield
In pentane at 20℃;	A 30% B 14%

...Expand

: 558-37-2
tert-butylethylene

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

Conditions

Conditions	Yield
With bromine; methyl cyclohexane at -60℃; und anschliessend mit Natriumamid in fluessigem Ammoniak bei -70grad;

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

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

Conditions

Conditions	Yield
With potassium hydroxide; ethanol; mineral oil at 200℃;

: 52418-50-5
4,4-dimethyl-2-pentynoic acid

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

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

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

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

Conditions

Conditions	Yield
With amine buffer; water at 25℃; Rate constant; μ = 0.10 M;

: 949091-15-0
3,3-dimethylbut-1-en-2-yl diethyl phosphate

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

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran

: 51779-49-8
2-tert-butyl-4-methyl-1,3-oxazin-6-one

A: 630-18-2
tert-butyl isocyanide

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

C: 463-49-0
1,2-propanediene

D: 75-05-8
acetonitrile

E: 74-99-7
prop-1-yne

Conditions

Conditions	Yield
at -263.2℃; Mechanism; Irradiation;

...Expand

: 542-28-9
3,4,5,6-tetrahydro-2H-pyran-2-one

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

: 1005-56-7
phenylcarbonochloridothioate

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

Conditions

Conditions	Yield
With pyridine; dmap 1.) THF, 75 min, from -70 deg C to r.t.; 2.) acetonitrile, 1.5 h; Yield given. Multistep reaction;

...Expand

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

A: 591-50-4
iodobenzene

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

Conditions

Conditions	Yield
With tetrabutyl-ammonium chloride; tetrabutylammonium perchlorate In acetonitrile at 25℃; Rate constant; var. solvents and var. concentration of reagents;

: 246023-20-1
1,1-dichloro-3,3-dimethyl2-butanol methanesulfonate

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

Conditions

Conditions	Yield
With methyllithium In tetrahydrofuran at -30 - 0℃; for 1h; Elimination;	78 % Chromat.

: 263904-19-4
1,1,1-trichloro-3,3-dimethyl-2-butanol methanesulfonate

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

Conditions

Conditions	Yield
With methyllithium In tetrahydrofuran; diethyl ether at -10 - 0℃; for 1h; Elimination;	81 % Chromat.

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

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

Conditions

Conditions	Yield
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%

: 50-00-0
formaldehyd

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

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

Conditions

Conditions	Yield
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%

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

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

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

Conditions

Conditions	Yield
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%

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

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

Conditions

Conditions	Yield
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%

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

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

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

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78 - -18℃; Addition;	100%

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

: 111-26-2
hexan-1-amine

: 201230-82-2
carbon monoxide

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

Conditions

Conditions	Yield
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%

...Expand

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

: 201230-82-2
carbon monoxide

: 103-49-1
dibenzylamine

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

Conditions

Conditions	Yield
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%

...Expand

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

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

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

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane at -78℃;	100%

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

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

Conditions

Conditions	Yield
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%

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

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

Conditions

Conditions	Yield
With copper(ll) bromide; palladium(II) bromide In acetonitrile; benzene at 20℃; for 4h;	100%

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

: 622-79-7
benzyl azide

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

Conditions

Conditions	Yield
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%

: 870011-18-0
acetaldehyde o-iodophenyl ethyl acetal

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

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

Conditions

Conditions	Yield
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;

: 149732-36-5
4-iodobenzo[b]thiophene-2-carboxamidine hydrochloride

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

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

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

Conditions

Conditions	Yield
With CuI; bis(triphenylphosphine)palladium(II)-chloride In triethylamine	100%

...Expand

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

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

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

Conditions

Conditions	Yield
In hexane 60°C (in dark, 4 h), evapn. (vac.); hexane addn., crystn. (-18°C, overnight);	100%

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

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

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

Conditions

Conditions	Yield
In hexane 60°C (in dark, 7 h), evapn. (vac.); hexane addn., crystn. (-18°C, overnight);	100%

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

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

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

Conditions

Conditions	Yield
In dichloromethane Ar-atmosphere; stirring (40°C, 20 h); evapn., detd. by (1)H and (31)P NMR spectroscopy;	100%

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

: [FeCl(μ3-NPEt3)]4

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

Conditions

Conditions	Yield
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%

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

Conditions

Conditions	Yield
In further solvent(s) byproducts: C2H4; C6D5Cl, 23°C;	100%

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

: [CoBr(NP(C2H5)3)]4

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

Conditions

Conditions	Yield
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%

: 612833-66-6
1-(benzyloxy)-4-bromo-2-iodobenzene

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

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

Conditions

Conditions	Yield
With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine In tetrahydrofuran at 20℃; for 10h;	100%

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

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

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

Conditions

Conditions	Yield
In benzene react. with 5 equiv. of tBuCCH in C6H6 at room temp.; Me2S from intermediate removed under reduced pressure; NMR;	100%

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

: 590-86-3
isovaleraldehyde

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

Conditions

Conditions	Yield
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;

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

: 7646-78-8
tin(IV) chloride

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

Conditions

Conditions	Yield
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;

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

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

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

Conditions

Conditions	Yield
With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine In tetrahydrofuran at 40℃; Sonogashira reaction; Inert atmosphere;	100%

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

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

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

Conditions

Conditions	Yield
With copper(I) trifluoromethanesulfonate toluene adduct (1/1); tributyl-amine In toluene at 20℃; for 0.333333h; stereoselective reaction;	100%

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

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

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

Conditions

Conditions	Yield
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%

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

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

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

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran for 12h; Sonogashira Cross-Coupling; Reflux; Inert atmosphere;	100%

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

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

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

Conditions

Conditions	Yield
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%

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

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

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

Conditions

Conditions	Yield
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%

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

: C14H12BrNO2

: C20H21NO2

Conditions

Conditions	Yield
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%

3,3-Dimethyl-1-butyne Specification

The 3,3-Dimethy-1-butyne, with the CAS registry number 917-92-0, is also known as tert-Butylacetylene. It belongs to the product categories of Pharmaceutical Intermediates; Acetylenes; Acetylenic Hydrocarbons. Its EINECS registry number is 213-035-3. This chemical's molecular formula is C₆H₁₀ and molecular weight is 82.1436. Its IUPAC name is called 3,3-dimethylbut-1-yne. 3,3-Dimethyl-1-butyne is colourless liquid which can be used as drugs intermediates for terbinafine and also can be used in organic synthesis.

Physical properties about 3,3-Dimethyl-1-butyne are: (1)ACD/LogP: 2.444; (2)ACD/LogD (pH 5.5): 2.44; (3)ACD/LogD (pH 7.4): 2.44; (4)ACD/BCF (pH 5.5): 42.40; (5)ACD/BCF (pH 7.4): 42.40; (6)ACD/KOC (pH 5.5): 508.70; (7)ACD/KOC (pH 7.4):508.70; (8)Index of Refraction: 1.411; (9)Molar Refractivity: 27.64 cm³; (10)Molar Volume: 111.389 cm³; (11)Polarizability: 10.957 10-24cm³; (12)Surface Tension: 23.3850002288818 dyne/cm; (13)Density: 0.737 g/cm³; (14)Flash Point: -41.238 °C; (15)Enthalpy of Vaporization: 27.075 kJ/mol; (16)Boiling Point: 37.699 °C at 760 mmHg; (17)Vapour Pressure: 480.921997070313 mmHg at 25°C

Preparation of 3,3-Dimethyl-1-butyne: 3-Dimethyl-1-butyne can be prepared by 1,1-dichloro-3,3-dimethyl-butane. This reaction will need reagent sodium amide and mineral oil. The reaction temperature is 90 - 95 °C.

Uses of 3,3-Dimethyl-1-butyne: 3-Dimethy-1-butyne can be used to produce 2,2,7,7-tetramethyl-octa-3,5-diyne at temperature of 55 - 65 °C. This reaction will need reagent CuCl, NH₄Cl and diluted HCl.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC(C)(C)C#C
(2)InChI: InChI=1S/C6H10/c1-5-6(2,3)4/h1H,2-4H3
(3)InChIKey: PPWNCLVNXGCGAF-UHFFFAOYSA-N

Product Name

3,3-Dimethyl-1-butyne

Synthetic route

3,3-Dimethyl-1-butyne Specification

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