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2,2-Dimethylbutane, also known as neoheptane, is an organic compound belonging to the alkane class. It has the chemical formula C7H16 and is characterized by a carbon backbone with two methyl groups attached to the second carbon atom from either end. This hydrocarbon is widely used in organic synthesis and as a component in gasoline.

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  • 75-83-2 Structure
  • Basic information

    1. Product Name: 2,2-Dimethylbutane
    2. Synonyms: 2,2-Dimethylbutane;3,3-Dimethylbutane; NSC 74126; Neohexane
    3. CAS NO:75-83-2
    4. Molecular Formula: C6H14
    5. Molecular Weight: 86.17536
    6. EINECS: 200-906-8
    7. Product Categories: N/A
    8. Mol File: 75-83-2.mol
  • Chemical Properties

    1. Melting Point: -115℃
    2. Boiling Point: 50 ºC
    3. Flash Point: -48 ºC
    4. Appearance: Liquid.
    5. Density: 0.649
    6. Vapor Pressure: 324mmHg at 25°C
    7. Refractive Index: 1.383
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. Water Solubility: insoluble
    11. CAS DataBase Reference: 2,2-Dimethylbutane(CAS DataBase Reference)
    12. NIST Chemistry Reference: 2,2-Dimethylbutane(75-83-2)
    13. EPA Substance Registry System: 2,2-Dimethylbutane(75-83-2)
  • Safety Data

    1. Hazard Codes:  F:Flammable;
    2. Statements: R11:; R38:; R51/53:; R65:; R67:;
    3. Safety Statements: S16:; S29:; S33:; S61:; S62:; S9:;
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 75-83-2(Hazardous Substances Data)

75-83-2 Usage

Uses

Used in Organic Synthesis:
2,2-Dimethylbutane is used as a reagent in various organic synthesis processes for its unique structural properties and ability to undergo chemical reactions.
Used in Gasoline Production:
2,2-Dimethylbutane is used as a component in gasoline to improve its performance and efficiency. Its presence in gasoline contributes to better combustion and reduced emissions.
Used in Chemical Industry:
2,2-Dimethylbutane is used as a solvent in the chemical industry for its ability to dissolve a wide range of substances and facilitate various chemical reactions.
However, it is important to note that 2,2-dimethylbutane can pose health risks, including respiratory irritation, dizziness, and skin irritation. Additionally, it has significant fire and explosion risks, necessitating careful storage and handling to ensure safety.

Check Digit Verification of cas no

The CAS Registry Mumber 75-83-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 5 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 75-83:
(4*7)+(3*5)+(2*8)+(1*3)=62
62 % 10 = 2
So 75-83-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H14/c1-5-6(2,3)4/h5H2,1-4H3

75-83-2 Well-known Company Product Price

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  • Aldrich

  • (39740)  2,2-Dimethylbutane  ≥99.0% (GC)

  • 75-83-2

  • 39740-100ML

  • 287.82CNY

  • Detail
  • Aldrich

  • (39740)  2,2-Dimethylbutane  ≥99.0% (GC)

  • 75-83-2

  • 39740-500ML

  • 1,223.82CNY

  • Detail
  • Aldrich

  • (39740)  2,2-Dimethylbutane  ≥99.0% (GC)

  • 75-83-2

  • 39740-2.5L

  • 7,330.05CNY

  • Detail
  • Aldrich

  • (D151408)  2,2-Dimethylbutane  99%

  • 75-83-2

  • D151408-100G

  • 631.80CNY

  • Detail
  • Aldrich

  • (D151408)  2,2-Dimethylbutane  99%

  • 75-83-2

  • D151408-1KG

  • 4,130.10CNY

  • Detail
  • Aldrich

  • (D151408)  2,2-Dimethylbutane  99%

  • 75-83-2

  • D151408-5GA

  • 28,197.00CNY

  • Detail

75-83-2SDS

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 2,2-Dimethylbutane

1.2 Other means of identification

Product number -
Other names Butane, 2,2-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:75-83-2 SDS

75-83-2Synthetic route

tert-butylethylene
558-37-2

tert-butylethylene

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

Conditions
ConditionsYield
With nickel(II) bis(octanoate); hydrogen; 1,4-bis(2,6-diisopropylphenyl)-2,3-dimethyl-1,4-diazabuta-1,3-diene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In benzene-d6 at 50℃; under 3040.2 Torr; for 5h;98%
With C28H32PZr(1+)*C19H3BF15(1-); hydrogen at 20℃; for 2h; Reagent/catalyst; Glovebox; Schlenk technique;86%
With borane-ammonia complex; Pd(SIPr)(PCy3) In isopropyl alcohol at 50℃; for 16h; Inert atmosphere; Glovebox;69%
tert-butylethylene
558-37-2

tert-butylethylene

2-methyl indoline
6872-06-6

2-methyl indoline

A

2-methyl-1H-indole
95-20-5

2-methyl-1H-indole

B

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

Conditions
ConditionsYield
With (PSCOP)IrHCl; sodium t-butanolate In para-xylene at 120℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;A 96%
B n/a
tert-butylethylene
558-37-2

tert-butylethylene

chlorotriisopropylsilane
6485-79-6

chlorotriisopropylsilane

A

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

B

((E)-3,3-Dimethyl-but-1-enyl)-triisopropyl-silane

((E)-3,3-Dimethyl-but-1-enyl)-triisopropyl-silane

Conditions
ConditionsYield
<(phen)PdCH3(Et2O)>+- In dichloromethane at 25℃; for 24h; Yields of byproduct given;A n/a
B 94%
triethyl borane
97-94-9

triethyl borane

tert-butyl alcohol
75-65-0

tert-butyl alcohol

A

Isobutane
75-28-5

Isobutane

B

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane 1.) -30 deg C 2.) room temp.;A 92.5%
B 7.5%
2-methyl-but-2-ene
513-35-9

2-methyl-but-2-ene

tetramethylsilane
75-76-3

tetramethylsilane

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

Conditions
ConditionsYield
With hydrogenchloride; aluminium trichloride In dichloromethane at 20℃; for 1h;92%
isochromane
493-05-0

isochromane

tert-butylethylene
558-37-2

tert-butylethylene

A

1H-isochromene
253-35-0

1H-isochromene

B

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

Conditions
ConditionsYield
With (PSCOP)IrHCl; sodium t-butanolate In para-xylene at 120℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;A 91%
B n/a
3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

Conditions
ConditionsYield
With hydrogen; K-10 montmorillonite; platinum In diethylene glycol dimethyl ether under 37503 Torr; for 20h; Reduction;60%
With hydrogen; aluminum oxide; nickel at 190℃;46%
With ethanol; sulfuric acid at 50℃; Electrolysis.elektrolytische Reduktion an einer Cadmiumkathode;
With molybdenum (IV) sulfide Hydrogenation.unter hohem Druck;
Multi-step reaction with 2 steps
1: water; alcohol; hydrazine hydrate
2: potassium hydroxide; platinized fired clay / 180 °C
View Scheme
2-methyltetrahydrofuran
96-47-9

2-methyltetrahydrofuran

tert-butylethylene
558-37-2

tert-butylethylene

A

2-methylfuran
534-22-5

2-methylfuran

B

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

Conditions
ConditionsYield
With (PSCOP)IrHCl; sodium t-butanolate In para-xylene at 150℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;A 57%
B n/a
1-(1-Cyclohexen-1-yl)pyrrolidine
1125-99-1

1-(1-Cyclohexen-1-yl)pyrrolidine

tert-butylethylene
558-37-2

tert-butylethylene

A

1-phenylpyrrole
635-90-5

1-phenylpyrrole

B

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

C

N-(1-cyclohexen-1-yl)-1H-pyrrole
62672-96-2

N-(1-cyclohexen-1-yl)-1H-pyrrole

Conditions
ConditionsYield
With (PSCOP)IrHCl; sodium t-butanolate In para-xylene at 150℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;A 16%
B n/a
C 54%
2,3-Dihydrobenzofuran
496-16-2

2,3-Dihydrobenzofuran

tert-butylethylene
558-37-2

tert-butylethylene

A

1-benzofurane
271-89-6

1-benzofurane

B

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

C

2,2'-bibenzofuranyl
41014-29-3

2,2'-bibenzofuranyl

Conditions
ConditionsYield
With (PSCOP)IrHCl; sodium t-butanolate In para-xylene at 120℃; for 6h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;A 11%
B n/a
C 37%
hexane
110-54-3

hexane

A

3-methylpentane
96-14-0

3-methylpentane

B

2-Methylpentane
107-83-5

2-Methylpentane

C

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

D

2,3-dimethylbutane
79-29-8

2,3-dimethylbutane

Conditions
ConditionsYield
platinum at 250℃; Product distribution; Further Variations:; Catalysts; Temperatures;A 22.1%
B 34.8%
C 12.9%
D 9%
With hydrogen at 215℃; under 7500.75 Torr; Catalytic behavior; Kinetics; Reagent/catalyst; Temperature; Flow reactor; Overall yield = 62.1 %;A n/a
B n/a
C 6.7%
D 8%
Pt-Al2O3-Cl at 100 - 140℃; under 15001.2 Torr; Product distribution;
octane
111-65-9

octane

tert-butylethylene
558-37-2

tert-butylethylene

A

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

B

oct-1-ene
111-66-0

oct-1-ene

Conditions
ConditionsYield
at 200℃; for 1h; Catalytic behavior; Kinetics; Temperature; Time;A n/a
B 16%
aluminum oxide; {4-Me2N-C6H2-2,6-[OP(t-Bu)2]2}IrH2 at 125℃; for 0.166667 - 4h; Product distribution / selectivity;
aluminum oxide; {4-Me2N-C6H2-2,6-[OP(t-Bu)2]2}IrH2 at 125℃; for 0.25 - 4h; Product distribution / selectivity;
{4-Me2N-C6H2-2,6-[OP(t-Bu)2]2}IrH2 at 125℃; for 0.0833333 - 4h; Product distribution / selectivity;
With (PSCOP)IrHCl; sodium t-butanolate at 100℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube; regioselective reaction;
methane
34557-54-5

methane

A

3,3-dimethylpentane
562-49-2

3,3-dimethylpentane

B

2,2-dimethylhexane
590-73-8

2,2-dimethylhexane

C

tetramethyl-2,2,3,3 butane
594-82-1

tetramethyl-2,2,3,3 butane

D

3-ethyl-3-methyl-pentane
1067-08-9

3-ethyl-3-methyl-pentane

E

tetraethylmethane
1067-20-5

tetraethylmethane

F

2,2,3,3-tetramethyl-hexane
13475-81-5

2,2,3,3-tetramethyl-hexane

G

2,4-dimethylhexane
589-43-5

2,4-dimethylhexane

H

ethane
74-84-0

ethane

I

propane
74-98-6

propane

J

Isobutane
75-28-5

Isobutane

K

2,2-dimethylpropane
463-82-1

2,2-dimethylpropane

L

methylbutane
78-78-4

methylbutane

M

2-Methylpentane
107-83-5

2-Methylpentane

N

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

O

triptane
464-06-2

triptane

P

2,2-dimethylpentane
590-35-2

2,2-dimethylpentane

Q

2,2,3,3-tetramethylpentane
7154-79-2

2,2,3,3-tetramethylpentane

R

hydrogen
1333-74-0

hydrogen

Conditions
ConditionsYield
With water at 84℃; Product distribution / selectivity; Photolysis;A 1.89%
B 1.45%
C 9.67%
D 1.72%
E 5.82%
F 2.18%
G 1.45%
H 0.17%
I 6.34%
J 4.51%
K 15.7%
L 4.01%
M 0.4%
N 6.41%
O 3.52%
P 1.2%
Q 9.66%
R 3.44%
at 84℃; Product distribution / selectivity; Photolysis; 24 psig;A 2.26%
B 1.83%
C 7.61%
D 1.75%
E 9.61%
F 1.56%
G 1.82%
H 0.035%
I 7.34%
J 5.28%
K 12.2%
L 2.1%
M 0.97%
N 7.04%
O 3.05%
P 2.35%
Q 6.46%
R 0.219%
pentane
109-66-0

pentane

A

Isobutane
75-28-5

Isobutane

B

methylbutane
78-78-4

methylbutane

C

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

Conditions
ConditionsYield
antimony pentafluoride; zirconium(IV) oxide at 0℃; under 50 Torr; Product distribution; also 2-methylbutane, var conditions, var. catalysts;A 12.6%
B 10.1%
C 0.1%
hexane
110-54-3

hexane

A

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

B

2,3-dimethylbutane
79-29-8

2,3-dimethylbutane

Conditions
ConditionsYield
With hydrogen; tungsten-zirconia-platinum catayst In water at 287.768℃; Product distribution / selectivity;A 9.377%
B 7.065%
With hydrogen at 220℃; under 20 Torr;
methylbutane
78-78-4

methylbutane

ethene
74-85-1

ethene

A

2-Methylhexane
591-76-4

2-Methylhexane

B

2,3-dimethyl pentane
565-59-3

2,3-dimethyl pentane

C

3-methylpentane
96-14-0

3-methylpentane

D

2-Methylpentane
107-83-5

2-Methylpentane

E

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

F

2,3-dimethylbutane
79-29-8

2,3-dimethylbutane

Conditions
ConditionsYield
water; fluorosulphonic acid at -15℃; for 1.5h; Product distribution;A 5.8%
B 6.2%
C 8%
D n/a
E 6.5%
F n/a
triptane
464-06-2

triptane

A

2,2-dimethylpropane
463-82-1

2,2-dimethylpropane

B

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

C

2,3-dimethylbutane
79-29-8

2,3-dimethylbutane

D

C1, C3, i-C4, i-C5

C1, C3, i-C4, i-C5

Conditions
ConditionsYield
nickel at 231.9℃; under 41.5 Torr; for 0.0833333h; Product distribution; Mechanism; hydrogenolysis;A 1.6%
B 1%
C 0.031%
D n/a
hexane
110-54-3

hexane

A

methylbutane
78-78-4

methylbutane

B

3-methylpentane
96-14-0

3-methylpentane

C

2-Methylpentane
107-83-5

2-Methylpentane

D

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

E

2,3-dimethylbutane
79-29-8

2,3-dimethylbutane

F

pentane
109-66-0

pentane

Conditions
ConditionsYield
With hydrogen at 180℃; under 11251.1 Torr; for 0.5h;A 0.6%
B n/a
C n/a
D n/a
E n/a
F 0.3%
tetrachloromethane
56-23-5

tetrachloromethane

tertiary butyl chloride
507-20-0

tertiary butyl chloride

diethylzinc
557-20-0

diethylzinc

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

A

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

B

2,3-dimethylbutane
79-29-8

2,3-dimethylbutane

Conditions
ConditionsYield
With nickel; copper at 250℃; Hydrogenation;
With nickel-copper at 250℃; Hydrogenation;
2-methyl-2-butylchloride
594-36-5

2-methyl-2-butylchloride

methylmagnesium chloride
676-58-4

methylmagnesium chloride

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

Conditions
ConditionsYield
With dibutyl ether at 50℃;
2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

rac-[Zr(ethylenebis(tetrahydro)indenyl)(Me)(NHCMe3)]

rac-[Zr(ethylenebis(tetrahydro)indenyl)(Me)(NHCMe3)]

rac-[Zr(ethylenebis(tetrahydro)indenyl)(CH2CH2C(CH3)3)(NHCMe3)]

rac-[Zr(ethylenebis(tetrahydro)indenyl)(CH2CH2C(CH3)3)(NHCMe3)]

Conditions
ConditionsYield
In neat (no solvent) byproducts: CH4; heating of mixt. of Zr(Me)(NHCMe3)((C9H10)2CH2CH2) and CH3CH2CMe3 at 75°C for 24 h;98%
2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

HCo3(CO)9

HCo3(CO)9

4,4-dimethylpentanal
926-36-3

4,4-dimethylpentanal

Conditions
ConditionsYield
In hexane at -15℃;77%
2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

isobutyric Acid
79-31-2

isobutyric Acid

trimethylolpropane tri(2-methylpropanoate)
14253-02-2

trimethylolpropane tri(2-methylpropanoate)

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 120℃; for 6h;72%
2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

2,2,2-tribromoethyl 2-(4-bromophenyl)-2-diazoacetate

2,2,2-tribromoethyl 2-(4-bromophenyl)-2-diazoacetate

C16H20Br4O2

C16H20Br4O2

Conditions
ConditionsYield
With Rh2[R-tris(p-tBuC6H4)TPCP]4 In dichloromethane Reflux; enantioselective reaction;70%
2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

[hydrido(hydridotris(3,5-dimethylpyrazolyl)borate)dimetylplatinum(IV)]

[hydrido(hydridotris(3,5-dimethylpyrazolyl)borate)dimetylplatinum(IV)]

[(hydridotris(3,5-dimethylpyrazolyl)borate)Pt(η2-neohexene)H]

[(hydridotris(3,5-dimethylpyrazolyl)borate)Pt(η2-neohexene)H]

Conditions
ConditionsYield
With B(C6F5)3 In further solvent(s) byproducts: CH4; (Ar); std. drybox technique; tert-butylethane was added to mixt. of Pt complex and B(C6F5)3 (1 equiv.); mixt. was stirred at 35°C for 3 d; solvent removed (vac.); chromd. (alumina, CH2Cl2); recrystd. (CH2Cl2/methanol, -30°C);65%
2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

1-methyl-4-((phenylsulfonyl)ethynyl)benzene
82721-80-0

1-methyl-4-((phenylsulfonyl)ethynyl)benzene

1-methyl-4-(3,3,4-trimethylpent-1-yn-1-yl)benzene

1-methyl-4-(3,3,4-trimethylpent-1-yn-1-yl)benzene

Conditions
ConditionsYield
With pyridine-4-carbonitrile; 4-cyanopyridine N-oxide; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane at 50℃; for 12h; Inert atmosphere; Schlenk technique;64%
2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

Cp(*)W(NO)(η(2)-CPhCH2)(CH2Si(CH3)3)
164400-22-0

Cp(*)W(NO)(η(2)-CPhCH2)(CH2Si(CH3)3)

Cp*W(NO)(η(2)-CH(η(2)-Ph)CH2CH(tBu)CH2)

Cp*W(NO)(η(2)-CH(η(2)-Ph)CH2CH(tBu)CH2)

Conditions
ConditionsYield
In neat (no solvent) N2 or Ar-atmosphere; 54°C (24 h), evapn. (vac., 1 h); Et2O addn., filtering, concg. (vac.), crystn. (-30°C, 24 h); elem. anal.;59%
2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

benzoyl azide
582-61-6

benzoyl azide

A

N-(3,3-dimethylbutan-2-yl)benzamide
114459-70-0

N-(3,3-dimethylbutan-2-yl)benzamide

B

N-(3,3-dimethylbutyl)benzamide

N-(3,3-dimethylbutyl)benzamide

Conditions
ConditionsYield
With [IPr2*NN]Cu(η2-C6H6) In fluorobenzene at 20℃; Inert atmosphere; Glovebox; Sealed tube;A 4%
B 53%
2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

phenyl isocyanate
103-71-9

phenyl isocyanate

A

2-{2-(3,3-dimethyl)butyl}benzoxazole
1361973-98-9

2-{2-(3,3-dimethyl)butyl}benzoxazole

B

2-(2,2-dimethylbutyl)benzoxazole

2-(2,2-dimethylbutyl)benzoxazole

C

2-(3,3-dimethyl-butyl)-1H-benzoxazole

2-(3,3-dimethyl-butyl)-1H-benzoxazole

Conditions
ConditionsYield
With di-tert-butyl peroxide; copper diacetate In acetonitrile at 120℃; for 10h; Inert atmosphere; Sealed tube; regioselective reaction;A 50%
B 13%
C 18%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

C13H15NO3
1402842-99-2

C13H15NO3

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 2h;45%
2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

A

perfluoroisobutylene
354-92-7

perfluoroisobutylene

B

perfluoro(2,3-dimethylbutane)
354-96-1

perfluoro(2,3-dimethylbutane)

C

perfluoroisohexane
355-04-4

perfluoroisohexane

D

perfluoro(3-methylpentane)
865-71-4

perfluoro(3-methylpentane)

E

perfluoro(2-methylcyclopentane)
1805-22-7

perfluoro(2-methylcyclopentane)

F

perfluoro(2,2-dimethylbutane)
112156-74-8

perfluoro(2,2-dimethylbutane)

Conditions
ConditionsYield
cobalt (III) fluoride at 360℃; for 3h; Product distribution;A 7%
B 4%
C 18%
D 16%
E 12%
F 43%
2,2-Dimethylbutane
75-83-2

2,2-Dimethylbutane

[platinum(IV)(trimethyl)(((4-tert-butyl-2,6-dimethylphenyl)NC(CH3))2CH)]
646535-41-3

[platinum(IV)(trimethyl)(((4-tert-butyl-2,6-dimethylphenyl)NC(CH3))2CH)]

[Pt(CH(C(CH3)NC6H2(CH3)2C(CH3)3)2)(H)(CH2CHC(CH3)3)]
646535-49-1

[Pt(CH(C(CH3)NC6H2(CH3)2C(CH3)3)2)(H)(CH2CHC(CH3)3)]

Conditions
ConditionsYield
In further solvent(s) heating in neohexane at 35°C for 110-200 h;40%

75-83-2Relevant articles and documents

Mechanistic Studies of the Reactions of 3,3-Dimethylbut-1-ene with Deuterium over Supported-metal Catalysts

Brown, Ronald,Kemball, Charles

, p. 2519 - 2526 (1993)

The reactions of 3,3-dimethylbut-1-ene with deuterium have been followed over a number of silica-supported metal catalysts at 254 K and the products analysed by mass spectrometry (MS) and deuterium NMR spectroscopy.The main reaction was the formation of the alkane, 2,2-dimethylbutane, in which extensive redistribution of H and D atoms had occurred in the ethyl group.It was possible to make a complete analysis of all 12 isotopic alkanes, i.e. (CH3)3CCX2CX3 where X represents H or D, in the products formed over supported Pd and Rh using both the NMR and MS results.Relatively little exchange of alkene occurred but it was most noticeable over Pd/SiO2.The results were interpreted in terms of a mechanistic model involving three types of adsorbed species: alkene, 1-alkyl and 2-alkyl.Any adsorbed alkene may either be desorbed or form one of the alkyls, both alkyls may either be desorbed as alkane product or revert to alkene.By choosing suitable parameters and solving 23 simultaneous equations, it was possible to obtain calculated distributions for the 12 isotopic products in good agreement with the experimental results.The presence of the tertiary butyl group has an influence on the relative stability of the adsorbed intermediates and also on the relative ease of activation (addition or removal) of primary and secondary H or D atoms.

Synthesis of a 14-electron iridium(III) complex with a xanthene-based bis(silyl) chelate ligand (xantsil): A distorted seesaw-shaped fourcoordinate geometry and reactions leading to 16-electron complexes

Komuro, Takashi,Furuyama, Keisuke,Kitano, Takeo,Tobita, Hiromi

, p. 686 - 694 (2014)

Synthesis, structure determination, and reactions of a 14-electron four-coordinate iridium(III) complex bearing a xanthene-based bis(silyl) chelate ligand, i.e., Ir{κ2(Si,Si)-xantsil}(PCy3)Cl (1a, xantsil = (9,9-dimethylxanthene-4,5-diyl)bis(dimethylsilyl)), are reported. A precursor of 1a, the 16-electron (dihydrido)iridium(V) complex Ir{κ2 (Si,Si)-xantsil}(H)2(PCy3)Cl (2), was prepared by the reaction of [IrCl-(coe)2]2 (coe = cyclooctene) with 4,5-bis(dimethylsilyl)-9,9-dimethylxanthene (xantsilH2) and PCy 3. Dehydrogenation reaction of 2 with 3,3-dimethylbut-1-ene, a hydrogen acceptor, afforded a mixture of 1a and its isomer 1b, abbreviated as 1a + 1b, together with 2,2-dimethylbutane. Single crystals obtained from a CH 2Cl2 solution of 1a + 1b contained only isomer 1a. X-ray crystal structure analysis of one of the crystals revealed that 1a adopts a distorted seesaw-shaped four-coordinate geometry where the coordinatively unsaturated metal center is stabilized by weak agostic interaction of two γ-C-H bonds of the PCy3 ligand. On the other hand, NMR spectroscopic analysis of 1a + 1b demonstrated that 1a is in fast equilibrium with a minor amount of 1b in solution. Replacement of the chloro ligand in complexes 1a + 1b by a triflato ligand with AgOTf (OTf = OSO2CF 3) afforded quantitatively a single product, i.e., the 16-electron iridiumetriflato complex Ir{κ3(Si,O,Si)-xantsil}(PCy 3)(OTf) (3). 1a + 1b and 16-electron complex 2 are interconvertible via oxidative addition of dihydrogen (from 1a + 1b to 2) and alkene hydrogenation (from 2 to 1a + 1b). Complexes 1a + 1b and 2 were found to catalyze hydrogenation of 3,3-dimethylbut-1-ene.

Formation of a C-C double bond from two aliphatic carbons. Multiple C-H activations in an iridium pincer complex

Polukeev, Alexey V.,Marcos, Rocío,Ahlquist, M?rten S. G.,Wendt, Ola F.

, p. 2060 - 2067 (2015)

The search for novel, atom-economic methods for the formation of C-C bonds is of crucial importance in synthetic chemistry. Especially attractive are reactions where C-C bonds are formed through C-H activation, but the coupling of unactivated, alkane-type Csp3-H bonds remains an unsolved challenge. Here, we report iridium-mediated intramolecular coupling reactions involving up to four unactivated Csp3-H bonds to give carbon-carbon double bonds under the extrusion of dihydrogen. The reaction described herein is completely reversible and the direction can be controlled by altering the reaction conditions. With a hydrogen acceptor present a C-C double bond is formed, while reacting under dihydrogen pressure leads to the reverse process, with some of the steps representing net Csp3-Csp3 bond cleavage. Mechanistic investigations revealed a conceptually-novel overall reactivity pattern where insertion or deinsertion of an Ir carbene moiety, formed via double C-H activation, into an Ir-C bond is responsible for the key C-C bond formation and cleavage steps.

Hydroformylation of olefins catalyzed by alkene complexes of platinum(0)

Botteghi, Carlo,Paganelli, Stefano

, p. C41 - C45 (1991)

In the presence of methanesulfonic acid the platinum(0) complex catalyses the hydroformylation of various olefins.In some cases there is quite good chemoselectivity and high regioselectivity towards n-aldehyde.

Synthesis of A Pincer-IrV Complex with A Base-Free Alumanyl Ligand and Its Application toward the Dehydrogenation of Alkanes

Morisako, Shogo,Watanabe, Seiya,Ikemoto, Satoru,Muratsugu, Satoshi,Tada, Mizuki,Yamashita, Makoto

, p. 15031 - 15035 (2019)

A pincer-iridium complex bearing a Lewis-base-free X-type alumanyl ligand has been synthesized. X-ray diffraction, NMR and IR spectroscopy, as well as XANES analysis confirmed its tetrahydrido-IrV structure and Lewis acidity at the Al center as supported by DFT calculations. The resulting complex was applied as a catalyst for the transfer dehydrogenation of cyclooctane.

Boosting homogeneous chemoselective hydrogenation of olefins mediated by a bis(silylenyl)terphenyl-nickel(0) pre-catalyst

Lücke, Marcel-Philip,Yao, Shenglai,Driess, Matthias

, p. 2909 - 2915 (2021/03/14)

The isolable chelating bis(N-heterocyclic silylenyl)-substituted terphenyl ligand [SiII(Terp)SiII] as well as its bis(phosphine) analogue [PIII(Terp)PIII] have been synthesised and fully characterised. Their reaction with Ni(cod)2(cod = cycloocta-1,5-diene) affords the corresponding 16 VE nickel(0) complexes with an intramolecularη2-arene coordination of Ni, [E(Terp)E]Ni(η2-arene) (E = PIII, SiII; arene = phenylene spacer). Due to a strong cooperativity of the Si and Ni sites in H2activation and H atom transfer, [SiII(Terp)SiII]Ni(η2-arene) mediates very effectively and chemoselectively the homogeneously catalysed hydrogenation of olefins bearing functional groups at 1 bar H2pressure and room temperature; in contrast, the bis(phosphine) analogous complex shows only poor activity. Catalytic and stoichiometric experiments revealed the important role of the η2-coordination of the Ni(0) site by the intramolecular phenylene with respect to the hydrogenation activity of [SiII(Terp)SiII]Ni(η2-arene). The mechanism has been established by kinetic measurements, including kinetic isotope effect (KIE) and Hammet-plot correlation. With this system, the currently highest performance of a homogeneous nickel-based hydrogenation catalyst of olefins (TON = 9800, TOF = 6800 h?1) could be realised.

Photo-Initiated Cobalt-Catalyzed Radical Olefin Hydrogenation

Sang, Sier,Unruh, Tobias,Demeshko, Serhiy,Domenianni, Luis I.,van Leest, Nicolaas P.,Marquetand, Philipp,Schneck, Felix,Würtele, Christian,de Zwart, Felix J.,de Bruin, Bas,González, Leticia,V?hringer, Peter,Schneider, Sven

, p. 16978 - 16989 (2021/08/09)

Outer-sphere radical hydrogenation of olefins proceeds via stepwise hydrogen atom transfer (HAT) from transition metal hydride species to the substrate. Typical catalysts exhibit M?H bonds that are either too weak to efficiently activate H2 or too strong to reduce unactivated olefins. This contribution evaluates an alternative approach, that starts from a square-planar cobalt(II) hydride complex. Photoactivation results in Co?H bond homolysis. The three-coordinate cobalt(I) photoproduct binds H2 to give a dihydrogen complex, which is a strong hydrogen atom donor, enabling the stepwise hydrogenation of both styrenes and unactivated aliphatic olefins with H2 via HAT.

Synthesis and reactivity of nitridorhenium complexes incorporating the mercaptoethylsulfide (SSS) ligand

Ison, Elon A.,Lambic, Nikola S.,Sommer, Roger D.

, p. 6127 - 6134 (2020/05/25)

A method for the preparation of nitridorhenium(v) complexes of the form (SSS)Re(N)(L) (where SSS = 2-mercaptoethylsulfide and L = PPh3andt-BuNC) has been described. These complexes react with Lewis acids allowing for the isolation of adducts. The lack of a significant steric profile on the SSS ligand combined with enhanced nucleophilicity of the nitrido group does not allow for the effective formation of frustrated Lewis pairs with these complexes and as a result these species are poor catalysts for the hydrogenation of unactivated olefins.

Highly Active Superbulky Alkaline Earth Metal Amide Catalysts for Hydrogenation of Challenging Alkenes and Aromatic Rings

Eyselein, Jonathan,F?rber, Christian,Grams, Samuel,Harder, Sjoerd,Knüpfer, Christian,Langer, Jens,Martin, Johannes,Thum, Katharina,Wiesinger, Michael

supporting information, p. 9102 - 9112 (2020/03/30)

Two series of bulky alkaline earth (Ae) metal amide complexes have been prepared: Ae[N(TRIP)2]2 (1-Ae) and Ae[N(TRIP)(DIPP)]2 (2-Ae) (Ae=Mg, Ca, Sr, Ba; TRIP=SiiPr3, DIPP=2,6-diisopropylphenyl). While monomeric 1-Ca was already known, the new complexes have been structurally characterized. Monomers 1-Ae are highly linear while the monomers 2-Ae are slightly bent. The bulkier amide complexes 1-Ae are by far the most active catalysts in alkene hydrogenation with activities increasing from Mg to Ba. Catalyst 1-Ba can reduce internal alkenes like cyclohexene or 3-hexene and highly challenging substrates like 1-Me-cyclohexene or tetraphenylethylene. It is also active in arene hydrogenation reducing anthracene and naphthalene (even when substituted with an alkyl) as well as biphenyl. Benzene could be reduced to cyclohexane but full conversion was not reached. The first step in catalytic hydrogenation is formation of an (amide)AeH species, which can form larger aggregates. Increasing the bulk of the amide ligand decreases aggregate size but it is unclear what the true catalyst(s) is (are). DFT calculations suggest that amide bulk also has a noticeable influence on the thermodynamics for formation of the (amide)AeH species. Complex 1-Ba is currently the most powerful Ae metal hydrogenation catalyst. Due to tremendously increased activities in comparison to those of previously reported catalysts, the substrate scope in hydrogenation catalysis could be extended to challenging multi-substituted unactivated alkenes and even to arenes among which benzene.

Zero valent iron complexes as base partners in frustrated Lewis pair chemistry

Fraser, Craig,Tinnermann, Hendrik,Young, Rowan D.

supporting information, p. 15184 - 15189 (2020/11/18)

The prototypical iron(0) complex [Fe(CO)3(PMe3)2] (1) forms a frustrated Lewis pair (FLP) with B(C6F5)3 (BCF). In this FLP, the iron complex acts as the Lewis base partner, and the borane as the Lewis acid partner. This FLP is able to cleave H-H, H-Cl, H-O and H-S bonds in H2, HCl, H2O and HSPh. The FLP 1/BCF is shown to catalyze the hydrogenation of alkenes under mild conditions, where terminal alkenes are preferentially reduced. Mechanistic studies using D2 gas suggest that a branched intermediate in an alkene insertion cycle or an ionic cycle is favored for this catalytic reaction.

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