463-82-1

Basic information

• Product Name: Neopentane
• Synonyms: 1,1,1-Trimethylethane;2,2-Dimethylpropane;Neopentane;Tetramethylmethane;tert-Pentane
• CAS NO: 463-82-1
• Molecular Formula: C₅H₁₂
• Molecular Weight: 72.17
• EINECS: 207-343-7
• Mol File: 463-82-1.mol
• Article Data: 71

Chemical Properties

• Boiling Point: 7.2 ºC at 760 mmHg
• Flash Point: °C
• Appearance: /
• Density: 0.649 g/cm³
• Vapor Pressure: 1420mmHg at 25°C
• Refractive Index: 1.37
• CAS DataBase Reference: Neopentane(CAS DataBase Reference)
• NIST Chemistry Reference: Neopentane(463-82-1)
• EPA Substance Registry System: Neopentane(463-82-1)

Safety Data

• Hazardous Substances Data: 463-82-1(Hazardous Substances Data)

Usage

General Description

Neopentane is a branched-chain alkane with the chemical formula C5H12. It is a colorless, flammable gas with a boiling point of -9.5 °C and a melting point of -16.5 °C. Neopentane is commonly used as a propellant in aerosol sprays, as a refrigerant, and as a solvent. It is also used in the production of high-octane gasoline and as a chemical intermediate in the synthesis of various organic compounds. Neopentane is highly flammable and should be handled with care. It is considered to be non-toxic, but its high volatility means that it can pose a risk of explosion if not properly contained.

InChI:InChI=1/C5H12/c1-5(2,3)4/h1-4H3

Synthetic route

tris(cyclopentadienyl)thorium(IV) neopentyl → 2,2-dimethylpropane (463-82-1)

Conditions	Yield
In benzene-d6 Kinetics; thermolysis at 167 +/- 1°C;	100%

trans-neopentyl(trifluoromethanesulfonato)bis(trimethylphosphine)platinum(II) (116563-64-5) + toluene (108-88-3) → (trifluoromethanesulfonato)bis(trimethylphosphine)(m-tolyl)platinum(II) + (trifluoromethanesulfonato)bis(trimethylphosphine)(p-tolyl)platinum(II) + 2,2-dimethylpropane (463-82-1) + 1,1-dimethylcyclopropane (1630-94-0)

Conditions	Yield
In toluene Kinetics; thermolysis in toluene at 133°C for 80 min (Ar or N2);	A n/a B n/a C 99% D 1%

methane (34557-54-5) + [(η5-pentamethylcyclopentadienide)Sc(CH2C(CH3)3] (586367-34-2) → (eta.5-C5Me5)2ScCH3 (99707-15-0) + 2,2-dimethylpropane (463-82-1)

Conditions	Yield
In Cyclohexane-d12 Kinetics; under Ar, in the dark; in NMR tube; CH4 added to soln. of Sc complex in cyclohexane-d12 at 77 K; warmed to 11-50°C; not isolated; monitored by (1)H NMR spectra;	A 99% B 99%
In benzene-d6 Kinetics; under Ar, in the dark; in NMR tube; CH4 added to soln. of Sc complex in benzene-d6 at 77 K; warmed to 11-50°C; not isolated; monitored by (1)H NMR spectra;	A 99% B 99%

cyclopentadienylbis(neopentyl)indium(III) + tert-butyl alcohol (75-65-0) → 2,2-dimethylpropane (463-82-1) + [(neopentyl)2InO(t-Bu)]2 (614750-99-1)

Conditions	Yield
In diethyl ether under Ar; soln. of t-BuOH in Et2O added to In compd. (molar ratio 1:1) in Et2O at room temp.; stirred for 1 h; volatiles removed by vac. distn.; recrystd. from Et2O at -40°C; crystals washed with pentane at 0°C; elem. anal.;	A 0% B 98.3%

dineopentyl(bis(triphenylphosphine))palladium(II) → 2,2-dimethylpropane (463-82-1)

Conditions	Yield
With hydrogenchloride In toluene protonolysis with gaseous HCl;	98%

(CH2C(CH3)3)2Pt(P(C2D5)3)2 → 2,2-dimethylpropane (463-82-1) + ((CH2)2C(CH3)2)Pt(P(C2D5)3)2 (75095-31-7)

Conditions	Yield
In Cyclopentane; cyclohexane (Ar); a soln. of Pt-complex heated at 150°C for 24 min; quenched thermally at -196°C; evapd.; dissolved in acetonitrile;separated; evapd.;	A 98% B n/a

trineopentylaluminum*H2NCH3 (110638-22-7) → dineopentylaluminum(CH3NH) (110638-25-0) + 2,2-dimethylpropane (463-82-1)

Conditions	Yield
In neat (no solvent) Freshly sublimed ((CH3)3CCH2)3Al*CH3NH2 is heated under protective gas for 10 h at 96°C.; After cooling distn. of neopentane, vac. sublimation of residue at 80°C, elem. anal., mol wt.;	A 97% B n/a

cis-[bis-(dicyclohexylphosphino)ethane]hydridoneopentylplatinum(II) + 3-methyl-2-isopropyl-1-butene (111823-35-9) → {3-methyl-2-(2-propyl)-1-butene}{bis(dicyclohexylphosphino)ethane}platinum(0) (111848-52-3) + 2,2-dimethylpropane (463-82-1)

Conditions	Yield
In cyclohexane Kinetics; thermolysis of cis-hydridoneopentyl{bis(dicyclohexylphosphino)ethane}platinum(II) in 3-methyl-2-(2-propyl)-1-butene/cyclohexane via supposed {bis(dicyclohexylphosphino)ethane}platinum(0) at 69°C to completion;	A 97% B n/a

trineopentylindium (106136-98-5) + diphenylphosphane (829-85-6) → ((CH3)3CCH2)2In(P(C6H5)2) (110138-91-5) + 2,2-dimethylpropane (463-82-1)

Conditions	Yield
In benzene The mixt. of reagents in benzene was kept at 60°C for 3 d;; evapd., washed with benzene, pentane at -78°C;;	A 69.3% B 96.6%

tert-Butylacetic acid (1070-83-3) → 2,2-dimethylpropane (463-82-1)

Conditions	Yield
With hydrogen; silica gel; palladium at 330℃;	96%

cis-[bis-(dicyclohexylphosphino)ethane]hydridoneopentylplatinum(II) + tert-butylethylene (558-37-2) → (3,3-dimethyl-1-butene){bis(dicyclohexylphosphino)ethane}platinum(0) (105373-18-0) + 2,2-dimethylpropane (463-82-1)

Conditions	Yield
In cyclohexane Kinetics; thermolysis of cis-hydridoneopentyl{bis(dicyclohexylphosphino)ethane}platinum(II) in 3,3-dimethyl-1-butene/cyclohexane via supposed {bis(dicyclohexylphosphino)ethane}platinum(0) at 69°C for 2.2 h;	A >99 B 96%

dineopentyl(bis(diphenylphosphino)ethane)nickel(II) → 2,2-dimethylpropane (463-82-1)

Conditions	Yield
With hydrogenchloride In toluene protonolysis with gaseous HCl;	96%

2,2-dichloropropane (594-20-7) + methyltrichlorotitanium (2747-38-8) → 2,2-dimethylpropane (463-82-1)

Conditions	Yield
In dichloromethane at 0℃; for 1h;	95%

2,3-Dimethyl-2-butene (563-79-1) + cis-[bis-(dicyclohexylphosphino)ethane]hydridoneopentylplatinum(II) → (2,3-dimethyl-2-butene){bis(dicyclohexylphosphino)ethane}platinum(0) (111848-53-4) + 2,2-dimethylpropane (463-82-1)

Conditions	Yield
In cyclohexane Kinetics; thermolysis of cis-hydridoneopentyl{bis(dicyclohexylphosphino)ethane}platinum(II) in 2,3-dimethyl-2-butene/cyclohexane via supposed {bis(dicyclohexylphosphino)ethane}platinum(0) at 69°C to completion;	A 94% B >99

cis-[bis-(dicyclohexylphosphino)ethane]hydridoneopentylplatinum(II) + tricyclohexylphosphine (2622-14-2) → (tricyclohexylphosphine){bis(dicyclohexylphosphino)ethane}platinum(0) (111848-54-5) + 2,2-dimethylpropane (463-82-1)

Conditions	Yield
In cyclohexane Kinetics; thermolysis of cis-hydridoneopentyl{bis(dicyclohexylphosphino)ethane}platinum(II) in tricyclohexylphosphine/cyclohexane via supposed {bis(dicyclohexylphosphino)ethane}platinum(0) at 68.9°C to completion;	A 94% B >99

dineopentyl(bis(triphenylphosphine))nickel(II) → 2,2-dimethylpropane (463-82-1)

Conditions	Yield
With sulfuric acid -10°C; GLC;	93%

neopentyl iodide (15501-33-4) → 2,2,5,5-tetramethylhexane (1071-81-4) + 2,2-dimethylpropane (463-82-1) + 1,1-dimethylcyclopropane (1630-94-0)

Conditions	Yield
With tetrabutylammonium perchlorate; nickel(II) perchlorate; triphenylphosphine In acetonitrile at 25℃;	A 92% B 2.5% C 2.5%

tert-butyl methyl ether (1634-04-4) + dimethyl zinc(II) (544-97-8) → 2,2-dimethylpropane (463-82-1)

Conditions	Yield
With titanium tetrachloride In dichloromethane at 0℃; for 3h;	90%

neopentyl(η5-pentamethylcyclopentadienyl)bis(trimethylphosphine)ruthenium (87640-51-5) + toluene (108-88-3) → (η5-pentamethylcyclopentadienyl)-m-tolylbis(trimethylphosphine)ruthenium (114674-67-8) + 2,2-dimethylpropane (463-82-1)

Conditions	Yield
In toluene Ar atmosphere, 60°C, 24 h; volatiles removal (vacuum);	A 90% B n/a

cis-[bis-(dicyclohexylphosphino)ethane]hydridoneopentylplatinum(II) + tetramethylsilane (75-76-3) → cis-hydrido(trimethylsilylmethyl){bis(dicyclohexylphosphino)ethane}platinum(II) (105373-20-4) + 2,2-dimethylpropane (463-82-1)

Conditions	Yield
In cyclohexane Kinetics; thermolysis of cis-hydridoneopentyl{bis(dicyclohexylphosphino)ethane}platinum(II) in tetramethylsilane/cyclohexane via supposed {bis(dicyclohexylphosphino)ethane}platinum(0) at 69.8°C for 3 h;	A 85% B 83%

trans-neopentyl(trifluoromethanesulfonato)bis(trimethylphosphine)platinum(II) (116563-64-5) + benzene-d6 (1076-43-3) → ((CH3)3P)2Pt(C6(2)H5)(SO3CF3) + 2,2-dimethylpropane (463-82-1) + neopentane-d1 (4741-94-0) + 1,1-dimethylcyclopropane (1630-94-0)

Conditions	Yield
In benzene-d6 Kinetics; react. in a sealed 5-mm NMR tube, 133°C, 80 min (2 half-lives) (Ar or N2);	A n/a B 14% C 83% D 3%

dineopentyl(bis(triphenylphosphine))nickel(II) → bis(triphenylphosphine)-3,3-dimethylnickelacyclobutane + 2,2-dimethylpropane (463-82-1) + 1,1-dimethylcyclopropane (1630-94-0)

Conditions	Yield
In toluene inert atmosphere, -35°C, 70 h; pptn. of complex (hexane addn.), recrystn. (toluene/hexane); elem. anal.;	A 12% B 83% C 7.3%

dineopentyl(1,5-cyclooctadiene)platinum(II) → 1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) + 2,2,5,5-tetramethylhexane (1071-81-4) + 2,2-dimethylpropane (463-82-1) + (1Z,3Z,5Z)-Cycloocta-1,3,5-triene (1871-52-9)

Conditions	Yield
With tris(1-methylethyl)phosphine In Cyclopentane; cyclohexane 50 deg C,15 h; 126 deg C, 2 h; Further byproducts given;	A 80% B 36 % Chromat. C 106 % Chromat. D 14 % Chromat.

trineopentylaluminum*P(Ph2)H (110638-21-6) → dineopentylaluminum{Ph2phosphide} (110638-24-9) + 2,2-dimethylpropane (463-82-1)

Conditions	Yield
Trineopentylaluminum*P(Ph)2H is heated under protective gas at 180°C for 24 h.; Resulting solid Al-compd. is washed with pentane.;	A 78% B n/a

cis-dioxo ReO2(CH2CMe3)3 (116301-53-2) → ReO2(CH2tBu)(neopentylidene) (123154-26-7) + 2,2-dimethylpropane (463-82-1)

Conditions	Yield
In pyridine Irradiation (UV/VIS); photolysis for 1 h, using Pyrex glass-filtered light from a medium pressure mercury lamp;; Re-complex and neopentane were the only identifiable products, isolation of Re-complex by sublimation (40 ° C/ 10 E-4 torr);	A 76% B n/a
In acetonitrile Irradiation (UV/VIS); photolysis for 1 h, using Pyrex glass-filtered light from a medium pressure mercury lamp;; isolation of Re-complex by sublimation (40 ° C/ 10 E-4 torr);

(bis(triphenylphosphine))-3,3-dimethylpalladacyclobutane → 2,2-dimethylpropane (463-82-1) + ethene (74-85-1) + 1,1-dimethylcyclopropane (1630-94-0) + 3-Methyl-1-butene (563-45-1) + isobutene (115-11-7)

Conditions	Yield
In toluene inert atmosphere, thermal decompn. (85°C); GLC;	A 5% B 5% C 74% D 4% E 12%

(bis(triphenylphosphine))-3,3-dimethylpalladacyclobutane → methane (34557-54-5) + 2,2-dimethylpropane (463-82-1) + methylbutane (78-78-4) + 1,1-dimethylcyclopropane (1630-94-0) + isobutene (115-11-7)

Conditions	Yield
With hydrogen In toluene High Pressure; 5 atm H2, room temp., complete reaction at 52°C for 2 h; GLC;	A 4% B 69% C 6% D 14% E 6%

bis(triphenylphosphine)-3,3-dimethylnickelacyclobutane → methane (34557-54-5) + ethane (74-84-0) + 2,2-dimethylpropane (463-82-1) + 1,1-dimethylcyclopropane (1630-94-0) + isobutene (115-11-7)

Conditions	Yield
With hydrogen In toluene High Pressure; 5 atm H2, room temp., complete reaction at 52°C for 2 h; i-C4H8 and i-C5H12 also formed; GLC;	A 53% B 7% C 10% D 32% E 62%

cis-[bis-(dicyclohexylphosphino)ethane]hydridoneopentylplatinum(II) + 2,2,3,3-tetramethylcyclopropane (4127-47-3) → cis-hydrido(2,2,3,3-tetramethylcyclopropyl){bis(dicyclohexylphosphino)ethane}platinum(II) (105373-22-6) + cis-hydrido{(1,2,2-trimethylcyclopropyl)methyl}{bis(dicyclohexylphosphino)ethane}platinum(II) (111848-55-6) + 2,2-dimethylpropane (463-82-1)

Conditions	Yield
In further solvent(s) Kinetics; thermolysis of cis-hydridoneopentyl{bis(dicyclohexylphosphino)ethane}platinum(II) in 1,1,2,2-tetramethylcyclopropane via supposed {bis(dicyclohexylphosphino)ethane}platinum(0) at 35.0°C for 154 h;	A 56% B 12% C n/a
In further solvent(s) Kinetics; thermolysis of cis-hydridoneopentyl{bis(dicyclohexylphosphino)ethane}platinum(II) in 1,1,2,2-tetramethylcyclopropane via supposed {bis(dicyclohexylphosphino)ethane}platinum(0) at 44.9°C for 28.5 h;	A 54% B 12% C n/a

bis(triphenylphosphine)-3,3-dimethylnickelacyclobutane → 2,2-dimethylpropane (463-82-1) + ethene (74-85-1) + 1,1-dimethylcyclopropane (1630-94-0) + 3-Methyl-1-butene (563-45-1) + isobutene (115-11-7)

Conditions	Yield
With triphenylphosphine In toluene inert atmosphere, thermal decompn. (24°C, 5-fold molar excess PPh3); GLC;	A 2% B 28% C 11% D 7% E 52%
In toluene inert atmosphere, thermal decompn. (24°C); GLC;	A 6% B 15% C 47% D 6% E 26%

2,2-dimethylpropane (463-82-1) + D-(-)-quinic acid (77-95-2) → (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone (32384-42-2)

Conditions	Yield
With toluene-4-sulfonic acid In ethyl acetate at 0 - 78℃; for 12h;	92%

2,2-dimethylpropane (463-82-1) + 8-((2R,3R,4R,5R)-3,4-bishydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-fluoro-3-(2,2,2-trifluoroacetyl)pteridine-2,4(3H,8H)-dione → 8-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-6-fluoro-3-(2,2,2-trifluoroacetyl)-2,4,3,8-tetrahydropteridine-dione

Conditions	Yield
With sulfuric acid In acetone at 20 - 45℃; for 1h;	90%

2,2-dimethylpropane (463-82-1) + 8-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-6-fluoropteridine2,4(3H,8H)-dione → 6-fluoro-8-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)pteridine-2,4(3H,8H)-dione

Conditions	Yield
With sulfuric acid In acetone at 20 - 45℃; for 1h;	90%

2,2-dimethylpropane (463-82-1) → 2-methyl-2-butylchloride (594-36-5)

Conditions	Yield
With dichloromethane; antimony pentafluoride 1.) -78 deg C, 2 h, 2.) RT, 24 h;	88%

2,2-dimethylpropane (463-82-1) → methane (34557-54-5) + ethane (74-84-0) + propane (74-98-6) + Isobutane (75-28-5) + methylbutane (78-78-4)

Conditions	Yield
With hydrogen; platinum at 243℃; Product distribution; further reaction temperatures, catalysts;	A 2.7% B 1.5% C 1.5% D 6.7% E 87.8%
at 304℃; Product distribution; also from n-butane, other products,other temperatures, other catalysts;	A 7% B 1.7% C 2.4% D 15.6% E 73.3%
With hydrogen; NaY-500; palladium at 216℃; Product distribution; Kinetics; Thermodynamic data; other catalysts, other temperatures; activation energies;
With hydrogen In neat (no solvent) at 275℃; under 1225.5 Torr; Reagent/catalyst; Inert atmosphere;

pentamethylcyclopentadienyliridium(III) PMe3 dihydride (80146-01-6) + 2,2-dimethylpropane (463-82-1) → (C5(CH3)5)Ir(P(CH3)3)(C5H11)H

Conditions	Yield
In neat (no solvent) Irradiation (UV/VIS); dihydride Ir complex and C(CH3)4 irradiating for 5.3 h, cooling to -40°C, filtering, filtrate collecting, solvent removing in vacuo; identified by elem. anal., IR and NMR spectra;	83%
In further solvent(s) Irradiation (UV/VIS); irradn. in neopentane for 5.3 h;	80%
In further solvent(s) Irradiation (UV/VIS); soln. of complex in neopentane was irradiated for 36 h, then heated at 115°C for 21 h (inert atm.); cold chromy.(-80°C) on alumina III column, Et2O-hexane; elem. anal.;	40%
In neat (no solvent) Irradiation (UV/VIS); (1)H-, (13)C-NMR and IR spectroscopy;

Upstream product

• 74-84-0 ethane 
• 74-98-6 propane 
• 75-28-5 Isobutane 
• 106-97-8 n-butane 
• 503-17-3 dimethylacetylene 
• 116563-64-5 trans-neopentyl(trifluoromethanesulfonato)bis(trimethylphosphine)platinum(II) 
• 429-42-5 tetrabutylammonium tetrafluoroborate 
• 563-79-1 2,3-Dimethyl-2-butene 
• 558-37-2 tert-butylethylene 
• 4127-47-3 2,2,3,3-tetramethylcyclopropane 
• 111823-35-9 3-methyl-2-isopropyl-1-butene 
• 501-65-5 diphenyl acetylene 
• 34557-54-5 methane 
• 2622-14-2 tricyclohexylphosphine 

Downstream Products

• 1071-81-4 2,2,5,5-tetramethylhexane 
• 5434-27-5 1,3-dibromo-2,2-dimethyl-propane 
• 74-90-8 hydrogen cyanide 
• 753-89-9 neopentyl chloride 
• 630-17-1 2,2-dimethylpropyl bromide 
• 594-70-7 2-Methyl-2-nitropropane 
• 53333-76-9 2,2-dimethyl-propane-1-sulfonyl chloride 
• 24765-76-2 3-chloro-2,2-dimethylpropane-1-sulfonyl chloride 
• 354-92-7 perfluoroisobutylene 
• 594-91-2 perfluoroisopentane 
• 115-11-7 isobutene 
• 594-82-1 tetramethyl-2,2,3,3 butane 
• 1070-87-7 2,2,4,4-tetramethylpentane 
• 3522-94-9 2,2,5-trimethylhexane 

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PRODUCTION OF NEOPENTANE

Disclosed herein are processes for producing neopentane. The processes generally relate to demethylating neohexane and/or neoheptane to produce neopentane. The neohexane and/or neoheptane may be provided by the isomerization of C6-C7 paraffins.