142-82-5

Basic information

• Product Name: n-Heptane
• Synonyms: Heptanen;Eptani;Heptan;Dipropylmethane;1-Heptane;Skellysolve C;Heptyl hydride
• CAS NO: 142-82-5
• Molecular Formula: C₇H₁₆
• Molecular Weight: 100.23
• EINECS: 205-563-8
• Mol File: 142-82-5.mol
• Article Data: 335

Chemical Properties

• Melting Point: -91℃
• Boiling Point: 98.8 °C at 760 mmHg
• Flash Point: 30 °F
• Appearance: colourless liquid
• Density: 0.695 g/cm³
• Vapor Pressure: 45.2mmHg at 25°C
• Refractive Index: 1.394
• Water Solubility: practically insoluble
• CAS DataBase Reference: n-Heptane(CAS DataBase Reference)
• NIST Chemistry Reference: n-Heptane(142-82-5)
• EPA Substance Registry System: n-Heptane(142-82-5)

Safety Data

• Hazard Codes: F:Flammable;;
• Statements: R11:; R38:; R50/53:; R65:; R67:
• Safety Statements: S16:; S29:; S33:; S60:; S61:; S62:; S9:
• RIDADR: 1206
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 142-82-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H16/c1-3-5-7-6-4-2/h3-7H2,1-2H3

Synthetic route

1-Iodoheptane (4282-40-0) → n-heptane (142-82-5)

Conditions	Yield
With lithium aluminium tetrahydride In diethylene glycol dimethyl ether at 0℃; for 1h; Product distribution; other solvent;	100%
With ethanol; coppered zinc

Octanoic acid (124-07-2) → n-heptane (142-82-5)

Conditions	Yield
With palladium on silica gel; hydrogen at 300℃; under 760.051 Torr; for 4h; Temperature; Flow reactor;	100%
With hydrogen; silica gel; palladium at 330℃; Ni/Al2O3, 180 deg C;	97%
With Au0012O19676(00)Pd042(98)Si038; hydrogen at 260℃; under 760.051 Torr; Catalytic behavior; Reagent/catalyst;

1,2,6-heptatriene (3642-12-4) → n-heptane (142-82-5)

Conditions	Yield
With hydrogen; palladium on activated charcoal In 2,2,4-trimethylpentane Thermodynamic data; ΔHH;	100%

1-Iodoheptane (4282-40-0) + trimethylstannane (1631-73-8) + lithium diisopropyl amide (4111-54-0) → n-heptane (142-82-5) + hexamethyldistannane (661-69-8) + diisopropyl(trimethylstannyl)amine (1068-71-9)

Conditions	Yield
In hexane; cyclohexane to soln. of 1-iodoheptane (1.0 mmol) and TMTH (1.0 mmol) in hexane at 0°C added LDA (1.0 mmol, 1.6 M soln. in cyclohexane) under Ar, react. time 10 min; analyzed by GLPC;	A 99% B 0% C n/a
In hexane; cyclohexane to soln. of 1-iodoheptane (1.0 mmol) and TMTH (1.0 mmol) in hexane at 0°C added LDA (0.8 mmol, 1.6 M soln. in cyclohexane) under Ar, react. time 10 min; analyzed by GLPC;	A 98% B 0% C n/a
In hexane; cyclohexane to soln. of 1-iodoheptane (1.0 mmol) and TMTH (1.0 mmol) in hexane at 0°C added LDA (0.6 mmol, 1.6 M soln. in cyclohexane) under Ar, react. time 10 min; analyzed by GLPC;	A 94% B 0% C n/a
In hexane; cyclohexane to soln. of 1-iodoheptane (1.0 mmol) and TMTH (1.0 mmol) in hexane at 0°C added LDA (0.4 mmol, 1.6 M soln. in cyclohexane) under Ar, react. time 10 min; analyzed by GLPC;	A 84% B 0% C n/a
In hexane; cyclohexane to soln. of 1-iodoheptane (1.0 mmol) and TMTH (1.0 mmol) in hexane at 0°C added LDA (0.2 mmol, 1.6 M soln. in cyclohexane) under Ar, react. time 10 min; analyzed by GLPC;	A 74% B 0% C n/a

1-Bromoheptane (629-04-9) + trimethylstannane (1631-73-8) → n-heptane (142-82-5) + n-butyltrimethyltin (1527-99-7)

Conditions	Yield
With n-butyllithium In hexane n-BuLi (1.50 mmol, 2.40 M soln. in hexane) added to soln. of TMTH (1.50 mmol) in hexane under Ar, stirred for 3 h at room temp., 1-bromoheptane (1.50 mmol) added, heated to reflux for 2 h; analyzed by GC;	A 7% B 99%
With n-butyllithium In hexane 1-bromoheptane (1 equiv.) and TMTH (1 equiv.) in hexane cooled to 0°C under Ar, n-BuLi (1 equiv., 2.40 M in hexane) added, stirred for 5 min, quenched with water; analyzed by GC;	A 98% B 93%
With n-butyllithium In hexane to 1-bromoheptane (2.20 mmol) and TMTH (2.20 mmol) in hexane at 0°C under Ar added n-BuLi (2.20 mmol, in hexane) in four 0.55-mmol increments, stirred for 5 min; various product ratio (yields) for various amounts of n-BuLi increments added; analyzed by GC;

1-Heptyne (628-71-7) → 1-Heptene (592-76-7) + n-heptane (142-82-5)

Conditions	Yield
With quinoline; oct-1-ene; hydrogen; Lindlar's catalyst	A 98.3% B 1.7%
With hydrogen; silica gel; rhodium(1+) In ethanol; toluene at 40℃; under 1320.1 Torr; Product distribution;	A 32% B 1%
With hydrogen; copper at 200℃;

1-Iodoheptane (4282-40-0) + trimethylstannane (1631-73-8) → n-heptane (142-82-5) + n-butyltrimethyltin (1527-99-7)

Conditions	Yield
With n-butyllithium In hexane 1-iodoheptane (1 equiv.) and TMTH (1 equiv.) in hexane cooled to 0°C under Ar, n-BuLi (1 equiv., 2.40 M in hexane) added, stirred for 15 min, quenched with water; analyzed by GC;	A 92% B 98%

heptan-3-one (106-35-4) → n-heptane (142-82-5)

Conditions	Yield
With hydrogen; K-10 montmorillonite; platinum In diethylene glycol dimethyl ether under 37503 Torr; for 16h; Reduction;	97%

tricyclohexyltin hydride (6056-50-4) + 1-Bromoheptane (629-04-9) → (cyclo-C6H11)3SnC4H9 (7067-44-9) + n-heptane (142-82-5)

Conditions	Yield
With n-butyllithium In hexane 1-bromoheptane (1 equiv.) and TMTH (1 equiv.) in hexane cooled to 0°C under Ar, n-BuLi (1 equiv., 2.40 M in hexane) added, stirred for 15 min, quenched with water; analyzed by GC;	A n/a B 97%

n-pentyl methyl ketone (110-43-0) → n-heptane (142-82-5)

Conditions	Yield
With hydrogen; K-10 montmorillonite; platinum In diethylene glycol dimethyl ether under 37503 Torr; for 24h; Reduction;	96%

2-bromoheptane (1974-04-5) + trimethylstannane (1631-73-8) → n-heptane (142-82-5) + n-butyltrimethyltin (1527-99-7)

Conditions	Yield
With n-butyllithium In hexane 2-bromoheptane (1 equiv.) and TMTH (1 equiv.) in hexane cooled to 0°C under Ar, n-BuLi (1 equiv., 2.40 M in hexane) added, stirred for 5 min, quenched with water; analyzed by GC;	A 96% B 93%

1-Chloroheptane (629-06-1) + trimethylstannane (1631-73-8) → n-heptane (142-82-5) + n-butyltrimethyltin (1527-99-7)

Conditions	Yield
With n-butyllithium In hexane 1-chloroheptane (1 equiv.) and TMTH (1 equiv.) in hexane cooled to 0°C under Ar, n-BuLi (1 equiv., 2.40 M in hexane) added, stirred for 4 h, quenched with water; analyzed by GC;	A 6% B 93%
With n-butyllithium In hexane 1-chloroheptane (1 equiv.) and TMTH (1 equiv.) in hexane cooled to 0°C under Ar, n-BuLi (1 equiv., 2.40 M in hexane) added, stirred for 15 min, quenched with water; analyzed by GC;	A 0% B 36%

n-heptan1ol (111-70-6) → n-heptane (142-82-5)

Conditions	Yield
With hydrogen; AIOTfbpy-Pd In 1,2-dichloro-ethane at 200℃; under 37503.8 Torr; for 24h; Glovebox; Inert atmosphere;	92%
With hydrogen; Al(OH)(2,2'-bipyridine-5,5'-dicarboxylic acid)0.81(PdCl2)0.48(OTf)0.38 In 1,2-dichloro-ethane at 200℃; under 15001.5 Torr; for 24h; Autoclave;	78%

1-Heptyne (628-71-7) → 1-Heptene (592-76-7) + hept-3-ene (592-78-9) + hept-2-ene (592-77-8) + n-heptane (142-82-5)

Conditions	Yield
With hydrogen; palladium dichloride In N,N-dimethyl-formamide under 18751.5 Torr; for 0.416667h; Product distribution; Ambient temperature; various time;	A 89% B 1.8% C 2.9% D 6.3%

4-heptanone (123-19-3) → n-heptane (142-82-5)

Conditions	Yield
With hydrogen; aluminum oxide; nickel at 190℃;	88%
With molybdenum trisulfide at 300℃; under 73550.8 - 110326 Torr; Hydrogenation;
With cobalt(II) oxide; molybdenum trisulfide; decalin at 345℃; under 72079.8 Torr; Hydrogenation;
With hydrogenchloride; amalgamated zinc

Octanoic acid (124-07-2) → octane (111-65-9) + n-heptane (142-82-5)

Conditions	Yield
With hydrogen In water at 240℃; under 22502.3 Torr; for 12h; Catalytic behavior; Temperature; Reagent/catalyst; Autoclave;	A 5.9% B 87.4%
With hydrogen In dodecane at 350℃; under 30003 Torr; for 8h; Autoclave; chemoselective reaction;	A 83.2 %Chromat. B 9.1 %Chromat.

(Z)-hept-2-ene (6443-92-1) → n-heptane (142-82-5)

Conditions	Yield
With hydrogen In ethanol at 100℃; under 30003 Torr; Flow reactor; Green chemistry; chemoselective reaction;	87%

1-Chloroheptane (629-06-1) → n-heptane (142-82-5)

Conditions	Yield
With water; sodium iodide; nickel dichloride; zinc; sonication In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 1h; Product distribution;	85%
With water; sodium iodide; nickel dichloride; zinc; sonication In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 1h;	85%

1-Bromoheptane (629-04-9) + triethylcarbinyl bromide (73908-04-0) + trimethylstannane (1631-73-8) → 3-ethylpentane (617-78-7) + n-heptane (142-82-5) + 3-ethyl-2-pentene (816-79-5)

Conditions	Yield
With n-butyllithium In hexane n-BuLi (0.81 mmol, 0.70 M soln. in hexane) added to mixt. of 1-bromoheptane (0.81 mmol), 3-bromo-3-ethylpentane(0.81 mmol), and TMTH (0.81 mmol) in hexane under Ar, after 15 min of stirring at 0°C quenched with water; analyzed by GC;	A 84% B 5% C 11%

(E)-hept-2-ene (14686-13-6) → n-heptane (142-82-5)

Conditions	Yield
With hydrogen In ethanol at 100℃; under 30003 Torr; Flow reactor; Green chemistry; chemoselective reaction;	83%
With sodium tetrahydroborate; Octanoic acid; boron trifluoride diethyl etherate 1.) triglyme, 1 h, RT; 2.) triglyme, 210 deg C 1 h; Yield given. Multistep reaction;

2-hexyl-1,3-dithiolane (6008-84-0) + tri-n-butyl-tin hydride (688-73-3) → ethane (74-84-0) + n-heptane (142-82-5) + bis(tributyltin)sulfide (4808-30-4)

Conditions	Yield
2,2'-azobis(isobutyronitrile) In neat (no solvent) at 80℃; for 1.5h; Product distribution;	A n/a B 80% C n/a

Na(1+)*Ga(CH2CH2(CH2)4CH3)4(1-)=NaGa((CH2)6CH3)4 → sodium gallate + n-heptane (142-82-5)

Conditions	Yield
With water In hydrogenchloride hydrolyzed with 10% HCl;;	A n/a B 80%

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + 2-hydroxy-2'-nitro-4'-trifluoromethyl-3-α-cumyl-5-tert-octylazobenzene (286471-09-8) → 2-cumyl(1,1,3,3-tetramethyl-butyl)-6-[(5'-trifluoromethyl)-4,5-benzo-1,2,3-triazol-2-yl]-phenol + n-heptane (142-82-5)

Conditions	Yield
With sodium hydroxide In butanol, 2-; butanone Heating / reflux;	A 79.1% B n/a

Octanoic acid (124-07-2) → 1-Heptene (592-76-7) + n-heptane (142-82-5) + Octanal (124-13-0)

Conditions	Yield
With palladium on silica gel; hydrogen at 245℃; under 760.051 Torr; for 4h; Temperature; Flow reactor;	A 12% B 70% C 18%

1-Chloroheptane (629-06-1) + trimethylstannane (1631-73-8) + lithium diisopropyl amide (4111-54-0) → n-heptane (142-82-5) + hexamethyldistannane (661-69-8) + trimethyl(n-heptyl)tin (59344-40-0)

Conditions	Yield
In diethyl ether; cyclohexane 1-chloroheptane (1 equiv.) and TMTH (2 equiv.) in Et2O cooled to 0°C under Ar, LDA (1 equiv., 1.6 M soln. in cyclohexane) dropped in, stirred for 20-25 min at room temp., quenched with water; analyzed by GC;	A 2% B 68% C 27%
In hexane; cyclohexane 1-chloroheptane (1 equiv.) and TMTH (2 equiv.) in hexane cooled to 0°C under Ar, LDA (1 equiv., 1.6 M soln. in cyclohexane) dropped in, stirred for 20-25 min at room temp., quenched with water; analyzed by GC;	A 9% B 65% C 32%
In hexane; cyclohexane 1-chloroheptane (5 equiv.) and TMTH (2 equiv.) in hexane cooled to 0°C under Ar, LDA (1 equiv., 1.6 M soln. in cyclohexane) dropped in, stirred for 20-25 min at room temp., quenched with water; analyzed by GC;	A 8% B 34% C 63%
In diethyl ether; cyclohexane 1-chloroheptane (5 equiv.) and TMTH (2 equiv.) in Et2O cooled to 0°C under Ar, LDA (1 equiv., 1.6 M soln. in cyclohexane) dropped in, stirred for 20-25 min at room temp., quenched with water; analyzed by GC;	A 2% B 42% C 56%

chloroform (67-66-3) + n-hexylmagnesium chloride (44767-62-6) → n-heptane (142-82-5) + Tridecane (629-50-5) + 7-hexyltridecane (7225-66-3)

Conditions	Yield
With C31H37ClN3NiO2(1-)*Li(1+) In tetrahydrofuran at 25℃; for 0.333333h; Inert atmosphere;	A 9.3% B 65.2% C 21.4%
With C31H37ClFeN3O2 In tetrahydrofuran at 25℃; for 0.0833333h; Inert atmosphere;

n-heptane (142-82-5) + 1-(3-(tert-butyl)-4-hydroxyphenyl)ethan-1-one (16928-01-1) → 1-(5-bromo-3-tert-butyl-4-hydroxyphenyl)ethanone (153356-10-6)

Conditions	Yield
With N-Bromosuccinimide; sodium thiosulfate In water; acetonitrile	99.1%

[(ethyl acetate)3Mn6(O)2Piv10(2,4,4,5,5-pentamethyl-4,5-dihydro-1H-imidazolyl-3-oxide-1-oxyl)Mn6(O)2Piv10(ethyl acetate)3] + n-heptane (142-82-5) + 4,4,5,5-tetramethylimidazoline-1-oxyl-2-p-pyridyl-3-oxide (38987-16-5) → [Mn6(O)2Piv10(4,4,5,5-tetramethyl-2-(pyridine-4'-yl)-4,5-dihydro-1H-imidazolyl-3-oxide-1-oxyl)4]*0.5C7H16

Conditions	Yield
With heptane In dichloromethane Mn-compound dissolved under stirring in CH2Cl2; carefully dropped through a glass filter into a soln. of imidazole ligand in CH2Cl2; heptane added without stirring; stored at room temp. for a few days; filtered off; washed with cold heptane; dried in air; elem. anal.;	95%

n-heptane (142-82-5) + (μ-aqua)tetrakis(pivalato)tetrakis(pivalic acid)dicobalt + 2-(2-hydroxy-3-methoxy-5-nitrophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-1-oxyl → C58H94Co3N6O24*C7H16

Conditions	Yield
In acetone at 20℃; for 48h;	90%

tetrakis(acetonitrile)copper(I) tetrakis(pentafluorophenyl)borate (425370-02-1) + n-heptane (142-82-5) + 2-(1H-imidazol-4-yl)-N,N-bis((pyridin-2-yl)methyl)ethanamine (1198105-19-9) → [(2-(1H-imidazol-4-yl)-N,N-bis((pyridin-2-yl)methyl)ethanamine)Cu]B(C6F5)4*0.33(heptane)

Conditions	Yield
In tetrahydrofuran (inert atm.), Schlenk techniques; dissolving C17H19N5 and copper complexin C4H8O, stirring for 1 h at room temp.; filtration, pptn. by addn. of heptane, decantation, washing with heptane, drying under vacuum;	88%

copper(II) hexafluoro-2,4-pentanedionate + n-heptane (142-82-5) + 1-methyl-4-(4,4,5,5-tetramethyl-3-oxide-1-oxyl-4,5-dihydro-1-H-imidazol-2-yl)-1H-pyrazole → [Cu(hexafluoroacetylacetonate)2]3(4,4,5,5-tetramethyl-2-(1-methyl-1H-pyrazol-4-yl)-imidazoline-3-oxide-1-oxyl)2*heptane

Conditions	Yield
In n-heptane dissolving ligand and 1.5 equiv. of Cu complex in heptane with heating to 50°C; filtration, slow cooling to room temp., filtration, washing the crystalswith cold heptane, drying in air; elem. anal.;	87%

n-heptane (142-82-5) + [(η5-pentamethylcyclopentadienyl)(NO)(neopentyl)(η3-CH2CHCHPh)] → [(η5-pentamethylcyclopentadienyl)(NO)(n-heptyl)(η3-CH2CHCHPh)]

Conditions	Yield
In n-heptane byproducts: CMe4; (N2); using Schlenk techniques; stirring of mixt. of W(C5Me5)(CH2CMe3)(NO)(CH2CHCHPh) and n-heptane at 55°C for 3 ds; removal of solvent under reduced pressure, dissolving in pentane, transferring to the top of alumina column, deluting with 2:1 mixt. of pentane and Et2O, removal of solvents under vac., crystn. from pentane at -30°C overnight;	87%

1,1-Diphenylmethanol (91-01-0) + n-heptane (142-82-5) + [bis-5,5'-(1,3-propanediyldiimino)-2,2-dimethyl-4-hexene-3-onato]samarium[bis(trimethylsilyl)amido] → bis-5,5'-(1,3-propanediyldiimino)-2,2-dimethyl-4-hexene-3-one benzhydrol samarium(III) dimer heptane solvate

Conditions	Yield
In toluene under dry N2 atm. using Schlenk techniques; Sm complex dissolved in dry toluene; benzhydrol dissolved in toluene added with stirring; mixt. stirred at reflux overnight; cooled to ambient temp.; soln. concd. (vac.); solid recrystd. (heptane); crystals were obtained after 1 wk at -18°C; elem. anal.;	85.6%

tetrahydrofuran (109-99-9) + neodymium(III) chloride + hexane (110-54-3) + n-heptane (142-82-5) + (N-mesityl-6-(2,4,6-triisopropylphenyl)pyridine-2-aminide)Li(OEt)2 → {[(N-mesityl-6-(2,4,6-triisopropylphenyl)pyridine-2-aminide)Nd(THF)](μ2-Cl)3Li(THF)2}2

Conditions	Yield
Stage #1: tetrahydrofuran; neodymium(III) chloride; (N-mesityl-6-(2,4,6-triisopropylphenyl)pyridine-2-aminide)Li(OEt)2 at 20℃; for 24h; Schlenk technique; Stage #2: hexane; n-heptane In tetrahydrofuran Schlenk technique;	85%

Upstream product

• 617-78-7 3-ETHYLPENTANE 
• 2532-58-3 CIS-1,3-DIMETHYLCYCLOPENTANE 

Downstream Products

• 29943-42-8 Tetrahydro-4H-pyran-4-one 
• 216485-86-8 3-ISOPROPOXYPHENYLBORONIC ACID 
• 23687-27-6 8-Aminoisoquinoline 
• 20485-43-2 1-Methyl-1H-imidazole-2-carboxylic acid 
• 51630-58-1 Fenvalerate 
• 171887-03-9 N-(2-Amino-4,6-dichloro-5-pyrimidinyl)formamide 
• 56621-90-0 5-Amino-2-chloropyrimidine 
• 58-54-8 Ethacrynic acid 
• 215597-45-8 2-(AMINOMETHYL)CYCLOPROPANECARBOXYLIC ACID 
• 122453-72-9 2-(4-CHLOROPHENYL)-4-BROMO-1-METHYL-5-(TRIFLUOROMETHYL)-1H-PYRROLE-3-CARBONITRILE 
• 60835-73-6 4'-FORMYLBENZO-15-CROWN 5-ETHER 
• 31458-45-4 4,6-Diamino-2-pyrimidinol 
• 6299-85-0 2-(3-CHLOROPHENYL)MALONDIALDEHYDE 
• 39515-41-8 Fenpropathrin 
• 69739-34-0 Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester 
• 143-08-8 1-Nonanol 
• 4359-87-9 2,4,6-TRICHLORO-5-NITROPYRIMIDINE 
• 10320-42-0 2-Chloro-5-nitropyrimidine 
• 31301-51-6 2-Chloro-5-fluoropyridine 
• 990-91-0 Tetrabenzyl pyrophosphate 
• 142921-23-1 2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile 
• 157335-93-8 4,6-Dimethylpyrimidine-5-carboxylic acid 
• 931-59-9 Phenylsulfenylchloride 
• 143210-04-2 4-bromo-1-(bromomethyl)-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile 

Recommend Products

• 86467-49-4  heptanal-hydrazone 
• 124-41-4  sodium methylate 
• 112-27-6  2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 623-30-3  3-furan-2-yl-propenal 
• 592-76-7  1-Heptene 
• 123-99-9  azelaic acid 
• 110-54-3  hexane 
• 106-97-8  n-butane 
• 109-66-0  pentane 
• 109-72-8  n-butyllithium 
• 115-10-6  Dimethyl ether 
• 513-35-9  2-methyl-but-2-ene 
• 111-65-9  octane 
• 2359-09-3  5-t-butylisophthalic acid 

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