10042-59-8

Basic information

• Product Name: 2-PROPYL-1-HEPTANOL
• Synonyms: 2-propyl-1-heptano;2-propylheptanol;2-PROPYL-1-HEPTANOL;2-PROPYLHEPTAN-1-OL;1-Heptanol, 2-propyl-;2-n-Propyl-1-heptanol;2-Propylheptyl Alcohol
• CAS NO: 10042-59-8
• Molecular Formula: C₁₀H₂₂O
• Molecular Weight: 158.28
• EINECS: 233-126-1
• Product Categories: Aliphatics
• Mol File: 10042-59-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: -1.53°C (estimate)
• Boiling Point: 213.4°C (estimate)
• Flash Point: 87.141 °C
• Appearance: Light yellow oil
• Density: 0.8280
• Vapor Pressure: 0.0283mmHg at 25°C
• Refractive Index: 1.4360
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 15.09±0.10(Predicted)
• Water Solubility: Insoluble in water. Miscible with most common organic solvents.
• CAS DataBase Reference: 2-PROPYL-1-HEPTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PROPYL-1-HEPTANOL(10042-59-8)
• EPA Substance Registry System: 2-PROPYL-1-HEPTANOL(10042-59-8)

Safety Data

• RTECS: MJ4800000
• TSCA: Yes
• Hazardous Substances Data: 10042-59-8(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Oil

Uses

2-Propyl-1-heptanol (cas# 10042-59-8) is a compound useful in organic synthesis.

Preparation

2-Propyl Heptanol (2-PH) is the precursor to Di-propylheptylphthalate (DPHP): a similar component to Di-ethylhexylphthalate (DEHP) and Di-octyl-phtalate (DOP) which is made from 2-Ethyl Hexanol (2-EH). It is produced from the hydroformylation ("oxo synthesis") of C4 alkenes followed by hydrogenation of the resulting aldehyde. The production route is similar to that for 2-Ethylhexanol.

Application

2-propylheptanol is a branched C10 fatty alcohol. Mainly used as plasticizer alcohol (phthalic anhydride, trimellitic anhydride and adipic acid), and as raw material for making surfactants used in detergents or in industrial cleaning agents for hard surface cleaning. It is also used as raw material for lubricants and acrylates in adhesives applications.

Synthesis Reference(s)

The Journal of Organic Chemistry, 15, p. 54, 1950 DOI: 10.1021/jo01147a010

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H22O/c1-3-5-6-8-10(9-11)7-4-2/h10-11H,3-9H2,1-2H3

Synthetic route

pentan-1-ol (71-41-0) → 2-propylheptan-1-ol (10042-59-8)

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl) iridium; potassium tert-butylate; 1,7-Octadiene In para-xylene at 120℃; for 4h; Guerbet reaction;	71%

2-pentyl-pent-4-en-1-ol (346447-01-6) → 2-propylheptan-1-ol (10042-59-8)

Conditions	Yield
With ethanol; platinum Hydrogenation; dextrorotatory form of 4-oxymethyl-nonane;

pentan-1-ol (71-41-0) + sodium pentanolate (1941-84-0) → 2-propylheptan-1-ol (10042-59-8)

Conditions	Yield
With copper

2-propyl-1-heptene (33717-91-8) → 2-propylheptan-1-ol (10042-59-8)

Conditions	Yield
(i) NaBH4, AlCl3, diglyme, (ii) aq. NaOH, aq. H2O2; Multistep reaction;

pentan-1-ol (71-41-0) + potassium pentylate → 2-propylheptan-1-ol (10042-59-8)

Conditions	Yield
With nickel

high-density polyethylene, carbon content: 85.3 wt percent, hydrogen content: 14.7 wt percent, net calorific value: 10273 kcal/kg → 2-propylheptan-1-ol (10042-59-8)

Conditions	Yield
With air at 500℃; for 0.0277778h; Formation of xenobiotics;

nonan-4-one (4485-09-0) → 2-propylheptan-1-ol (10042-59-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) NaNH2, liq. NH3, (ii) /BRN= 1743603/, benzene 2: (i) NaBH4, AlCl3, diglyme, (ii) aq. NaOH, aq. H2O2 View Scheme

poly(2-propylheptyl acrylate) → 2-propylheptan-1-ol (10042-59-8) + 2-propyl-1-heptene (33717-91-8) + 2-propylheptyl acrylate (149021-58-9) + 2-propyleheptyl methacrylate (149855-64-1)

Conditions	Yield
at 450℃; Pyrolysis;

poly(2-propylheptyl acrylate) → 2-propylheptan-1-ol (10042-59-8) + methane (34557-54-5) + carbon dioxide (124-38-9) + carbon monoxide (201230-82-2) + 2-propylheptyl acrylate (149021-58-9) + 2-propyleheptyl methacrylate (149855-64-1)

Conditions	Yield
at 550℃; Pyrolysis;

poly(2-propylheptyl acrylate) → 2-propylheptan-1-ol (10042-59-8) + 2-propyl-1-heptene (33717-91-8) + 2-propylheptyl acrylate (149021-58-9)

Conditions	Yield
at 350℃; Pyrolysis;

2-propylheptenal (34880-43-8) → 2-propylheptan-1-ol (10042-59-8)

Conditions	Yield
With hydrogen; Ru/Al2O3 at 180℃; under 18751.9 Torr; Product distribution / selectivity;

pentanal (110-62-3) → 2-propylheptan-1-ol (10042-59-8) + pentan-1-ol (71-41-0)

Conditions	Yield
With hydrogen at 200℃; under 22502.3 Torr; for 6h; Catalytic behavior; Reagent/catalyst; Autoclave;
Stage #1: pentanal at 200℃; for 1.5h; Aldol Condensation; Autoclave; Inert atmosphere; Stage #2: With hydrogen under 30003 Torr; for 8h; Catalytic behavior; Pressure; Temperature; Autoclave;
With hydrogen at 200℃; under 22502.3 Torr; for 6h; Reagent/catalyst; Autoclave;

pentanal (110-62-3) → 2-propylheptan-1-ol (10042-59-8) + pentan-1-ol (71-41-0) + 2-propylheptenal (34880-43-8) + 2-(n-propyl)-heptanal (76058-49-6)

Conditions	Yield
With hydrogen at 200℃; under 22502.3 Torr; for 6h; Autoclave;
With hydrogen at 200℃; under 22502.3 Torr; for 6h; Autoclave;

pentanal (110-62-3) → 2-propylheptan-1-ol (10042-59-8) + pentan-1-ol (71-41-0) + 2-(n-propyl)-heptanal (76058-49-6)

Conditions	Yield
Stage #1: pentanal at 190℃; for 1.5h; Aldol Condensation; Autoclave; Inert atmosphere; Stage #2: With hydrogen under 15001.5 Torr; for 6h; Pressure; Autoclave;
With hydrogen at 200℃; under 22502.3 Torr; for 6h; Autoclave;

pentanal (110-62-3) + butyraldehyde (123-72-8) → 2-propylheptan-1-ol (10042-59-8) + 2-Ethylhexyl alcohol (104-76-7) + 2-propylhexanol (817-46-9) + 2-ethylheptanol (817-60-7)

Conditions	Yield
Stage #1: pentanal; butyraldehyde With sodium hydroxide In water at 20 - 130℃; for 3.25h; Stage #2: With hydrogen In water

2-propylheptan-1-ol (10042-59-8) + acrylic acid methyl ester (292638-85-8) → 2-propylheptyl acrylate (149021-58-9)

Conditions	Yield
With sodium methylate; dimethyltin dichloride; 4-methoxy-phenol In methanol; cyclohexane at 86 - 114℃; Solvent; Large scale;	99.6%

2-propylheptan-1-ol (10042-59-8) + acrylic acid (79-10-7) → 2-propylheptyl acrylate (149021-58-9)

Conditions	Yield
With dimethylphosphinic acid; toluene-4-sulfonic acid; 4-methoxy-phenol; copper dichloride In cyclohexane; water at 85 - 99℃; for 5h;	99%
With methanesulfonic acid; hypophosphorous acid; 4-methoxy-phenol; copper dichloride In cyclohexane; water at 60 - 75℃; for 2h; Reflux;	97%
With methanesulfonic acid In water at 120℃; Industrial scale;

2-propylheptan-1-ol (10042-59-8) + benzene-1,2-dicarboxylic acid (88-99-3) → di(2-propylheptyl) phthalate (53306-54-0)

Conditions	Yield
With titanium(IV) isopropylate at 170 - 220℃; under 760.051 Torr; for 4.5h; Inert atmosphere; Large scale;	99%
In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 6h; Reagent/catalyst; Solvent; Temperature;

2-propylheptan-1-ol (10042-59-8) → 4-(bromomethyl)nonane

Conditions	Yield
With sulfuric acid; hydrogen bromide at 109.84℃; for 3.5h;	95%

2-propylheptan-1-ol (10042-59-8) + trifluoromethylsulfonic anhydride (358-23-6) → 2-propyl-1-heptyl triflate (885501-50-8)

Conditions	Yield
In dichloromethane at 20℃; for 0.333333h;	94.1%
In dichloromethane at 20℃; for 0.333333h;	94.1%
In dichloromethane at 20℃; for 0.333333h;

2-propylheptan-1-ol (10042-59-8) → 2-propyl-1-heptyl triflate (885501-50-8)

Conditions	Yield
With trifluoromethanesulfonic acid anhydride In dichloromethane	94.1%
With trifluoromethanesulfonic acid anhydride In dichloromethane	94.1%

2-propylheptan-1-ol (10042-59-8) → tris(2-propyl-1-heptyl) phosphate

Conditions	Yield
With tetrabutoxytitanium; trichlorophosphate at 60 - 80℃; under 600.06 - 750.075 Torr; for 5h; Reagent/catalyst; Pressure; Green chemistry;	92.5%

2-propylheptan-1-ol (10042-59-8) + dimethyl 2,5-dimethylhexanedioate (19550-58-4) → di(2-propylheptyl)-2,5-dimethyladipate

Conditions	Yield
With sulfuric acid at 140℃; for 2h;	66.7%

2-propylheptan-1-ol (10042-59-8) + epichlorohydrin (106-89-8) → 1-chloro-3-(2-propyl-heptyloxy)-propan-2-ol

Conditions	Yield
Stage #1: 2-propylheptan-1-ol With boron trifluoride diethyl etherate at 20 - 50℃; Stage #2: epichlorohydrin at 50℃; for 4.5h;	60%
With tin(IV) chloride at 90℃; for 19h;
boron trifluoride diethyl etherate at 50℃; for 4.5h; Neat (no solvent);
With tin(ll) chloride at 90℃; for 19h;

2-propylheptan-1-ol (10042-59-8) + furan-2,5-dicarboxylic acid (3238-40-2) → 2,5-furandicarboxylic acid bis(2-propyl-heptyl) ester

Conditions	Yield
With sulfuric acid In water; toluene Reflux;	58%

2-propylheptan-1-ol (10042-59-8) + 2,5-tetrahydrofurandicarboxylic acid dimethyl ester → 2,5-tetrahydrofurandicarboxylic acid bis(2-propyl-heptyl) ester

Conditions	Yield
In tetrahydrofuran; n-heptane at 100 - 126℃; for 22h;	58%

3-methoxy-thiophene (17573-92-1) + 2-propylheptan-1-ol (10042-59-8) → C14H24OS

Conditions	Yield
With sodium hydrogen sulfate In toluene at 130℃; for 19h; Inert atmosphere; Schlenk technique;	55.4%

2-propylheptan-1-ol (10042-59-8) → 2-propyl-heptanoyl chloride

Conditions	Yield
With potassium permanganate; sulfuric acid und Behandeln des Reaktionsprodukts mit Thionylchlorid;

2-propylheptan-1-ol (10042-59-8) → bis-(2-propyl-heptyloxy)-disulfane (3542-42-5)

Conditions	Yield
With disulfur dichloride; triethylamine In dichloromethane at 5 - 15℃;

2-propylheptan-1-ol (10042-59-8) + phosphorus pentabromide (7789-69-7) → 4-(bromomethyl)nonane

Conditions	Yield
dextrorotatory form of 4-oxymethyl-nonane;

2-propylheptan-1-ol (10042-59-8) → C28H38N3(1+)*CF3SO3(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94.1 percent / CH2Cl2 / 0.33 h / 20 °C 2: CH2Cl2 / 12 h / 20 °C View Scheme

2-propylheptan-1-ol (10042-59-8) → C36H44N3(1+)*CF3SO3(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94.1 percent / CH2Cl2 / 0.33 h / 20 °C 2: CH2Cl2 / 4 h / 20 °C View Scheme

2-propylheptan-1-ol (10042-59-8) → 2-{4-[3,5-dimethyl-1-(2-propyl-heptyl)-1H-pyridin-4-ylidene]-3,5-dimethyl-cyclohexa-2,5-dienylidene}-malononitrile

Conditions	Yield
Multi-step reaction with 2 steps 1.1: CH2Cl2 / 0.33 h / 20 °C 2.1: CH2Cl2 / 12 h / 20 °C 2.2: 66.9 percent / sodium methoxide / methanol; CH2Cl2 / 0.17 h / 20 °C View Scheme

2-propylheptan-1-ol (10042-59-8) → 2-[4-(2-{4-[3,5-dimethyl-1-(2-propyl-heptyl)-1H-pyridin-4-ylidene]-3,5-dimethyl-cyclohexa-2,5-dienylidene}-ethylidene)-cyclohexa-2,5-dienylidene]-malononitrile

Conditions	Yield
Multi-step reaction with 2 steps 1.1: CH2Cl2 / 0.33 h / 20 °C 2.1: CH2Cl2 / 4 h / 20 °C 2.2: 65.7 percent / sodium methoxide / methanol; CH2Cl2 / 0.17 h / 20 °C View Scheme

2-propylheptan-1-ol (10042-59-8) + oxiranyl-methanol (556-52-5) → C13H28O3

Conditions	Yield
boron trifluoride diethyl etherate In xylene at 80℃; for 5h;

Upstream product

• 110-62-3 pentanal 
• 123-72-8 butyraldehyde 
• 34880-43-8 2-propylheptenal 
• 4485-09-0 nonan-4-one 
• 71-41-0 pentan-1-ol 
• 33717-91-8 2-propylhept-1-ene 
• 1941-84-0 sodium pentanolate 
• 346447-01-6 2-pentyl-pent-4-en-1-ol 

Downstream Products

• 53306-54-0 di(2-propylheptyl) phthalate 
• 6422-86-2 di(2-ethylhexyl)terephthalate 

Relevant articles and documents

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[IrCl(cod)]2 and [Cp*IrCl2]2 complexes catalyzed efficiently the Guerbet reaction of primary alcohols to β-alkylated dimer alcohols in good yields. For instance, the reaction of 1-butanol in the presence of [Cp*IrCl2]2 (1 mol %), t-BuOK (40 mol %), and 1,7-octadiene (10 mol %) produced 2-ethyl-1-hexanol in 93% yield. Various primary alcohols undergo the Guerbet reaction under the influence of Ir complexes to give the corresponding dimer alcohols in good yields. This method provides an alternative direct route to β-alkylated primary alcohols which are prepared by aldol condensation of aldehydes followed by hydrogenation.

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