25462-23-1

Basic information

• Product Name: 2-N-PENTYLPROPANE-1,3-DIOL
• Synonyms: 2-pentyl-3-propanediol;2-PENTYL-1,3-PROPANEDIOL;2-N-AMYLPROPANE-1,3-DIOL;2-N-PENTYLPROPANE-1,3-DIOL;1,1-BIS(HYDROXYMETHYL)HEXANE;2-Pentylpropane-1,3-diol
• CAS NO: 25462-23-1
• Molecular Formula: C₈H₁₈O₂
• Molecular Weight: 146.23
• Product Categories: Propanes/propenes
• Mol File: 25462-23-1.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 255.8 °C at 760 mmHg
• Flash Point: 117.3 °C
• Appearance: /
• Density: 0.938 g/cm³
• Vapor Pressure: 0.00242mmHg at 25°C
• Refractive Index: 1.452
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.55±0.10(Predicted)
• CAS DataBase Reference: 2-N-PENTYLPROPANE-1,3-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-N-PENTYLPROPANE-1,3-DIOL(25462-23-1)
• EPA Substance Registry System: 2-N-PENTYLPROPANE-1,3-DIOL(25462-23-1)

Safety Data

• Statements: 20/21-65
• Safety Statements: 23-36/37/39
• Hazardous Substances Data: 25462-23-1(Hazardous Substances Data)

Usage

General Description

2-N-PENTYLPROPANE-1,3-DIOL, also known as diisopropylcarbinol, is a chemical compound with the molecular formula C8H18O2. It is a colorless, odorless liquid at room temperature and is commonly used as a solvent and in the production of pharmaceuticals and cosmetics. It is a type of alcohol and is classified as a diol, meaning it contains two hydroxyl (OH) groups. 2-N-PENTYLPROPANE-1,3-DIOL is flammable and should be handled with care. It is also known for its ability to act as a chiral auxiliary in asymmetric synthesis, making it valuable in organic chemistry.

InChI:InChI=1/C8H18O2/c1-2-3-4-5-8(6-9)7-10/h8-10H,2-7H2,1H3

Synthetic route

diethyl n-pentylmalonate (6065-59-4) → 2-pentylpropane-1,3-diol (25462-23-1)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 3.33333h; Reflux;	92%
With lithium aluminium tetrahydride In diethyl ether for 1h; Reduction; Heating;	83%
Stage #1: diethyl n-pentylmalonate With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Stage #2: With sodium hydroxide; water	82%

formaldehyd (50-00-0) + heptanal (111-71-7) → 2-pentylpropane-1,3-diol (25462-23-1)

Conditions	Yield
Stage #1: formaldehyd; heptanal; L-proline In N,N-dimethyl-formamide at 20℃; Stage #2: With sodium tetrahydroborate In methanol at 0℃; Further stages.;	57%

5-bromopentylmalonic acid diethyl ester (1906-95-2) → 2-pentylpropane-1,3-diol (25462-23-1) + (bromo-5 pentyl)-2 propanediol-1,3 (115694-04-7)

Conditions	Yield
With lithium aluminium tetrahydride; bromine; sodium carbonate 1.) 10 deg C, 1 h, ether; 2.) water; Yield given. Multistep reaction. Yields of byproduct given;

Acetic acid 2-acetoxymethyl-3-cyclohexyl-propyl ester (110230-66-5) → 2-pentylpropane-1,3-diol (25462-23-1) + Acetic acid 2-hydroxymethyl-heptyl ester (138513-51-6)

Conditions	Yield
In water; isopropyl alcohol pig pancreatic lipase, pH 7 buffer (K2HPO4-KH2PO4);

1-Bromopentane (110-53-2) + sodium cyclohexylmalonic acid ester → 2-pentylpropane-1,3-diol (25462-23-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / NaOEt / ethanol / 2 h / Heating 2: 83 percent / LiAlH4 / diethyl ether / 1 h / Heating View Scheme

1-Bromopentane (110-53-2) + silver fluoride → 2-pentylpropane-1,3-diol (25462-23-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Na 2: LiAlH4 / diethyl ether / 18 h / 35 °C View Scheme
Multi-step reaction with 2 steps 1: NaOEt / ethanol 2: 1, LiAlH4; 2.) dil. HCl / 1.) ether View Scheme

1,5-dibromo-pentane (111-24-0) + zinc → 2-pentylpropane-1,3-diol (25462-23-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) bromine, sodium / 1.) ethanol, 60 deg C, 1 h; 2.) ether, 0 deg C 2: 1.) bromine, lithium aluminium hydride; 2.) 10percent sodium carbonate / 1.) 10 deg C, 1 h, ether; 2.) water View Scheme

(E)-1-Acetoxy-2-(acetoxymethyl)-3-cyclohexylidenepropane (133490-88-7) → 2-pentylpropane-1,3-diol (25462-23-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / H2 / 10percent Pd-C / ethanol / Ambient temperature 2: H2O; propan-2-ol / pig pancreatic lipase, pH 7 buffer (K2HPO4-KH2PO4) View Scheme

diethyl malonate (105-53-3) → 2-pentylpropane-1,3-diol (25462-23-1)

Conditions	Yield
With sulfuric acid In sodium-dried diethyl ether; diethyl ether; water

Pentylmalonsaeure-dimethylester (39520-21-3) → 2-pentylpropane-1,3-diol (25462-23-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Reflux;

1-Bromopentane (110-53-2) → 2-pentylpropane-1,3-diol (25462-23-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran 2: lithium aluminium tetrahydride / tetrahydrofuran / Reflux View Scheme

2-pentylpropane-1,3-diol (25462-23-1) → 1,3-dichloro-2-pentylpropane (1160187-81-4)

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride at 100 - 110℃;	85%

2-pentylpropane-1,3-diol (25462-23-1) + hypochlorous acid 4-methylbenzene sulfonic anhydride (103057-51-8) → C22H30O6S2 (111241-42-0)

Conditions	Yield
In pyridine for 16h; Ambient temperature;	81%

2-pentylpropane-1,3-diol (25462-23-1) + 4-Carboxybenzaldehyde (619-66-9) → 4-(5-n-pentyl-trans-1,3-dioxane-2-yl)-benzoic acid (81288-02-0)

Conditions	Yield
toluene-4-sulfonic acid In benzene	80%

2-pentylpropane-1,3-diol (25462-23-1) + 2',4',6'-trimethyl-[1,1'-biphenyl]-4-carbaldehyde (106359-72-2) → trans-5-pentyl-2-(2’,4’,6’-trimethyl-[1,1’-biphenyl]-4-yl)-1,3-dioxane

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 120℃; Inert atmosphere;	79%

2-pentylpropane-1,3-diol (25462-23-1) + 4-(hexyloxy)benzaldehyde (5736-94-7) → 2-(4-Hexyloxy-phenyl)-5-pentyl-[1,3]dioxane (74800-59-2) + 2-(4-Hexyloxy-phenyl)-5-pentyl-[1,3]dioxane (81221-08-1)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	A 60% B n/a

2-pentylpropane-1,3-diol (25462-23-1) + 4-(n-heptyloxy)benzaldehyde (27893-41-0) → 2-(4-Heptyloxy-phenyl)-5-pentyl-[1,3]dioxane (74800-60-5) + 2-(4-Heptyloxy-phenyl)-5-pentyl-[1,3]dioxane (81221-09-2)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	A 60% B n/a

2-pentylpropane-1,3-diol (25462-23-1) + 4-nonyloxy-benzaldehyde (50262-46-9) → 2-(4-Nonyloxy-phenyl)-5-pentyl-[1,3]dioxane (74800-61-6) + 2-(4-Nonyloxy-phenyl)-5-pentyl-[1,3]dioxane (81221-10-5)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	A 60% B n/a

2-pentylpropane-1,3-diol (25462-23-1) + 4-(n-pentyloxy)benzaldehyde (5736-91-4) → 5-Pentyl-2-(4-pentyloxy-phenyl)-[1,3]dioxane (74800-58-1) + 5-Pentyl-2-(4-pentyloxy-phenyl)-[1,3]dioxane (81221-07-0)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	A 60% B n/a

2-pentylpropane-1,3-diol (25462-23-1) + 4-propoxybenzaldehyde (5736-85-6) → 5-Pentyl-2-(4-propoxy-phenyl)-[1,3]dioxane (74800-56-9) + 5-Pentyl-2-(4-propoxy-phenyl)-[1,3]dioxane (81221-05-8)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	A 60% B n/a

2-pentylpropane-1,3-diol (25462-23-1) + p-butoxybenzaldehyde (5736-88-9) → 2-(4-Butoxy-phenyl)-5-pentyl-[1,3]dioxane (74800-57-0) + 2-(4-Butoxy-phenyl)-5-pentyl-[1,3]dioxane (81221-06-9)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	A 60% B n/a

2-pentylpropane-1,3-diol (25462-23-1) + 4-bromo-benzaldehyde (1122-91-4) → 2-(4-bromophenyl)-5-pentyl-1,3-dioxane (156684-80-9) + 2-(4-bromo-phenyl)-5-pentyl-[1,3]dioxane

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 3h; Cycloaddition; Heating;	A 50% B n/a

2-pentylpropane-1,3-diol (25462-23-1) + 2,3-difluoro-4-ethoxy-[trans-4-(2,3-difluorophenoxymethyl)cyclohexyl]benzaldehyde → 2-(4-((trans-4-(4-ethoxy-2,3-difluorophenyl)cyclohexyl)methoxy)-2,3-difluorophenyl)-5-pentyl-1,3-dioxane

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 2h; Reflux;	48.3%

2-pentylpropane-1,3-diol (25462-23-1) + 3'-fluoro[1,1'-biphenyl]-4-carbaldehyde (400750-63-2) → 3-fluoro-4'-(5-n-pentyl-1,3-dioxane-2-yl)-1,1'-biphenyl

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 2h; Inert atmosphere; Reflux;	48%

2-pentylpropane-1,3-diol (25462-23-1) + 4-(trans-4-butylcyclohexanecarbonyloxy)benzaldehyde (79285-01-1) → 4-Butyl-cyclohexanecarboxylic acid 4-(5-pentyl-[1,3]dioxan-2-yl)-phenyl ester

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	45%

2-pentylpropane-1,3-diol (25462-23-1) + Heptanoic acid 4-formylphenyl ester (50262-52-7) → trans-2-(4-Heptanoyloxyphenyl)-5-pentyl-1,3-dioxane + cis-2-(4-Heptanoyloxyphenyl)-5-pentyl-1,3-dioksane

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating; Yields of byproduct given;	A 34% B n/a
With toluene-4-sulfonic acid In benzene Heating; Yield given; Title compound not separated from byproducts;	A 34% B n/a

4-hydroxybenzotrifluoride (402-45-9) + 2-pentylpropane-1,3-diol (25462-23-1) → 2-(4-trifluoromethyl-phenoxymethyl)-heptan-1-ol (851528-56-8)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 6.5h;	31%

2-pentylpropane-1,3-diol (25462-23-1) + Decyl p-formylcinnamate (156144-74-0) → Decyl p-(5-pentyl-1,3-dioxan-2-yl)cinnamate

Conditions	Yield
	28%

2-pentylpropane-1,3-diol (25462-23-1) + 4''-(4-ethoxy-2,3,2''-trifluoro-1,1'-terphenyl)carbaldehyde (1130351-42-6) → 1-(4-ethoxy-2,3,2''-trifluoro-1,1'-terphenyl)-trans-4-pentyl-2,6-dioxane

Conditions	Yield
toluene-4-sulfonic acid In toluene for 2h; Reflux;	24.9%

2-pentylpropane-1,3-diol (25462-23-1) + 2-bromo-pentanoic acid 4-formyl-phenyl ester (220801-73-0) → 2-bromo-pentanoic acid 4-(5-pentyl-[1,3]dioxan-2-yl)-phenyl ester + 2-bromo-pentanoic acid 4-(5-pentyl-[1,3]dioxan-2-yl)-phenyl ester

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating; Yields of byproduct given;	A 21% B n/a
With toluene-4-sulfonic acid In benzene Heating; Yield given; Title compound not separated from byproducts;	A 21% B n/a

2-pentylpropane-1,3-diol (25462-23-1) + 2-chloro-heptanoic acid 4-formyl-phenyl ester (220801-72-9) → 2-chloro-heptanoic acid 4-(5-pentyl-[1,3]dioxan-2-yl)-phenyl ester + 2-chloro-heptanoic acid 4-(5-pentyl-[1,3]dioxan-2-yl)-phenyl ester

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating; Yields of byproduct given;	A 21% B n/a
With toluene-4-sulfonic acid In benzene Heating; Yield given; Title compound not separated from byproducts;	A 21% B n/a

2-pentylpropane-1,3-diol (25462-23-1) + p-cyanocinnamaldehyde (41917-85-5) → 4-[(E)-2-(5-Pentyl-[1,3]dioxan-2-yl)-vinyl]-benzonitrile (95759-39-0)

Conditions	Yield
With CH3C6H4SO3H Yield given;

2-pentylpropane-1,3-diol (25462-23-1) + Di-spiro<5.1.5.2>pentadecan-3,7,11-trione (117221-94-0) → trans-3,17-Dipentyl-1,5,15,19-tetraoxatetraspiro<5.2.1.2.5.2.2.2>pentacosan-10-on (139564-58-2, 139628-97-0)

Conditions	Yield
With toluene-4-sulfonic acid In chloroform Heating;

2-pentylpropane-1,3-diol (25462-23-1) + N-(Dimethoxymethyl)-4-pentylpiperidin (89129-94-2) → trans-4-Pentyl-1-(trans-5-pentyl-1,3-dioxan-2-yl)-piperidin

Conditions	Yield
at 40℃; for 3h; Yield given;

2-pentylpropane-1,3-diol (25462-23-1) → 2-n-pentyl-3-bromo-1-propanol (95400-56-9)

Conditions	Yield
With hydrogen bromide In sulfuric acid at 70 - 75℃;
With sulfuric acid; hydrogen bromide at 70 - 75℃; for 18h; Yield given;

2-pentylpropane-1,3-diol (25462-23-1) → 2-n-pentyl-1,3-dibromopropane (89074-70-4)

Conditions	Yield
With sulfuric acid; hydrogen bromide at 95 - 100℃; for 18h; Yield given;

2-pentylpropane-1,3-diol (25462-23-1) + terephthalaldehyde, (623-27-8) → C24H38O4 (81221-47-8)

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;

Upstream product

• 1906-95-2 5-bromopentylmalonic acid diethyl ester 
• 105-53-3 diethyl malonate 
• 110-53-2 1-Bromopentane 
• 39520-21-3 Pentylmalonsaeure-dimethylester 
• 133490-88-7 (E)-1-Acetoxy-2-(acetoxymethyl)-3-cyclohexylidenepropane 
• 111-24-0 1,5-dibromo-pentane 
• 50-00-0 formaldehyd 
• 111-71-7 heptanal 
• 110230-66-5 Acetic acid 2-acetoxymethyl-3-cyclohexyl-propyl ester 
• 6065-59-4 diethyl n-pentylmalonate 

Downstream Products

• 60435-70-3 (S)-(+)-2-methyl-1-heptanol 
• 128441-03-2 (R)-(-)-2-methyl-1-heptanol 
• 81288-02-0 4-(5-n-pentyl-trans-1,3-dioxane-2-yl)-benzoic acid 
• 96184-66-6 trans-4-(trans-5-pentyl-m-dioxan-2-yl)cyclohexanecarbonitrile 
• 851528-56-8 2-(4-trifluoromethyl-phenoxymethyl)-heptan-1-ol 
• 95400-62-7 cis 2-(p-cyanophenyl)-5-(n-pentyl)-1,3-oxathiane 
• 95400-62-7 trans 2-(p-cyanophenyl)-5-(n-pentyl)-1,3-oxathiane 
• 127113-77-3 Toluene-4-sulfonic acid 3-pentyl-cyclobutylmethyl ester 
• 104660-73-3 C₂₅H₃₄O₆S₂ 

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