3913-02-8

Basic information

• Product Name: 2-BUTYL-1-OCTANOL
• Synonyms: 2-butyl-1-octano;2-Butyloctyl alcohol;2-butyloctylalcohol;5-(Hydroxymethyl)undecane;Isododecyl alcohol;Michel XO-150-12;2-BUTYL-1-OCTANOL;2-BUTYLOCTAN-1-OL
• CAS NO: 3913-02-8
• Molecular Formula: C₁₂H₂₆O
• Molecular Weight: 186.33
• EINECS: 223-470-0
• Product Categories: Alcohols;C9 to C30;Oxygen Compounds
• Mol File: 3913-02-8.mol
• Article Data: 17

Chemical Properties

• Melting Point: -80°C(lit.)
• Boiling Point: 145-149 °C(lit.)
• Flash Point: 113 °C
• Appearance: clear liquid
• Density: 0.833 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00476mmHg at 25°C
• Refractive Index: 1.4400 to 1.4440
• PKA: 15.09±0.10(Predicted)
• Water Solubility: 1mg/L at 23℃
• Stability: Stable. Incompatible with strong oxidizing agents. Combustible.
• CAS DataBase Reference: 2-BUTYL-1-OCTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BUTYL-1-OCTANOL(3913-02-8)
• EPA Substance Registry System: 2-BUTYL-1-OCTANOL(3913-02-8)

Safety Data

• Hazard Codes: N
• Statements: 50-50/53
• Safety Statements: 57-61
• RIDADR: UN 3082 9 / PGIII
• WGK Germany: 2
• RTECS: RH0885000
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 3913-02-8(Hazardous Substances Data)

Usage

Chemical Properties

liquid

Uses

2-Butyl-1-octanol (BuOA) has been used to synthesize:2-butyl-1-octyl-methacrylate (BOMA)3,5,5-trimethyl-1-hexyl methacrylate (TMHMA) hydrophobic polyesters in miniemulsion in the presence of large amounts of waterIt has also been used as an extraction solvent in extractive fed-batch experiments.

Definition

ChEBI: A primary alcohol that is 1-octanol substituted by a butyl group at position 2. Metabolite observed in cancer metabolism.

General Description

2-Butyl-1-octanol (BuOA) is a long-chain glass forming monohydroxy alcohol.

Safety Profile

Mildly toxic by ingestion, A skin and eye irritant. See also ALCOHOLS. Combustible when exposed to heat or flame. Incompatible with oxidizing materials. To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid and irritating fumes.

InChI:InChI=1/C12H26O/c1-3-5-7-8-10-12(11-13)9-6-4-2/h12-13H,3-11H2,1-2H3

Synthetic route

2-butyloctanoic acid (27610-92-0) → 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;	94%
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;	99 %Spectr.
With samarium diiodide; tributyl-amine; water In tetrahydrofuran at 23℃; Kinetics; Concentration; Inert atmosphere; chemoselective reaction;

hexan-1-ol (111-27-3) → 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
With zinc(II) oxide; sodium hydroxide at 210℃; for 3h; Temperature; Inert atmosphere;	86%
With dichloro(pentamethylcyclopentadienyl) iridium; potassium tert-butylate; 1,7-Octadiene In para-xylene at 120℃; for 4h; Guerbet reaction;	77%
With dicarbonyl(η4-3,4-bis(4-methoxyphenyl)-2,5-diphenylcyclopenta-2,4-dienone)(iodine)ruthenium[1,3 -dimethylimidazolium]; p-benzoquinone; sodium hydroxide at 150℃; for 4h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	30.6%

methyl 2-butyloctanoate (53692-86-7) → 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h; Cooling with ice;	83%
With isopropyl alcohol In hexane at 0 - 20℃; for 0.583333h; Bouveault-Blanc Reduction; Inert atmosphere;	73%
With methanol; thulium(II) iodide In tetrahydrofuran at 23℃; Inert atmosphere; Schlenk technique;	63 %Spectr.
With samarium diiodide; water; triethylamine In tetrahydrofuran Inert atmosphere; chemoselective reaction;

1-Decanol (112-30-1) + hexan-1-ol (111-27-3) → 2-(n-butyl)octanol (3913-02-8) + 2-hexyldecan-1-ol (2425-77-6) + 5-hydroxymethyl-pentadecane (21078-85-3) + 2-octyldodecan-1-ol (5333-42-6)

Conditions	Yield
With potassium hydroxide at 255℃; for 6h; Reagent/catalyst; Dean-Stark; Inert atmosphere;	A 8.4% B n/a C n/a D 39.1%

octanol (111-87-5) + hexan-1-ol (111-27-3) → 2-hexadecyleicosyl alcohol (17658-63-8) + 2-(n-butyl)octanol (3913-02-8) + 2-hexyl-1-octanol (19780-79-1) + 2-butyl-1-decanol (21078-81-9, 123518-89-8)

Conditions	Yield
With potassium hydroxide at 225℃; for 6h; Dean-Stark; Inert atmosphere;	A 22.32% B 19.2% C n/a D n/a

hexanal (66-25-1) + benzyl alcohol (100-51-6) → 2-(n-butyl)octanol (3913-02-8) + (±)-2-benzyl-1-hexanol (7500-73-4)

Conditions	Yield
With potassium hydroxide

hexanal (66-25-1) → 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
With potassium hydroxide
With calcium carbide at 110℃;
Multi-step reaction with 3 steps 1: L-lysine / chloroform-d1 / 20 °C / Inert atmosphere 2: glucose dehydrogenase; NADPH; D-glucose; ene reductase from gluconobacter oxydans / methanol; aq. phosphate buffer / 24 h / 20 °C / pH 7 / Inert atmosphere; Enzymatic reaction 3: alcohol dehydrogenase rhodococcus sp.; glucose dehydrogenase; NADPH; D-glucose / methanol; aq. phosphate buffer / 24 h / 20 °C / pH 7 / Inert atmosphere; Enzymatic reaction View Scheme

2-butyl-octanoic acid dimethylamide → 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; tert-butyl alcohol

2-butyl-1-octene (5698-48-6) → 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
With zirconocene dichloride; oxygen; diisobutylaluminum chloride 1.) 40 deg C, 4 h, 2.) 4 h; Yield given. Multistep reaction;

hexanal (66-25-1) + benzylalcoholic KOH → 2-(n-butyl)octanol (3913-02-8) + 2-butyl-3-phenyl-propanol-(1)

sodium hexanolate (19779-06-7) + hexanal (66-25-1) + hexan-1-ol (111-27-3) → 2-(n-butyl)octanol (3913-02-8) + hexanoic acid (142-62-1) + 2-butyl-oct-2ξ-en-1-ol

hexanal (66-25-1) + calcium carbide → 2-(n-butyl)octanol (3913-02-8) + 5-formyl-undecene-(5) + 2-butyl-octanediol-(1.3)-monocaproate + caproic acid ester of 2-butyl-octanol-(1)

Conditions	Yield
at 115℃;

hexan-1-ol (111-27-3) + KOH + aluminium → 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
at 270℃; under 14710.2 Torr;

hexan-1-ol (111-27-3) + KOH + magnesium → 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
at 270℃; under 14710.2 Torr;

hexan-1-ol (111-27-3) + sodium → 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
at 230 - 290℃; unter Druck;

tetrachloromethane (56-23-5) + hexan-1-ol (111-27-3) + zinc dust + ZnO → 2-(n-butyl)octanol (3913-02-8) + 2-butyl-octen-(2)-ol-(1)

Conditions	Yield
at 205℃; under 1471.02 Torr;

butan-1-ol (71-36-3) + hexan-1-ol (111-27-3) + zinc + ZnO → 2-Ethylhexyl alcohol (104-76-7) + 2-(n-butyl)octanol (3913-02-8) + 2-ethyl-octanol-(1) + 2-butyl-hexanol-(1)

butyl-n-hexyl-acetic acid ethyl ester → 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
With ethanol; sodium

ethanol (64-17-5) + 2-butyl-octanoic acid ethyl ester + sodium → 2-(n-butyl)octanol (3913-02-8)

hexan-1-ol (111-27-3) → 2-(n-butyl)octanol (3913-02-8) + 2-butyl-octen-(2)-ol-(1)

Conditions	Yield
With sodium hydroxide anschliessendes Erhitzen in Gegenwart von Zinkstaub+Zinkoxyd auf 205grad unter ca. 2 at Druck unter Abtrennen des gebildeten Wassers;

2-butyl-1-octanal (88015-70-7) → 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
With glucose dehydrogenase; D-glucose; alcohol dehydrogenase rhodococcus sp.; NADPH In methanol; aq. phosphate buffer at 20℃; for 24h; pH=7; Solvent; Inert atmosphere; Enzymatic reaction;

2-(n-butyl)-2-octenal (64935-38-2, 99915-14-7, 13019-16-4) → 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
Stage #1: 2-butyl-oct-2-en-1-al With methanol; 5%-palladium/activated carbon at 50℃; under 7500.75 Torr; Large scale; Stage #2: With sodium tetrahydroborate at 50℃; for 1h; Temperature; Large scale;	4.5 kg

1-hexene (592-41-6) + trimethylaluminum (75-24-1) → 2-methylhexan-1-ol (624-22-6) + 2-(n-butyl)octanol (3913-02-8) + C13H28O + C19H40O

Conditions	Yield
Stage #1: 1-hexene; trimethylaluminum With (η5–neomenthylindenyl)2ZrCl2 In dichloromethane at 20℃; for 72h; Inert atmosphere; Stage #2: With oxygen In dichloromethane at 0℃; for 26h;

1-hexene (592-41-6) + trimethylaluminum (75-24-1) → 2-(n-butyl)octanol (3913-02-8) + 1-deuterio-2-methylhexane (75854-77-2) + C13H27(2)H + C19H39(2)H

Conditions	Yield
Stage #1: 1-hexene; trimethylaluminum With (η5–neomenthylindenyl)2ZrCl2 In dichloromethane at 20℃; for 72h; Inert atmosphere; Stage #2: With hydrogen chloride In dichloromethane; water-d2 at 0℃;

1-bromo-hexane (111-25-1) → 2-(n-butyl)octanol (3913-02-8)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: sodium methylate / N,N-dimethyl-formamide / 0.5 h / 80 °C / Large scale 1.2: 2 h / 120 °C / Large scale 2.1: sodium methylate / N,N-dimethyl-formamide / 0.5 h / 80 °C / Large scale 2.2: 2 h / 120 °C / Large scale 3.1: lithium chloride / N,N-dimethyl-formamide; water / 24 h / 160 °C / Large scale 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice View Scheme

Hexylmalonsaeure-dimethylester (122459-92-1) → 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium methylate / N,N-dimethyl-formamide / 0.5 h / 80 °C / Large scale 1.2: 2 h / 120 °C / Large scale 2.1: lithium chloride / N,N-dimethyl-formamide; water / 24 h / 160 °C / Large scale 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice View Scheme

dimethyl 2-butyl-2-hexylmalonate → 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium chloride / N,N-dimethyl-formamide; water / 24 h / 160 °C / Large scale 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice View Scheme

ethanol (64-17-5) + hexan-1-ol (111-27-3) → octanol (111-87-5) + 2-Ethylhexyl alcohol (104-76-7) + 2-ethyloctane-1-ol (20592-10-3) + 1-Decanol (112-30-1) + 2-(n-butyl)octanol (3913-02-8)

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium tert-butylate; 1,7-Octadiene In tetrahydrofuran at 100℃; for 24h; Inert atmosphere; Overall yield = 19 percent; Overall yield = 25 mg;

2-(n-butyl)octanol (3913-02-8) + 4-dodecyloxy-4'-hydroxybenzil (1219732-61-2) → 4-dodecyloxy-4'-(2-butyloctyloxy)benzil (1219732-56-5)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 2h; Mitsunobu reaction;	100%

2-(n-butyl)octanol (3913-02-8) + dimethyl 5,5'-dibromo-[2,2'-bithiophene]-4,4'-dicarboxylate → bis(2-butyloctyl) 5,5'-dibromo-[2,2'-bithiophene]-4,4'-dicarboxylate

Conditions	Yield
With dmap; oxo[hexa(trifluoroacetato)]tetrazinc In toluene at 110℃; Inert atmosphere; Molecular sieve;	99.8%
With dmap; oxo[hexa(trifluoroacetato)]tetrazinc In toluene at 100℃; Inert atmosphere; Molecular sieve; Schlenk technique; Sealed tube;	81.6%

fumaryl dichloride (627-63-4) + 2-(n-butyl)octanol (3913-02-8) → di(2-butyloctyl) fumarate (1142924-23-9)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 24h; Inert atmosphere;	99%

2-(n-butyl)octanol (3913-02-8) → 5-(bromomethyl)undecane (85531-02-8)

Conditions	Yield
With bromine; triphenylphosphine In dichloromethane at 0 - 20℃; Inert atmosphere;	95.3%
With 1H-imidazole; carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 3h; Cooling with ice;	90%
With bromine; triphenylphosphine In dichloromethane at 0 - 20℃; Inert atmosphere; Schlenk technique;	88.1%

2-(n-butyl)octanol (3913-02-8) → 5-(iodomethyl)undecane (1256345-37-5)

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 2h;	95%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 2h;	95%

2-(n-butyl)octanol (3913-02-8) + 2-decyltetradecanoic acid (93778-52-0) → 2-decyl-tetradecanoic acid 2-butyl-octyl ester

Conditions	Yield
With toluene-4-sulfonic acid at 80 - 83℃; for 24h;	93.4%

2-(n-butyl)octanol (3913-02-8) + p-toluenesulfonyl chloride (98-59-9) → 2-butyloctyl 4-methylbenzenesulfonate

Conditions	Yield
With triethylamine In dichloromethane at 5 - 20℃;	93%

P,P-dichlorophenylphosphine oxide (824-72-6) + 2-(n-butyl)octanol (3913-02-8) → 2-butyl-1-octyl phenylphosphonic acid (141024-65-9)

Conditions	Yield
Stage #1: P,P-dichlorophenylphosphine oxide; 2-(n-butyl)octanol With pyridine at 5 - 10℃; for 1.5 - 8.5h; Stage #2: With hydrogenchloride; water pH=1;	90%

2-(n-butyl)octanol (3913-02-8) + 4,4'-dihydroxybenzil (33288-79-8) → 4,4'-di(2-butyloctyloxy)benzil (1219732-57-6)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 2h; Mitsunobu reaction;	90%

2-(n-butyl)octanol (3913-02-8) + 4,9-dimethoxynaphtho[1,2-b:5,6-b’]dithiophene → 4,9-bis(2-butyl-1-octyl)naphtho[1,2-b:5,6-b’]dithiophene

Conditions	Yield
With toluene-4-sulfonic acid In water at 200℃; Inert atmosphere;	90%

2-bromothiophene-3-carboxylic acid (24287-95-4) + 2-(n-butyl)octanol (3913-02-8) → 2-butyloctyl 2-bromo-3-thiophenecarboxylate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;	90%

2-bromothiophene-4-carboxylic acid (100523-84-0) + 2-(n-butyl)octanol (3913-02-8) → C17H27BrO2S

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide	85%

azelaic acid (123-99-9) + 2-(n-butyl)octanol (3913-02-8) → di-2-butyloctyl azelate

Conditions	Yield
With sulfuric acid In toluene at 120 - 130℃; for 4h; Dean-Stark;	83%

4-methoxy-3-pyrrolin-2-one (69778-83-2) + 2-(n-butyl)octanol (3913-02-8) → 4-(2-butyloctyloxy)-1,5-dihydropyrrol-2-one (914275-86-8)

Conditions	Yield
With methanesulfonic acid at 80℃; for 24h;	82%

2-(n-butyl)octanol (3913-02-8) + 4'-methyl-biphenyl-4-carboxylic acid (720-73-0) → 2-butyloctyl 4’-methylbiphenyl-4-caboxylate

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 18h; Dean-Stark;	79%

2-(n-butyl)octanol (3913-02-8) + dimethyl 2,5-dibromothieno[3,2-b]thiophene-3,6-dicarboxylate → bis(2-butyloctyl) 2,5-dibromothieno[3,2-b] thiophene-3,6-dicarboxylate

Conditions	Yield
With Ti(acac)2 In toluene at 110℃; for 10h; Inert atmosphere;	79%

2-(n-butyl)octanol (3913-02-8) + 4,5-dichlorophthalic acid (56962-08-4) → bis(2-butyloctyl)-4,5-dichlorophthalate (1030871-33-0)

Conditions	Yield
With sulfuric acid In toluene Heating;	78%

2-(n-butyl)octanol (3913-02-8) + 2,3,9,10,16,17,23,24-(29H,31H)-Phthalocyanineoctacarboxylic acid (58334-40-0) → 2,3,9,10,16,17,23,24-octakis(2-butyloctyl-1-oxycarbonyl)-(29H,31H)-phthalocyanine (944909-73-3)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 48h; Heating;	78%
With toluene-4-sulfonic acid In toluene Heating;

Upstream product

• 66-25-1 hexanal 
• 100-51-6 benzyl alcohol 
• 5698-48-6 2-butyl-1-octene 
• 56-23-5 tetrachloromethane 
• 111-27-3 hexan-1-ol 
• 71-36-3 butan-1-ol 
• 64-17-5 ethanol 
• 122459-92-1 Hexylmalonsaeure-dimethylester 
• 111-25-1 1-bromo-hexane 
• 592-41-6 1-hexene 
• 75-24-1 trimethylaluminum 
• 64935-38-2 2-butyl-oct-2-en-1-al 
• 111-87-5 octanol 
• 112-30-1 1-Decanol 

Downstream Products

• 1030871-33-0 bis(2-butyloctyl)-4,5-dichlorophthalate 
• 104-15-4 toluene-4-sulfonic acid 
• 3055-97-8 heptaethylene glycol monododecyl ether 
• 217655-07-7 2-butyloctan-1-amine 
• 5698-48-6 2-butyl-1-octene 
• 112-41-4 1-dodecene 
• 4542-57-8 dilauryl ether 
• 1638802-04-6 3-(2-butyloctyl)thiophene 

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