115-84-4

Basic information

• Product Name: 2-BUTYL-2-ETHYL-1,3-PROPANEDIOL
• Synonyms: 2-N-BUTYL-2-ETHYL-1,3-PROPANEDIOL;2-ETHYL-2-(HYDROXYMETHYL)-1-HEXANOL;2-ETHYL-2-BUTYL-1,3-PROPANEDIOL;2-ETHYL-2-BUTYL-1,3-PROPANEDIOLE;2-BUTYL-2-ETHYL-1,3-PROPANEDIOL;3,3-BIS(HYDROXYMETHYL)HEPTANE;2-butyl-2-ethyl-3-propanediol;2-butyl-2-ethyl-propane-1,3-diol
• CAS NO: 115-84-4
• Molecular Formula: C₉H₂₀O₂
• Molecular Weight: 160.25
• EINECS: 204-111-7
• Product Categories: Organic Building Blocks;Oxygen Compounds;Polyols;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 115-84-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 41-44 °C(lit.)
• Boiling Point: 178 °C50 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: white crystalline solid
• Density: 0,93 g/cm3
• Vapor Pressure: 0.00159mmHg at 25°C
• Refractive Index: 1.4587
• Solubility: almost transparency in Methanol
• PKA: 14.54±0.10(Predicted)
• CAS DataBase Reference: 2-BUTYL-2-ETHYL-1,3-PROPANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BUTYL-2-ETHYL-1,3-PROPANEDIOL(115-84-4)
• EPA Substance Registry System: 2-BUTYL-2-ETHYL-1,3-PROPANEDIOL(115-84-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 1
• RTECS: TY3605000
• Hazardous Substances Data: 115-84-4(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 115-84-4 differently. You can refer to the following data:
1. Synthesis of lubricants, emulsifying agents, insect repellents, plastics.
2. 2-Butyl-2-ethyl-1,3-propanediol was used in the synthesis of polyesters.

General Description

2-Butyl-2-ethyl-1,3-propanediol undergoes bulk polycondensation with diacid monomer (terephthalic acid) to yield poly(ethylene terephthalate) copolymers.

InChI:InChI=1/C9H20O2/c1-3-5-6-9(4-2,7-10)8-11/h10-11H,3-8H2,1-2H3

Synthetic route

formaldehyd (50-00-0) + d,l-2-ethylhexanal (123-05-7) → 2-butyl-2-ethylpropane-1,3-diol (115-84-4)

Conditions	Yield
With potassium hydroxide
With potassium hydroxide In ethanol
With potassium hydroxide at 15 - 30℃;

ethyl-butyl-malonic acid diethyl ester (596-76-9) → 2-butyl-2-ethylpropane-1,3-diol (115-84-4) + 2-ethyl-2-hydroxymethyl-hexanoic acid ethyl ester

Conditions	Yield
With copper chromite; ethanol at 150℃; under 257428 Torr; Hydrogenation;

formaldehyd (50-00-0) + d,l-2-ethylhexanal (123-05-7) + alcoholic KOH → 2-butyl-2-ethylpropane-1,3-diol (115-84-4)

ethanol (64-17-5) + ethyl-butyl-malonic acid diethyl ester (596-76-9) + copper chromite → 2-butyl-2-ethylpropane-1,3-diol (115-84-4) + 2-ethyl-2-hydroxymethyl-hexanoic acid ethyl ester

Conditions	Yield
at 150℃; under 257428 Torr; Hydrogenation;

ethyl-butyl-malonic acid diethyl ester (596-76-9) → 2-butyl-2-ethylpropane-1,3-diol (115-84-4) + 2-hydroxymethyl-2-ethyl-caproic acid

Conditions	Yield
With copper chromite; ethanol at 150℃; under 250073 Torr; Hydrogenation;

formaline + d,l-2-ethylhexanal (123-05-7) → 2-butyl-2-ethylpropane-1,3-diol (115-84-4)

Conditions	Yield
With sodium hydroxide In water for 6h; Aldol Condensation; Sodium hydroxide is added into reaction mixture continuously and incrementally;

2,2-dimethyl-3-hydroxypropionaldehyde (597-31-9) + 2-butyl-2-ethylpropane-1,3-diol (115-84-4) → 2-(5-butyl-5-ethyl[1,3]dioxane-2-yl)-2-methylpropane-1-ol

Conditions	Yield
With nafion NR-50 In benzene Dean-Stark;	99%

Elaidic acid (112-79-8) + 2-butyl-2-ethylpropane-1,3-diol (115-84-4) → C45H84O4

Conditions	Yield
toluene-4-sulfonic acid In toluene at 80 - 140℃; for 6h; Heating / reflux;	98%

2-butyl-2-ethylpropane-1,3-diol (115-84-4) + methyl 3-(3-tert-butyl-4-hydroxyphenyl)propionate (36837-50-0) → 3-[3-tert-butyl-4-(5-butyl-5-ethyl-1,3,2-dioxaphosphorinan-2-yloxy)-phenyl]-propionic acid methyl ester

Conditions	Yield
Stage #1: 2-butyl-2-ethylpropane-1,3-diol With phosphorus trichloride In toluene at 60℃; for 1.5h; Stage #2: methyl 3-(3-tert-butyl-4-hydroxyphenyl)propionate With triethylamine In toluene at 80℃; for 2.5h;	94%

2-butyl-2-ethylpropane-1,3-diol (115-84-4) + tert-butylchlorodiphenylsilane (58479-61-1) → 2-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethyl-hexan-1-ol

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 9h; Substitution;	92%

2-butyl-2-ethylpropane-1,3-diol (115-84-4) + propargyl bromide (106-96-7) → 3,3-bis((prop-2-yn-1-yloxy)methyl)heptane

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium hydroxide In tetrahydrofuran; toluene at 70℃; for 24h;	88%

2,3-dimethoxythiophene (51792-34-8) + 2-butyl-2-ethylpropane-1,3-diol (115-84-4) → 3-butyl-3-ethyl-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 110℃; for 24h;	80%

2-butyl-2-ethylpropane-1,3-diol (115-84-4) + chloroformic acid ethyl ester (541-41-3) → 2-butyl-2-ethyltrimethylene carbonate (40998-16-1)

Conditions	Yield
Stage #1: 2-butyl-2-ethylpropane-1,3-diol With triethylamine In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: chloroformic acid ethyl ester In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;	73%

3-(3-tert-butyl-4-hydroxy-phenyl)-propionic acid 6-[3-(3-tert-butyl-4-hydroxy-phenyl)-propionyloxy]-hexyl ester (934371-86-5) + 2-butyl-2-ethylpropane-1,3-diol (115-84-4) → 4-[3-tert-butyl-4-(5-butyl-5-ethyl-[1,3,2]dioxaphosphinan-2-yloxy)-phenyl]-butyric acid 6-{3-[3-tert-butyl-4-(5-butyl-5-ethyl-[1,3,2]dioxaphosphinan-2-yloxy)-phenyl]-propionyloxy}-hexyl ester

Conditions	Yield
Stage #1: 2-butyl-2-ethylpropane-1,3-diol With phosphorus trichloride In toluene at 60℃; for 1.25h; Stage #2: 3-(3-tert-butyl-4-hydroxy-phenyl)-propionic acid 6-[3-(3-tert-butyl-4-hydroxy-phenyl)-propionyloxy]-hexyl ester With triethylamine In toluene at 80℃; for 2.25h;	59%

diazoacetic acid ethyl ester (623-73-4) + 2-butyl-2-ethylpropane-1,3-diol (115-84-4) → diethyl 5-butyl-5-ethyl-3,7-dioxaazelaate (108444-74-2)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane 1.) r.t., 1 h, 2.) 45 deg C, 1.5 h;	58.6%

phosgene (75-44-5) + 2-butyl-2-ethylpropane-1,3-diol (115-84-4) → 2-butyl-2-ethyltrimethylene carbonate (40998-16-1)

Conditions	Yield
With antipyrine; chloroform; toluene

phosgene (75-44-5) + 2-butyl-2-ethylpropane-1,3-diol (115-84-4) → 4-ethyl-4-butyl-2,6-dioxa-heptanedioic acid diamide (1471-51-8)

Conditions	Yield
With antipyrine; chloroform; toluene und Behandeln der Reaktionsloesung mit Ammoniak;
(i), (ii) aq. NH3; Multistep reaction;

vinyl acetate (108-05-4) + 2-butyl-2-ethylpropane-1,3-diol (115-84-4) → 5-ethyl-5-butyl-2-methyl-[1,3]dioxane (707-30-2)

Conditions	Yield
With methanol; boron trifluoride; mercury(II) oxide

poly(methacrylic acid) (79-41-4) + 2-butyl-2-ethylpropane-1,3-diol (115-84-4) → 3,3-bis-methacryloyloxymethyl-heptane (15422-98-7)

Conditions	Yield
With sulfuric acid; benzene

2-butyl-2-ethylpropane-1,3-diol (115-84-4) + nonanoic acid (112-05-0) → 3,3-bis-nonanoyloxymethyl-heptane (1637-17-8)

Conditions	Yield
With toluene; benzenesulfonic acid unter Entfernen des entstehenden Wassers;

2-butyl-2-ethylpropane-1,3-diol (115-84-4) + ethyl 3,3-diethoxypropanoate (10601-80-6) → (5-ethyl-5-butyl-[1,3]dioxan-2-yl)-acetic acid ethyl ester (86310-74-9)

Conditions	Yield
With sodium hydrogen sulfate Entfernen des entstehenden Aethanols;

2-butyl-2-ethylpropane-1,3-diol (115-84-4) → 3,3-bis-bromomethyl-heptane (855952-10-2)

Conditions	Yield
With phosphorus tribromide at 70℃;

2-butyl-2-ethylpropane-1,3-diol (115-84-4) + n-tetradecanoic acid (544-63-8) → 3,3-bis-myristoyloxymethyl-heptane (122218-25-1)

Conditions	Yield
With toluene; benzenesulfonic acid unter Entfernen des entstehenden Wassers;

2-butyl-2-ethylpropane-1,3-diol (115-84-4) + benzenesulfonyl chloride (98-09-9) → 3,3-bis-benzenesulfonyloxymethyl-heptane

2-butyl-2-ethylpropane-1,3-diol (115-84-4) + stearic acid (57-11-4) → 3,3-bis-stearoyloxymethyl-heptane (121255-47-8)

Conditions	Yield
With toluene; benzenesulfonic acid

2-butyl-2-ethylpropane-1,3-diol (115-84-4) → 2-bromo-5-butyl-5-ethyl-[1,3,2]dioxaphosphinane (21992-81-4)

Conditions	Yield
With phosphorus tribromide In dichloromethane

phosgene (75-44-5) + 2-butyl-2-ethylpropane-1,3-diol (115-84-4) + dimethyl amine (124-40-3) → N.N.N'.N'-Tetramethyl-2-aethyl-2-butyl-propandiol-(1.3)-dicarbamat (97497-30-8)

Conditions	Yield
(i) PhNMe2, (ii) /BRN= 605257/; Multistep reaction;

phosgene (75-44-5) + 2-butyl-2-ethylpropane-1,3-diol (115-84-4) + isopropylamine (75-31-0) → N,N'-Diisopropyl-2-ethyl-2-butyl-propandiol-(1.3)-dicarbamat (98308-96-4)

Conditions	Yield
(i) PhNMe2, (ii) /BRN= 605259/; Multistep reaction;

2-butyl-2-ethylpropane-1,3-diol (115-84-4) + dimethylsilicon dichloride (75-78-5) → 5-butyl-5-ethyl-2,2-dimethyl-[1,3,2]dioxasilinane (18002-55-6)

Conditions	Yield
With triethylamine

phosgene (75-44-5) + 2-butyl-2-ethylpropane-1,3-diol (115-84-4) + methylamine (74-89-5) → N,N'-Dimethyl-2-aethyl-2-butyl-propandiol-(1.3)-dicarbamat (96900-97-9)

Conditions	Yield
(i) PhNMe2, (ii) /BRN= 741851/; Multistep reaction;

2-butyl-2-ethylpropane-1,3-diol (115-84-4) + phosphorus tribromide (7789-60-8) → 3,3-bis-bromomethyl-heptane (855952-10-2)

Conditions	Yield
at 70℃;

Upstream product

• 123-05-7 d,l-2-ethylhexanal 
• 596-76-9 ethyl-butyl-malonic acid diethyl ester 
• 64-17-5 ethanol 
• 50-00-0 formaldehyd 

Downstream Products

• 1471-51-8 2-Aethyl-2-butyl-propandiol-(1,3)-dicarbamat 
• 1193512-81-0 C₂₄H₃₂N₂O₅S 
• 1193512-80-9 C₂₂H₂₈FNO₃S 
• 1193512-78-5 C₂₂H₂₆FNO₅S 
• 1193512-79-6 C₂₂H₂₆FNO₅S 
• 1193512-77-4 C₂₂H₂₆FNO₅S 
• 1193512-76-3 C₂₂H₂₈FNO₅S 
• 1193512-75-2 C₂₂H₂₈FNO₃S 
• 1193512-74-1 C₂₂H₂₆FNO₄S 
• 1025019-31-1 C₃₈H₅₁N₃O₁₂S₂*H₃N 
• 1025019-41-3 C₄₄H₅₇N₃O₁₂S 
• 1025019-24-2 C₃₈H₅₁N₃O₉S 
• 1025009-40-8 volixibat 
• 101051-51-8 (+/-)-2-Ethyl-2-(hydroxymethyl)-hexanoic acid 

Relevant articles and documents

Process for the production of 2-butyl-2-ethyl-1,3-propanediol

The present invention concerns a process for producing 2-butyl-2-ethyl-1,3-propanediol. According to the process, a reaction mixture is formed, containing 2-ethylhexanal and formaldehyde, into which an hydroxide compound is fed, whereby 2-ethylhexanal and formaldehyde are reacted to to produce 2-butyl-2-ethyl-1,3-propanediol. According to the invention, the hydroxide compound is incrementally fed into the reaction mixture. Preferably the hydroxide compound is fed at least at two input rates, in such a way that the heat production of the reaction between 2-ethylhexanal and formaldehyde immediately after each increase of the input rate of the hydroxide compound, is at least almost the same. The invention allows for the production of BEPD in a controlled and safe manner, with excellent yields.