7426-71-3

Basic information

• Product Name: butylidynetrimethanol
• Synonyms: butylidynetrimethanol;2-(Hydroxymethyl)-2-propyl-1,3-propanediol;2-(HydroxyMethyl)-2-propylpropane-1,3-diol
• CAS NO: 7426-71-3
• Molecular Formula: C₇H₁₆O₃
• Molecular Weight: 148.20014
• EINECS: 231-065-5
• Mol File: 7426-71-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 306.8 °C at 760 mmHg
• Flash Point: 151.2 °C
• Appearance: /
• Density: 1.084 g/cm³
• Vapor Pressure: 6.98E-05mmHg at 25°C
• Refractive Index: 1.483
• CAS DataBase Reference: butylidynetrimethanol(CAS DataBase Reference)
• NIST Chemistry Reference: butylidynetrimethanol(7426-71-3)
• EPA Substance Registry System: butylidynetrimethanol(7426-71-3)

Safety Data

• Hazardous Substances Data: 7426-71-3(Hazardous Substances Data)

Usage

General Description

Butylidynetrimethanol, also known as pentaerythritol, is an organic compound which is a white, crystalline, solid substance. This odorless compound has various applications, notably in the production of alkyd resins, varnishes, polyvinyl chloride stabilizers, olefins antioxidant, and synthetic lubricants. It may also be used as a starting material for manufacturing plasticizers, certain types of explosives, and rosin esters for use in printing inks and adhesives. The substance is known for its low toxicity and minimal environmental impact. It is usually created through the reaction of acetaldehyde and formaldehyde under alkaline conditions. It has a melting point of about 260 degrees Celsius and a boiling point of about 276 degrees Celsius at 100 mm Hg. Its chemical formula is C5H12O4.

InChI:InChI=1/C7H16O3/c1-2-3-7(4-8,5-9)6-10/h8-10H,2-6H2,1H3

Synthetic route

formaldehyd (50-00-0) + pentanal (110-62-3) → 2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3)

Conditions	Yield
With sodium hydroxide In acetonitrile at 60 - 80℃; for 1h;	52%
With potassium hydroxide In ethanol; water at 50℃; Cooling with ice;	10%
(i) NaOH, (ii) nBuOH, (heating); Multistep reaction;
With sodium hydroxide In acetonitrile
With sodium hydroxide In acetonitrile at 20 - 80℃; for 0.833333h; Inert atmosphere;	6.6 g

formaldehyd (50-00-0) + dibutyl ether (142-96-1) → 2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3)

Conditions	Yield
Irradiation.mit UV-Licht;

formaldehyd (50-00-0) + dibutyl ether (142-96-1) → 2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) + 2-propyl-propane-1,3-diol (2612-28-4)

Conditions	Yield
Irradiation.mit UV-Licht;
anschliessend Betrahlen der Reaktionsloesung mit UV;

2-n-propyl-2-hydroxymethyl-propan-1,3-diol triacetate (14274-62-5) → 2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3)

Conditions	Yield
With sodium In methanol

C7H13O3(3-)*Sb(3+) → 2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3)

Conditions	Yield
With water-d2 In dimethylsulfoxide-d6 Glovebox;

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) + antimony(III) tert-butoxide → C7H13O3(3-)*Sb(3+)

Conditions	Yield
In tetrahydrofuran at 22℃; Inert atmosphere; Sealed tube;	70.4%

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → 3-hydroxymethyl-3-n-propyl oxetane (107829-94-7)

Conditions	Yield
With potassium carbonate; Diethyl carbonate at 125℃; for 3h;	38%
With potassium carbonate; Diethyl carbonate at 125℃; for 6h; Inert atmosphere;	3.7 g

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) + methyl 5-t-butyl-2,3-dimethyl-4-hydroxyphenylacetate (56823-74-6) → (5-tert-Butyl-4-hydroxy-2,3-dimethyl-phenyl)-acetic acid 2,2-bis-[2-(5-tert-butyl-4-hydroxy-2,3-dimethyl-phenyl)-acetoxymethyl]-pentyl ester (56823-89-3)

Conditions	Yield
With lithium hydride

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → 1-chloro-2,2-bis-chloromethyl-pentane (13722-71-9)

Conditions	Yield
With pyridine; thionyl chloride

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → 4-n-propyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane (18644-16-1)

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) + acetone (67-64-1) → 5-hydroxymethyl-2,2-dimethyl-5-propyl-1,3-dioxane (109383-31-5)

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → 2,2-dimethyl-5-propyl-1,3-dioxan-5-ylmethyl N,N,N',N'-tetraethylphosphorodiamidite (676447-84-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2 h / 90 - 100 °C View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → O-(2,2-dimethyl-5-propyl-1,3-dioxan-5-ylmethyl) N,N,N',N'-tetraethylphosphorodiamidothioate (676447-87-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 2 h / 90 - 100 °C 2: 64 percent / sulfur View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → O-(2,2-dimethyl-5-propyl-1,3-dioxan-5-ylmethyl) N,N,N',N'-tetraethylphosphorodiamidoselenoate (676447-90-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 2 h / 90 - 100 °C 2: 72 percent / selenium View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → O-[2,2-bis(myristoyloxymethyl)pentyl] N,N,N',N'-tetraethylphosphorodiamidothioate

Conditions	Yield
Multi-step reaction with 4 steps 1: 2 h / 90 - 100 °C 2: 64 percent / sulfur 3: ZnCl2 / 20 °C View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → O-[2,2-bis(myristoyloxymethyl)pentyl] N,N,N',N'-tetraethylphosphorodiamidoselenoate

Conditions	Yield
Multi-step reaction with 4 steps 1: 2 h / 90 - 100 °C 2: 72 percent / selenium 3: ZnCl2 / 20 °C View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → O-[2,2-bis(stearoyloxymethyl)pentyl] N,N,N',N'-tetraethylphosphorodiamidothioate

Conditions	Yield
Multi-step reaction with 4 steps 1: 2 h / 90 - 100 °C 2: 64 percent / sulfur 3: ZnCl2 / 20 °C View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → O-[2,2-bis(stearoyloxymethyl)pentyl] N,N,N',N'-tetraethylphosphorodiamidoselenoate

Conditions	Yield
Multi-step reaction with 4 steps 1: 2 h / 90 - 100 °C 2: 72 percent / selenium 3: ZnCl2 / 20 °C View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) + methanesulfonyl chloride (124-63-0) → 2-hydroxymethyl-2-n-propylpropan-1,3-diol trimethanesulphonate

Conditions	Yield
In pyridine; diethyl ether

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → 4-propyl-1-(3,5-difluorophenyl)-2,6,7-trioxabicyclo[2.2.2]octane (1401904-32-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: Diethyl carbonate; potassium carbonate / 6 h / 125 °C / Inert atmosphere 2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere 3: boron trifluoride diethyl etherate / dichloromethane / 24 h / -70 - 20 °C / Inert atmosphere View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → 1-(4-(bromodifluoromethyl)-3,5-difluorophenyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane (1401904-34-4)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: Diethyl carbonate; potassium carbonate / 6 h / 125 °C / Inert atmosphere 2.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere 3.1: boron trifluoride diethyl etherate / dichloromethane / 24 h / -70 - 20 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -70 °C / Inert atmosphere 4.2: 1 h / -70 °C / Inert atmosphere View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → 1-(4-(difluoro(3,4,5-trifluorophenoxy)methyl)-3,5-difluorophenyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane (1401904-29-7)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: Diethyl carbonate; potassium carbonate / 6 h / 125 °C / Inert atmosphere 2.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere 3.1: boron trifluoride diethyl etherate / dichloromethane / 24 h / -70 - 20 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -70 °C / Inert atmosphere 4.2: 1 h / -70 °C / Inert atmosphere 5.1: potassium carbonate; tetrabutyl phosphonium bromide / n-heptane; water / 10 h / 82 - 85 °C / Inert atmosphere View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → (3-propyloxetane-3-yl)methyl 4-((3,4,5-trifluorophenoxy)methyl)cyclohexanecarboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1: Diethyl carbonate; potassium carbonate / 6 h / 125 °C / Inert atmosphere 2: 1-(4'-(bromodifluoromethyl)-2,3',5'-trifluoro-[1,1'-biphenyl]-4-yl)-4-pentyl-2,6,7-trioxabicyclo[2.2.2]octane; dmap / dichloromethane / 20 h / 20 °C View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → 4-propyl-1-(4-((3,4,5-trifluorophenoxy)methyl)cyclohexyl)-2,6,7-trioxabicyclo[2.2.2]octane

Conditions	Yield
Multi-step reaction with 3 steps 1: Diethyl carbonate; potassium carbonate / 6 h / 125 °C / Inert atmosphere 2: 1-(4'-(bromodifluoromethyl)-2,3',5'-trifluoro-[1,1'-biphenyl]-4-yl)-4-pentyl-2,6,7-trioxabicyclo[2.2.2]octane; dmap / dichloromethane / 20 h / 20 °C 3: boron trifluoride diethyl etherate / dichloromethane / 15 h / -70 - 20 °C / Inert atmosphere View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → 1-(3-propyloxetane-3-yl)methyl 4-(3,4,5-trifluorophenyl)cyclohexane-1,4-dicarboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1: Diethyl carbonate; potassium carbonate / 6 h / 125 °C / Inert atmosphere 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 h / 20 °C / Inert atmosphere View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → 3,4,5-trifluorophenyl 4-(4-propyl-2,6,7-trioxabicyclo[2.2.2]octane-1-yl)cyclohexanecarboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: Diethyl carbonate; potassium carbonate / 6 h / 125 °C / Inert atmosphere 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 h / 20 °C / Inert atmosphere 3: boron trifluoride diethyl etherate / dichloromethane / 22 h / -70 - 20 °C / Inert atmosphere View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → 4-(3,4,5-trifluorophenyl)cyclohexanecarboxylate(3-propyloxetane-3-yl)methyl

Conditions	Yield
Multi-step reaction with 2 steps 1: Diethyl carbonate; potassium carbonate / 6 h / 125 °C / Inert atmosphere 2: pyridine / tetrahydrofuran / 20 h / 20 °C / Inert atmosphere View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → 4-propyl-1-(4-(3,4,5-trifluorophenyl)cyclohexyl)-2,6,7-trioxabicyclo[2.2.2]octane

Conditions	Yield
Multi-step reaction with 3 steps 1: Diethyl carbonate; potassium carbonate / 6 h / 125 °C / Inert atmosphere 2: pyridine / tetrahydrofuran / 20 h / 20 °C / Inert atmosphere 3: boron trifluoride diethyl etherate / dichloromethane / 15 h / -70 - 20 °C / Inert atmosphere View Scheme

2-(hydroxymethyl)-2-propylpropane-1,3-diol (7426-71-3) → 3,5-difluorobenzoate(3-propyloxetane-3-yl)methyl (1401904-30-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: Diethyl carbonate; potassium carbonate / 6 h / 125 °C / Inert atmosphere 2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere View Scheme

Upstream product

• 14274-62-5 2-n-propyl-2-hydroxymethyl-propan-1,3-diol triacetate 
• 50-00-0 formaldehyd 
• 110-62-3 pentanal 
• 142-96-1 dibutyl ether 

Downstream Products

• 1401904-30-0 3,5-difluorobenzoate(3-propyloxetane-3-yl)methyl 
• 1401904-34-4 1-(4-(bromodifluoromethyl)-3,5-difluorophenyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane 
• 18644-16-1 4-n-propyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 
• 56823-89-3 (5-tert-Butyl-4-hydroxy-2,3-dimethyl-phenyl)-acetic acid 2,2-bis-[2-(5-tert-butyl-4-hydroxy-2,3-dimethyl-phenyl)-acetoxymethyl]-pentyl ester 

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