78-26-2

Basic information

• Product Name: 2-Methyl-2-propyl-1,3-propanediol
• Synonyms: methyl-2-propyl-2-propanediol-1,3;2-METHYL-2-PROPYL-1,3-PROPANEDIOL,99%;2-Propyl-2-methyl-1,3-propanediol;Pentane-2,2-dimethanol;2,2-Dimethylolpentane2,2-Bis(hydroxymethyl)pentane;2,2-Bis(hydroxymethyl)pentane 2,2-Dimethylolpentane;Carisoprodol iMpurity C;2-Methyl-2-propyl-1,3-propanediol 98%
• CAS NO: 78-26-2
• Molecular Formula: C₇H₁₆O₂
• Molecular Weight: 132.2
• EINECS: 201-099-5
• Product Categories: Pharmaceutical Intermediates;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Polyols;(intermediate of meprobamate or carisoprodol);Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 78-26-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 57-59 °C(lit.)
• Boiling Point: 230 °C753 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: white crystalline solid
• Density: 0.9744 (rough estimate)
• Vapor Pressure: 0.00999mmHg at 25°C
• Refractive Index: 1.4474 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.57±0.10(Predicted)
• BRN: 1734432
• CAS DataBase Reference: 2-Methyl-2-propyl-1,3-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-2-propyl-1,3-propanediol(78-26-2)
• EPA Substance Registry System: 2-Methyl-2-propyl-1,3-propanediol(78-26-2)

Safety Data

• Hazard Codes: Xn
• Statements: 36-22
• Safety Statements: 22-24/25-39-26
• WGK Germany: 1
• RTECS: TY9386000
• Hazardous Substances Data: 78-26-2(Hazardous Substances Data)

Usage

Synthesis

2-Methyl-2-pentenal was hydrogenated at 100°C and 1.3-1.5MPa with a yield of 80%. After obtaining 2-methylpentenal, it was added to 36% formaldehyde, and the reaction was carried out at room temperature. Sodium hydroxide solution was added dropwise. The reaction was exothermic, and the temperature was naturally raised to 70 °C, then heated to 90 °C, added for 1 h, cooled to 60 °C and left to separate layers. The upper layer was washed with water, the washings were combined with the lower layer, and extracted with benzene. The extract and the upper layer were combined, and benzene was recovered by distillation, followed by distillation under reduced pressure to collect a fraction at 160°C (14.7kPa), which was 2-methyl-2-propyl-1,3-propanediol,yield 93%.

Uses

A intermediate in the synthesis of Carisoprodol

InChI:InChI=1/C7H16O2/c1-3-4-7(2,5-8)6-9/h8-9H,3-6H2,1-2H3

Synthetic route

5-Methyl-5-n-propyl-1,3-dioxan-2-one (7148-50-7) → methanol (67-56-1) + 2-methyl-2-propyl-1,3-propanediol (78-26-2)

Conditions	Yield
With (bis[(2-diisopropylphosphino)ethyl]amine)Mn(CO)2Br; hydrogen; sodium t-butanolate In tetrahydrofuran at 120℃; under 22502.3 Torr; for 26h; Schlenk technique; Glovebox; Autoclave;	A 94% B 98%

formaldehyd (50-00-0) + 2-methylvaleraldehyde (123-15-9) → 2-methyl-2-propyl-1,3-propanediol (78-26-2)

Conditions	Yield
With potassium hydroxide; water

methylpropylpropanedioic acid diethyl ester (55898-43-6) → 2-methyl-2-propyl-1,3-propanediol (78-26-2)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether
Stage #1: methylpropylpropanedioic acid diethyl ester With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h; Stage #2: With water In tetrahydrofuran

meprobamate (57-53-4) → 2-methyl-2-propyl-1,3-propanediol (78-26-2)

Conditions	Yield
With hydrogenchloride determination of concentration by ammonia selective electrodes;

formaldehyd (50-00-0) + 2-methylvaleraldehyde (123-15-9) + KOH-solution → 2-methyl-2-propyl-1,3-propanediol (78-26-2)

2-methyl-2-propyl-1,3-propanediol (78-26-2) + Octanoic acid (124-07-2) → Octanoic acid 2-methyl-2-octanoyloxymethyl-pentyl ester

Conditions	Yield
With pyridine; <(chlorosulfinyloxy)methylene>dimethylammonium chloride In dichloromethane at 20℃; for 6h;	98%
With toluene-4-sulfonic acid Heating; Yield given;

2-Ethylhexanoic acid (149-57-5) + 2-methyl-2-propyl-1,3-propanediol (78-26-2) → 2-methyl-2-propyl-1,3-propane-diol bis(2-ethylhexanoate)

Conditions	Yield
With pyridine; <(chlorosulfinyloxy)methylene>dimethylammonium chloride In dichloromethane at 20℃; for 6h;	98%

lauric acid (143-07-7) + 2-methyl-2-propyl-1,3-propanediol (78-26-2) → Dodecanoic acid 2-dodecanoyloxymethyl-2-methyl-pentyl ester

Conditions	Yield
With pyridine; <(chlorosulfinyloxy)methylene>dimethylammonium chloride In dichloromethane at 20℃; for 6h;	97%
With toluene-4-sulfonic acid Heating; Yield given;

2-methyl-2-propyl-1,3-propanediol (78-26-2) + 1-decanoic acid (334-48-5) → Decanoic acid 2-decanoyloxymethyl-2-methyl-pentyl ester

Conditions	Yield
With pyridine; <(chlorosulfinyloxy)methylene>dimethylammonium chloride In dichloromethane at 20℃; for 6h;	96%
With toluene-4-sulfonic acid Heating; Yield given;

2-methyl-2-propyl-1,3-propanediol (78-26-2) + hexanoic acid (142-62-1) → Hexanoic acid 2-hexanoyloxymethyl-2-methyl-pentyl ester

Conditions	Yield
With pyridine; <(chlorosulfinyloxy)methylene>dimethylammonium chloride In dichloromethane at 20℃; for 6h;	96%
With toluene-4-sulfonic acid Heating; Yield given;

2-methyl-2-propyl-1,3-propanediol (78-26-2) → 2-methyl-2-[(nitrooxy)methyl]pentyl nitrate (10605-24-0)

Conditions	Yield
With nitric acid; acetic anhydride at 15 - 20℃; for 1h;	90%
With nitric acid; acetic anhydride at 15 - 20℃; for 1h; Cooling with ice;

2-methyl-2-propyl-1,3-propanediol (78-26-2) + N-isopropylformamide (16741-46-1) → N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate (25462-17-3)

Conditions	Yield
With dihydrogen peroxide; dicyclohexyl-carbodiimide at 30℃; for 4h; Temperature; Reagent/catalyst;	82%

2,3-dimethoxythiophene (51792-34-8) + 2-methyl-2-propyl-1,3-propanediol (78-26-2) → 3-methyl-3-propyl-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-methyl-2-propyl-1,3-propanediol (78-26-2) + vanadium(V) oxychloride (7727-18-6) → {(VOCl)(μ-OCH2C(CH3)(n-C3H7)CH2O)}4

Conditions	Yield
In dichloromethane byproducts: HCl; (Ar or N2); to a soln. of 2-methyl-2-propyl-1,3-propanediol added a soln. of VOCl3 and stirred for 30 min; pentane added; stirred for 1 h; evapd.; filtered; elem. anal.;	77.4%

methylphosphonic acid dichloroanhydride (676-97-1) + 2-methyl-2-propyl-1,3-propanediol (78-26-2) → C8H17O3P

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 15h;	69%

2-methyl-2-propyl-1,3-propanediol (78-26-2) + urea (57-13-6) → meprobamate (57-53-4)

Conditions	Yield
With iron(II) bromide In 1,4-dioxane at 150℃; for 6h; Inert atmosphere; Sealed tube;	65%
With propan-1-ol; aluminum isopropoxide
With aluminum tri-n-butoxide; butan-1-ol
With lead acetate at 160℃;

2-methyl-2-propyl-1,3-propanediol (78-26-2) + 3,4-bis(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide (66074-00-8) → 4-((2-(hydroxymethyl)-2-methylpentyl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 5℃; for 0.5h;	63%

2-methyl-2-propyl-1,3-propanediol (78-26-2) + C19H24O7 → C26H38O8

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h;	55.1%

2-hydroxyhex-4-en-3-one + 2-methyl-2-propyl-1,3-propanediol (78-26-2) → 2-hydroxyethyl-5-methyl-2-(1-propenyl)-5-propyl-1,3-dioxane

Conditions	Yield
In cyclohexane	40%

C6H4NCH2CHCCH2 (491-35-0) + 2-methyl-2-propyl-1,3-propanediol (78-26-2) → C17H23NO2

Conditions	Yield
With dipotassium peroxodisulfate; sulfuric acid; silver nitrate In water; acetone at 50℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;	32%

phosgene (75-44-5) + 2-methyl-2-propyl-1,3-propanediol (78-26-2) → 5-Methyl-5-n-propyl-1,3-dioxan-2-one (7148-50-7)

Conditions	Yield
With antipyrine; chloroform

phosgene (75-44-5) + 2-methyl-2-propyl-1,3-propanediol (78-26-2) → meprobamate (57-53-4)

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

phosgene (75-44-5) + 2-methyl-2-propyl-1,3-propanediol (78-26-2) → 2-methyl-1-phenylcarbamoyloxy-2-(phenylcarbamoyloxy-methyl)-pentane (25457-67-4)

Conditions	Yield
und anschliessend mit Anilin;

phosgene (75-44-5) + 2-methyl-2-propyl-1,3-propanediol (78-26-2) → 1-(4-ethoxy-phenylcarbamoyloxy)-2-[(4-ethoxy-phenylcarbamoyloxy)-methyl]-2-methyl-pentane (25648-74-2)

Conditions	Yield
anschliessend Behandeln mit p-Phenetidin;

diphenylacetic acid chloride (1871-76-7) + 2-methyl-2-propyl-1,3-propanediol (78-26-2) → diphenyl-acetic acid-(2-hydroxymethyl-2-methyl-pentyl ester) (102472-07-1) + 2,2-bis-(diphenylacetoxy-methyl)-pentane (121376-21-4)

Conditions	Yield
With pyridine; tetrachloromethane

3,3-Dimethylacryloyl chloride (3350-78-5) + 2-methyl-2-propyl-1,3-propanediol (78-26-2) → 2,2-bis-[(3-methyl-crotonoyloxy)-methyl]-pentane

Conditions	Yield
With pyridine; diethyl ether

2-methyl-2-propyl-1,3-propanediol (78-26-2) + 4-methylvaleroyl chloride (38136-29-7) → 2,2-bis-(4-methyl-valeryloxymethyl)-pentane (111528-86-0)

Conditions	Yield
With pyridine; diethyl ether

2-methyl-2-propyl-1,3-propanediol (78-26-2) → 1-bromo-2-bromomethyl-2-methyl-pentane (89796-29-2)

Conditions	Yield
With phosphorus tribromide

2-methyl-2-propyl-1,3-propanediol (78-26-2) → 2-Methylpentanoic acid (97-61-0, 22160-39-0)

Conditions	Yield
With potassium permanganate

2-methyl-2-propyl-1,3-propanediol (78-26-2) → 2-hydroxymethyl-2-methyl-valeric acid (15240-86-5)

Conditions	Yield
With sodium hydroxide; potassium permanganate

2-methyl-2-propyl-1,3-propanediol (78-26-2) → 1-(4-methoxy-phenylcarbamoyloxy)-2-[(4-methoxy-phenylcarbamoyloxy)-methyl]-2-methyl-pentane (118899-17-5)

Conditions	Yield
With COCl2 anschliessend Behandeln mit p-Anisidin;

2-methyl-2-propyl-1,3-propanediol (78-26-2) + benzyl chloride (100-44-7) → 3-benzyloxy-2-methyl-2-propyl-propan-1-ol (108239-67-4)

Conditions	Yield
With sodium hydroxide

Upstream product

• 50-00-0 formaldehyd 
• 123-15-9 2-methylvaleraldehyde 
• 7148-50-7 5-Methyl-5-n-propyl-1,3-dioxan-2-one 
• 57-53-4 meprobamate 
• 55898-43-6 methylpropylpropanedioic acid diethyl ester 

Downstream Products

• 102472-07-1 diphenyl-acetic acid-(2-hydroxymethyl-2-methyl-pentyl ester) 
• 121376-21-4 2,2-bis-(diphenylacetoxy-methyl)-pentane 
• 57-53-4 meprobamate 
• 7148-50-7 5-Methyl-5-n-propyl-1,3-dioxan-2-one 
• 1729-14-2 N,N'-Diisopropyl-2-methyl-2-propyl-propandiol-(1.3)-dicarbamat 
• 25649-06-3 N.N.N'.N'-Tetra-(β-chlor-ethyl)-2-methyl-2-propyl-1.3-dicarbamoyloxy-propan 
• 25648-73-1 N,N'-Dibenzyl-2-methyl-2-propyl-1,3-dicarbamoyloxy-propan 
• 25652-09-9 N,N'-Dimethoxy-N,N',2-trimethyl-2-propyl-1,3-dicarbamoyloxy-propan 
• 67-56-1 methanol 
• 105-30-6 2-methylpentan-1-ol 
• 123-15-9 2-methylvaleraldehyde 
• 115570-48-4 1,3-bis-(4-nitrophenoxy)-2-methyl-2-propylpropane 
• 25462-17-3 N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate 
• 25648-74-2 1-(4-ethoxy-phenylcarbamoyloxy)-2-[(4-ethoxy-phenylcarbamoyloxy)-methyl]-2-methyl-pentane 

Relevant articles and documents

Application of the ammonia selective electrode: Determination of meprobamate by decomposition with acid

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