57018-52-7

Basic information

• Product Name: 1-TERT-BUTOXY-2-PROPANOL
• Synonyms: 1-TERT-BUTOXY-2-PROPANOL;ARCOSOLV(R) PTB;PROPYLENE GLYCOL 1-TERT-BUTYL ETHER;PROPYLENE GLYCOL TERTIARY BUTYL ETHER;(1,1-dimethylethoxy)-propano;1-(1,1-dimethylethoxy)-2-propano;1-(1,1-dimethylethoxy)-2-Propanol;1-tert-butoxy-propan-2-ol
• CAS NO: 57018-52-7
• Molecular Formula: C₇H₁₆O₂
• Molecular Weight: 132.2
• EINECS: 406-180-0
• Product Categories: Alcohols;Building Blocks;C7 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 57018-52-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: -56°C(lit.)
• Boiling Point: 143-145 °C(lit.)
• Flash Point: 112 °F
• Appearance: Clear colorless liquid with an ethereal odor.
• Density: 0.874 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.000356mmHg at 25°C
• Refractive Index: n20/D 1.413(lit.)
• PKA: 14.51±0.20(Predicted)
• Water Solubility: Soluble in water
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, acids, water, dehydrating agents. Slightly air sensitive.
• CAS DataBase Reference: 1-TERT-BUTOXY-2-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-TERT-BUTOXY-2-PROPANOL(57018-52-7)
• EPA Substance Registry System: 1-TERT-BUTOXY-2-PROPANOL(57018-52-7)

Safety Data

• Hazard Codes: Xi
• Statements: 10-41
• Safety Statements: 26-39
• RIDADR: UN 1987 3/PG 3
• WGK Germany: 1
• RTECS: UB3772000
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 57018-52-7(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

1-(1,1-Dimethylethoxy)-2-propanol is a useful reagent for organic synthesis.

General Description

Clear colorless liquid with an ethereal odor.

Air & Water Reactions

Highly flammable. Sensitive to heat and prolonged exposure to air. Water soluble.

Reactivity Profile

1-TERT-BUTOXY-2-PROPANOL is incompatible with acids, oxidizing agents, oxygen (prolonged contact), water and dehydrating agents. .

Fire Hazard

1-TERT-BUTOXY-2-PROPANOL is combustible.

InChI:InChI=1/C8H18O.C3H8O2/c1-7(2,3)9-8(4,5)6;1-3(5)2-4/h1-6H3;3-5H,2H2,1H3

Synthetic route

propylene glycol (57-55-6) + tert-butyl alcohol (75-65-0) → 1-tert-butoxy-2-propanol (57018-52-7)

Conditions	Yield
With Amberlyst15 In hexane at 40℃; for 7h;	84.8%

propylene glycol (57-55-6) + isobutene (115-11-7) → 1-tert-butoxy-2-propanol (57018-52-7)

Conditions	Yield
With Amberlyst15 In toluene at 35℃; for 5h;	72.3%

2-<2-(2-hydroxypropoxy)-ethyl>-4-methyl-1,3-dioxolane (89769-15-3) + tert-butyl alcohol (75-65-0) → 2-tert-butoxy-1-propanol (94023-15-1) + 1-tert-butoxy-2-propanol (57018-52-7) + 1,2-di-tert-butoxypropane + cis-2-(2-tert-butoxyethyl)-4-methyl-1,3-dioxolane

Conditions	Yield
With sulfuric acid for 5h; Heating; Further byproducts given;	A 0.15% B 0.65 g C 0.08 g D n/a
With sulfuric acid for 5h; Heating; Further byproducts given;	A 0.15 g B 0.65% C 0.08 g D n/a
With sulfuric acid for 5h; Heating; Further byproducts given;	A 0.15 g B 1.27 g C 0.08 g D n/a

potassium tert-butylate (865-47-4) + methyloxirane (75-56-9, 16033-71-9) → 1-tert-butoxy-2-propanol (57018-52-7)

Conditions	Yield
In toluene; tert-butyl alcohol

methyloxirane (75-56-9, 16033-71-9) + tert-butyl alcohol (75-65-0) → 1-tert-butoxy-2-propanol (57018-52-7)

Conditions	Yield
With sodium hydroxide for 72h; Heating; Yield given;

2-<2-(2-hydroxypropoxy)-ethyl>-4-methyl-1,3-dioxolane (89769-15-3) + tert-butyl alcohol (75-65-0) → 2-tert-butoxy-1-propanol (94023-15-1) + 1-tert-butoxy-2-propanol (57018-52-7) + 1,2-di-tert-butoxypropane + trans-2-(2-tert-butoxyethyl)-4-methyl-1,3-dioxolane

Conditions	Yield
With sulfuric acid for 5h; Heating; Further byproducts given;	A 0.15 g B 1.27 g C 0.08 g D n/a

ethanol (64-17-5) + isopropyl alcohol (67-63-0) + methyloxirane (75-56-9, 16033-71-9) + tert-butyl alcohol (75-65-0) → propylene glycol monoethyl ether (1569-02-4) + 1-isopropoxy-2-propanol (3944-36-3) + 1-tert-butoxy-2-propanol (57018-52-7)

Conditions	Yield
Trimethyl borate; hydrogen fluoride In water for 0.5h;

phosphotungestic acid (1343-93-7) + propylene glycol (57-55-6) + isobutene (115-11-7) → 1-tert-butoxy-2-propanol (57018-52-7)

tert-butyl glycidyl ether (7580-85-0) → 1-tert-butoxy-2-propanol (57018-52-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / Reflux 2: diethyl ether / 0 °C View Scheme

tert-butoxyacetaldehyde (28047-97-4) + methylmagnesium bromide (75-16-1) → 1-tert-butoxy-2-propanol (57018-52-7)

Conditions	Yield
In diethyl ether at 0℃;

methyloxirane (75-56-9, 16033-71-9) + tert-butyl alcohol (75-65-0) → 2-tert-butoxy-1-propanol (94023-15-1) + 1-tert-butoxy-2-propanol (57018-52-7)

Conditions	Yield
With trigonal Mo-V-O oxide at 100℃; for 12h;

1-tert-butoxy-2-propanol (57018-52-7) + ethoglucid (1954-28-5) → C19H38O8

Conditions	Yield
With tin(IV) chloride at 80℃; for 4.5h;	94.7%

1-tert-butoxy-2-propanol (57018-52-7) + ethylaluminum dichloride (563-43-9) → [Cl2Al(OCH(CH3)CH2OC(CH3)3)]2 (463966-50-9)

Conditions	Yield
In hexane (Ar); addn. of a soln. of alcohol in hexane to a soln. of aluminium compd. in hexane at 0°C; evapn., drying in vac., recrystn. (hexane); elem. anal.;	94%

Isopropenyl acetate (108-22-5) + 1-tert-butoxy-2-propanol (57018-52-7) → (R)-2-O-acetyl-1-O-tert-butylpropane-1,2-diol (136579-69-6)

Conditions	Yield
With Novozym 435; dicarbonyl(chloro)(η5-pentaphenylcyclopentadienyl)ruthenium(II); potassium tert-butylate; sodium carbonate In toluene at 75℃; for 120h; Time; Enzymatic reaction;	92%
With novozyme 435; dicarbonyl(chloro)(η5-pentaphenylcyclopentadienyl)ruthenium(II); potassium tert-butylate; sodium carbonate In tetrahydrofuran; toluene at 75℃; for 120h; Catalytic behavior; Time; Resolution of racemate; Inert atmosphere;	68%

1-tert-butoxy-2-propanol (57018-52-7) + tris(dimethylamino)aluminum (14314-61-5) → 3C7H15O2(1-)*Al(3+)

Conditions	Yield
at 23 - 60℃; for 18.25h;	84%

1-tert-butoxy-2-propanol (57018-52-7) + trimethylaluminum (75-24-1) → [(CH3)2Al(OCH(CH3)CH2OC(CH3)3)]2

Conditions	Yield
In hexane; toluene (Ar); addn. of a soln. of alcohol in toluene to a soln. of aluminium compd. in hexane at -78°C, stirring for 0.5 h, slow warming to room temp.; evapn., crystn. (hexane, -5°C, 5 d); elem. anal.;	83%

gallium tris(dimethylamide) + 1-tert-butoxy-2-propanol (57018-52-7) → 3C7H15O2(1-)*Ga(3+)

Conditions	Yield
In toluene at 23 - 60℃; for 18.25h;	81%

1-tert-butoxy-2-propanol (57018-52-7) + indium (III) tris(hexamethyldisilyl) amide → In(3+)*3C7H15O2(1-)

Conditions	Yield
In toluene at 23 - 60℃; for 18.25h;	81%

vinyl acetate (108-05-4) + 1-tert-butoxy-2-propanol (57018-52-7) → (R)-2-O-acetyl-1-O-tert-butylpropane-1,2-diol (136579-69-6) + (S)-1-tert-butoxy-2-propanol (136656-76-3)

Conditions	Yield
In various solvent(s) lipase from Pseudomonas fluorescens (SAM-1); pH 7;

1-tert-butoxy-2-propanol (57018-52-7) → (R)-2-O-acetyl-1-O-tert-butylpropane-1,2-diol (136579-69-6) + (S)-1-tert-butoxy-2-propanol (136656-76-3)

Conditions	Yield
In various solvent(s) lipase from Pseudomonas fluorescens (SAM-1); pH 7;

1-tert-butoxy-2-propanol (57018-52-7) → tert-butoxy-2-propanone (28047-99-6)

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid In dichloromethane at 20℃; for 6h;	95 % Turnov.
With acetic anhydride; pyridinium chlorochromate In dichloromethane at 20℃; Molecular sieve;

1-tert-butoxy-2-propanol (57018-52-7) + 5-(1-hydroxy-2-methylpropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (84794-38-7) → 4-methyl-3-oxo-pentanoic acid 2-tert-butoxy-1-methyl-ethyl ester (575838-16-3)

Conditions	Yield
In toluene Heating;

1-tert-butoxy-2-propanol (57018-52-7) + 5-(1-hydroxy-2-phenyl-butylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione → 3-oxo-4-phenyl-hexanoic acid 2-tert-butoxy-1-methyl-ethyl ester

Conditions	Yield
In toluene Heating;

2-amino-8-quinolinol (70125-16-5) + 1-tert-butoxy-2-propanol (57018-52-7) → 8-(2-tert-butoxy-1-methyl-ethoxy)-quinolin-2-ylamine

Conditions	Yield
With PS-PPh3; dibenzyl azodicarboxylate In tetrahydrofuran Mitsunobu reaction;

5-(6-(azidocarbonyl)-5-isopropylpyrrolo[2,1-f][1,2,4]triazin-4-ylamino)-2,4-difluoro-N-methoxybenzamide (658085-52-0) + 1-tert-butoxy-2-propanol (57018-52-7) → [4-(2,4-difluoro-5-methoxycarbamoyl-phenylamino)-5-isopropyl-pyrrolo[2,1-f][1,2,4]triazin-6-yl]-carbamic acid 2-tert-butoxy-1-methyl-ethyl ester

Conditions	Yield
In N,N-dimethyl-formamide at 85℃; for 2h; Curtius rearrangement;

1-tert-butoxy-2-propanol (57018-52-7) + methyl 4-hydroxy-3-chlorobenzoate (3964-57-6) → 4-(1-tert-butoxy-2-propoxy)-3-chlorobenzoic acid methyl ester (570408-03-6)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 1h;

1-tert-butoxy-2-propanol (57018-52-7) + p-toluenesulfonyl chloride (98-59-9) → TsOCH(CH3)CH2OC(CH3)3 (304874-42-8)

Conditions	Yield
With pyridine at 5℃; for 2h;

4-chloro-7-methoxyquinoline (68500-37-8) + 1-tert-butoxy-2-propanol (57018-52-7) → 4-(1-tert-butoxypropan-2-yloxy)-7-methoxyquinoline (1051315-81-1)

Conditions	Yield
Stage #1: 1-tert-butoxy-2-propanol With sodium hydride In N,N-dimethyl-formamide at 23℃; for 0.166667h; Stage #2: 4-chloro-7-methoxyquinoline In N,N-dimethyl-formamide at 37℃; for 18h;

potassium hexacyanidocobaltate(III) + nitroprusside + poly(propyleneoxide) + 1-tert-butoxy-2-propanol (57018-52-7) + zinc(II) chloride (7646-85-7) → Catalyst Complex B

1-tert-butoxy-2-propanol (57018-52-7) → C11H20O3

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 20 °C / Molecular sieve 2.1: sodium hydride / tetrahydrofuran / 0 °C 2.2: 20 °C View Scheme

1-tert-butoxy-2-propanol (57018-52-7) → C11H21NO3

Conditions	Yield
Multi-step reaction with 3 steps 1.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 20 °C / Molecular sieve 2.1: sodium hydride / tetrahydrofuran / 0 °C 2.2: 20 °C 3.1: isopropylmagnesium chloride / tetrahydrofuran / 0 - 20 °C View Scheme

1-tert-butoxy-2-propanol (57018-52-7) → C16H24O2 (1392278-12-4)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: acetic anhydride; pyridinium chlorochromate / dichloromethane / 20 °C / Molecular sieve 2.1: sodium hydride / tetrahydrofuran / 0 °C 2.2: 20 °C 3.1: isopropylmagnesium chloride / tetrahydrofuran / 0 - 20 °C 4.1: tetrahydrofuran; diethyl ether / 0 °C 5.1: [2,2]bipyridinyl; silver hexafluoroantimonate; palladium dichloride / methanol; water / 60 °C / Inert atmosphere View Scheme

Upstream product

• 865-47-4 potassium tert-butylate 
• 75-56-9 methyloxirane 
• 1343-93-7 phosphotungestic acid 
• 57-55-6 propylene glycol 
• 115-11-7 isobutene 
• 75-65-0 tert-butyl alcohol 
• 28047-97-4 tert-butoxyacetaldehyde 
• 75-16-1 methylmagnesium bromide 
• 7580-85-0 tert-butyl glycidyl ether 
• 64-17-5 ethanol 
• 67-63-0 isopropyl alcohol 
• 89769-15-3 2-<2-(2-hydroxypropoxy)-ethyl>-4-methyl-1,3-dioxolane 

Downstream Products

• 1392278-12-4 C₁₆H₂₄O₂ 
• 3246-80-8 9-phenyl-9H-xanthene 
• 28047-99-6 tert-butoxy-2-propanone 
• 304874-42-8 TsOCH(CH₃)CH₂OC(CH₃)3 
• 570408-03-6 4-(1-tert-butoxy-2-propoxy)-3-chlorobenzoic acid methyl ester 
• 136579-69-6 (R)-2-O-acetyl-1-O-tert-butylpropane-1,2-diol 
• 136656-76-3 (S)-1-tert-butoxy-2-propanol 

Relevant articles and documents

METHOD FOR PRODUCING 1-ALKOXY-2-ALKANOL COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing 1-alkoxy-2-alkanol compounds from 1,2-alkanediol compounds with good yields while suppressing the by-production of 1,2-dialkoxyalkane compounds. SOLUTION: The present invention provides a method for producing 1-alkoxy-2-alkanol compounds represented by formula (3) by making the reaction between 1,2-alkanediol compounds and tertiary alcohol compounds represented by formula (2) to occur in the presence of acidic catalysts (R1-R4 are each a C1-4 alkyl group). SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Palladium-catalyzed asymmetric quaternary stereocenter formation

An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β-disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl2, PhBOX, and AgSbF 6, and provides products in up to 99 % enantiomeric excess, with good yields. Based on this strategy, (-)-α-cuparenone has been prepared in only two steps. Copyright

Synthesis of low molecular weight ethylene propylene glycol ethers via olefin addition to the corresponding glycol

A selective process for the synthesis of ethers of polyols involves reacting an olefin and a polyol in the presence of a heteropoly acid catalyst at a temperature of 25 to 200oC and a pressure of up to 7MPa.