865-48-5

Basic information

• Product Name: Sodium tert-butoxide
• Synonyms: sodiumt-butoxide,stb;sodiumt-butoxide,stb,in;sodiumt-butoxide,stb,intetrahydrofuran;sodium 2-methylpropan-2-olate;SODIUM TERTIARY BUTOXIDE;SODIUM TERT-BUTOXIDE;SODIUM TERT-BUTYLATE;SODIUM T-BUTOXIDE
• CAS NO: 865-48-5
• Molecular Formula: C₄H₉NaO
• Molecular Weight: 96.1
• EINECS: 212-741-9
• Product Categories: Chemical Synthesis;Organic Bases;Synthetic Reagents;Organic BasesMicro/Nanoelectronics;Solution Deposition Precursors;metal alkoxide;Organics;Pharmaceutical Intermediates;Indoles
• Mol File: 865-48-5.mol
• Article Data: 18

Chemical Properties

• Melting Point: 180 °C
• Boiling Point: 180°C/1mmHg
• Flash Point: 12°C
• Appearance: white to off-white/Powder
• Density: 1,104 g/cm3
• Vapor Pressure: 46mmHg at 25°C
• Refractive Index: n20/D1.413
• Storage Temp.: Flammables area
• Solubility: very slightly in Tetrahydrofuran
• Water Solubility: reacts
• Sensitive: Air Sensitive & Hygroscopic
• BRN: 3654215
• CAS DataBase Reference: Sodium tert-butoxide(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium tert-butoxide(865-48-5)
• EPA Substance Registry System: Sodium tert-butoxide(865-48-5)

Safety Data

• Hazard Codes: F,C,Xi
• Statements: 11-14-34-37-35-36/37/38-40-19
• Safety Statements: 26-36/37/39-43-45-7/8-8-16-36
• RIDADR: UN 3206 4.2/PG 2
• WGK Germany: 3
• F: 1-3-10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 865-48-5(Hazardous Substances Data)

Usage

Chemical Properties

white to light tan crystalline powder

Uses

Sodium tert-butoxide is used as a strong base and a non-nucleophilic base. In organic synthesis, it serves as an intermediate in various reactions like condensation, rearrangement and ring-opening. Further, it finds use in agrochemicals, pharmaceuticals, colorants, aroma chemicals, detergents and biodiesel. It acts as a catalyst in polymerization and isomerization reactions.

Flammability and Explosibility

Highlyflammable

Purification Methods

Its solubility in tert-BuOH is 0.208M at 30.2o and 0.382M at 60o, and it is quite soluble in tetrahydrofuran (32g/100g). It should not be used if it has a brown colour. [Feuer J Am Chem Soc 78 4364 1956, Hurd Inorg Synth I 87 1939, IR: Seubold J Org Chem 21 156 1956, Beilstein 1 IV 1609.]

InChI:InChI=1/C4H9O.Na/c1-4(2,3)5;/h1-3H3;/q-1;+1

Synthetic route

tert-butyl alcohol (75-65-0) → sodium t-butanolate (865-48-5)

Conditions	Yield
With sodium amide In water; toluene at 105℃; for 2h; Temperature; Solvent;	99%
With sodium; sodium hydride In 5,5-dimethyl-1,3-cyclohexadiene at 97 - 132℃; for 12.7h; Temperature; Inert atmosphere;	99.8%
With sodium amide at 85℃; for 10h;	76.3%

1-methyl-pyrrolidin-2-one (872-50-4) + tert-butyl alcohol (75-65-0) → sodium t-butanolate (865-48-5)

2,5-di-tert-butyl-7-trifluoromethyl-phenanthridinium; trifluoro-methanesulfonate + sodium t-butanolate (865-48-5) → 6-tert-butoxy-2,5-di-tert-butyl-7-trifluoromethyl-5,6-dihydro-phenanthridine

Conditions	Yield
In tetrahydrofuran-d8 at -78℃;	100%

Ce(OCMe3)(NO3)3(THF)2 (121314-35-0) + sodium t-butanolate (865-48-5) → sodium nitrate (7631-99-4) + Ce(OCMe3)4(THF)2 (122423-58-9)

Conditions	Yield
In tetrahydrofuran exclusion of air and water, stirred for 20 h, 3 equiv. of NaOCMe3; centrifuged, removal of solvent;	A 100% B 80-95

[CuCl(ClIPr)] (1268526-51-7) + sodium t-butanolate (865-48-5) → C31H43Cl2CuN2O (1268526-52-8)

Conditions	Yield
In tetrahydrofuran at 20℃; Inert atmosphere;	100%

water (7732-18-5) + pyridin-2-ylboronic acid dimethyl ester (136805-54-4) + sodium t-butanolate (865-48-5) → sodium trihydroxy(2-pyridyl)borate

Conditions	Yield
at 35℃; for 0.0166667h; Sonication;	100%

ammonium cerium (IV) nitrate (16774-21-3) + sodium t-butanolate (865-48-5) → sodium nitrate (7631-99-4) + Ce(OCMe3)(NO3)3(THF)2 (121314-35-0) + tert-butyl alcohol (75-65-0)

Conditions	Yield
In tetrahydrofuran byproducts: NH3; exclusion of air and water, stirred for 2 h; filtered (NaNO3), removal of solvent from filtrate, extn. (toluene), removal of solvent; elem. anal.;	A 99% B 56% C n/a

6-bromo-4-(4-methylphenyl)-2-(2-methylpropyl)quinoline-3-carbonitrile (660451-32-1) + sodium t-butanolate (865-48-5) → 6-tert-butoxy-4-(4-methylphenyl)-2-(2-methylpropyl)quinoline-3-carbonitrile (1262394-32-0)

Conditions	Yield
With palladium diacetate; 2,2'-bis(diphenylphosphino)biphenyl In tert-butyl alcohol at 70℃; for 15h; Inert atmosphere;	99%

C35H49N3O2PPdS(1+)*C32H12BF24(1-) + sodium t-butanolate (865-48-5) → 3Na(1+)*3C28H41N2P*3Pd(2+)*3C7H7NO2S(2-)*3C4H10O*3C32H12BF24(1-)

Conditions	Yield
at 23℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox;	99%

C40H51N3O2PPdS(1+)*C32H12BF24(1-) + sodium t-butanolate (865-48-5) → 3Na(1+)*3C28H41N2P*3Pd(2+)*3C12H9NO2S(2-)*3C4H10O*3C32H12BF24(1-)

Conditions	Yield
at 23℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox;	99%

m-bromobenzoic aldehyde (3132-99-8) + trimethylsilylazide (4648-54-8) + sodium t-butanolate (865-48-5) → [(tert-butoxy)(3-bromophenyl)methoxy]trimethylsilane

Conditions	Yield
In tetrahydrofuran; benzene at 20℃; for 1h;	99%

trimethylsilylazide (4648-54-8) + ortho-bromobenzaldehyde (6630-33-7) + sodium t-butanolate (865-48-5) → [(tert-butoxy)(2-bromophenyl)methoxy]trimethylsilane

Conditions	Yield
In tetrahydrofuran; benzene at 20℃; for 1h;	99%

trimethylsilylazide (4648-54-8) + 4-cyanobenzaldehyde (105-07-7) + sodium t-butanolate (865-48-5) → 4-[(tert-butoxy)[(trimethylsilyl)oxy]methyl]benzonitrile

Conditions	Yield
In tetrahydrofuran; benzene at 20℃; for 1h;	99%

trimethylsilylazide (4648-54-8) + benzaldehyde (100-52-7) + sodium t-butanolate (865-48-5) → [(tert-butoxy)(phenyl)methoxy]trimethylsilane

Conditions	Yield
In tetrahydrofuran; benzene at 20℃; for 1h;	99%

trimethylsilylazide (4648-54-8) + 3-methoxy-benzaldehyde (591-31-1) + sodium t-butanolate (865-48-5) → [(tert-butoxy)(3-methoxyphenyl)methoxy]trimethylsilane

Conditions	Yield
In tetrahydrofuran; benzene at 20℃; for 1h;	99%

trimethylsilylazide (4648-54-8) + β-naphthaldehyde (66-99-9) + sodium t-butanolate (865-48-5) → [(tert-butoxy)(naphthalen-2-yl)methoxy]trimethylsilane

Conditions	Yield
In tetrahydrofuran; benzene at 20℃; for 1h;	99%

(E)-3-phenylpropenal (14371-10-9) + trimethylsilylazide (4648-54-8) + sodium t-butanolate (865-48-5) → (E)-((1-(tert-butoxy)-3-phenylallyl)oxy)trimethylsilane

Conditions	Yield
In tetrahydrofuran; benzene at 20℃; for 1h;	99%

trimethylsilylazide (4648-54-8) + α-methyl-trans-cinnamaldehyde (15174-47-7) + sodium t-butanolate (865-48-5) → (E)-((1-(tert-butoxy)-2-methyl-3-phenylallyl)oxy)trimethylsilane

Conditions	Yield
In tetrahydrofuran; benzene at 20℃; for 1h;	99%

trimethylsilylazide (4648-54-8) + sodium t-butanolate (865-48-5) + cyclohexanecarbaldehyde (2043-61-0) → [(tert-butoxy)(cyclohexyl)methoxy]trimethylsilane

Conditions	Yield
In tetrahydrofuran; benzene at 20℃; for 1h;	99%

tert-butyldimethylsilyl cyanide (56522-24-8) + 4-chlorobenzaldehyde (104-88-1) + sodium t-butanolate (865-48-5) → [(tert-butoxy)(4-chlorophenyl)methoxy](tert-butyl)dimethylsilane

Conditions	Yield
In tetrahydrofuran; benzene at 20℃; for 1h;	99%

trimethylsilylazide (4648-54-8) + 4-chlorobenzaldehyde (104-88-1) + sodium t-butanolate (865-48-5) → [(tert-butoxy)(4-chlorophenyl)methoxy]trimethylsilane

Conditions	Yield
In tetrahydrofuran; benzene at 20℃; for 1h;	99%

trimethylsilylazide (4648-54-8) + 3-Chlorobenzaldehyde (587-04-2) + sodium t-butanolate (865-48-5) → [(tert-butoxy)(3-chlorophenyl)methoxy]trimethylsilane

Conditions	Yield
In tetrahydrofuran; benzene at 20℃; for 1h;	99%

(4-bromophenyl)(phenyl)methanone (90-90-4) + sodium t-butanolate (865-48-5) → 4-tert-butoxybenzophenone

Conditions	Yield
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 6h;	98%
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 6h;	98%
With palladium diacetate; tri-tert-butyl phosphine In xylene at 120℃; for 1h; Substitution; Suzuki coupling;	94%
With bis(1,5-cyclooctadiene)nickel (0); 1,2-bis-(diphenylphosphino)ethane In toluene at 95℃; for 18h;	93%
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel (0) In toluene at 95℃; for 18h; Product distribution; other reagent;	67%

4-bromobenzenecarbonitrile (623-00-7) + sodium t-butanolate (865-48-5) → tert-butyl 4-cyanophenyl ether (185259-36-3)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 120℃; for 12h; Product distribution; other reagents;	98%
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel (0) In toluene at 100℃; for 17h;	59%

4-chlorobenzophenone (134-85-0) + sodium t-butanolate (865-48-5) → 4-tert-butoxybenzophenone

Conditions	Yield
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 4h;	98%
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 4h;	98%
With palladium diacetate; tri-tert-butyl phosphine In xylene at 120℃; for 3h; Substitution; Suzuki coupling;	92%
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 95℃; for 12h; Product distribution; other reagents, temperature, reaction time;	84%
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel (0) In toluene at 95℃; for 10h;	69%

para-nitrophenyl bromide (586-78-7) + sodium t-butanolate (865-48-5) → 4-tert-butoxy-1-nitrobenzene (2109-72-0)

Conditions	Yield
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 9h;	98%
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 9h;	98%
tris(dibenzylideneacetone)dipalladium (0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 12h; Etherification;	95%

bromobenzene (108-86-1) + sodium t-butanolate (865-48-5) → t-butyl phenyl ether (6669-13-2)

Conditions	Yield
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 23h;	97%
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 17h;	96%
With palladium diacetate; tri-tert-butyl phosphine In xylene at 120℃; for 2h; Substitution; Suzuki coupling;	89%

4-(benzoyloxy)morpholine (5765-65-1) + sodium t-butanolate (865-48-5) → benzoic acid tert-butyl ester (774-65-2)

Conditions	Yield
In 1,4-dioxane-d8 at 25℃; for 2h; Inert atmosphere;	97%

Upstream product

• 75-65-0 tert-butyl alcohol 
• 872-50-4 1-methyl-pyrrolidin-2-one 

Downstream Products

• 59862-83-8 tert-butyl 5-bromofuran-2-carboxylate 
• 90612-88-7 5-hydroxy-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 13901-77-4 1-methyl-2,3,5-triphenyl-1H-pyrrole 
• 2201-23-2 1-phenyl-1-cyclohexanecarbonitrile 
• 29072-93-3 n-propyl t-butyl ether 
• 1471-04-1 allyl tert-butyl ether 
• 13895-74-4 ethyl 2-cyano-2-(2,6-dimethyl-4H-pyran-4-ylidene)acetate 
• 104741-75-5 1-(tert-butoxycarbonyloxy)-4-methylbenzene 
• 87661-18-5 1,1-dimethylethyl cyclopentanecarboxylate 
• 3422-01-3 tert-butyl phenylcarbamate 
• 90972-20-6 (3,5-dimethyl-4-nitro-phenyl)-methyl sulfide 
• 61019-03-2 5-methoxy-1,3-dimethyl-2-nitrobenzene 
• 637-92-3 Ethyl tert-butyl ether 
• 65321-36-0 t-butyl nicotinate 

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Sodium tert-butoxide and preparation method thereof

The invention discloses sodium tert-butoxide and a preparation method thereof. The preparation method comprises the following steps: (1) taking methylbenzene or heptanes as a reaction medium, adding sodium amide and tertiary butanol, mixing and stirring to dissolve to obtain a mixed solution; (2) heating the mixed solution to 70-110 DEG C for reaction to obtain a crude product of sodium tert-butoxide till the reaction is completed; (3) rectifying the crude product of the sodium tert-butoxide to obtain a finished product of the sodium tert-butoxide. The preparation method disclosed by the invention has relaxed reaction conditions, is small in danger in the production process, simple in aftertreatment process of products and short in drying time, and the product yield is up to 99% or above.

Preparation method of di-tert-butyl dicarbonate

The invention relates to a preparation method of di-tert-butyl dicarbonate and belongs to the technical field of synthesis of pharmaceutical intermediates. The preparation method comprises the following steps: adding metal sodium into xylol; heating to obtain sodium sand; then dropwise adding tert-butyl alcohol and carrying out pumping filtration to obtain sodium tert-butoxide; dissolving the sodium tert-butoxide into petroleum ether; introducing carbon dioxide and reacting to obtain a monoester sodium salt solution; adding a catalyst and slowly dropwise adding diphosgene to react; after reacting, standing and carrying out the pumping filtration; and washing with water, drying, distilling, cooling and crystallizing to obtain the di-tert-butyl dicarbonate. According to the preparation method, the sodium tert-butoxide is prepared from the metal sodium and the di-tert-butyl dicarbonate is prepared from the sodium tert-butoxide; a pumping filtration method is used for replacing a previous distillation method, so that the process is simpler and more energy is saved; the petroleum ether is used for replacing n-hexane and toluene, so that the production cost is reduced and a product is easier to purify; and finally, after the reaction, the pumping filtration is carried out and then water washing is carried out, so that the amount of wastewater is reduced and the environment-friendly treatment cost is reduced.