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

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

Uses

Used in Organic Synthesis:
Sodium tert-butoxide is used as a strong base in organic synthesis for facilitating various reactions like condensation, rearrangement, and ring-opening. Its non-nucleophilic nature makes it a suitable base for these reactions.
Used in Agrochemicals:
Sodium tert-butoxide is used as a catalyst in the production of agrochemicals, aiding in the synthesis of various compounds used in agriculture.
Used in Pharmaceuticals:
In the pharmaceutical industry, sodium tert-butoxide is used as a catalyst in the synthesis of various drugs, contributing to the development of new medications.
Used in Colorants and Aroma Chemicals:
Sodium tert-butoxide is utilized as a catalyst in the production of colorants and aroma chemicals, helping to create a wide range of colors and fragrances for various applications.
Used in Detergents and Biodiesel:
Sodium tert-butoxide is used as a catalyst in the production of detergents and biodiesel, contributing to the development of more effective and environmentally friendly products.
Used in Polymerization and Isomerization Reactions:
Sodium tert-butoxide acts as a catalyst in polymerization and isomerization reactions, playing a crucial role in the synthesis of various polymers and isomers.

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 
• 1694-31-1 tert-butyl acetoacetate 
• 18166-43-3 tris(tert-butoxy)silanol 
• 18765-23-6 O{Si(Ot-bu)3}2 
• 13901-77-4 1-methyl-2,3,5-triphenyl-1H-pyrrole 
• 18846-14-5 hexa-o-tolyl-disiloxane 
• 18105-64-1 tri-tert-butoxy-chloro-silane 
• 2201-23-2 1-phenyl-1-cyclohexanecarbonitrile 
• 4984-82-1 cyclopentadienyl sodium 
• 637-92-3 Ethyl tert-butyl ether 
• 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 

Relevant articles and documents

DESIGN, SYNTHESIS, AND PHOTOPHYSICAL PROPERTIES OF A NOVEL NIR II DYE FOR BIOLOGICAL IMAGING AND OPTOELECTRONIC DEVICES

In one aspect, the disclosure relates to fluorescent dyes that absorb and emit in the near infrared II (NIR II) range of the electromagnetic spectrum, methods of making same, compositions comprising same and methods of using the compositions to perform imaging on biological samples, and optoelectronic devices using the dyes. The dyes are small organic molecules that are inexpensive and facile to produce, can be water-soluble, have tunable properties, and are biocompatible and/or possess low toxicity.

Novel process for preparing sodium tert-butoxide by using xylene as solvent

The invention belongs to the technical field of manufacturing of fine chemical intermediates, particularly relates to a novel process for preparing sodium tert-butoxide by using dimethylbenzene as a solvent, and solves the technical problems that a traditional sodium tert-butoxide synthesis method in the prior art directly uses tert-butyl alcohol as a solvent, metal sodium is easy to oxidize, sodium sheets are easy to gather, the reaction contact area is reduced, the stirring load of a reaction kettle is indirectly increased, and the like. The novel process for preparing the sodium tert-butoxide by using the xylene as the solvent comprises the steps of preparation before reaction including reaction kettle cleaning, drying and gas replacement; adding materials for reaction, specifically, melting metal sodium in xylene, adding sodium hydride for dissolving under the protection of inert gas, and then adding tert-butyl alcohol for reaction; obtaining a product, specifically, removing sodium hydride after the reaction is finished, and recovering xylene; and obtaining the product sodium tert-butoxide. The preparation process is simple, the preparation condition is mild, the reaction safety is high, and the product purity is high.

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.

Sodium tert-butoxide production technology

Sodium tert-butoxide is a main chemical material. The brief production process comprises the following steps: adding metered 99% sodium amide into a reaction vessel, simultaneously slowly dropwise adding a certain amount of 99% anhydrous tert-butanol, stirring after dropwise adding, controlling temperature of the reaction vessel to 85 DEG C, carrying out thermal insulation and carrying out reflux reaction for 10 h; and carrying out distillation after the reaction, distilling off tert-butanol (reused in the reaction vessel) until there is no fraction, cooling to room temperature, discharging, and packaging to obtain a 98% sodium tert-butoxide finished product. The whole reaction yield is 76.3%. Three-stage condensation is adopted, including two-stage chilled brine condensation and first-stage water-cooling. Tert-butanol (boiling point is 82.8 DEG C) adopts three-stage condensation, condenser area is 20 m, and tert-butanol condensation efficiency is 98%.

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.

Preparation method for low residual granular sodium alkoxide or potassium alcoholate

The invention provides a preparation method for low residual granular sodium alkoxide or potassium alcoholate. The method includes using sodium or potassium and alcohol as raw materials, mixing the mixture with a solvent, reacting in inert gas atmosphere by using a microwave heating method, and removing the residual alcohol and solvent in the presence of microwave after the reaction to get the granular sodium alkoxide or potassium alcoholate. The microwave frequency is 2450 +/- 50 MHz. The method can prepare sodium alkoxide or potassium alcoholate with low residual solvent, and the prepared sodium alkoxide or potassium alcoholate is large granular solid, so that the development from powdered product to granular product can be realized, and the problems of residual solvent and potential risk troubled human for a long time can be overcome.

Amide acetals in the synthesis of pyridothienopyrimidines

Methyl 3-amino-4-arylaminothieno[2,3-b]pyridine-2-carboxylates containing various substituents in the benzene ring were synthesized by the Thorpe-Ziegler reaction of 4-arylamino-2-chloropyridine-3-carbonitriles with methyl thioglycolates. The influence of the substituent in the benzene ring, acetal structure, the solvent and the process temperature on the reactions of obtained compounds with amide acetals was studied. It was established that reactions with dimethylacetamide dimethylacetal in toluene smoothly results in amidine derivatives, viz., methyl 4-arylamino-3-[1-(dimethylamino)ethylidene] aminothieno[2,3-b]pyridine-2-carboxylates, regardless of the substituent in the benzene ring. Analogous reaction of p-fluoroderivative with dimethylacetamide dimethylacetal in refluxing anhydrous ethanol leads to intramolecular cyclocondensation to produce substituted pyridothienopyrimidines, viz., 5H-1-thia-3,5,8-triazaacenaphthenes, in good yields. Amidine derivatives were the major products in the case of the coupling of aminothienopyridines with dimethylformamide dimethylacetal under the same conditions. A new approach to the synthesis of substituted pyridothienopyrimidines, viz., 3H-1-thia-3,5,8- triazaacenaphthylenes, based on the prolonged heating of methyl 4-arylamino-3-[1-(dimethylamino)ethylidene]aminothieno[2,3-b] pyridine-2-carboxylates in the excess of acetic anhydride was elaborated. Putative mechanisms of the processes concerned are given.

5-Oxo-5,8-dihydro-pyrido-pyrimidines as inhibitors of c-fms kinase

The invention addresses the current need for selective and potent protein tyrosine kinase inhibitors by providing potent inhibitors of c-fms kinase. The invention is directed to the novel compounds of Formula I: or a solvate, hydrate, tautomer or pharmaceutically acceptable salt thereof, wherein:W, A, Y, n, Z, and R102 are described in the specification.

5-Oxo-5,8-dihydro-pyrido-pyrimidines as inhibitors of c-fms kinase

The invention addresses the current need for selective and potent protein tyrosine kinase inhibitors by providing potent inhibitors of c-fms kinase. The invention is directed to the novel compounds of Formula I: or a solvate, hydrate, tautomer or pharmaceutically acceptable salt thereof, wherein: W, A, Y, Z, R101 and R200 are described in the specification.

Novel aminophenyl ketone derivatives

Novel heteroaryl aminophenyl ketone derivatives which are inhibitors of MAP kinases, in particular the p38 MAP kinase, are useful as anti-inflammatory agents in the prophylaxis or treatment of inflammatory diseases or conditions.