57699-45-3

Basic information

• Product Name: 4-(TERT-BUTOXY)BENZALDEHYDE
• Synonyms: P-TERT-BUTOXYBENZALDEHYDE;4-(TERT-BUTOXY)BENZALDEHYDE;4-(TERT-BUTYLOXY)BENZALDEHYDE;4-(tert-Butoxy)benzaldehyde,98%;1-tert-Butoxy-4-formylbenzene;4-(1,1-Dimethylethoxy)benzaldehyde;4-[(2-methylpropan-2-yl)oxy]benzaldehyde;4-tert-Butoxybenzaldehyde
• CAS NO: 57699-45-3
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.23
• EINECS: 260-909-5
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;C10 to C21;Carbonyl Compounds
• Mol File: 57699-45-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 87-92°C 1,5mm
• Flash Point: 87-92°C/1.5mm
• Appearance: clear yellow-green/liquid
• Density: 1.023 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00552mmHg at 25°C
• Refractive Index: n20/D 1.534
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Insoluble in water
• Sensitive: Air Sensitive
• BRN: 5499455
• CAS DataBase Reference: 4-(TERT-BUTOXY)BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(TERT-BUTOXY)BENZALDEHYDE(57699-45-3)
• EPA Substance Registry System: 4-(TERT-BUTOXY)BENZALDEHYDE(57699-45-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 57699-45-3(Hazardous Substances Data)

Usage

General Description

4-(tert-butoxy)benzaldehyde is a compound with the molecular formula C13H16O2. It is an aldehyde containing a benzene ring with a tert-butoxy group attached to the fourth carbon. This chemical is commonly used as a fragrance and flavoring agent in the production of perfumes and cosmetics. It is also utilized in the synthesis of pharmaceuticals, dyes, and other organic compounds. 4-(tert-butoxy)benzaldehyde has a strong and sweet floral odor and is considered to be a versatile and valuable chemical in various industries due to its aromatic and chemical properties.

InChI:InChI=1/C11H14O2/c1-11(2,3)13-10-6-4-9(8-12)5-7-10/h4-8H,1-3H3

Synthetic route

4-bromo-benzaldehyde (1122-91-4) + sodium t-butanolate (865-48-5) → p-tert-butoxybenzaldehyde (57699-45-3)

Conditions	Yield
With palladium diacetate; tri-tert-butyl phosphine In xylene at 120℃; for 1h; Substitution; Suzuki coupling;	91%

potassium tert-butylate (865-47-4) + 4-fluorobenzaldehyde (459-57-4) → p-tert-butoxybenzaldehyde (57699-45-3)

Conditions	Yield
In dimethyl sulfoxide for 0.166667h; Heating; Irradiation;	75%

tertiary butyl chloride (507-20-0) + 4-hydroxy-benzaldehyde (123-08-0) → p-tert-butoxybenzaldehyde (57699-45-3)

Conditions	Yield
With zinc at 25℃; for 1h; Etherification;	72%

potassium tert-butylate (865-47-4) + 4-chlorobenzaldehyde (104-88-1) → p-tert-butoxybenzaldehyde (57699-45-3)

Conditions	Yield
In dimethyl sulfoxide for 2h; Heating; Irradiation;	68%

4-chlorobenzaldehyde (104-88-1) + sodium t-butanolate (865-48-5) → benzaldehyde (100-52-7) + p-tert-butoxybenzaldehyde (57699-45-3)

Conditions	Yield
With palladium diacetate; tri-tert-butyl phosphine In xylene at 120℃; for 2h; Substitution; Suzuki coupling;	A n/a B 60%

di-tert-butyl dicarbonate (24424-99-5) + 4-hydroxy-benzaldehyde (123-08-0) → p-tert-butoxybenzaldehyde (57699-45-3)

Conditions	Yield
scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 5h; Product distribution; Further Variations:; Catalysts; Solvents; Temperatures;	48%

t-butyl bromide (507-19-7) + 4-hydroxy-benzaldehyde (123-08-0) → p-tert-butoxybenzaldehyde (57699-45-3)

Conditions	Yield
With zinc trifluoromethanesulfonate; zinc In toluene at 40℃; for 12h; Sealed tube; Schlenk technique; Molecular sieve;	46%

2,2-diethoxy acetic acid (20461-86-3) + 4-tert-butoxybromobenzene (60876-70-2) → p-tert-butoxybenzaldehyde (57699-45-3)

Conditions	Yield
With nickel(II) chloride hexahydrate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide at 20℃; for 0.6h; Schlenk technique; Inert atmosphere; Flow reactor;	45%

4-hydroxy-benzaldehyde (123-08-0) + isobutene (115-11-7) → p-tert-butoxybenzaldehyde (57699-45-3)

Conditions	Yield
With Amberlyst 15 In benzene for 17h; Yield given;

(4-(tert-butoxy)phenyl)methanol (51503-08-3) → p-tert-butoxybenzaldehyde (57699-45-3)

Conditions	Yield
With oxoammonium resin In dichloromethane at 20℃; for 1h;
With polystyrene-supported 5-hydroxy-2-iodoxybenzoic acid In dichloromethane at 20℃; for 3h;	95 % Chromat.
With oxygen; 6C68H44ClMnN12*8Zn(2+)*12C2F6NO4S2(1-)*4F6P(1-); Flavin mononucleotide; NADH In water; N,N-dimethyl-formamide; acetonitrile at 35℃; under 760.051 Torr; for 10h;	22 %Chromat.

p-tert-butoxybenzaldehyde (57699-45-3) → 4-hydroxy-benzaldehyde (123-08-0)

Conditions	Yield
With sodium iodide; cerium(III) chloride In acetonitrile at 40℃; for 6h;	100%

2,4-imidazolidinedione (461-72-3) + p-tert-butoxybenzaldehyde (57699-45-3) + 3-amino-2-propanol (78-96-6, 1674-56-2) → 5-(4-tert-butoxybenzylidene)hydantoin

Conditions	Yield
In water	98%

4-bromobenzenecarbonitrile (623-00-7) + p-tert-butoxybenzaldehyde (57699-45-3) → 4-(4-(tert-butoxy)benzoyl)benzonitrile

Conditions	Yield
With Ni(dmbpy)Br2; sodium carbonate In acetone at 25℃; for 8h; Sealed tube; Inert atmosphere; Irradiation;	98%

methylmagnesium chloride (676-58-4) + sodium hydrogencarbonate (144-55-8) + p-tert-butoxybenzaldehyde (57699-45-3) → 1-(p-tert.-butoxyphenyl)-ethan-1-ol

Conditions	Yield
With sulfuric acid In tetrahydrofuran; water	97.9%

p-tert-butoxybenzaldehyde (57699-45-3) + allyl bromide (106-95-6) → 1-(4-(tert-butyl)phenyl)but-3-en-1-ol (106027-36-5)

Conditions	Yield
With manganese; iodine In tetrahydrofuran Heating;	97%

p-tert-butoxybenzaldehyde (57699-45-3) + acetophenone (98-86-2) → 4-t-butoxychalcone

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; for 20h;	97%

N,N-dimethylglycine methyl ester (7148-06-3) + p-tert-butoxybenzaldehyde (57699-45-3) → (E/Z)-methyl 3-(4-tert-butoxyphenyl)-2-dimethylaminoacrylate (1431505-83-7)

Conditions	Yield
With sodium hydride In methanol; diethyl ether at 0 - 20℃; for 18h;	93%

2-(N,N-dimethylamino)ethanol (108-01-0) + p-tert-butoxybenzaldehyde (57699-45-3) → p-tert.-butoxybenzaldehyde-cyanohydrin (79686-52-5)

Conditions	Yield
With hydrogen isocyanide In diethyl ether	92%

p-tert-butoxybenzaldehyde (57699-45-3) + tert-butylamine (75-64-9) → N-4-t-butoxybenzylidene-t-butylamine

Conditions	Yield
With titanium tetrachloride In diethyl ether; toluene at 0℃; for 0.25h; Glovebox; Inert atmosphere; Schlenk technique;	92%

1-(2-chlorophenyl)ethanone (2142-68-9) + p-tert-butoxybenzaldehyde (57699-45-3) → (E)-3-(4-(tert-butoxy)phenyl)-1-(2-chlorophenyl)prop-2-en-1-one

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃;	91%

2-acetylpyridine (1122-62-9) + p-tert-butoxybenzaldehyde (57699-45-3) → (E)-3-(4-(tert-butoxy)phenyl)-1-(pyridin-2-yl)prop-2-en-1-one

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃;	91%

2-Acetylthiophene (88-15-3) + p-tert-butoxybenzaldehyde (57699-45-3) → (E)-3-(4-(tert-butoxy)phenyl)-1-(thiophen-2-yl)prop-2-en-1-one

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃;	90%

p-tert-butoxybenzaldehyde (57699-45-3) + tetraethyl (anthracene-9,10-diylbis(methylene))bis(phosphonate) (60974-92-7) → C38H38O2

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 8h;	90%

p-tert-butoxybenzaldehyde (57699-45-3) + acetophenone (98-86-2) → (E)-3-(4-(tert-butoxy)phenyl)-1-phenylprop-2-en-1-one

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃;	88%

p-tert-butoxybenzaldehyde (57699-45-3) + 1-triphenylphosphoranylidene-2-propanone (1439-36-7) → (E)-4-(4-tert-butoxyphenyl)-but-3-en-2-one

Conditions	Yield
In toluene for 2h; Reflux;	88%

o-hydroxyacetophenone (118-93-4) + p-tert-butoxybenzaldehyde (57699-45-3) → (E)-3-(4-(tert-butoxy)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃;	87%

2-Acetylpyrrole (1072-83-9) + p-tert-butoxybenzaldehyde (57699-45-3) → (E)-3-(4-(tert-butoxy)phenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃;	84%

2,4-imidazolidinedione (461-72-3) + p-tert-butoxybenzaldehyde (57699-45-3) → (5Z)-5-(4-tert-butoxybenzylidene)imidazolidine-2,4-dione (1256244-64-0)

Conditions	Yield
With sodium hydrogencarbonate; ethanolamine In ethanol; water pH=7; Reflux; stereoselective reaction;	83.4%
Stage #1: 2,4-imidazolidinedione With sodium hydrogencarbonate; ethanolamine In water at 70 - 90℃; pH=7; Stage #2: p-tert-butoxybenzaldehyde In ethanol; water for 10h; pH=7; Reflux; regioselective reaction;

1-(2-ethoxyphenyl)ethanone (2142-67-8) + p-tert-butoxybenzaldehyde (57699-45-3) → (E)-3-(4-(tert-butoxy)phenyl)-1-(2-ethoxylphenyl)prop-2-en-1-one

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃;	82%

2-Methoxyacetophenone (579-74-8) + p-tert-butoxybenzaldehyde (57699-45-3) → (E)-3-(4-(tert-butoxy)phenyl)-1-(2-methoxylphenyl)prop-2-en-1-one

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃;	81%

4-hydroxy[1]benzopyran-2-one (1076-38-6) + p-tert-butoxybenzaldehyde (57699-45-3) + malononitrile (109-77-3) → C23H20N2O4

Conditions	Yield
With piperidine In ethanol for 2h;	80%

3,5-dimethoxy-α,α-dimethylbenzylcarbazate (39508-00-4) + p-tert-butoxybenzaldehyde (57699-45-3) → C23H32N2O5 (1130218-39-1)

Conditions	Yield
Stage #1: 3,5-dimethoxy-α,α-dimethylbenzylcarbazate; p-tert-butoxybenzaldehyde In tetrahydrofuran at 20℃; Stage #2: With sodium cyanoborohydride; acetic acid In tetrahydrofuran for 24h;	78%

4-Aminoacetophenone (99-92-3) + p-tert-butoxybenzaldehyde (57699-45-3) → (E)-1-(4-aminophenyl)-3-(4-(tert-butoxy)phenyl)prop-2-en-1-one

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃;	78%

3,3-dimethyl-butan-2-one (75-97-8) + p-tert-butoxybenzaldehyde (57699-45-3) → (E)-1-(4-(tert-butoxy)phenyl)-4,4-dimethylpent-1-en-3-one

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃;	77%
With potassium hydroxide In methanol; water at 20℃; Cooling with ice;	77%

4-Chloro-1,2-phenylenediamine (95-83-0) + p-tert-butoxybenzaldehyde (57699-45-3) → 2-(4-(tert-butoxy)phenyl)-5-chloro-1H-benzo[d]imidazole

Conditions	Yield
In methanol at 20℃; for 0.0166667h;	75%

p-tert-butoxybenzaldehyde (57699-45-3) + cyclopentanone (120-92-3) → (2E,5E)-2,5-bis(4-tert-butoxybenzylidene)cyclopentanone (1158188-85-2)

Conditions	Yield
With sodium methylate In methanol at 20℃;	74.5%

p-tert-butoxybenzaldehyde (57699-45-3) + 4,4'-dihydrazinodiphenyl sulfone (14052-65-4) → C34H38N4O4S

Conditions	Yield
In 1,4-dioxane at 60℃; for 2h;	73%

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 115-11-7 isobutene 
• 865-47-4 potassium tert-butylate 
• 459-57-4 4-fluorobenzaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 865-48-5 sodium t-butanolate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 507-19-7 t-butyl bromide 
• 20461-86-3 2,2-diethoxy acetic acid 
• 60876-70-2 4-tert-butoxybromobenzene 
• 51503-08-3 (4-(tert-butoxy)phenyl)methanol 
• 507-20-0 tertiary butyl chloride 
• 1122-91-4 4-bromo-benzaldehyde 

Downstream Products

• 143589-82-6 1(R,S)-(p-tert-butoxyphenyl)ethylamine 
• 79686-52-5 p-tert.-butoxybenzaldehyde-cyanohydrin 
• 155904-35-1 3-(4-tert-butoxy-phenyl)-acrylic acid 
• 1257525-25-9 (2S)-trimethylsilyloxy(4-tert-butoxyphenyl)acetonitrile 
• 1256244-64-0 (5Z)-5-(4-tert-butoxybenzylidene)imidazolidine-2,4-dione 
• 1400684-94-7 3-(4-(tert-butoxy)phenyl)-N-methoxy-N-methylpropanamide 
• 941293-00-1 3-(4-tert-butoxyphenyl)propionaldehyde 
• 21323-98-8 3-(4-tert-butoxyphenyl)-propionic acid 
• 727716-46-3 3-(4-tert-butoxyphenyl)propionic acid benzyl ester 
• 1400685-19-9 (E)-benzyl 2-(4-(tert-butoxy)benzyl)but-2-enoate 
• 1449400-12-7 (2E)-3-(4-tert-butoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one 
• 1449400-14-9 (2E)-3-(4-tert-butoxyphenyl)-1-(4-chlorophenyl)prop-2-en-1-one 
• 1449400-24-1 (2E)-3-(4-tert-butoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one 
• 1444605-47-3 4-(4-tert-butoxybenzylamino)benzoic acid 

Relevant articles and documents

Zn- And Cu-catalyzed coupling of tertiary alkyl bromides and oxalates to forge challenging C?O, C?S, and C?N bonds

We describe here the facile construction of sterically hindered tertiary alkyl ethers and thioethers via the Zn(OTf)2catalyzed coupling of alcohols/phenols with unactivated tertiary alkyl bromides and the Cu(OTf)2-catalyzed thiolation of unactivated tertiary alkyl oxalates with thiols. The present protocol represents one of the most effective unactivated tertiary C(sp3)? heteroatom bond-forming conditions via readily accessible Lewis acid catalysis that is surprisingly less developed.

Visible-Light-Promoted Nickel- and Organic-Dye-Cocatalyzed Formylation Reaction of Aryl Halides and Triflates and Vinyl Bromides with Diethoxyacetic Acid as a Formyl Equivalent

A simple formylation reaction of aryl halides, aryl triflates, and vinyl bromides under synergistic nickel- and organic-dye-mediated photoredox catalysis is reported. Distinct from widely used palladium-catalyzed formylation processes, this reaction proceeds by a two-step mechanistic sequence involving initial in situ generation of the diethoxymethyl radical from diethoxyacetic acid by a 4CzIPN-mediated photoredox reaction. The formyl-radical equivalent then undergoes nickel-catalyzed substitution reactions with aryl halides and triflates and vinyl bromides to form the corresponding aldehyde products. Significantly, besides aryl bromides, less reactive aryl chlorides and triflates and vinyl halides serve as effective substrates for this process. Since the mild conditions involved in this reaction tolerate a plethora of functional groups, the process can be applied to the efficient preparation of diverse aromatic aldehydes.

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