939-97-9

Basic information

• Product Name: 4-tert-Butylbenzaldehyde
• Synonyms: benzaldehyde,-(1,1-dimethylethyl)-;p-tert-butylbenzaldehyde(p-tbb);4-t-BUTYL BENZALDEHYDE;P-TERTIARY-BUTYL BENZALDEHYDE;para TertiaryButyl Benzaldehyde;4-tert-Butylbenzaldehyde 98%;PARA-TERTBUTYLBENZALDEHYDE;p-tert.Butylbenzaldehyd
• CAS NO: 939-97-9
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.23
• EINECS: 213-367-9
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het;Pharmaceutical Intermediate;C10 to C21;Carbonyl Compounds;Building Blocks;C10-C12;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Synthetic Flavours & Fragrances
• Mol File: 939-97-9.mol
• Article Data: 272

Chemical Properties

• Melting Point: 245-246 °C
• Boiling Point: 130 °C25 mm Hg(lit.)
• Flash Point: 214 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.97 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0372mmHg at 25°C
• Refractive Index: n20/D 1.53(lit.)
• Storage Temp.: Store below +30°C.
• Explosive Limit: 1.3-5.6%(V)
• Water Solubility: Soluble in water.
• Sensitive: Air & Light Sensitive
• BRN: 1906461
• CAS DataBase Reference: 4-tert-Butylbenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-tert-Butylbenzaldehyde(939-97-9)
• EPA Substance Registry System: 4-tert-Butylbenzaldehyde(939-97-9)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 22-43-50/53
• Safety Statements: 36/37-60-61
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 2
• F: 8-9-23
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 939-97-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 939-97-9 differently. You can refer to the following data:
1. Used for preparing isoxazolyl penicillin derivatives. 4-tert-Butylbenzaldehyde is suitable for use in a kinetic study to evaluate the kinetic constants (KI) for inhibition of mushroom tyrosinase by 4-substituted benzaldehydes. It is also an important intermediate for the synthesis of medicines, dyes, flavor and fragrance compounds.
2. 4-tert-Butylbenzaldehyde is suitable for use in a kinetic study to evaluate the kinetic constants (KI) for inhibition of mushroom tyrosinase by 4-substituted benzaldehydes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 37, p. 3973, 1972 DOI: 10.1021/jo00797a058Tetrahedron Letters, 32, p. 4291, 1991 DOI: 10.1016/S0040-4039(00)92151-8

General Description

4-tert-Butylbenzaldehyde is an important intermediate for the synthesis of medicines, dyes, flavor and fragrance compounds. It is reported to be formed during the partial oxidation of 4-tert-butyltoluene by hydrogen peroxide in glacial acetic acid, catalyzed by bromide ions in combination with cobalt(II) acetate or cerium(III) acetate. Schiff base reaction between 4-tert-butylaniline and 4-tert-butylbenzaldehyde in ethanol has been carried out on-chip in the matrix assisted laser desorption ionization (MALDI) chamber, the formed imine was detected in real time.

InChI:InChI=1/C11H14O/c1-11(2,3)10-6-4-9(8-12)5-7-10/h4-8H,1-3H3

Synthetic route

4-tert-Butylbenzyl alcohol (877-65-6) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With 1H-imidazole; sodium periodate; manganese(III)-porphyrin complex immobilized on polystyrene In water; acetonitrile at 20℃; for 1.16667h;	100%
With oxygen In 1,3,5-trimethyl-benzene at 60℃; under 760.051 Torr; for 7h; Solvent; Reagent/catalyst;	100%
With titanium(IV) oxide; oxygen at 29.84℃; under 760.051 Torr; for 6h; Sealed tube; Irradiation;	99%

p-tert-butyl benzoyl chloride (1710-98-1) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With polymethylhydrosiloxane; trifuran-2-yl-phosphane; tetrabutyl ammonium fluoride; potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water at 20℃; for 1h;	99%
With diethylene glycol dimethyl ether; lithium tri-t-butoxyaluminum hydride
With hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal In ethyl acetate at 25℃; under 760 Torr; for 1.75h; Yield given;
Multi-step reaction with 2 steps 1: dichloromethane / 0.5 h / 20 °C / Cooling with ice 2: Schwartz's reagent / tetrahydrofuran / 0.5 h / 20 °C View Scheme

4-tert-Butylstyrene (1746-23-2) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With p-PPh2-C6H4-(OCH2CH2)n-O-C6H4-PPh2-p; ozone Product distribution; various catalysts;	98%
Stage #1: 4-tert-Butylstyrene With oxygen; ozone In dichloromethane at -78℃; Stage #2: With poly(ethylene glycol)-triphenylphosphine In dichloromethane at -78 - 20℃;	98%
With oxygen; benzoic acid; sodium nitrite In toluene at 80℃; for 20h; Reagent/catalyst; Solvent; Temperature;	82%

4-tert-butyl benzene carbaldehyde oxime (180261-48-7) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With iron(III) chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In water; toluene at 60℃; under 760.051 Torr; for 3h;	98%

(4-tert-butylbenzyloxy)trimethylsilane (624286-50-6) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With trinitratocerium(IV) bromate for 0.7h; Heating;	97%
With copper(II) nitrate trihydrate; water; silica gel; potassium bromide at 90℃; for 0.5h; Neat (no solvent);	87%

1-bromo-4-tert-butylbenzene (3972-65-4) + carbon monoxide (201230-82-2) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium diacetate; propyl di-tert-butylphosphinite In toluene at 100℃; under 3750.38 Torr; for 20h; Inert atmosphere;	97%

4-tert-butylbenzyl chloride (19692-45-6) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With 1-dodecyl-3-methylimidazolium iron chloride; periodic acid at 30℃; for 1.5h;	96%
With potassium hydroxide; cetyltrimethylammonim bromide; potassium nitrate In water for 4h; pH=10 - 11; Reflux;	90%
With potassium nitrite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; potassium bromide In water for 4h; Reflux;	90%
With sodium nitrate; acetic acid In water for 3.5h; Reflux;	90%
With hexamethylenetetramine; sulfuric acid; sodium carbonate In ethanol; water; toluene	11.8 g (60%)

4-tert-butyltoluene (98-51-1) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In fluorobenzene; dimethyl sulfoxide at 80℃; for 8h;	95%
With ammonium cerium(IV) nitrate In water; acetic acid at 85 - 95℃; for 1.5h;	94%
With carbon tetrabromide; oxygen In acetonitrile at 20℃; for 3h; Irradiation; Green chemistry;	90%

1,1-bis(4-t-butylphenyl)methane (19099-48-0) + 1-azidononane (80077-60-7) → 4-tert-Butylbenzaldehyde (939-97-9) + 4-tert-butyl-N-nonylaniline (1225826-38-9)

Conditions	Yield
With water; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; iron(II) chloride at 60℃; for 5h;	A 85% B 94%

N-(4-tert-butylbenzyl)-4-tert-butylaniline → 4-tert-Butylbenzaldehyde (939-97-9) + 4-tert-Butylaniline (769-92-6)

Conditions	Yield
Stage #1: N-(4-tert-butylbenzyl)-4-tert-butylaniline With oxygen; toluene-4-sulfonic acid; dimethyl sulfoxide In toluene at 100℃; for 119h; Green chemistry; Stage #2: With hydrogenchloride In water at 20℃; for 1h; Reagent/catalyst; Temperature; Green chemistry;	A 93% B 94%

formic acid (64-18-6) + 1-tert-butyl-4-iodobenzene (35779-04-5) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
Stage #1: formic acid; 1-tert-butyl-4-iodobenzene With palladium diacetate; acetic anhydride; tricyclohexylphosphine In N,N-dimethyl-formamide at 30℃; for 1h; Inert atmosphere; Green chemistry; Stage #2: With triethylamine In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere; Green chemistry;	93%
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; tricyclohexylphosphine In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube;	72%

4-tert-butyltoluene (98-51-1) → 4-tert-Butylbenzaldehyde (939-97-9) + 4-(1,1-dimethylethyl)benzoic acid (98-73-7)

Conditions	Yield
With N-hydroxyphthalimide; oxygen; cobalt(II) acetate In acetic acid at 25℃; under 760 Torr; for 20h;	A 2% B 91%
With N-hydroxyphthalimide; oxygen; cobalt(II) acetate In acetonitrile at 25℃; under 760 Torr; for 20h;	A 4% B 77%
With oxygen; acetic acid; N-hydroxyphthalimide at 100℃; for 6h; Product distribution / selectivity;	A 3.8% B 66.5%

potassium tert-butyltrifluoroboranuide + 4-bromo-benzaldehyde (1122-91-4) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With dipotassium hydrogenphosphate; nickel(II) bis(2,2,6,6-tetramethylheptane-3,5-dionate); Ir(dF(CF3)ppy)2(bpy)PF6; zinc dibromide In N,N-dimethyl acetamide at 27℃; for 48h; Inert atmosphere; Irradiation;	91%

1-(bromomethyl)-4-(1,1-dimethylethyl)benzene (18880-00-7) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With potassium hydrogencarbonate; dimethyl sulfoxide for 0.0583333h; Microwave irradiation;	90%
With carbon dioxide; copper(II) nitrate
With ethanol; carbon dioxide; hexamethylenetetramine
With 4-methylmorpholine N-oxide at 20℃; for 4h; Reflux;	246.6 mg
Multi-step reaction with 2 steps 1: eosin y; oxygen / dimethyl sulfoxide / 12 h / 25 °C / Irradiation 2: eosin y / dimethyl sulfoxide / 24 h / 80 °C / Irradiation View Scheme

4-(1,1-dimethylethyl)-benzenemethanamine (39895-55-1) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With cercosporin; oxygen In methanol at 20℃; Schlenk technique; Irradiation; Green chemistry; chemoselective reaction;	89%
With copper(I) 2-hydroxy-3-methylbenzoate; oxygen; ascorbic acid In N,N-dimethyl acetamide at 45℃; for 2h; chemoselective reaction;	70%
With dipotassium peroxodisulfate; tris(bipyridine)ruthenium(II) dichloride hexahydrate; water In acetonitrile at 20℃; for 12h; Sealed tube; Irradiation; Green chemistry;

tert-butylisonitrile (119072-55-8, 7188-38-7) + 1-tert-butyl-4-iodobenzene (35779-04-5) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
Stage #1: tert-butylisonitrile; 1-tert-butyl-4-iodobenzene With triethylsilane; palladium diacetate; sodium carbonate; CyJohnPhos In N,N-dimethyl-formamide at 65℃; for 8h; Inert atmosphere; Sealed tube; Green chemistry; Stage #2: With water Green chemistry;	88%

C14H20S2 → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With eosin y In water; acetonitrile at 20℃; for 4h; Irradiation;	88%

4-t-butylphenylacetic acid (32857-63-9) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With oxygen; copper diacetate In dimethyl sulfoxide at 120℃; for 18h; Sealed tube;	87%
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20 - 25℃; for 6h; Irradiation;	76%
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; N,N,N',N'-tetramethylguanidine In acetonitrile at 20℃; for 6h; Irradiation;	55%
With water; copper dichloride at 250℃; under 30003 Torr; for 0.17h; Sealed tube; Green chemistry;	94 %Chromat.

4-tert-butylbenzyl mercaptan (49543-63-7) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With dipotassium peroxodisulfate; tetrakis(pyridine)silver(II) peroxodisulfate; oxygen In N,N-dimethyl-formamide at 23℃; under 760.051 Torr; Irradiation;	87%

1-(1,1-dimethylethyl)-4-(methoxymethyl)benzene (3395-87-7) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With nitric acid In dichloromethane at 20℃; for 1h;	86%

1-tert-butyl-4-iodobenzene (35779-04-5) + 9-methyl-9H-fluorene-9-carbonyl chloride (82102-37-2) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With dichloro(1,5-cyclooctadiene)palladium(II); N-Methyldicyclohexylamine; potassium formate; tetra-(n-butyl)ammonium iodide; tricyclohexylphosphine tetrafluoroborate; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate In acetonitrile at 80℃; for 18h; Sealed tube; Glovebox; Inert atmosphere;	86%

1-bromo-4-tert-butylbenzene (3972-65-4) + carbon dioxide (124-38-9) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With rhodium(III) iodide; dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); hydrogen; acetic anhydride; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 24h; Autoclave;	85%
With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 100℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry;	81%

4-(tert-butyl)benzoyl fluoride → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With triethylsilane; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 20h; Inert atmosphere; Sealed tube;	85%

1-tert-butoxymethyl-4-tert-butylbenzene (72390-21-7) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With N-hydroxyphthalimide; nitrogen(II) oxide In acetonitrile at 60℃; for 10h;	84%
	84%

methanol (67-56-1) + (E)-1,1'-(1,2-ethenediyl)bis(4-butyl)benzene (79135-54-9, 114530-47-1, 123356-27-4, 64392-50-3) → 4-tert-Butylbenzaldehyde (939-97-9) + methyl 4-tert-butylbenzoate (26537-19-9)

Conditions	Yield
With iodine; oxygen; trifluoroacetic acid In ethyl acetate for 20h; Solvent; Reagent/catalyst; Irradiation;	A 84% B 7 %Spectr.

3-(4-(tert-butyl)phenyl)acrylaldehyde (84434-23-1) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With pyrrolidine; water In acetonitrile at 20℃; for 12h; Inert atmosphere;	83%

(4-t-butylphenyl)(chloro)methyl p-tolyl sulfoxide → 4-tert-Butylbenzaldehyde (939-97-9) + di(p-tolyl) disulfide (103-19-5)

Conditions	Yield
In 1,4-dioxane for 12h; Heating;	A 82% B 66%

carbon monoxide (201230-82-2) + 1-tert-butyl-4-iodobenzene (35779-04-5) → 4-tert-Butylbenzaldehyde (939-97-9)

Conditions	Yield
With rhodium(III) chloride trihydrate; hydrogen; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 90℃; under 7500.75 Torr; for 12h; Autoclave;	81%

4-tert-Butylbenzaldehyde (939-97-9) → 4-(1,1-dimethylethyl)benzoic acid (98-73-7)

Conditions	Yield
With hydrogen bromide; oxygen In acetonitrile at 20℃; for 5h; UV-irradiation;	100%
With tert.-butylhydroperoxide; potassium tert-butylate In water at 60℃; for 5h;	96%
With N-Bromosuccinimide; oxygen In ethyl acetate at 20℃; Irradiation;	93%

4-tert-Butylbenzaldehyde (939-97-9) → 4-tert-Butylbenzyl alcohol (877-65-6)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 25℃; for 0.5h;	100%
With sodium tetrahydroborate In ethanol at 20℃; for 0.5h; Inert atmosphere;	100%
With sodium tetrahydroborate In ethanol at 20℃; for 0.5h; Inert atmosphere;	100%

4-tert-Butylbenzaldehyde (939-97-9) + diethylzinc (557-20-0) → 1-(4-tert-butylphenyl)propan-1-ol (127896-25-7)

Conditions	Yield
With (R,R)-(2,4,6-Me3C6H2-CH=N-CH(Ph))2; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane 1.) -78 deg C, 4 h, 2.) -20 deg, 1 h;	100%
With (1R,2R)-N,N'-bis[(2,4,6-trimethylphenyl)methylene]-1,2-cyclohexane-diamine; (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol In hexane; dichloromethane at -78 - -20℃; for 5h;	100%
With titanium(IV) isopropylate at 80℃; for 1h; Time; Inert atmosphere;	60 %Chromat.
With magnesium chloride at 80℃; for 0.5h; Reagent/catalyst; Inert atmosphere;	24.2 %Chromat.

4-tert-Butylbenzaldehyde (939-97-9) + 1-(2,4-dichlorophenyl)ethan-1-one (2234-16-4) → 3-(4-tert-butyl-phenyl)-1-(2,4-dichloro-phenyl)-propenone

Conditions	Yield
With sodium hydroxide for 1.5h;	100%

4-tert-Butylbenzaldehyde (939-97-9) + 1-amino-2-propene (107-11-9) → Allyl-[1-(4-tert-butyl-phenyl)-meth-(E)-ylidene]-amine (250376-72-8)

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 20h;	100%

N-[3-fluoro-4-(4-morpholinyl)phenyl]-N-(4-piperidinylmethyl)-N'-(tetrahydro-2H-pyran-4-yl)urea (856889-57-1) + 4-tert-Butylbenzaldehyde (939-97-9) → N-[(1-{[4-(1,1-dimethylethyl)phenyl]methyl}-4-piperidinyl)methyl]-N-[3-fluoro-4-(4-morpholinyl)phenyl]-N'-(tetrahydro-2H-pyran-4-yl)urea

Conditions	Yield
With MP-triacetoxyborohydride In dichloromethane at 20℃; for 18h; MP-triacetoxyborohydride;	100%

4-tert-Butylbenzaldehyde (939-97-9) + vinyl magnesium bromide (1826-67-1) → 1-(4-(tert-butyl)phenyl)prop-2-en-1-ol (863029-85-0)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;	100%
Stage #1: 4-tert-Butylbenzaldehyde; vinyl magnesium bromide In tetrahydrofuran at 20℃; for 20h; Heating / reflux; Stage #2: With water; ammonium chloride
In tetrahydrofuran at 0℃; for 1h;

4-tert-Butylbenzaldehyde (939-97-9) + 2-(3-methoxyphenyl)-1-ethanamine (2039-67-0) → (4-tert-butyl-benzyl)-[2-(3-methoxy-phenyl)-ethyl]-amine

Conditions	Yield
Stage #1: 4-tert-Butylbenzaldehyde; 2-(3-methoxyphenyl)-1-ethanamine With potassium carbonate In methanol at 20℃; for 2h; Heating / reflux; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 3h; Heating / reflux; Stage #3: With hydrogenchloride In methanol; water	100%

4-tert-Butylbenzaldehyde (939-97-9) + 2-(3-Fluorophenyl)ethylamine (404-70-6) → (4-tert-butyl-benzyl)-[2-(3-fluoro-phenyl)-ethyl]-amine

Conditions	Yield
Stage #1: 4-tert-Butylbenzaldehyde; 2-(3-Fluorophenyl)ethylamine In methanol at 20℃; for 2.5h; Heating / reflux; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 3.08h; Heating / reflux; Stage #3: With hydrogenchloride In methanol; water at 20℃;	100%

4-tert-Butylbenzaldehyde (939-97-9) + 2-(3-chlorophenyl)ethylamine (13078-79-0) → (4-tert-butyl-benzyl)-[2-(3-chloro-phenyl)-ethyl]-amine (875305-16-1)

Conditions	Yield
Stage #1: 4-tert-Butylbenzaldehyde; 2-(3-chlorophenyl)ethylamine In methanol at 20℃; for 3h; Heating / reflux; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 4.08h; Heating / reflux; Stage #3: With hydrogenchloride In methanol; water at 20℃;	100%

4-tert-Butylbenzaldehyde (939-97-9) + 4-fluoro-2-phenethylamine (1583-88-6) → (4-tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amine (875305-06-9)

Conditions	Yield
Stage #1: 4-tert-Butylbenzaldehyde; 4-fluoro-2-phenethylamine In methanol at 20℃; for 4.5h; Heating / reflux; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 2.08h; Heating / reflux; Stage #3: With hydrogenchloride In methanol; water at 20℃;	100%

4-tert-Butylbenzaldehyde (939-97-9) + 2-(p-tolyl)ethylamine (3261-62-9) → (4-tert-butyl-benzyl)-(2-p-tolyl-ethyl)-amine (875305-08-1)

Conditions	Yield
Stage #1: 4-tert-Butylbenzaldehyde; 2-(p-tolyl)ethylamine In methanol at 20℃; for 3h; Heating / reflux; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 2.38h; Heating / reflux; Stage #3: With hydrogenchloride In methanol; water at 20℃;	100%

2-(2-fluoro-5-trifluoromethyl-phenyl)-ethylamine hydrochloride (875305-55-8) + 4-tert-Butylbenzaldehyde (939-97-9) → (4-tert-butyl-benzyl)-[2-(2-fluoro-5-trifluoromethyl-phenyl)-ethyl]-amine (875305-54-7)

Conditions	Yield
Stage #1: 2-(2-fluoro-5-trifluoromethyl-phenyl)-ethylamine hydrochloride; 4-tert-Butylbenzaldehyde With potassium carbonate In methanol at 20℃; for 3h; Heating / reflux; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 2.58h; Heating / reflux;	100%

4-tert-Butylbenzaldehyde (939-97-9) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → C30H42N2 (1217526-91-4)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

4-tert-Butylbenzaldehyde (939-97-9) + methylamine (74-89-5) → C12H17N (144023-42-7)

Conditions	Yield
at 20℃; for 12h;	100%

2-(4-Chloro-3-Ethyl-Phenyl)-Ethyl-Amine-Hydrochloride (945717-05-5) + 4-tert-Butylbenzaldehyde (939-97-9) → [1-(4-tert-butyl-phenyl)-meth-(E)-ylidene]-[2-(4-chloro-3-ethyl-phenyl)-ethyl]-amine (1352659-88-1)

Conditions	Yield
Stage #1: 2-(4-Chloro-3-Ethyl-Phenyl)-Ethyl-Amine-Hydrochloride With sodium hydroxide In water; ethyl acetate Stage #2: 4-tert-Butylbenzaldehyde In ethyl acetate at 20℃; for 2h;	100%
With sodium hydroxide In water; ethyl acetate at 20℃; for 2h;	100%

4-tert-Butylbenzaldehyde (939-97-9) + tert-butyl 1-(2-bromobenzyl)hydrazine-1-carboxylate → C23H29BrN2O2

Conditions	Yield
In ethanol at 20℃;	100%

4-tert-Butylbenzaldehyde (939-97-9) + allylmagnesium bromide (1730-25-2) → 1-(4-(tert-butyl)phenyl)but-3-en-1-ol (106027-36-5)

Conditions	Yield
In tetrahydrofuran; diethyl ether at 0 - 20℃;	100%
With indium In tetrahydrofuran; diethyl ether at 0℃; Inert atmosphere;

malonic acid (141-82-2) + 4-tert-Butylbenzaldehyde (939-97-9) → 4-tert-butyl-trans-cinnamic acid (1208-65-7)

Conditions	Yield
Stage #1: malonic acid; 4-tert-Butylbenzaldehyde With piperidine; pyridine Knoevenagel-Doebner reaction; Reflux; Stage #2: With hydrogenchloride In water Cooling with ice; optical yield given as %de;	99%
With piperidine; pyridine for 2h; Knoevenagel condensation; Reflux;	88%
With piperidine; pyridine	87%

4-tert-Butylbenzaldehyde (939-97-9) + (1R,2R)-1,2-diaminocyclohexane tartrate → (1R,2R)-N,N'-bis(4-tert-butylbenzylidene)-1,2-diaminocyclohexane

Conditions	Yield
With potassium carbonate In ethanol; water for 5.5h; Heating;	99%
With potassium carbonate

ethyl 2-diethoxyphosphorylpropionate (3699-66-9) + 4-tert-Butylbenzaldehyde (939-97-9) → ethyl (E)-3-(4-(tert-butyl)phenyl)-2-methylacrylate

Conditions	Yield
Stage #1: ethyl 2-diethoxyphosphorylpropionate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: 4-tert-Butylbenzaldehyde In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;	99%
Stage #1: ethyl 2-diethoxyphosphorylpropionate With sodium hydride In tetrahydrofuran at 0 - 25℃; Stage #2: 4-tert-Butylbenzaldehyde In tetrahydrofuran for 1h; Heating;
With sodium hydride In tetrahydrofuran; mineral oil at -78 - 20℃; for 3h;

4-tert-Butylbenzaldehyde (939-97-9) → 4-tert-butyl benzonitrile (4210-32-6)

Conditions	Yield
With ammonium sulfate; sodium carbonate; sulfur In dimethyl sulfoxide at 120℃; for 10h; Sealed tube;	99%
With pyridine; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ammonium peroxydisulfate; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; ammonium carbamate In water; acetonitrile at 20℃; for 24h; Irradiation; Sealed tube;	98%
Stage #1: 4-tert-Butylbenzaldehyde With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane at 26℃; for 0.0833333h; Stage #2: With 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In dichloromethane at 26℃; for 18h;	97%

3-(diethoxyphosphorylmethyl)-4-methoxybenzamide (858124-31-9) + 4-tert-Butylbenzaldehyde (939-97-9) → 3-[(E)-2-(4-tert-butylphenyl)vinyl]-4-methoxybenzamide

Conditions	Yield
With sodium tert-pentoxide In N,N-dimethyl-formamide at 20℃; for 1h; Horner-Wadsworth-Emmons olefination;	99%

4-tert-Butylbenzaldehyde (939-97-9) + girard's reagent T (123-46-6) + diisopropyl (2-oxo-2-(pyrrolidin-1-yl)ethyl)phosphonate (66932-77-2) → C16H26N3O(1+)*Cl(1-) + C17H23NO (535945-57-4) + di-isopropylphosphonate anion

Conditions	Yield
Stage #1: 4-tert-Butylbenzaldehyde; diisopropyl (2-oxo-2-(pyrrolidin-1-yl)ethyl)phosphonate With potassium tert-butylate In tetrahydrofuran at 20℃; for 6h; Horner-Wadsworth-Emmons Olefination; Stage #2: girard's reagent T In tetrahydrofuran; methanol stereoselective reaction;	A n/a B 99% C n/a

4-tert-Butylbenzaldehyde (939-97-9) → 4-tert-butyltoluene (98-51-1)

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 25℃; under 760.051 Torr; for 0.833333h;	99%

1.3-propanedithiol (109-80-8) + 4-tert-Butylbenzaldehyde (939-97-9) → C14H20S2

Conditions	Yield
With silica gel; toluene-4-sulfonic acid In dichloromethane Reflux;	99%
With boron trifluoride diethyl etherate In dichloromethane Inert atmosphere;
With boron trifluoride diethyl etherate In dichloromethane at 0 - 25℃;

4-tert-Butylbenzaldehyde (939-97-9) + cyclohexylamine (108-91-8) → (E)-N-(4-tert-butylbenzylidene)cyclohexanamine

Conditions	Yield
In neat (no solvent) at 60℃; for 0.0666667h; Microwave irradiation;	99%

pentanonitrile (110-59-8) + 4-tert-Butylbenzaldehyde (939-97-9) → N-(4-(tert-butyl)benzyl)pentan-1-aminium chloride

Conditions	Yield
Stage #1: pentanonitrile; 4-tert-Butylbenzaldehyde With hydrogen In 2-methyltetrahydrofuran at 100℃; under 11251.1 Torr; for 20h; High pressure; Autoclave; Stage #2: With hydrogenchloride In diethyl ether	99%

Upstream product

• 18880-00-7 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene 
• 1710-98-1 p-tert-butyl benzoyl chloride 
• 507-20-0 tertiary butyl chloride 
• 71-43-2 benzene 
• 877-65-6 p-tert-butylbenzyl alcohol 
• 67-56-1 methanol 
• 98-51-1 4-tert-butyltoluene 
• 594-19-4 tert.-butyl lithium 
• 100-52-7 benzaldehyde 
• 50-00-0 formaldehyd 
• 253185-03-4 tert-butylbenzene 
• 201230-82-2 carbon monoxide 
• 154318-75-9 4-tert-butylphenyl triflate 
• 25891-31-0 triformylamine 

Downstream Products

• 13586-68-0 p-tert-butyl-α-methyl-3-phenylprop-2-enal 
• 55047-62-6 (E)-4-(4′-tert-butylphenyl)-3-buten-2-one 
• 36524-19-3 2-[(E)-2-(4-tert-Butyl-phenyl)-vinyl]-benzo[c]phenanthrene 
• 75485-50-6 4-tert.-Butyl-benzoylbromid 
• 90672-08-5 (4-tert-Butyl-phenyl)-(3-methyl-isothiazol-5-yl)-methanol 
• 158010-17-4 ethyl (E)-3-[4-(tert-butylphenyl)]-2-propenoate 
• 127033-97-0 (E)-3-(4-tert-Butyl-phenyl)-1-(3,4,5-trimethoxy-phenyl)-propenone 
• 99327-11-4 (E)-2-methoxy-1-(4-tert-butylphenyl)-2-buten-1-ol 
• 131178-82-0 3,3-diphenyl-5-(4-tert-butylphenyl)-1,2,4-trioxolane 
• 74518-95-9 (E)-1-(tert-butyl)-4-(4-nitrostyryl)benzene 
• 122439-68-3 1-(4-tert-Butyl-phenyl)-2-methyl-but-3-en-1-ol 
• 124652-44-4 (E,Z)-1,8-Bis(4-<2-(4-tert-butylphenyl)ethenyl>phenyl)naphthalin 
• 124652-43-3 (E,E)-1,8-Bis(4-<2-(4-tert-butylphenyl)ethenyl>phenyl)naphthalin 
• 141172-11-4 (Z)-1-(4-tert-butylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene 

Relevant articles and documents

Preparation, characterization and catalytic performance of bimetallic Ti-Co-MCM-41 catalysts

Ti-Co-MCM-41 molecular sieve catalysts were synthesized using the impregnation method. The catalysts were characterized by X-ray diffraction, UV-visible, Fourier transform infrared spectroscopy and low temperature N2 adsorption-desorption. Their performance in 4-tert-butylbenzaldehyde synthesis was evaluated in mild conditions by oxygen oxidation 4-tert-butyltoluene. The results showed that the catalysts had large surface area and pore size and contained titanium and cobalt with four ligands, which formed the catalysts of high catalytic activity. The conversion rate of 4-tert-butyl toluene was improved by 38%, the selectivity of 4-tert-butyl benzaldehyde was improved by 85% and the yield of 4-tert-butyl benzaldehyde was up to 35%.

Selective oxidation of benzylic alcohols with molecular oxygen catalyzed by copper-manganese oxide nanoparticles

The catalytic activity of copper-manganese (CuMn) mixed oxide nanoparticles (Cu/Mn = 1:1) prepared by co-precipitation method has been studied for the selective oxidation of benzyl alcohol and its derivatives to the corresponding aldehydes using molecular

Efficient catalysis of a redox reaction by an artificial enzyme

-

Inhibition of the Cobalt Acetate/Bromide-Catalyzed Hydrogen Peroxide Oxidation of 4-tert-Butyltoluene

The hydrogen peroxide oxidation of 4-tert-butyltoluene to 4-tert-butylbenzaldhyde, an important fragrance intermediate, catalyzed by cobalt acetate and bromide in acetic acid was investigated again. The initial stages of the reaction appear to be rapid and quantitative, but after approximately 25-30% conversion, the process ceases. Overoxidation to 4-tert-butylbenzoic acid does not occur. It appears that both water and the aldehyde product itself inhibit further oxidation. An engineering solution to remove the product continuously seems required for process optimization.

A Metal–Organic Framework as a Multiphoton Excitation Regulator for the Activation of Inert C(sp3)?H Bonds and Oxygen

The activation and oxidization of inert C(sp3)?H bonds into value-added chemicals affords attractively economic and ecological benefits as well as central challenge in modern chemistry. Inspired by the natural enzymatic transformation, herein,

Method for generating benzaldehyde by catalyzing alpha-monosubstituted styrene to be oxidized by N-hydroxyphthalimide

The invention discloses a method for generating benzaldehyde by catalyzing alpha-mono-substituted styrene to be oxidized through N-hydroxyphthalimide. According to the method, N-hydroxyphthalimide isused as a catalyst, oxygen is used as an oxidizing agent, and an alpha mono-substituted styrene compound is oxidized in an organic solvent to obtain the benzaldehyde derivative. The method has the advantages of simple reaction operation, low cost, mild conditions, high yield, no heavy metal pollution and the like.