5779-95-3

Basic information

• Product Name: 3,5-Dimethylbenzaldehyde
• Synonyms: 3,5-DIMETHYLBENZALDEHYDE;M-XYLENE-5-CARBOXALDEHYDE;3,5-DIMETHYLBENZALDEHYDE 99+%;3,5-Dimethylbenzaldehyde, 98+%;3,5-Dimethylbenzaldehyde, 97+%
• CAS NO: 5779-95-3
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.18
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;C9;Carbonyl Compounds;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 5779-95-3.mol
• Article Data: 100

Chemical Properties

• Melting Point: 8-10 °C
• Boiling Point: 232 °C(lit.)
• Flash Point: 210 °F
• Appearance: clear colorless to yellow liquid
• Density: 0.998 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.11mmHg at 25°C
• Refractive Index: n20/D 1.538(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: Not miscible with water.
• Sensitive: Air Sensitive
• BRN: 2038840
• CAS DataBase Reference: 3,5-Dimethylbenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dimethylbenzaldehyde(5779-95-3)
• EPA Substance Registry System: 3,5-Dimethylbenzaldehyde(5779-95-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 5779-95-3(Hazardous Substances Data)

Usage

Description

3,5-Dimethylbenzaldehyde is an organic compound with the chemical formula C9H10O. It is a clear colorless to yellow liquid and is known for its distinct aromatic smell. 3,5-Dimethylbenzaldehyde is an aromatic aldehyde derived from benzene, with two methyl groups attached at the 3rd and 5th positions. It is widely used in various industries due to its unique chemical properties and versatile applications.

Uses

Used in Chemical Synthesis:
3,5-Dimethylbenzaldehyde is used as a key intermediate in the production of various chemicals. For instance, it is used to produce 2,3-bis-(3,5-dimethyl-phenyl)-succinonitrile by heating along with the reagent NaCN and solvent H2O, methanol. This synthesized compound has potential applications in the chemical and pharmaceutical industries.
Used in Flavor and Fragrance Industry:
3,5-Dimethylbenzaldehyde is used as a flavoring agent and a fragrance ingredient in the food, beverage, and cosmetic industries. Its distinct aromatic smell makes it a valuable component in creating various scents and flavors for different products.
Used in Pharmaceutical Industry:
Due to its chemical properties, 3,5-Dimethylbenzaldehyde can be utilized in the synthesis of pharmaceutical compounds. It can serve as a building block for developing new drugs or improving the efficacy of existing ones.
Used in Dye and Pigment Industry:
3,5-Dimethylbenzaldehyde's chemical structure also makes it suitable for use in the dye and pigment industry. It can be employed in the production of various dyes and pigments, contributing to the coloration of textiles, plastics, and other materials.

InChI:InChI=1/C9H10O/c1-7-3-8(2)5-9(4-7)6-10/h3-6H,1-2H3

Synthetic route

3,5-dimethylbenzyl alcohol (27129-87-9) → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; oxygen; nitric acid at 20℃; for 5h;	99%
With dihydrogen peroxide In tetrahydrofuran; water at 70℃; for 5h;	94.5%
With potassium tetrakis-μ-pyrophosphitodiplatinate(II); tetrabutyl-ammonium chloride In dichloromethane; water at 20℃; for 8h; Inert atmosphere; Irradiation;	89%

(E)-N-(3,5-dimethylbenzylidene)aniline → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With hydrogenchloride; water In diethyl ether; toluene at 20℃; for 2h; Inert atmosphere;	98%

tert-butylisonitrile (119072-55-8, 7188-38-7) + 3,5-dimethylphenyl iodide (22445-41-6) → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
Stage #1: tert-butylisonitrile; 3,5-dimethylphenyl iodide 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;	97%

5-bromo-1,3-xylene (556-96-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
Stage #1: 5-bromo-1,3-xylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; for 1.33333h; Inert atmosphere; Stage #3: With water In tetrahydrofuran; hexane	95%

3,5-dimethylbenzoic acid (499-06-9) → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With dipotassium hydrogenphosphate; fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane; dimethyl dicarbonate In acetonitrile at 20℃; for 6h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;	93%
With P(p-CH3OC6H4)3; methylphenylsilane; 2,2-dimethylpropanoic anhydride; bis(dibenzylideneacetone)-palladium(0) In toluene at 80℃; for 20h; Schlenk technique; Inert atmosphere;	71%
With maleic anhydride; Dimethylphenylsilane; nickel(II) acetate tetrahydrate; 2,2'-Bipyrimidine In tetrahydrofuran at 100℃; for 12h; Schlenk technique; Inert atmosphere;	71%
Multi-step reaction with 2 steps 1: indium (III) iodide / toluene / 2 h / 60 °C / Inert atmosphere; Sealed tube 2: indium (III) iodide; dihydrogen peroxide / toluene; water / 15 h / 20 °C / Inert atmosphere; Sealed tube View Scheme

3,5-dimethylbenzyliodide (35509-95-6) → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With vanadia; periodic acid; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 70℃; for 4h; Reagent/catalyst; Green chemistry;	91%

1-bromomethyl-3,5-dimethylbenzene (27129-86-8) → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With 2-nitropropane; sodium ethanolate	87%
With dihydrogen peroxide In ethanol for 6h; Heating;	85%
With sodium 2-nitropropane In ethanol at 60℃; for 3h;	84%

carbon monoxide (201230-82-2) + 3,5-dimethylphenyl iodide (22445-41-6) → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With triethylsilane; palladium diacetate; sodium hydrogencarbonate; sodium carbonate at 20℃; under 760.051 Torr; for 33h;	87%
With bis-triphenylphosphine-palladium(II) chloride; formic acid; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 60℃; under 760 Torr; Carbonylation; Electrochemical reaction;	82%

1,3,5-trimethyl-benzene (108-67-8) → 3,5-dimethylbenzyl nitrate (15285-43-5) + 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With ammonium cerium(IV) nitrate In acetonitrile at 40℃; for 1h; Mechanism; Irradiation;	A 85% B n/a
With ammonium cerium(IV) nitrate In acetonitrile at 40℃; for 1h; Irradiation;	A 85% B n/a

3,5-dimethylbenzyl chloride (2745-54-2) → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With 2-nitropropane; sodium ethanolate In ethanol for 2h; Heating;	83%

formic acid (64-18-6) + 3,5-dimethylphenyl iodide (22445-41-6) → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
Stage #1: 3,5-dimethylphenyl iodide With iodine; triethylamine; triphenylphosphine In dichloromethane; toluene at 20℃; for 0.0833333h; Sealed tube; Green chemistry; Stage #2: formic acid In dichloromethane; toluene at 70℃; for 1.5h; Sealed tube; Green chemistry;	83%

3,5-dimethyl benzoyl fluoride → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With triethylsilane; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 20h; Inert atmosphere; Sealed tube;	82%

N,3,5-trimethyl-N-(methyloxy)benzamide (252199-44-3) → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
Stage #1: N,3,5-trimethyl-N-(methyloxy)benzamide With chloromagnesium dimethylaminoborohydride In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere; Stage #2: With acetaldehyde; acetic acid In tetrahydrofuran; pentane for 0.25h; Inert atmosphere; Further stages;	81%
Stage #1: N,3,5-trimethyl-N-(methyloxy)benzamide With chloromagnesium dimethylaminoborohydride In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere; Stage #2: With acetaldehyde; acetic acid In tetrahydrofuran; pentane for 0.25h; Inert atmosphere;

1,3,5-trimethyl-benzene (108-67-8) → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With pyridinium chlorochromate In acetonitrile for 3h; Heating;	79%
With iron(III) sulfate In water; acetonitrile for 12h; Irradiation; Sealed tube;	72%
With iron(III) sulfate; water In acetonitrile at 20℃; for 12h; UV-irradiation;	72%

1,3,5-trimethyl-benzene (108-67-8) → 3,5-dimethylbenzaldehyde (5779-95-3) + 3,5-dimethylbenzyl alcohol (27129-87-9)

Conditions	Yield
With sulfuric acid; water; oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile for 1.33333h; Quantum yield; Reagent/catalyst; Irradiation;	A 77% B 19%
With oxygen for 24h; Ambient temperature; Irradiation; Yield given. Yields of byproduct given;
With cobalt(II) 5,10,15,20-tetraphenylporphyrin; trifluorormethanesulfonic acid; water; oxygen In [D3]acetonitrile at 24.84℃; for 8h; Catalytic behavior; Time; UV-irradiation;

carbon monoxide (201230-82-2) + 3,5-dimethylphenyl iodide (22445-41-6) → 3,5-dimethylbenzaldehyde (5779-95-3) + m-xylene (108-38-3)

Conditions	Yield
With hydrogen; potassium carbonate In 1,4-dioxane at 120 - 140℃; under 30003 Torr; for 20h; Autoclave;	A 71% B 6%

p-benzoquinone (106-51-4) + 1,3,5-trimethyl-benzene (108-67-8) → 3,5-dimethylbenzaldehyde (5779-95-3) + 2-(3,5-Dimethyl-benzyl)-[1,4]benzoquinone

Conditions	Yield
With sodium persulfate; sulfuric acid; silver nitrate In water at 60℃; for 0.5h;	A 1% B 70%

1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide (33070-58-5) + 1,3,5-trimethyl-benzene (108-67-8) → 3,5-dimethylbenzaldehyde (5779-95-3) + 3,5-dimethylbenzyl alcohol (27129-87-9)

Conditions	Yield
at 135℃; for 2h;	A 21% B 69%

C17H20N2O → 3,5-dimethylbenzoic acid (499-06-9) + 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With hydrogenchloride; water for 0.25h;	A 34% B 67%

N-formylformamide (18197-22-3) + m-xylene (108-38-3) → 3,5-dimethylbenzaldehyde (5779-95-3) + N-[Bis(3,5-dimethylphenyl)methyl]formamid

Conditions	Yield
With aluminium trichloride In chlorobenzene at 0 - 60℃; for 5h; Condensation; formylation;	A n/a B 65%

1,3,5-trimethyl-benzene (108-67-8) → 3,5-dimethylbenzoic acid (499-06-9) + 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With oxygen; 9,10-Dicyanoanthracene; Paraquat; iron(II) chloride In methanol; acetonitrile for 8h; Ambient temperature; Irradiation;	A 26% B 61%
With oxygen at 100℃; in diffusem Licht;
With dmap; oxygen; benzyl bromide In acetonitrile at 160℃; under 7500.75 Torr; for 3h; Autoclave;

1,3,5-trimethyl-benzene (108-67-8) → 3,5-dimethylbenzoic acid (499-06-9) + 3,5-dimethylbenzaldehyde (5779-95-3) + 3,5-dimethylbenzyl alcohol (27129-87-9)

Conditions	Yield
With N-hydroxyphthalimide; oxygen; cobalt(II) acetate In acetic acid at 25℃; under 760 Torr; for 30h;	A 51% B 21% C 2%
With N-hydroxyphthalimide; oxygen; cobalt(II) acetate In acetic acid at 25℃; under 760 Torr; for 20h;	A 39% B 26% C 2%
With air; Pt2 In acetonitrile Product distribution; Ambient temperature; Irradiation; relative rate;	A 12 % Chromat. B 65 % Chromat. C 10 % Chromat.

acetic acid (64-19-7) + 1,3,5-trimethyl-benzene (108-67-8) → 3,5-dimethylbenzaldehyde (5779-95-3) + 3,5-dimethylbenzyl acetate (5159-42-2)

Conditions	Yield
With air; copper diacetate; cobalt(II) acetate; sodium bromide at 150℃; under 15200 Torr; for 1h;	A 11% B 49%
With cobalt(III) acetate at 60℃; for 2h; Mechanism; Product distribution; other temperature;	A 9 % Chromat. B 91 % Chromat.

1,3,5-trimethyl-benzene (108-67-8) → 3,5-dimethylbenzaldehyde (5779-95-3) + 3,5-dimethylbenzyl acetate (5159-42-2)

Conditions	Yield
With air; copper diacetate; cobalt(II) acetate; acetic acid; sodium bromide at 150℃; under 15200 Torr; for 1h;	A 11% B 49%

para-iodoanisole (696-62-8) + 1,3,5-trimethyl-benzene (108-67-8) → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With C14H9N4O(1-); potassium tert-butylate at 120℃; for 24h; Inert atmosphere;	41%

3,5-dimethylbenzyliodide (35509-95-6) → 3,5-dimethylbenzoic acid (499-06-9) + 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With sodium periodate In N,N-dimethyl-formamide at 150℃; for 1h; Reagent/catalyst; Inert atmosphere;	A 21% B 41%
Multi-step reaction with 3 steps 1: 3 h / 100 °C 2: pyridine; sodium amide / water / 20 °C / Reflux 3: water; hydrogenchloride / 0.25 h View Scheme

1-(azidomethyl)-3,5-dimethylbenzene (222716-36-1) → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With sodium dithionite; spermwhale myoglobin (H64V,V68A) In methanol; aq. phosphate buffer at 20℃; for 24h; pH=7; Catalytic behavior;	37%
With di[(2,4-bis-tert-butyl-1-methoxy-3-neopentylcyclopentadienyl)dichlororuthenium(III)]; water In acetonitrile at 75℃; for 5h; Inert atmosphere;	75 %Chromat.
With sodium dithionite In methanol; aq. phosphate buffer at 20℃; for 24h; pH=7; Catalytic behavior; Enzymatic reaction;

acetic acid (64-19-7) + trifluoroacetic acid (76-05-1) + 1,3,5-trimethyl-benzene (108-67-8) → 3,5-dimethylbenzaldehyde (5779-95-3) + mesityl acetate (19082-49-6) + 3,5-dimethylbenzyl trifluoroacetate (52040-88-7) + 3,5-dimethylbenzyl acetate (5159-42-2)

Conditions	Yield
With KCu(III)(biuret)2 for 2h; Product distribution; Heating;	A 0.7% B 0.2% C 2% D 28%

(+/-)-(E)-hept-4-en-3-ol (35077-65-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3,5-dimethylbenzaldehyde (5779-95-3)

Conditions	Yield
With trichlorophosphate for 6h; Heating;	18%

3,5-dimethylbenzaldehyde (5779-95-3) → 3,5-dimethyl-benzaldehyde oxime (75601-36-4)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In methanol at 20 - 27℃; for 2h;	100%
With hydroxylamine hydrochloride; sodium hydroxide In water; tert-butyl alcohol at 20℃; for 0.5h;
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 25℃; for 1h; Inert atmosphere; Cooling with ice;
With hydroxylamine hydrochloride; sodium hydroxide In water; tert-butyl alcohol at 20℃; for 1h;
With hydroxylamine hydrochloride; sodium hydroxide In water; tert-butyl alcohol at 20℃; for 1h;

3,5-dimethylbenzaldehyde (5779-95-3) + (2-aminoethyl)diphenylphosphane (4848-43-5) → (E)-N-[(3,5-dimethylphenyl)methylene]-N-[2-(diphenylphosphino)ethyl]amine

Conditions	Yield
In ethanol at 65℃; for 4h; Argon atmosphere;	100%
In ethanol at 65℃; for 4h;	100%

3,5-dimethylbenzaldehyde (5779-95-3) + cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) → C26H34N2 (1217526-72-1)

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

3,5-dimethylbenzaldehyde (5779-95-3) + 4-trimethylsilylethynyl aniline (75867-39-9) → C20H23NSi

Conditions	Yield
Molecular sieve;	100%

3,5-dimethylbenzaldehyde (5779-95-3) → 3,5-dimethylbenzyl alcohol (27129-87-9)

Conditions	Yield
With C30H37ClN4ORu; hydrogen; sodium t-butanolate In toluene at 105℃; under 4500.45 Torr; for 20h; Glovebox; Sealed tube;	99%
With methanol; C25H29ClNO2Rh; caesium carbonate at 90℃; for 1h;	66%
With acid bei der elektrolytischen Reduktion;
With methanol; sodium tetrahydroborate at 0℃; for 0.166667h;

3,5-dimethylbenzaldehyde (5779-95-3) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (2E)-3-(3,5-dimethyl-phenyl)-acrylic acid ethyl ester (865484-89-5)

Conditions	Yield
In dichloromethane for 24h; Heating;	99%

3,5-dimethylbenzaldehyde (5779-95-3) → 3,5-dimethylbenzyl 3,5-dimethylbenzoate (55000-47-0)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); 1,3-bis-(2,6-diisopropylphenyl)-4,5-dichloroimidazol-2-ylidene In toluene at 23 - 60℃; Tishchenko reaction; Inert atmosphere;	99%
With C18BF16(1-)*C34H53F2NiOP2(1+) In toluene at 20℃; for 1h; Glovebox; Inert atmosphere;	93%

3,5-dimethylbenzaldehyde (5779-95-3) + benzylamine (100-46-9) → N-benzyl-3,5-dimethylbenzaldimine (848132-07-0)

Conditions	Yield
With magnesium sulfate In tetrahydrofuran at 20℃; for 5h;	98%

3,5-dimethylbenzaldehyde (5779-95-3) + ethyl potassium malonate (6148-64-7) → (2E)-3-(3,5-dimethyl-phenyl)-acrylic acid ethyl ester (865484-89-5)

Conditions	Yield
With piperidine; dmap; acetic acid In N,N-dimethyl-formamide at 0 - 60℃; optical yield given as %de; diastereoselective reaction;	98%
Stage #1: 3,5-dimethylbenzaldehyde; ethyl potassium malonate With dmap In N,N-dimethyl-formamide Inert atmosphere; Stage #2: With piperidine; acetic acid at 60℃; Inert atmosphere;

3,5-dimethylbenzaldehyde (5779-95-3) + (1R,2R,3S,5R)-2,3-pinane diol (22422-34-0) → C19H26O2 (1338323-31-1)

Conditions	Yield
With pyridinium p-toluenesulfonate In toluene Reflux; Inert atmosphere;	98%

3,5-dimethylbenzaldehyde (5779-95-3) + 2-amino-benzenethiol (137-07-5) → 2-(3,5-dimethylphenyl)benzo[d]thiazole (152355-90-3)

Conditions	Yield
In water at 23℃; Irradiation;	98%
With silver(l) oxide In water for 0.133333h; Microwave irradiation;	92%
With β‐cyclodextrin In water at 60 - 65℃; Green chemistry;	79%

5-bromo-1,3-xylene (556-96-7) + 3,5-dimethylbenzaldehyde (5779-95-3) → bis(3,5-dimethylphenyl)methanol (21945-78-8)

Conditions	Yield
Stage #1: 5-bromo-1,3-xylene With iodine; magnesium In tetrahydrofuran for 4h; Reflux; Stage #2: 3,5-dimethylbenzaldehyde In tetrahydrofuran for 18h;	98%
Stage #1: 5-bromo-1,3-xylene With iodine; magnesium In tetrahydrofuran Inert atmosphere; Heating; Stage #2: 3,5-dimethylbenzaldehyde In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	78%

3-chloro-1,1-diethoxy-propane (35573-93-4) + 3,5-dimethylbenzaldehyde (5779-95-3) → 1-(3,5-dimethylphenyl)-4,4-diethoxybutan-1-ol (1258208-42-2)

Conditions	Yield
Stage #1: 3-chloro-1,1-diethoxy-propane With magnesium; ethylene dibromide In tetrahydrofuran at 15 - 25℃; Stage #2: 3,5-dimethylbenzaldehyde In tetrahydrofuran at -40 - 0℃; for 2.5h;	97%

3,5-dimethylbenzaldehyde (5779-95-3) + tert-butyldimethyl(3-phenyl-3-(trimethylsilyl)prop-1-yn-1-yl)silane → trans-tert-butyl(5-(3,5-dimethylphenyl)-4-phenyl-4,5-dihydrofuran-2-yl)dimethylsilane

Conditions	Yield
Stage #1: 3,5-dimethylbenzaldehyde; tert-butyldimethyl(3-phenyl-3-(trimethylsilyl)prop-1-yn-1-yl)silane In 1,2-dichloro-ethane at 25℃; for 0.416667h; Stage #2: With tert-butyl alcohol In 1,2-dichloro-ethane at 60℃; for 3h;	97%

2-methallyltrimethylsilane (18292-38-1) + 3,5-dimethylbenzaldehyde (5779-95-3) → (1R)-1-(3,5-dimethylphenyl)-3-methyl-3-buten-1-ol

Conditions	Yield
Stage #1: 2-methallyltrimethylsilane; 3,5-dimethylbenzaldehyde With 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene; (R)-3,3'-bis[4-methyl-3,5-dinitrophenyl]-1,1'-binaphthyl-2,2'-disulfonimide In toluene at -78℃; for 72h; Hosomi-Sakurai Reaction; Inert atmosphere; Stage #2: With hydrogenchloride In water; toluene at -78 - 20℃; enantioselective reaction;	96%

3,5-dimethylbenzaldehyde (5779-95-3) + 3-methyl-2-pyrazoline-5-one (108-26-9) + triethyl phosphite (122-52-1) → C17H25N2O4P

Conditions	Yield
With choline chloride; urea at 25 - 80℃; for 0.466667h; Green chemistry;	96%

3,5-dimethylbenzaldehyde (5779-95-3) + acetone (67-64-1) → C12H14O (1242166-10-4)

Conditions	Yield
With morpholin-4-ium 2,2,2-trifluoroacetate at 75℃; Aldol condensation; Sealed vial; optical yield given as %de; diastereoselective reaction;	95%

3,5-dimethylbenzaldehyde (5779-95-3) → 3,5-dimethylbenzamide (5692-35-3)

Conditions	Yield
With tert.-butylhydroperoxide; titanium superoxide; saccharin In 1,4-dioxane; hexane at 90℃; for 1h; Green chemistry;	95%
With hydroxylamine hydrochloride; caesium carbonate In water; dimethyl sulfoxide at 125℃; for 48h;	57%

2-acetylpyridine (1122-62-9) + 3,5-dimethylbenzaldehyde (5779-95-3) → 3-(3′,5′-dimethylphenyl)-1-(pyridin-2′-yl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In methanol; water at 5℃; for 8h;	95%
With sodium hydroxide In methanol; water at 20℃; for 6h; Aldol Condensation;	90%

3,5-dimethylbenzaldehyde (5779-95-3) + edaravone (89-25-8) + triethyl phosphite (122-52-1) → C23H29N2O4P

Conditions	Yield
With choline chloride; urea at 25 - 80℃; for 0.333333h; Green chemistry;	95%

3,5-dimethylbenzaldehyde (5779-95-3) + phenyl BODIPY → C37H35BF2N2

Conditions	Yield
With piperidine; acetic acid In N,N-dimethyl-formamide at 150℃; for 0.833333h; Inert atmosphere; Irradiation;	95%
With piperidine; acetic acid for 0.75h; Microwave irradiation;	93%

3,5-dimethylbenzaldehyde (5779-95-3) + (methoxymethyl)triphenylphosphonium chloride (4009-98-7) → 1-(2-methoxyvinyl)-3,5-dimethylbenzene

Conditions	Yield
Stage #1: (methoxymethyl)triphenylphosphonium chloride With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: 3,5-dimethylbenzaldehyde In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique;	95%

3,5-dimethylbenzaldehyde (5779-95-3) + C15H12FNO2 → C24H22FNO3

Conditions	Yield
With disodium hydrogenphosphate; 3-(2,6-diisopropylphenyl)-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate In dimethyl sulfoxide at 20℃; Irradiation;	95%

6-amino-1-hexanol (4048-33-3) + 3,5-dimethylbenzaldehyde (5779-95-3) → C20H33NO3

Conditions	Yield
Stage #1: 6-amino-1-hexanol; 3,5-dimethylbenzaldehyde In methanol at 20℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol for 2h; Inert atmosphere;	95%

3,5-dimethylbenzaldehyde (5779-95-3) + (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (144222-34-4) → C30H30N2O2S

Conditions	Yield
With sodium sulfate In methanol for 8h; Heating;	94%

3,5-dimethylbenzaldehyde (5779-95-3) + benzyl bromide (100-39-0) → (E)-1-(-3,5-dimethylphenyl)-2-phenylethene (40477-38-1)

Conditions	Yield
Stage #1: benzyl bromide With triethyl phosphite at 150℃; for 3h; Inert atmosphere; Stage #2: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #3: 3,5-dimethylbenzaldehyde In N,N-dimethyl-formamide; mineral oil at 20℃; for 18h; Inert atmosphere;	94%

Upstream product

• 50-00-0 formaldehyd 
• 27129-86-8 1-bromomethyl-3,5-dimethylbenzene 
• 34696-73-6 3,5-dimethyphenylmagnesium bromide 
• 109-94-4 formic acid ethyl ester 
• 108-67-8 1,3,5-trimethyl-benzene 
• 15285-43-5 3,5-dimethylbenzyl nitrate 
• 14250-96-5 2-methyl-2-pentenal 
• 107-02-8 acrolein 
• 123-73-9 crotonaldehyde 
• 2745-54-2 3,5-dimethylbenzyl chloride 
• 64-19-7 acetic acid 
• 76-05-1 trifluoroacetic acid 
• 35077-65-7 (+/-)-(E)-hept-4-en-3-ol 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 5379-18-0 rac-1-(3,5-dimethylphenyl)ethan-1-ol 
• 27129-87-9 3,5-dimethylbenzyl alcohol 
• 713147-74-1 3,5-dimethyl-2-nitrobenzaldehyde 
• 500540-48-7 1,2-bis-(3,5-dimethyl-phenyl)-2-hydroxy-ethanone 
• 36412-05-2 3,5-dimethyl-benzaldehyde-(2,4-dinitro-phenylhydrazone) 
• 16134-72-8 3,3',5-Trimethyl-diphenylcarbinol 
• 16134-70-6 3,4',5-Trimethyl-diphenylcarbinol 
• 13863-27-9 (E)-1,2-bis(3,5-dimethylphenyl)ethene 
• 36393-47-2 2-[(E)-2-(3,5-Dimethyl-phenyl)-vinyl]-benzo[c]phenanthrene 
• 78710-55-1 3,5-dimethylbenzyl amine 
• 108546-02-7 5,10,15,20-tetrakis(3,5-dimethylphenyl)porphyrin 
• 106116-41-0 2-(3,5-Dimethylbenzyliden)-2,3-dihydro-5,7-dimethyl-1H-inden-1-on 
• 106116-40-9 2-(3,5-Dimethylbenzyliden)-2,3-dihydro-5,7-dimethoxy-1H-inden-1-on 
• 154808-87-4 2,3-bis(3,5-dimethylphenyl)succinonitrile 

Relevant articles and documents

Ferric ion concentration-controlled aerobic photo-oxidation of benzylic C–H bond with high selectivity and conversion

A Fe(III)-promoted highly selective photo-oxidation of benzylic C–H bond delivering relative carbonyl products is reported. By altering the concentration of ferric salt, methylarenes can be selectively oxidized under UV irradiation to furnish aromatic aldehydes or acids, respectively. By this protocol, the oxidation of ethylarenes provides the corresponding acetophenones. The reaction is inferred to involve divergent pathways in different concentrations of catalyst for the alternative selectivity between aldehydes and aicds. The reusable catalyst, high conversion and selectivity make this oxidation a green and economic protocol for the synthesis of aromatic carbonyl compounds.

Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis

A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.

LIGHT INDUCED CATALYTIC C-H OXYGENATION OF ALKANES

A method of oxygenating a benzylic C-H bond is provided. The method comprises light induced activation of an initiator and subsequent reaction with oxygen, resulting in the formation of free radicals. Subsequently, free radicals catalyze the reaction of the benzylic C-H bond with oxygen, thereby forming an oxygenated compound.