4-Difluoromethoxy-3-hydroxybenzaldehyde supplier

Name
4-Difluoromethoxy-3-hydroxybenzaldehyde
EINECS 216-149-1
CAS No. 151103-08-1
Article Data40
CAS DataBase
Density 1.883g/cm³
Solubility
Melting Point 85-90°C
Formula C8H6 F2 O3
Boiling Point °Cat760mmHg
Molecular Weight 188.131
Flash Point °C
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes R36/37/38;
Molecular Structure
Hazard Symbols Xi
Synonyms 3-Hydroxy-4-difluoromethoxybenzaldehyde;4-(Difluoromethoxy)-3-hydroxybenzaldehyde
PSA 46.53000
LogP 1.80610

Synthetic route

: 683-98-7
methyl bromodifluoroacetate

: 139-85-5
3,4-dihydroxybenzaldehyde

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
With hydroxylamine In water; acetonitrile at 45℃; Concentration; Reagent/catalyst;	90.3%

: 162401-70-9
4-(difluoromethoxy)-3-methoxybenzaldehyde

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one	88.3%
With lithium chloride In N,N-dimethyl-formamide Reagent/catalyst; Reflux;	28%
Multi-step reaction with 2 steps 1.1: orthoformic acid triethyl ester / boron trifluoride diethyl etherate / diethyl ether / 24 h / Heating / reflux 2.1: lithium diphenylphosphide / tetrahydrofuran / 3 - 4 h 2.2: pH 3 - 4 View Scheme

: 773093-32-6
C11H12F2O4

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
Stage #1: C11H12F2O4 With lithium diphenylphosphide In tetrahydrofuran for 3 - 4h; Stage #2: With hydrogenchloride; water pH=3 - 4;	83%

: 1514-87-0
metyhyl chlorodifluoroacetate

: 139-85-5
3,4-dihydroxybenzaldehyde

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
With tetrabutylammonium hydrogen sulfide; sodium hydroxide at 60 - 65℃; for 3h; Concentration;	79.4%
With caesium carbonate In N,N-dimethyl-formamide at 20 - 90℃; for 0.5h; Reagent/catalyst; Time; Microwave irradiation; Green chemistry;	57%
With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 0.5h; Microwave irradiation;	57%

: 1895-39-2
sodium chlorodifluoroacetate

: 139-85-5
3,4-dihydroxybenzaldehyde

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
With sodium carbonate In water; N,N-dimethyl-formamide at 80℃; for 6h;	57.5%
With sodium hydroxide In water; N,N-dimethyl-formamide at 120℃; for 2h;	46%
Stage #1: sodium chlorodifluoroacetate; 3,4-dihydroxybenzaldehyde With sodium hydroxide In water; N,N-dimethyl-formamide at 120℃; for 2h; Stage #2: With hydrogenchloride In water	44%

: 87189-16-0
potassium 2-bromo-2,2-difluoroacetate

: 139-85-5
3,4-dihydroxybenzaldehyde

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
With sodium hydroxide In water; N,N-dimethyl-formamide at 70℃; for 2h;	53%

: 1514-87-0
metyhyl chlorodifluoroacetate

: 139-85-5
3,4-dihydroxybenzaldehyde

A: 127842-54-0
3,4-bis-(difluoromethoxy)-benzaldehyde

B: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 65℃; for 3h; Inert atmosphere;	A 20% B 45%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 16h;	A 13% B 21%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 16h;	A 13% B 21%

...Expand

: 577968-58-2
3-(benzyloxy)-4-(difluoromethoxy)benzaldehyde

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethyl acetate under 760.051 Torr; for 1h;	43.7%

: 75-45-6
Chlorodifluoromethane

: 139-85-5
3,4-dihydroxybenzaldehyde

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In N,N-dimethyl-formamide for 0.166667h;	37%
With potassium carbonate In N,N-dimethyl-formamide at 80 - 85℃; for 4.5h;	25%
With potassium carbonate In N,N-dimethyl-formamide at 75 - 80℃;	25.3%
Stage #1: 3,4-dihydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20 - 85℃; Stage #2: Chlorodifluoromethane In N,N-dimethyl-formamide for 8 - 10h; Inert atmosphere;

: 139-85-5
3,4-dihydroxybenzaldehyde

: 76-04-0
2-chloro-2,2-difluoroacetic acid

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
Stage #1: 3,4-dihydroxybenzaldehyde; 2-chloro-2,2-difluoroacetic acid With sodium hydroxide In N,N-dimethyl-formamide at 55℃; for 16h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide pH=1.0;	24%

: 7732-18-5
water

: 139-85-5
3,4-dihydroxybenzaldehyde

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide In 1,4-dioxane	19%

: 139-85-5
3,4-dihydroxybenzaldehyde

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
With potassium carbonate	18%

: 75-45-6
Chlorodifluoromethane

: 139-85-5
3,4-dihydroxybenzaldehyde

A: 127842-54-0
3,4-bis-(difluoromethoxy)-benzaldehyde

B: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
Stage #1: Chlorodifluoromethane; 3,4-dihydroxybenzaldehyde With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In DMF (N,N-dimethyl-formamide); water for 0.05h; Stage #2: With hydrogenchloride In DMF (N,N-dimethyl-formamide); water

...Expand

: 121-33-5
vanillin

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: potassium carbonate / 1-methyl-pyrrolidin-2-one View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 90 °C 2: lithium chloride / N,N-dimethyl-formamide / Reflux View Scheme

: 667-27-6
Ethyl bromodifluoroacetate

: 139-85-5
3,4-dihydroxybenzaldehyde

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
With sodium hydroxide In water; N,N-dimethyl-formamide at 70℃; for 2h;	3.43 g

: 1-(difluoromethoxy)-3-methyl-6-nitro-4-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-3-ium trifluoromethanesulfonate

: 100-83-4
meta-hydroxybenzaldehyde

A: 2-(difluoromethoxy)-3-hydroxybenzaldehyde

B: 2-(difluoromethoxy)-5-hydroxybenzaldehyde

C: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate In acetonitrile at 23℃; for 12h; Irradiation; Overall yield = 60 %Spectr.;
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate In acetonitrile at 23℃; for 12h; Irradiation; Glovebox; Sealed tube; Inert atmosphere; Overall yield = 60 percentSpectr.;
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; lithium carbonate In 1,2-dichloro-ethane; acetonitrile at 60℃; for 20h; Sealed tube; Overall yield = 68 percentSpectr.;

...Expand

: 621-59-0
isovanillin

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 25 °C 2: ethanethiol; sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / 70 °C / Cooling with ice 3: potassium carbonate / N,N-dimethyl-formamide; water / 120 °C 4: hydrogen; 5%-palladium/activated carbon / ethyl acetate / 1 h / 760.05 Torr View Scheme

: 6346-05-0
3-benzyloxy-4-methoxybenzaldehyde

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanethiol; sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / 70 °C / Cooling with ice 2: potassium carbonate / N,N-dimethyl-formamide; water / 120 °C 3: hydrogen; 5%-palladium/activated carbon / ethyl acetate / 1 h / 760.05 Torr View Scheme

: 50773-56-3
3-benzyloxy-4-hydroxybenzaldehyde

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide; water / 120 °C 2: hydrogen; 5%-palladium/activated carbon / ethyl acetate / 1 h / 760.05 Torr View Scheme

: 100-39-0
benzyl bromide

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 577968-58-2
3-(benzyloxy)-4-(difluoromethoxy)benzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 3h;	100%
With potassium carbonate In acetonitrile at 20 - 30℃; for 4h;	99.4%
With potassium carbonate In acetonitrile at 80℃; for 3h; Inert atmosphere;	95%
With potassium carbonate In acetonitrile at 20℃; for 4h;

: 137-43-9
Cyclopentyl bromide

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 153587-14-5
3-Cyclopentyloxy-4-difluoromethoxybenzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide)	100%
With potassium carbonate In N-methyl-acetamide	89%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 65℃; for 22h;	87%

: 106-96-7
propargyl bromide

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 4-difluoromethoxy-3-propargyloxybenzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 16h; Reflux;	100%

: 7051-34-5
cyclopropylcarbinyl bromide

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 151103-09-2
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde

Conditions

Conditions	Yield
Stage #1: 4-difluoromethoxy-3-hydroxybenzaldehyde With potassium carbonate; potassium iodide In dimethyl sulfoxide at 70℃; for 1h; Stage #2: cyclopropylcarbinyl bromide In dimethyl sulfoxide at 70℃; for 4h;	99%
With trimethylbenzylammonium bromide; potassium carbonate; potassium iodide In tetrahydrofuran at 0℃; Concentration; Reflux;	98.5%
With potassium carbonate In tetrahydrofuran at 0℃; for 14h; Heating / reflux;	97%

: 701-45-1
2-bromo-1-fluoro-4-nitrobenzene

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 3-(2-bromo-4-nitrophenoxy)-4-(difluoromethoxy)benzaldehyde

Conditions

Conditions	Yield
With potassium fluoride In dimethyl sulfoxide at 90℃; for 2h;	97.9%
With potassium fluoride In dimethyl sulfoxide at 100 - 120℃;	66%

: 3355-28-0
1-Bromo-2-butyne

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 1164145-11-2
3-(but-2-ynyloxy)-4-difluoromethoxybenzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 16h; Heating / reflux;	97%

: 76-83-5
trityl chloride

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 959860-02-7
3-trityloxy-4-difluoromethoxybenzaldehyde

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 1h;	91%

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 913985-07-6
4-difluoromethoxy-3-hydroxybenzoic acid

Conditions

Conditions	Yield
With sodium chlorite; aminosulfonic acid In water; acetonitrile at 0 - 30℃;	90.4%
With sodium chlorite; aminosulfonic acid In water; acetic acid at 10 - 20℃;	77%

: 584-26-9
1-acetyl-2-thiohydantoin

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 1447755-95-4
5-(4-(difluoromethoxy)-3-hydroxybenzylidene)-2-thioxoimidazolidin-4-one

Conditions

Conditions	Yield
With sodium acetate; acetic acid for 5h; Reflux;	84.8%

: 453-20-3
3-Hydroxytetrahydrofuran

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 4-(difluoromethoxy)-3-[(tetrahydro-3-furanyl)oxy]benzaldehyde

Conditions

Conditions	Yield
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; Mitsunobu reaction;	84%

: [2H2]bromomethyl-[1-2H]cyclopropane

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 3-([1-2H]cyclopropyl[2H2]methoxy)-4-difluoromethoxybenzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 75℃; for 3h;	83%

: 109-64-8
1,3-dibromo-propane

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 1422361-81-6
3-(3-bromopropoxy)-4-(difluoromethoxy)benzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 1.5h; Reflux; Inert atmosphere;	81%

: 110-52-1
1,4-dibromo-butane

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 1422361-77-0
3-(4-bromobutoxy)-4-(difluoromethoxy)benzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 1.5h; Reflux; Inert atmosphere;	75.8%
With potassium carbonate In acetonitrile for 4h; Reflux;

: 67-56-1
methanol

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 1159429-52-3
3-hydroxy-4-(difluoromethoxy)-benzoic acid methyl ester

Conditions

Conditions	Yield
With Oxone at 50 - 55℃; for 3h;	70%
With Oxone at 50 - 55℃; for 3h;	70%

: 701-45-1
2-bromo-1-fluoro-4-nitrobenzene

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 685873-93-2
4-(difluoromethoxy)-8-nitrodibenzo[b,d]furan-1-carbaldehyde

Conditions

Conditions	Yield
Stage #1: 2-bromo-1-fluoro-4-nitrobenzene; 4-difluoromethoxy-3-hydroxybenzaldehyde With sodium carbonate In N,N-dimethyl-formamide at 90℃; for 2h; Stage #2: With sodium acetate; palladium diacetate In N,N-dimethyl-formamide at 90 - 130℃; for 2h; Product distribution / selectivity;	67%

: 99768-12-4
4-methoxycarbonylphenylboronic acid

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 1422361-86-1
methyl 4-(2-(difluoromethoxy)-5-formylphenoxy)benzoate

Conditions

Conditions	Yield
With pyridine; copper diacetate In dichloromethane at 20℃; for 15h;	67%

: 99839-30-2
3-bromo-4-chloropyridine-1-oxide

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 1086277-95-3
3-[(3-bromo-pyridin-N-oxide-4-yl)oxyl]-4-(difluoromethoxy)benzaldehyde

Conditions

Conditions	Yield
Stage #1: 4-difluoromethoxy-3-hydroxybenzaldehyde With potassium fluoride In dimethyl sulfoxide at 100 - 110℃; for 0.5 - 1h; Stage #2: 3-bromo-4-chloropyridine-1-oxide In dimethyl sulfoxide at 20 - 110℃; for 16 - 18h;	65%

: 13931-37-8
propyl 5-bromopentanoate

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 1422361-74-7
propyl 5-[2-(difluoromethoxy)-5-formylphenoxy]pentanoate

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 4h; Inert atmosphere; Reflux;	60.8%

: C30H21N15O3

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: C54H33F6N15O9

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; Claisen-Schmidt Condensation;	60%

: 109384-19-2
t-butyl 4-hydroxy piperidine-1-carboxylate

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 1093411-52-9
4-(2-difluoromethoxy-5-formylphenoxy)piperidine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; Mitsunobu reaction;	54%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 151103-08-1
4-difluoromethoxy-3-hydroxybenzaldehyde

: 1093411-51-8
4-difluoromethoxy-3-(tetrahydropyran-4-yloxy)benzaldehydehyde

Conditions

Conditions	Yield
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; Mitsunobu reaction;	28%

4-Difluoromethoxy-3-hydroxybenzaldehyde Chemical Properties

Systematic Name: 4-(Difluoromethoxy)-3-hydroxybenzaldehyde
SMILES: FC(F)Oc1ccc(cc1O)C=O
InChI: InChI=1/C8H6F2O3/c9-8(10)13-7-2-1-5(4-11)3-6(7)12/h1-4,8,12H
InChIKey: ZLIKNROJGXXNJG-UHFFFAOYAO
Empirical Formula: C₈H₆F₂O₃
Molecular Weight: 188.1282
Nominal Mass: 188
Average Mass: 188.1282
Monoisotopic Mass: 188.0285
Index of Refraction: 1.533
Molar Refractivity: 41.85 cm³
Molar Volume: 134.8 cm³
Surface Tension: 40.6 dyne/cm
Density: 1.395 g/cm³
Flash Point: 123.5 °C
Enthalpy of Vaporization: 54.02 kJ/mol
Boiling Point: 280.6 °C at 760 mmHg
Vapour Pressure: 0.0022 mmHg at 25 °C
Product Categories of 4-Difluoromethoxy-3-hydroxybenzaldehyde (CAS NO.151103-08-1): Aldehydes; Phenyls & Phenyl-Het; Phenyls & Phenyl-Het

4-Difluoromethoxy-3-hydroxybenzaldehyde Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
Hazard Note of 4-Difluoromethoxy-3-hydroxybenzaldehyde (CAS NO.151103-08-1): Irritant

4-Difluoromethoxy-3-hydroxybenzaldehyde Specification

4-Difluoromethoxy-3-hydroxybenzaldehyde (CAS NO.151103-08-1), its Synonyms are Benzaldehyde, 4-(difluoromethoxy)-3-hydroxy- ; 4-(Difluoromethoxy)-3-hydroxybenzaldehyde 97% ; 4-Difluoromethoxy-3-hydroxy-benzald; ehyde ; 4-(Difluoromethoxy)-3-hydroxybenzaldehyde .

Product Name

4-Difluoromethoxy-3-hydroxybenzaldehyde

Synthetic route

4-Difluoromethoxy-3-hydroxybenzaldehyde Chemical Properties

4-Difluoromethoxy-3-hydroxybenzaldehyde Safety Profile

4-Difluoromethoxy-3-hydroxybenzaldehyde Specification

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