3-Formyl-4-hydroxybenzonitrile supplier

Name
3-Formyl-4-hydroxybenzonitrile
EINECS
CAS No. 74901-29-4
Article Data17
CAS DataBase
Density 1.329 g/cm³
Solubility
Melting Point 147 °C(Solv: methanol (67-56-1); water (7732-18-5))
Formula C₈H₅NO₂
Boiling Point 241.351 °C at 760 mmHg
Molecular Weight 147.133
Flash Point 99.766 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Hydroxy-5-cyanobenzaldehyde;Benzonitrile, 3-formyl-4-hydroxy;5-Cyanosalicylaldehyde;Benzonitrile, 3-formyl-4-hydroxy- (9CI);3-Formyl-4-hydroxybenzonitril;
PSA 61.09000
LogP 1.07638

Synthetic route

: 21962-53-8
5-cyano-2-methoxybenzaldehyde

: 74901-29-4
5-cyanosalicylaldehyde

Conditions

Conditions	Yield
With lithium chloride In DMF (N,N-dimethyl-formamide)	86%
With boron tribromide In dichloromethane at 20℃; for 10h; Inert atmosphere;	71%

: 100-97-0
hexamethylenetetramine

: 767-00-0
4-cyanophenol

: 74901-29-4
5-cyanosalicylaldehyde

Conditions

Conditions	Yield
With methanesulfonic acid; water; trifluoroacetic acid at 70 - 80℃; for 10h; Duff Aldehyde Synthesis;	64%
With trifluoroacetic acid at 100℃; for 7h;	41%
In trifluoroacetic acid at 100℃; for 7h;	31%
With trifluoroacetic acid at 0 - 100℃; for 16h;	19%
With trifluoroacetic acid for 5h; Inert atmosphere; Reflux;	17%

: 50-00-0
formaldehyd

: 767-00-0
4-cyanophenol

A: 74901-29-4
5-cyanosalicylaldehyde

B: 161196-99-2
4-(Methoxymethoxy)-1-benzonitrile

Conditions

Conditions	Yield
With triethylamine; magnesium chloride In acetonitrile for 44h; Heating; Yields of byproduct given;	A 24% B n/a
With triethylamine; magnesium chloride In acetonitrile for 44h; Heating; Yield given;	A 24% B n/a

...Expand

: copper(l) cyanide

: 1761-61-1
5-bromosalicyclaldehyde

: 74901-29-4
5-cyanosalicylaldehyde

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 150℃; for 5h; Inert atmosphere;	21%

: 544-92-3
copper(I) cyanide

: 1761-61-1
5-bromosalicyclaldehyde

: 74901-29-4
5-cyanosalicylaldehyde

Conditions

Conditions	Yield
With 1-Methylpyrrolidine for 0.5h; Heating;	17%
With CuCN In N,N-dimethyl-formamide for 3h; Heating;

: 767-00-0
4-cyanophenol

: 141-78-6
ethyl acetate

: 74901-29-4
5-cyanosalicylaldehyde

Conditions

Conditions	Yield
With hexamethylenetetramine; sulfuric acid In dichloromethane; water; trifluoroacetic acid	13%

: 67-66-3
chloroform

: 767-00-0
4-cyanophenol

A: 74901-29-4
5-cyanosalicylaldehyde

B: 4-Cyanophenyl formate

C: 4-cyanophenyl dichloromethyl ether

Conditions

Conditions	Yield
for 5h; Irradiation; Yield given. Yields of byproduct given;

...Expand

: 2973-78-6
3-bromo-4-hydroxybenzylaldehyde

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 74901-29-4
5-cyanosalicylaldehyde

Conditions

Conditions	Yield
Stage #1: 3-bromo-4-hydroxybenzylaldehyde With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 20℃; Stage #3: With water In tetrahydrofuran

: 146137-79-3
4-fluoro-3-formylbenzonitrile

: 74901-29-4
5-cyanosalicylaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium methylate / 20 °C 2: boron tribromide / dichloromethane / 10 h / 20 °C / Inert atmosphere View Scheme

: 767-00-0
4-cyanophenol

: 76-05-1
trifluoroacetic acid

: 74901-29-4
5-cyanosalicylaldehyde

Conditions

Conditions	Yield
With hexamethylenetetramine

: 7658-80-2
2-methylbenzohydrazide

: 74901-29-4
5-cyanosalicylaldehyde

: 2-methyl-N'-(5-cyano-2-hydroxybenzylidene)benzohydrazide

Conditions

Conditions	Yield
With acetic acid In methanol at 20℃;	99%

: 74901-29-4
5-cyanosalicylaldehyde

: 2,4-dibromobenzohydrazide

: 2,4-dibromo-N'-(5-cyano-2-hydroxybenzylidene)benzohydrazide

Conditions

Conditions	Yield
With acetic acid In methanol at 20℃;	99%

: 74901-29-4
5-cyanosalicylaldehyde

: 68471-55-6
(2,3-dihydro-1H-pyrrol-1-yl)(phenyl)methanone

: (3aR,4R,9aS)-1-benzoyl-6-cyano-4-hydroxy-1,2,3,3a,4,9a-hexahydrochromeno[2,3-b]pyrrole

Conditions

Conditions	Yield
Stage #1: N-benzoyl-2-pyrroline With Ti(4+)4C3H7O(1-)2H2O*2C20H14O2 at 40℃; for 0.5h; Inert atmosphere; Stage #2: 5-cyanosalicylaldehyde In o-xylene at 40℃; for 3h; Inert atmosphere; stereoselective reaction;	91%
With titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol In o-xylene; water at 40℃; for 3h; Inert atmosphere;	91%
Stage #1: 5-cyanosalicylaldehyde With [(R)-(+)-1,1'-bi(2-naphthol)]Ti(Oi-Pr)2 In water at 40℃; for 0.5h; Inert atmosphere; Stage #2: N-benzoyl-2-pyrroline With sodium In o-xylene; water at 40℃; for 3h; Inert atmosphere;	91%

: 54060-30-9
3-acetylenephenylamine

: 74901-29-4
5-cyanosalicylaldehyde

: (E)-3-(((3-ethynylphenyl)imino)methyl)-4-hydroxybenzonitrile

Conditions

Conditions	Yield
In ethanol at 20℃;	86%

: 655-86-7
2,3-diaminephenazine

: 74901-29-4
5-cyanosalicylaldehyde

: 4-hydroxy-3-(1H-imidazo[4,5-b]phenazin-2-yl)benzonitrile

Conditions

Conditions	Yield
In dimethyl sulfoxide at 120℃; for 6h;	86%

: 74901-29-4
5-cyanosalicylaldehyde

: N-(3-sulfonatopropyl)-2,3,3-trimethyl-3H-indolium

: C22H22N2O4S

Conditions

Conditions	Yield
In ethanol for 12h; Knoevenagel Condensation; Reflux; Inert atmosphere;	82%

: 74901-29-4
5-cyanosalicylaldehyde

: 5970-45-6
zinc(II) acetate dihydrate

: 95-54-5
1,2-diamino-benzene

: N,N'-(o-phenylene)bis(5-cyanosalicylideneiminato)zinc

Conditions

Conditions	Yield
In methanol for 24h;	80%

...Expand

: 74901-29-4
5-cyanosalicylaldehyde

: 106-93-4
ethylene dibromide

: 1448673-59-3
4-(2-bromoethoxy)-3-formylbenzonitrile

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 2h; Reflux;	76%

: 74901-29-4
5-cyanosalicylaldehyde

: 101-48-4
phenylacetaldehyde dimethyl acetal

: 149-73-5
trimethyl orthoformate

: 6-cyano-2,4-dimethoxy-3-phenylchromane

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In toluene at 40℃; for 1h; Inert atmosphere;	76%

...Expand

: 74901-29-4
5-cyanosalicylaldehyde

: 95-54-5
1,2-diamino-benzene

: N,N'-(o-phenylene)bis(5-cyanosalicylideneimine)

Conditions

Conditions	Yield
In methanol for 24h;	75%

: 118-12-7
1,3,3-Trimethyl-2-methyleneindoline

: 74901-29-4
5-cyanosalicylaldehyde

: 19253-37-3
6-cyano-1',3',3'-trimethylspiro[2H-1-benzopyran-2,2-indoline]

Conditions

Conditions	Yield
In ethanol for 3h; cyclocondensation; Heating;	74%

: 74901-29-4
5-cyanosalicylaldehyde

: N1-(1H-benzo[d]imidazol-2-yl)-N2-ethylethane-1,2-diamine

: 3-(((2-((1H-benzo[d]imidazol-2-yl)amino)ethyl)(ethyl)amino)methyl)-4 hydroxybenzonitrile

Conditions

Conditions	Yield
Stage #1: 5-cyanosalicylaldehyde; N1-(1H-benzo[d]imidazol-2-yl)-N2-ethylethane-1,2-diamine In methanol at 25℃; for 6h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 25℃; for 16h;	74%

: 31101-37-8
2-(piperidin-1-yl)thiazole-4(5H)-one

: 74901-29-4
5-cyanosalicylaldehyde

: 1181081-60-6
4-hydroxy-3-{[(5Z)-4-oxo-2-(piperidin-1-yl)-4,5-dihydro-1,3-thiazol-5-ylidene]methyl}benzonitrile

Conditions

Conditions	Yield
With ammonium acetate; acetic acid at 100℃;	72%

: 3393-45-1
5,6-dihydro-pyran-2-one

: 74901-29-4
5-cyanosalicylaldehyde

: 1006900-86-2
1,3,4,4a-tetrahydro-1-oxopyrano[4,3-b]chromene-8-carbonitrile

Conditions

Conditions	Yield
With dmap In dimethyl sulfoxide at 60℃; for 72h;	71%

: 60512-56-3
1-(2,2-dibromovinyl)-4-methylbenzene

: 74901-29-4
5-cyanosalicylaldehyde

: 4-oxo-2-p-tolyl-4H-chromene-6-carbonitrile

Conditions

Conditions	Yield
With chlorocarbonylbis(triphenylphosphine)rhodium(I); potassium carbonate In N,N-dimethyl acetamide at 90℃; for 5h; Schlenk technique; Inert atmosphere;	67%

: 2680-03-7
N,N-Dimethylacrylamide

: 74901-29-4
5-cyanosalicylaldehyde

: 4-hydroxy-3-methyl-2-oxo-2H-chromene-6-carbonitrile

Conditions

Conditions	Yield
With dicarbonyl(acetylacotonato)rhodium(I); caesium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere; Schlenk technique;	65%

: 371-96-0, 37468-00-1
(E)-3,3,3-trifluoro-1-nitroprop-1-ene

: 74901-29-4
5-cyanosalicylaldehyde

: 3-nitro-2-(trifluoromethyl)-2H-chromene-6-carbonitrile

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 12h;	65%

: 74901-29-4
5-cyanosalicylaldehyde

: 140-88-5
ethyl acrylate

: 4-hydroxy-3-methyl-2-oxo-2H-chromene-6-carbonitrile

Conditions

Conditions	Yield
With dicarbonyl(acetylacotonato)rhodium(I); sodium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique;	64%

: 352015-03-3
(R)-2-amino-1,1-di(2-methoxyphenyl)-1-propanol

: 74901-29-4
5-cyanosalicylaldehyde

: 4-Hydroxy-3-{[(E)-(R)-2-hydroxy-2,2-bis-(2-methoxy-phenyl)-1-methyl-ethylimino]-methyl}-benzonitrile

Conditions

Conditions	Yield
In toluene for 1h; Heating;	62%

: 74901-29-4
5-cyanosalicylaldehyde

: 57019-81-5
5-methoxy-1,2,3,3-tetramethyl-3H-indolium iodide

: 5'-methoxy-1',3',3'-trimethylspiro[chromene-2,2'-indoline]-6-carbonitrile

Conditions

Conditions	Yield
With piperidine In ethanol for 19h; Reflux;	60%

: 74901-29-4
5-cyanosalicylaldehyde

: 248936-99-4
1-(3-bromopropyl)-3,3-dimethyl-2-methyleneindoline

: 1255640-66-4
1'-(3-bromopropyl)-3',3'-dimethyl-6-cyanospiro[(2H)-1-benzopyran-2,2'-indoline]

Conditions

Conditions	Yield
In tetrahydrofuran for 16h; Inert atmosphere; Heating;	58%

: 74901-29-4
5-cyanosalicylaldehyde

: 1401912-27-3
6-cyano-[1,2,3]benzoxathiazine-2,2-dioxide

Conditions

Conditions	Yield
With formic acid; isocyanate de chlorosulfonyle In N,N-dimethyl acetamide; acetonitrile at 0 - 20℃; for 12h;	50%

: 74901-29-4
5-cyanosalicylaldehyde

: 141-78-6
ethyl acetate

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 337520-37-3
5-cyano-2-hydroxycinnamaldehyde

Conditions

Conditions	Yield
In dichloromethane; toluene	44%

...Expand

: 74901-29-4
5-cyanosalicylaldehyde

: 1895-39-2
sodium chlorodifluoroacetate

: 2,2-difluoro-3-hydroxy-2,3-dihydro-1-benzofuran-5-carbonitrile

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 95℃; for 0.583333h; Inert atmosphere;	41%
With sodium carbonate In N,N-dimethyl-formamide at 95℃; for 0.5h; Inert atmosphere;	41%

: 74901-29-4
5-cyanosalicylaldehyde

: 2170-06-1
1-Phenyl-2-(trimethylsilyl)acetylene

: 149-73-5
trimethyl orthoformate

: 2-methoxy-2-phenyl-3-trimethylsilyl-2H-1-benzopyran-6-carbonitrile

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane for 16h; Inert atmosphere; Reflux;	35%

...Expand

: 2049-67-4
diethyl glutaconate

: 74901-29-4
5-cyanosalicylaldehyde

: ethyl 6-cyano-2-carboethoxymethylchromene-3-carboxylate

Conditions

Conditions	Yield
With piperidine In ethanol for 6h; Heating;	27%

: 74901-29-4
5-cyanosalicylaldehyde

: 501-65-5
diphenyl acetylene

: 149-73-5
trimethyl orthoformate

: 6-carbonitrile-2-methoxy-2,3-diphenyl-2H-1-benzopyran

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In toluene at 60℃; for 15h; Inert atmosphere; regioselective reaction;	23%

...Expand

3-Formyl-4-hydroxybenzonitrile Chemical Properties

Product Name: 3-Formyl-4-hydroxybenzonitrile
Synonyms of 3-Formyl-4-hydroxybenzonitrile (CAS NO.74901-29-4): Benzonitrile, 3-formyl-4-hydroxy ; Benzonitrile, 3-formyl-4-hydroxy- (9CI) ; 3-Formyl-4-hydroxybenzonitril ; 2-Hydroxy-5-cyanobenzaldehyde ; 5-Cyanosalicylaldehyde
CAS NO: 74901-29-4
Molecular Formula of 3-Formyl-4-hydroxybenzonitrile (CAS NO.74901-29-4): C₈H₅NO₂
Molecular Weight: 147.1308
Molecular Structure:

ProductCategories: ALDEHYDE
Polar Surface Area: 61.09 Å²
Index of Refraction: 1.599
Molar Refractivity: 37.818 cm³
Molar Volume: 110.727 cm³
Surface Tension: 65.851 dyne/cm
Density of 3-Formyl-4-hydroxybenzonitrile (CAS NO.74901-29-4): 1.329 g/cm³
Flash Point: 99.766 °C
Enthalpy of Vaporization: 49.769 kJ/mol
Boiling Point: 241.351 °C at 760 mmHg
Vapour Pressure: 0.023 mmHg at 25°C

Product Name

3-Formyl-4-hydroxybenzonitrile

Synthetic route

3-Formyl-4-hydroxybenzonitrile Chemical Properties

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