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10035-16-2

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10035-16-2 Usage

Chemical Properties

Colorless to light yellow liqui

Uses

1-Benzofuran-5-carbaldehyde is a building block used as a reactant in the synthetic preparation of benzofuranyl oxadiazoles as inhibitors of glycogen synthase kinase-3β with good brain permeability. It is also used in the synthesis of pyrroloquinolone PDE5 inhibitors used for clinical studies on erectile dysfunction.

Check Digit Verification of cas no

The CAS Registry Mumber 10035-16-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,0,3 and 5 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 10035-16:
(7*1)+(6*0)+(5*0)+(4*3)+(3*5)+(2*1)+(1*6)=42
42 % 10 = 2
So 10035-16-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H6O2/c10-6-7-1-2-9-8(5-7)3-4-11-9/h1-6H

10035-16-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Benzofuran-5-carbaldehyde

1.2 Other means of identification

Product number -
Other names 5-benzofurancarboxaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:10035-16-2 SDS

10035-16-2Synthetic route

2,3-dihydro-benzofuran-5-carbaldehyde
55745-70-5

2,3-dihydro-benzofuran-5-carbaldehyde

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chlorobenzene at 80℃; for 1h;83%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chlorobenzene at 20 - 80℃; for 1h; Inert atmosphere;75%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chlorobenzene at 80℃; for 1h;60%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chlorobenzene at 80℃; for 4h; Cooling with ice;55%
benzo[b]furan-5-carbonitrile
79002-39-4

benzo[b]furan-5-carbonitrile

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
Stage #1: benzo[b]furan-5-carbonitrile With diisobutylaluminium hydride In n-heptane; dichloromethane at -20 - -15℃; for 0.166667h;
Stage #2: With hydrogenchloride; water In n-heptane; dichloromethane
78%
Stage #1: benzo[b]furan-5-carbonitrile With diisobutylaluminium hydride In n-heptane; dichloromethane at -20 - -15℃; for 0.166667h;
Stage #2: With hydrogenchloride; water In n-heptane; dichloromethane at 20℃;
78%
With diisobutylaluminium hydride In dichloromethane at -15℃; for 0.166667h;
5-bromobenzofuran
23145-07-5

5-bromobenzofuran

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

N,N-dimethyl-formamide

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
Stage #1: 5-bromobenzofuran With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 2h;
Stage #2: N,N-dimethyl-formamide In diethyl ether; pentane for 1h;
75%
With tert.-butyl lithium In diethyl ether; pentane at -78 - 8℃; for 0.833333h;70%
Stage #1: 5-bromobenzofuran With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 0.333333h;
Stage #2: N,N-dimethyl-formamide In diethyl ether; pentane at -78 - 20℃; for 0.5h; Product distribution / selectivity;
70%
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
Stage #1: 5-bromobenzofuran With tert.-butyl lithium In diethyl ether at -78℃; for 0.333333h;
Stage #2: N,N-dimethyl-formamide In diethyl ether at -25 - 20℃; for 3h;
67%
Stage #1: 5-bromobenzofuran With tert.-butyl lithium In diethyl ether at -78℃; for 0.333333h;
Stage #2: N,N-dimethyl-formamide In diethyl ether at -25 - 20℃;
67%
3-ethynyl-4-methoxybenzaldehyde
160625-49-0

3-ethynyl-4-methoxybenzaldehyde

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium chloride at 130℃; for 1.5h;58%
3-(prop-1-enyl)-4-(prop-1-enyloxy)benzaldehyde
863659-50-1

3-(prop-1-enyl)-4-(prop-1-enyloxy)benzaldehyde

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 90℃; for 3h;50%
4-hydroxy-3-(2-propen-1-yl)benzaldehyde
41052-88-4

4-hydroxy-3-(2-propen-1-yl)benzaldehyde

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 89 percent / K2CO3 / acetone / 2 h / 60 °C
2: 82 percent / [RuClH(CO)(PPh3)3] / CH2Cl2 / 14 h / 65 °C
3: 50 percent / ((Mes)2C3H5N2)Cl2Ru=CHPh / toluene / 3 h / 90 °C
View Scheme
4-(2-propenyloxy)benzaldehyde
40663-68-1

4-(2-propenyloxy)benzaldehyde

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 41 percent / 0.17 h / 250 °C / microwave irradiation
2: 89 percent / K2CO3 / acetone / 2 h / 60 °C
3: 82 percent / [RuClH(CO)(PPh3)3] / CH2Cl2 / 14 h / 65 °C
4: 50 percent / ((Mes)2C3H5N2)Cl2Ru=CHPh / toluene / 3 h / 90 °C
View Scheme
3-allyl-4-allyloxybenzaldehyde
136433-45-9

3-allyl-4-allyloxybenzaldehyde

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / [RuClH(CO)(PPh3)3] / CH2Cl2 / 14 h / 65 °C
2: 50 percent / ((Mes)2C3H5N2)Cl2Ru=CHPh / toluene / 3 h / 90 °C
View Scheme
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

n-nonyl halide

n-nonyl halide

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: K2CO3 / acetone
2: 41 percent / 0.17 h / 250 °C / microwave irradiation
3: 89 percent / K2CO3 / acetone / 2 h / 60 °C
4: 82 percent / [RuClH(CO)(PPh3)3] / CH2Cl2 / 14 h / 65 °C
5: 50 percent / ((Mes)2C3H5N2)Cl2Ru=CHPh / toluene / 3 h / 90 °C
View Scheme
4-bromo-phenol
106-41-2

4-bromo-phenol

isobutyl halide

isobutyl halide

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF
2: polyphosphoric acid / benzene / Heating
3: 1.) t-BuLi / 1.) Et2O, -78 deg C, 2.) Et2O
View Scheme
1-bromo-4-(2,2-diethoxyethoxy)benzene
112598-18-2

1-bromo-4-(2,2-diethoxyethoxy)benzene

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: polyphosphoric acid / benzene / Heating
2: 1.) t-BuLi / 1.) Et2O, -78 deg C, 2.) Et2O
View Scheme
isovanillin
621-59-0

isovanillin

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 85 percent / ethyldiisopropylamine / CH2Cl2 / 0.67 h / -78 - 20 °C
2: 88 percent / Pd(PPh3)2Cl2, Et3N / dimethylformamide / 1.5 h / 90 °C
3: 68 percent / K2CO3 / methanol / 8.5 h / Ambient temperature
4: 58 percent / LiCl, HMPA / 1.5 h / 130 °C
View Scheme
4-methoxy-3-[2-(trimethylsilyl)ethynyl]benzaldehyde
160625-48-9

4-methoxy-3-[2-(trimethylsilyl)ethynyl]benzaldehyde

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 68 percent / K2CO3 / methanol / 8.5 h / Ambient temperature
2: 58 percent / LiCl, HMPA / 1.5 h / 130 °C
View Scheme
4-methoxy-3-trifluoromethanesulfonyloxybenzaldehyde
157790-73-3

4-methoxy-3-trifluoromethanesulfonyloxybenzaldehyde

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 88 percent / Pd(PPh3)2Cl2, Et3N / dimethylformamide / 1.5 h / 90 °C
2: 68 percent / K2CO3 / methanol / 8.5 h / Ambient temperature
3: 58 percent / LiCl, HMPA / 1.5 h / 130 °C
View Scheme
5-bromobenzofuran
23145-07-5

5-bromobenzofuran

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Conditions
ConditionsYield
With hydrogenchloride; iodine; magnesium In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide
5-bromobenzofuran
23145-07-5

5-bromobenzofuran

4-bromo-phenol
106-41-2

4-bromo-phenol

Bromoacetaldehyde diethyl acetal
2032-35-1

Bromoacetaldehyde diethyl acetal

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

5-hydroxymethylbenzo[b]furan
31823-05-9

5-hydroxymethylbenzo[b]furan

Conditions
ConditionsYield
Stage #1: benzofuran-5-carbaldehyde With sodium tetrahydroborate In methanol Cooling with ice;
Stage #2: With ammonium chloride In methanol Saturated solution;
100%
With sodium tetrahydroborate In methanol at 0℃; for 0.166667h;96%
With 2,2'-bi(1,3,6,2-dioxazaborocane); water at 20℃; for 18h; Inert atmosphere; Sealed tube;86%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

benzofuran-5-yl-(3-ethoxy-4-methoxy-phenyl)-methanol
878495-90-0

benzofuran-5-yl-(3-ethoxy-4-methoxy-phenyl)-methanol

Conditions
ConditionsYield
Stage #1: 1-Bromo-3-ethoxy-4-methoxybenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h;
Stage #2: benzofuran-5-carbaldehyde In tetrahydrofuran at -78℃; for 1h;
Stage #3: With water In isopropyl alcohol
100%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

ethyl 2-(bis(2-isopropylphenoxy)phosphoryl)acetate
188945-44-0

ethyl 2-(bis(2-isopropylphenoxy)phosphoryl)acetate

(Z)-ethyl 3-(benzofuran-5-yl)acrylate
1499179-57-5

(Z)-ethyl 3-(benzofuran-5-yl)acrylate

Conditions
ConditionsYield
Stage #1: ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate With N-benzyl-trimethylammonium hydroxide In tetrahydrofuran; methanol at -78℃; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;
Stage #2: benzofuran-5-carbaldehyde In tetrahydrofuran; methanol at -78℃; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; diastereoselective reaction;
96%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

C13H12O3

C13H12O3

Conditions
ConditionsYield
In dichloromethane at 40℃; for 20h;96%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

benzo[b]furan-5-carbonitrile
79002-39-4

benzo[b]furan-5-carbonitrile

Conditions
ConditionsYield
With ammonium sulfate; sodium carbonate; sulfur In dimethyl sulfoxide at 120℃; for 10h; Sealed tube;96%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

4-{4-(methylamino)thieno[3,2-d]pyrimidin-2-yl}benzohydrazide

4-{4-(methylamino)thieno[3,2-d]pyrimidin-2-yl}benzohydrazide

N'-[(benzofuran-5-yl)methylene]-4-{4-(methylamino)thieno[3,2-d]pyrimidin-2-yl}benzohydrazide

N'-[(benzofuran-5-yl)methylene]-4-{4-(methylamino)thieno[3,2-d]pyrimidin-2-yl}benzohydrazide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 120℃; for 1h; Inert atmosphere;93%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

methylamine
74-89-5

methylamine

benzofuran-5-yl-N-methylmethanamine
389845-58-3

benzofuran-5-yl-N-methylmethanamine

Conditions
ConditionsYield
Stage #1: benzofuran-5-carbaldehyde; methylamine In methanol; ethanol for 3h;
Stage #2: With sodium tetrahydroborate In methanol at 20℃;
Stage #3: With water In methanol
91%
Stage #1: benzofuran-5-carbaldehyde; methylamine In methanol; water at 0℃; for 0.916667h;
Stage #2: With sodium tetrahydroborate In methanol; water for 0.75h;
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

benzofuran-5-carbaldehyde oxime
1018038-52-2

benzofuran-5-carbaldehyde oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 3h;91%
With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 12h;
With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 3h;4.6 g
With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 16h;
BARBITURIC ACID
67-52-7

BARBITURIC ACID

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

5-(1-benzofuran-5-ylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

5-(1-benzofuran-5-ylmethylidene)pyrimidine-2,4,6(1H,3H,5H)-trione

Conditions
ConditionsYield
In 2-methyl-propan-1-ol for 0.75h; Reflux; Green chemistry;91%
In 2-methyl-propan-1-ol for 0.75h; Reflux;91%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

2,3-dibromo-2,3-dihydro-benzofuran-5-carbaldehyde

2,3-dibromo-2,3-dihydro-benzofuran-5-carbaldehyde

Conditions
ConditionsYield
With bromine In chloroform at 20℃; for 1h;90%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

(1,3-benzothiazol-2-ylsulfonyl)fluoromethyl n-propyl ketone
1149578-23-3

(1,3-benzothiazol-2-ylsulfonyl)fluoromethyl n-propyl ketone

(Z)-2-fluoro-1-(1-benzofuran-5-yl)-1-hexen-3-one
1184134-88-0

(Z)-2-fluoro-1-(1-benzofuran-5-yl)-1-hexen-3-one

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; dichloromethane at 0 - 5℃; for 8h; Julia Olefin synthesis; stereoselective reaction;90%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate
90965-06-3

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate

5-ethynylbenzo[b]furane
1158745-04-0

5-ethynylbenzo[b]furane

Conditions
ConditionsYield
With potassium carbonate In methanol at 20℃; for 12h;90%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

5-vinyl-1-benzofuran

5-vinyl-1-benzofuran

Conditions
ConditionsYield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Wittig Olefination; Inert atmosphere;
Stage #2: benzofuran-5-carbaldehyde In tetrahydrofuran at 20℃; for 3h; Wittig Olefination; Inert atmosphere;
86%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

5-(difluoromethyl)-7-(3-piperidyl)-[1,2,4]triazolo[1,5-a]pyrimidine hydrochloride

5-(difluoromethyl)-7-(3-piperidyl)-[1,2,4]triazolo[1,5-a]pyrimidine hydrochloride

7-[1-(benzofuran-5-ylmethyl)-3-piperidyl]-5-(difluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine hydrochloride

7-[1-(benzofuran-5-ylmethyl)-3-piperidyl]-5-(difluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidine hydrochloride

Conditions
ConditionsYield
Stage #1: benzofuran-5-carbaldehyde; 5-(difluoromethyl)-7-(3-piperidyl)-[1,2,4]triazolo[1,5-a]pyrimidine hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 2h; Inert atmosphere;
Stage #3: With hydrogenchloride In diphenylether Inert atmosphere;
86%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

4-(trifluoromethyl)phenylmagnesium bromide
402-51-7

4-(trifluoromethyl)phenylmagnesium bromide

benzofuran-5-yl(4-(trifluoromethyl)phenyl)methanol

benzofuran-5-yl(4-(trifluoromethyl)phenyl)methanol

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Schlenk technique;85%
tryptamine
61-54-1

tryptamine

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

1-benzofuran-5-yl-2,3,4,9-tetrahydro-1H-β-carboline
199678-72-3

1-benzofuran-5-yl-2,3,4,9-tetrahydro-1H-β-carboline

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane for 48h;83%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

2′-hydroxy-6′-methoxymethoxyacetophenone
78646-28-3

2′-hydroxy-6′-methoxymethoxyacetophenone

(E)-3-Benzofuran-5-yl-1-(2-hydroxy-6-methoxymethoxy-phenyl)-propenone

(E)-3-Benzofuran-5-yl-1-(2-hydroxy-6-methoxymethoxy-phenyl)-propenone

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃;82%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

buta-1,3-diene
106-99-0

buta-1,3-diene

phenylboronic acid
98-80-6

phenylboronic acid

(E)-1-(benzofuran-5-yl)-5-phenylpent-3-en-1-ol

(E)-1-(benzofuran-5-yl)-5-phenylpent-3-en-1-ol

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0) In tetrahydrofuran; toluene at 20℃; for 6h; Sealed tube; Inert atmosphere; diastereoselective reaction;82%
2-thioxo-4-thiazolidinone
141-84-4

2-thioxo-4-thiazolidinone

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

(Z)-5-[(benzofuran-5-yl)methylene]-2-thioxothiazolidin-4-one

(Z)-5-[(benzofuran-5-yl)methylene]-2-thioxothiazolidin-4-one

Conditions
ConditionsYield
With ammonium acetate; acetic acid In acetonitrile for 2h; Inert atmosphere; Reflux;81.2%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

(2S,4R,5R)-5-amino-2-(bis(4-fluorophenyl)methyl)tetrahydro-2H-pyran-4-ol

(2S,4R,5R)-5-amino-2-(bis(4-fluorophenyl)methyl)tetrahydro-2H-pyran-4-ol

(2S,4R,5R)-5-((benzofuran-5-ylmethyl)amino)-2-(bis(4-fluorophenyl) methyl)tetrahydro-2H-pyran-4-ol

(2S,4R,5R)-5-((benzofuran-5-ylmethyl)amino)-2-(bis(4-fluorophenyl) methyl)tetrahydro-2H-pyran-4-ol

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In methanol; 1,2-dichloro-ethane81%
Stage #1: benzofuran-5-carbaldehyde; (2S,4R,5R)-5-amino-2-(bis(4-fluorophenyl)methyl)tetrahydro-2H-pyran-4-ol With acetic acid In 1,2-dichloro-ethane for 0.5h; Inert atmosphere;
Stage #2: With sodium cyanoborohydride In MeOH; 1,2-dichloro-ethane Inert atmosphere;
81%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

1-(7-methoxy-2-(2,4,6-trimethoxyphenyl)benzofuran-5-yl)ethanone

1-(7-methoxy-2-(2,4,6-trimethoxyphenyl)benzofuran-5-yl)ethanone

(E)-3-(benzofuran-5-yl)-1-(7-methoxy-2-(2,4,6-trimethoxyphenyl)benzofuran-5-yl)prop-2-en-1-one

(E)-3-(benzofuran-5-yl)-1-(7-methoxy-2-(2,4,6-trimethoxyphenyl)benzofuran-5-yl)prop-2-en-1-one

Conditions
ConditionsYield
With potassium hydroxide In methanol; water at 20℃; for 24h; Claisen-Schmidt Condensation;79%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

(5-methylpyrazine-2-yl)methylamine
132664-85-8

(5-methylpyrazine-2-yl)methylamine

C15H15N3O
1160051-86-4

C15H15N3O

Conditions
ConditionsYield
Stage #1: benzofuran-5-carbaldehyde; (5-methylpyrazine-2-yl)methylamine With sodium acetate; acetic acid In methanol at 20℃; for 0.5h;
Stage #2: With sodium tetrahydroborate In methanol for 0.5h;
Stage #3: With water; sodium hydrogencarbonate In methanol
75%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

(8-morpholin-4-yl-2-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-hydrazine
1313014-23-1

(8-morpholin-4-yl-2-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-hydrazine

N-benzofuran-5-ylmethylene-N'-(8-morpholin-4-yl-2-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-hydrazine
1313014-05-9

N-benzofuran-5-ylmethylene-N'-(8-morpholin-4-yl-2-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-hydrazine

Conditions
ConditionsYield
In ethanol at 20℃;71%
benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

(2RS,3SR)-2,3-dibromo-2,3-dihydrobenzofuran-5-carbaldehyde

(2RS,3SR)-2,3-dibromo-2,3-dihydrobenzofuran-5-carbaldehyde

Conditions
ConditionsYield
With bromine; acetic acid at 100℃; for 0.5h;70%
With bromine In chloroform at 20℃; Cooling;50%
(2S,4R,5R)-5-amino-2-benzhydryltetrahydro-2H-pyran-4-ol
869114-22-7

(2S,4R,5R)-5-amino-2-benzhydryltetrahydro-2H-pyran-4-ol

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

(2S,4R,5R)-2-benzhydryl-5-((benzofuran-5-ylmethyl)amino)tetrahydro-2H-pyran-4-ol

(2S,4R,5R)-2-benzhydryl-5-((benzofuran-5-ylmethyl)amino)tetrahydro-2H-pyran-4-ol

Conditions
ConditionsYield
Stage #1: (2S,4R,5R)-5-amino-2-benzhydryl-tetrahydropyran-4-ol; benzofuran-5-carbaldehyde With acetic acid In 1,2-dichloro-ethane for 0.5h; Inert atmosphere;
Stage #2: With sodium cyanoborohydride In MeOH; 1,2-dichloro-ethane Inert atmosphere;
69%
cis-(3S,6S)-(6-benzhydryl-tetrahydropyran-3-yl)-amine
869114-39-6

cis-(3S,6S)-(6-benzhydryl-tetrahydropyran-3-yl)-amine

benzofuran-5-carbaldehyde
10035-16-2

benzofuran-5-carbaldehyde

(3S,6S)-6-benzhydryl-N-(benzofuran-5-ylmethyl)tetrahydro-2H-pyran-3-amine

(3S,6S)-6-benzhydryl-N-(benzofuran-5-ylmethyl)tetrahydro-2H-pyran-3-amine

Conditions
ConditionsYield
Stage #1: cis-(3S,6S)-(6-benzhydryl-tetrahydropyran-3-yl)-amine; benzofuran-5-carbaldehyde With acetic acid In 1,2-dichloro-ethane for 0.5h;
Stage #2: With sodium cyanoborohydride In methanol; 1,2-dichloro-ethane
67%
Stage #1: cis-(3S,6S)-(6-benzhydryl-tetrahydropyran-3-yl)-amine; benzofuran-5-carbaldehyde With acetic acid In acetic acid; 1,2-dichloro-ethane for 0.5h; Inert atmosphere;
Stage #2: With sodium cyanoborohydride In MeOH; 1,2-dichloro-ethane Inert atmosphere;
67%

10035-16-2Relevant articles and documents

C-5 substituted heteroaryl-3-pyridinecarbonitriles as PKCθ inhibitors: Part II

Prashad, Amar S.,Wang, Daniel,Subrath, Joan,Wu, Biqi,Lin, Melissa,Zhang, Mei-Yi,Kagan, Natasha,Lee, Julie,Yang, Xiaoke,Brennan, Agnes,Chaudhary, Divya,Xu, Xin,Leung, Louis,Wang, Jack,Boschelli, Diane H.

, p. 5799 - 5802 (2009)

We previously reported that a 3-pyridinecarbonitrile analog with a furan substituent at C-5 and a 4-methylindol-5-ylamino substituent at C-4, 1, was a potent inhibitor of PKCθ (IC50 = 4.5 nM). Replacement of the C-5 furan ring of 1 with bicycli

Heterocyclic acene propanoic derivative as well as preparation method and application thereof

-

Paragraph 0188; 0190; 0191; 0192, (2018/01/09)

The invention relates to a heterocyclic acene propanoic derivative as well as a preparation method and application thereof. A structural formula of the derivative is shown in the description. The heterocyclic acene propanoic derivative shows agonist activ

Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

Nishikawa, Keisuke,Fukuda, Hiroshi,Abe, Masato,Nakanishi, Kazunari,Taniguchi, Tomoya,Nomura, Takashi,Yamaguchi, Chihiro,Hiradate, Syuntaro,Fujii, Yoshiharu,Okuda, Katsuhiro,Shindo, Mitsuru

, p. 132 - 147 (2014/01/06)

1-O-cis-Cinnamoyl-β-d-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA.

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