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29199-11-9

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29199-11-9 Usage

General Description

2-Mercaptobenzaldehyde is a chemical compound with the molecular formula C7H6OS. It is a yellow to brown solid with a strong odor similar to that of garlic. 2-Mercaptobenzaldehyde is used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and dyes. It is also utilized as a reagent in organic chemistry reactions, particularly in the production of thiols. Additionally, it has potential applications in the development of sensors and as a corrosion inhibitor. However, 2-Mercaptobenzaldehyde is toxic and may cause irritation to the skin, eyes, and respiratory system, making it important to handle and store with caution.

Check Digit Verification of cas no

The CAS Registry Mumber 29199-11-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,1,9 and 9 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 29199-11:
(7*2)+(6*9)+(5*1)+(4*9)+(3*9)+(2*1)+(1*1)=139
139 % 10 = 9
So 29199-11-9 is a valid CAS Registry Number.

29199-11-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-sulfanylbenzaldehyde

1.2 Other means of identification

Product number -
Other names Benzaldehyde,2-mercapto

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:29199-11-9 SDS

29199-11-9Synthetic route

2,2'-dithiodibenzaldehyde
55164-16-4

2,2'-dithiodibenzaldehyde

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
With tris-(2-carboxyethyl)-phosphine hydrochloride In dimethyl sulfoxide100%
With triphenylphosphine In methanol; water; N,N-dimethyl-formamide 1.) room temp., 30 min; 2.) ice-water bath, 30 min;80%
With water; triphenylphosphine In methanol; N,N-dimethyl-formamide at 20℃; for 0.5h;80%
o-hydroxymethyl thiophenol
4521-31-7

o-hydroxymethyl thiophenol

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
With dihydrogen peroxide In neat (no solvent) at 80℃; for 4h; Green chemistry;100%
Multi-step reaction with 2 steps
1: 54 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 20 °C
2: 80 percent / triphenylphosphine; water / methanol; dimethylformamide / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 54 percent / PCC / CH2Cl2 / 4 h / Ambient temperature
2: 80 percent / Ph3P / dimethylformamide; H2O; methanol / 1.) room temp., 30 min; 2.) ice-water bath, 30 min
View Scheme
2-(2-bromophenyl)-1,3-dioxolan
34824-58-3

2-(2-bromophenyl)-1,3-dioxolan

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
Stage #1: 2-(2-bromophenyl)-1,3-dioxolan With magnesium In tetrahydrofuran at 0℃; for 1h; Reflux;
Stage #2: With sulfur In tetrahydrofuran at 20℃;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; water for 2h; Reflux;
91%
thiophenol
108-98-5

thiophenol

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

N,N-dimethyl-formamide

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
Stage #1: thiophenol With n-butyllithium; N,N,N,N,-tetramethylethylenediamine
Stage #2: N,N-dimethyl-formamide
83%
Stage #1: thiophenol With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane
Stage #2: N,N-dimethyl-formamide In hexane
66%
Stage #1: thiophenol With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at 0 - 20℃; for 16h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In hexane at 0 - 20℃; for 20h; Inert atmosphere;
48%
o-Thioacetoxybenzaldehyde
119011-44-8

o-Thioacetoxybenzaldehyde

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
With titanium tetrachloride; zinc In dichloromethane at 25℃; for 0.166667h;82%
o-rhodano-benzaldehyde
85733-65-9

o-rhodano-benzaldehyde

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
With sodium hydroxide for 0.0833333h;70%
With sodium sulfide; water das Natriumsalz entsteht;
2-hydroxy-5-phenylcyclohex-1-enecarbaldehyde
1060749-49-6

2-hydroxy-5-phenylcyclohex-1-enecarbaldehyde

mer-hydrido(2-mercaptobenzoyl)tris(trimethylphosphine)cobalt(III)

mer-hydrido(2-mercaptobenzoyl)tris(trimethylphosphine)cobalt(III)

A

mer-hydrido(1-carbonyl-2-oxo-5-phenylyclohexenediyl)tris(trimethylphosphine)cobalt(III)
210900-83-7

mer-hydrido(1-carbonyl-2-oxo-5-phenylyclohexenediyl)tris(trimethylphosphine)cobalt(III)

B

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
In diethyl ether at -80 - 20℃; for 14h; Mechanism; Inert atmosphere; Schlenk technique;A 69%
B n/a
ethyl 2-sulfanylacetate
623-51-8

ethyl 2-sulfanylacetate

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

A

ethyl benzo[b]thiophene-2-carboxylate
17890-55-0

ethyl benzo[b]thiophene-2-carboxylate

B

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
With potassium tert-butylate In ammonia for 180h; Irradiation;A 55%
B 10%
With potassium tert-butylate 1.) NH3, irradiation, 180 min,; Yield given. Multistep reaction. Yields of byproduct given;
2,2'-dithiodibenzaldehyde
55164-16-4

2,2'-dithiodibenzaldehyde

methyl vinyl ketone
78-94-4

methyl vinyl ketone

A

2-formylthiophenol
29199-11-9

2-formylthiophenol

B

3-acetyl-4-hydroxythiochroman

3-acetyl-4-hydroxythiochroman

C

3-acetyl-2H-1-benzothiopyran

3-acetyl-2H-1-benzothiopyran

Conditions
ConditionsYield
With triphenylphosphine In chloroform at 20℃; for 96h;A 9%
B 52%
C 33.5%
2-[(phenylmethyl)thio]benzaldehyde
24852-71-9

2-[(phenylmethyl)thio]benzaldehyde

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
Stage #1: 2-[(phenylmethyl)thio]benzaldehyde With aluminum (III) chloride In benzene at 20℃; for 48.5h; Inert atmosphere;
Stage #2: With water In benzene Cooling with ice;
24%
O-(2-formylphenyl) N,N-dimethylcarbamothioate

O-(2-formylphenyl) N,N-dimethylcarbamothioate

A

2-formylthiophenol
29199-11-9

2-formylthiophenol

B

S-(2-formylphenyl) N,N-dimethylthiocarbamate
153511-19-4

S-(2-formylphenyl) N,N-dimethylthiocarbamate

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 230℃; for 15h; Miyazaki-Newman-Kwart rearrangement; Microwave irradiation;A 10%
B n/a
2-mercapto-N-methyl-N-phenylbenzamide
49848-22-8

2-mercapto-N-methyl-N-phenylbenzamide

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
With lithium aluminium tetrahydride
N-Formylpiperidine
2591-86-8

N-Formylpiperidine

thiophenol
108-98-5

thiophenol

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine 1.) hexane, a) 0 deg C, 0.5 h, b) RT, 17 h, 2.) hexane, 25 deg C, 18 h; Yield given; Multistep reaction;
Thiosalicylic acid
147-93-3

Thiosalicylic acid

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 96 percent / LiAlH4 / tetrahydrofuran / 20 °C
2: 54 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 20 °C
3: 80 percent / triphenylphosphine; water / methanol; dimethylformamide / 0.5 h / 20 °C
View Scheme
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux;
Multi-step reaction with 3 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere
2: pyridinium chlorochromate / dichloromethane / 4 h / 20 °C / Inert atmosphere
3: triphenylphosphine / water; N,N-dimethyl-formamide; methanol / 0.5 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
2: pyridinium chlorochromate / dichloromethane / 5 h / 20 °C
3: tris-(2-carboxyethyl)-phosphine hydrochloride / dimethyl sulfoxide
View Scheme
Multi-step reaction with 3 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: pyridinium chlorochromate / dichloromethane / 20 °C
3: triphenylphosphine / methanol; N,N-dimethyl-formamide; water / 1 h / 0 - 20 °C
View Scheme
1,2-bis(2-(hydroxymethyl)phenyl)disulfane
35190-71-7

1,2-bis(2-(hydroxymethyl)phenyl)disulfane

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 16 percent / PCC
2: 80 percent / Ph3P / dimethylformamide; H2O; methanol / 1.) room temp., 30 min; 2.) ice-water bath, 30 min
View Scheme
With triphenylphosphine In methanol; water; N,N-dimethyl-formamide for 1h;
2-aminobenzaldehyde
529-23-7

2-aminobenzaldehyde

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) sodium nitrite / 1) sulphuric acid, water, 0 deg C, 2) water, room temp., 1 h, 60 deg C, 30 min
2: 70 percent / sodium hydroxide / 0.08 h
View Scheme
Multi-step reaction with 2 steps
1: Diazotization.durch Umsetzung mit CuCNS
2: sodium sulfide; water / das Natriumsalz entsteht
View Scheme
N-(2-nitro-benzyl)-sulfanilic acid

N-(2-nitro-benzyl)-sulfanilic acid

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: Diazotization.durch Umsetzung mit CuCNS
3: sodium sulfide; water / das Natriumsalz entsteht
View Scheme
2-Fluorobenzaldehyde
446-52-6

2-Fluorobenzaldehyde

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
With sodium sulfide
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
With sodium sulfide nonahydrate In N,N-dimethyl acetamide at 80℃; for 0.5h; Inert atmosphere;
Multi-step reaction with 3 steps
1.1: potassium hydroxide / dimethyl sulfoxide / 0.33 h / 20 °C / Inert atmosphere
1.2: 1.5 h / 110 °C / Inert atmosphere
2.1: acetic acid; hydrogen bromide; dimethyl sulfoxide / water / 20 °C / Cooling with ice
3.1: triphenylphosphine / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
3.2: 0.17 h / Inert atmosphere
View Scheme
salicylaldehyde
90-02-8

salicylaldehyde

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate / acetonitrile / 0.17 h / 20 °C / Inert atmosphere
1.2: 24 h / 80 °C / Inert atmosphere
2.1: 1-methyl-pyrrolidin-2-one / 15 h / 230 °C / Microwave irradiation
View Scheme
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / toluene / Dean-Stark
2.1: magnesium / tetrahydrofuran / 1 h / 0 °C / Reflux
2.2: 20 °C
2.3: 2 h / Reflux
View Scheme
2-(tert-butylthio)benzaldehyde
65924-65-4

2-(tert-butylthio)benzaldehyde

2-formylthiophenol
29199-11-9

2-formylthiophenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: acetic acid; hydrogen bromide; dimethyl sulfoxide / water / 20 °C / Cooling with ice
2.1: triphenylphosphine / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere
2.2: 0.17 h / Inert atmosphere
View Scheme
2,2'-dithiodibenzaldehyde
55164-16-4

2,2'-dithiodibenzaldehyde

acrylonitrile
107-13-1

acrylonitrile

A

2-formylthiophenol
29199-11-9

2-formylthiophenol

B

4-hydroxythiochromane-3-carbonitrile

4-hydroxythiochromane-3-carbonitrile

Conditions
ConditionsYield
Stage #1: 2,2'-dithiodibenzaldehyde With triphenylphosphine In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: acrylonitrile In tetrahydrofuran for 0.166667h; Inert atmosphere;
2-formylthiophenol
29199-11-9

2-formylthiophenol

2,2'-dithiodibenzaldehyde
55164-16-4

2,2'-dithiodibenzaldehyde

Conditions
ConditionsYield
With triethylamine; phenylacetylene; copper(l) iodide In acetonitrile at 20℃; for 8h;100%
With oxygen; SiO2-Cl In dichloromethane at 0℃; for 0.166667h;98%
MoO2Cl2(DMSO)2 In dimethyl sulfoxide at 20℃; for 0.5h;91%
nitrostyrene
5153-67-3

nitrostyrene

2-formylthiophenol
29199-11-9

2-formylthiophenol

(2R,3R,4S)-3-nitro-2-phenylthiochroman-4-ol
1574615-20-5

(2R,3R,4S)-3-nitro-2-phenylthiochroman-4-ol

Conditions
ConditionsYield
With 2-{[(1S)-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}-1-phenylethanamino]methyl}-4,6-dibromophenol; nickel(II) acetate tetrahydrate In toluene at -40 - 20℃; for 15h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere; enantioselective reaction;99%
With 2-{[(1S)-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}-1-phenylethanamino]methyl}-4,6-dibromophenol; nickel diacetate In toluene at -40℃; for 15h;99%
1-chloro-4-(2-nitrovinyl)benzene
706-07-0

1-chloro-4-(2-nitrovinyl)benzene

2-formylthiophenol
29199-11-9

2-formylthiophenol

(2R,3R,4S)-2-(4-chlorophenyl)-3-nitrothiochroman-4-ol
1574615-21-6

(2R,3R,4S)-2-(4-chlorophenyl)-3-nitrothiochroman-4-ol

Conditions
ConditionsYield
With 2-{[(1S)-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}-1-phenylethanamino]methyl}-4,6-dibromophenol; nickel(II) acetate tetrahydrate In toluene at -40 - 20℃; for 15h; Inert atmosphere; enantioselective reaction;99%
3-chloroβ-nitrostyrene
37888-03-2, 3156-35-2

3-chloroβ-nitrostyrene

2-formylthiophenol
29199-11-9

2-formylthiophenol

(2R,3R,4S)-2-(3-chlorophenyl)-3-nitrothiochroman-4-ol
1574615-26-1

(2R,3R,4S)-2-(3-chlorophenyl)-3-nitrothiochroman-4-ol

Conditions
ConditionsYield
With 2-{[(1S)-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}-1-phenylethanamino]methyl}-4,6-dibromophenol; nickel(II) acetate tetrahydrate In toluene at -40 - 20℃; for 15h; Inert atmosphere; enantioselective reaction;99%
4-bromo-β-nitrostyrene
3156-37-4

4-bromo-β-nitrostyrene

2-formylthiophenol
29199-11-9

2-formylthiophenol

(2R,3R,4S)-2-(4-bromophenyl)-3-nitrothiochroman-4-ol
1574615-27-2

(2R,3R,4S)-2-(4-bromophenyl)-3-nitrothiochroman-4-ol

Conditions
ConditionsYield
With 2-{[(1S)-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}-1-phenylethanamino]methyl}-4,6-dibromophenol; nickel(II) acetate tetrahydrate In toluene at -40 - 20℃; for 15h; Inert atmosphere; enantioselective reaction;99%
3-bromo-β-nitro-styrene
115665-95-7, 15795-14-9

3-bromo-β-nitro-styrene

2-formylthiophenol
29199-11-9

2-formylthiophenol

(2R,3R,4S)-2-(3-bromophenyl)-3-nitrothiochroman-4-ol
1574615-29-4

(2R,3R,4S)-2-(3-bromophenyl)-3-nitrothiochroman-4-ol

Conditions
ConditionsYield
With 2-{[(1S)-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}-1-phenylethanamino]methyl}-4,6-dibromophenol; nickel(II) acetate tetrahydrate In toluene at -40 - 20℃; for 15h; Inert atmosphere; enantioselective reaction;99%
4-fluoro-β-nitrostyrene
5153-69-5, 706-08-1

4-fluoro-β-nitrostyrene

2-formylthiophenol
29199-11-9

2-formylthiophenol

(2R,3R,4S)-2-(4-fluorophenyl)-3-nitrothiochroman-4-ol
1574615-35-2

(2R,3R,4S)-2-(4-fluorophenyl)-3-nitrothiochroman-4-ol

Conditions
ConditionsYield
With 2-{[(1S)-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}-1-phenylethanamino]methyl}-4,6-dibromophenol; nickel(II) acetate tetrahydrate In toluene at -40 - 20℃; for 15h; Inert atmosphere; enantioselective reaction;99%
3-nitro-β-nitrostyrene
882-26-8

3-nitro-β-nitrostyrene

2-formylthiophenol
29199-11-9

2-formylthiophenol

(2S,3R,4R)-3-nitro-2-(3-nitrophenyl)thiochroman-4-ol
1574615-40-9

(2S,3R,4R)-3-nitro-2-(3-nitrophenyl)thiochroman-4-ol

Conditions
ConditionsYield
With 2-{[(1S)-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}-1-phenylethanamino]methyl}-4,6-dibromophenol; nickel(II) acetate tetrahydrate In toluene at -40 - 20℃; for 15h; Inert atmosphere; enantioselective reaction;99%
1-methoxy-3-(2-nitrovinyl)benzene
3179-09-7

1-methoxy-3-(2-nitrovinyl)benzene

2-formylthiophenol
29199-11-9

2-formylthiophenol

(2R,3R,4S)-2-(3-methoxyphenyl)-3-nitrothiochroman-4-ol
1574615-46-5

(2R,3R,4S)-2-(3-methoxyphenyl)-3-nitrothiochroman-4-ol

Conditions
ConditionsYield
With 2-{[(1S)-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}-1-phenylethanamino]methyl}-4,6-dibromophenol; nickel(II) acetate tetrahydrate In toluene at -40 - 20℃; for 15h; Inert atmosphere; enantioselective reaction;99%
1-methyl-3-(2-nitrovinyl)benzene
22568-43-0, 62248-93-5

1-methyl-3-(2-nitrovinyl)benzene

2-formylthiophenol
29199-11-9

2-formylthiophenol

(2S,3R,4R)-3-nitro-2-(m-tolyl)thiochroman-4-ol
1574615-52-3

(2S,3R,4R)-3-nitro-2-(m-tolyl)thiochroman-4-ol

Conditions
ConditionsYield
With 2-{[(1S)-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}-1-phenylethanamino]methyl}-4,6-dibromophenol; nickel(II) acetate tetrahydrate In toluene at -40 - 20℃; for 15h; Inert atmosphere; enantioselective reaction;99%
1-(2-thienyl)-2-nitroethene
34312-77-1

1-(2-thienyl)-2-nitroethene

2-formylthiophenol
29199-11-9

2-formylthiophenol

(2R,3R,4R)-3-nitro-2-(thiophen-2-yl)thiochroman-4-ol
1574615-57-8

(2R,3R,4R)-3-nitro-2-(thiophen-2-yl)thiochroman-4-ol

Conditions
ConditionsYield
With 2-{[(1S)-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}-1-phenylethanamino]methyl}-4,6-dibromophenol; nickel(II) acetate tetrahydrate In toluene at -40 - 20℃; for 15h; Inert atmosphere; enantioselective reaction;99%
3-(2-bromobenzylidene)oxindole
391614-10-1

3-(2-bromobenzylidene)oxindole

2-formylthiophenol
29199-11-9

2-formylthiophenol

2'-(2”-bromophenyl)-4'-hydroxyspiro[indoline-3,3'-thiochroman]-2-one

2'-(2”-bromophenyl)-4'-hydroxyspiro[indoline-3,3'-thiochroman]-2-one

Conditions
ConditionsYield
With 2C2H3O2(1-)*Ni(2+)*C49H45N5 In toluene at -40 - 20℃; for 30h; stereoselective reaction;99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

3-benzylidene-6-chloroindol-2-one
387343-81-9

3-benzylidene-6-chloroindol-2-one

6-chloro-4'-hydroxy-2'-phenylspiro[indoline-3,3'-thiochroman]-2-one

6-chloro-4'-hydroxy-2'-phenylspiro[indoline-3,3'-thiochroman]-2-one

Conditions
ConditionsYield
With 2C2H3O2(1-)*Ni(2+)*C49H45N5 In toluene at -40 - 20℃; for 30h; stereoselective reaction;99%
(E)-1-methoxy-4-(2-nitrovinyl)benzene
3179-10-0, 5576-97-6

(E)-1-methoxy-4-(2-nitrovinyl)benzene

2-formylthiophenol
29199-11-9

2-formylthiophenol

A

2-(4-methoxyphenyl)-3-nitro-thiochroman-4-ol

2-(4-methoxyphenyl)-3-nitro-thiochroman-4-ol

B

(2R,3R,4S)-2-(4-methoxyphenyl)-3-nitrothiochroman-4-ol
1574615-43-2

(2R,3R,4S)-2-(4-methoxyphenyl)-3-nitrothiochroman-4-ol

Conditions
ConditionsYield
With 2-{[(1S)-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}-1-phenylethanamino]methyl}-4,6-dibromophenol; nickel diacetate In toluene at -40℃; for 15h;A n/a
B 99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-phenylprop-2-en-1-one

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-phenylprop-2-en-1-one

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-4-hydroxy-2-phenylthiochroman-3-yl)methanone

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-4-hydroxy-2-phenylthiochroman-3-yl)methanone

Conditions
ConditionsYield
With C31H26F6N4O2 In dichloromethane at 0℃; Solvent; enantioselective reaction;99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(4-fluorophenyl)prop-2-en-1-one

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(4-fluorophenyl)prop-2-en-1-one

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-2-(4-fluorophenyl)-4-hydroxythiochroman-3-yl)methanone

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-2-(4-fluorophenyl)-4-hydroxythiochroman-3-yl)methanone

Conditions
ConditionsYield
With C31H26F6N4O2 In dichloromethane at 0℃; enantioselective reaction;99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

(E)-3-(4-bromophenyl)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)prop-2-en-1-one

(E)-3-(4-bromophenyl)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)prop-2-en-1-one

((2R,3S,4R)-2-(4-bromophenyl)-4-hydroxythiochroman-3-yl)(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)methanone

((2R,3S,4R)-2-(4-bromophenyl)-4-hydroxythiochroman-3-yl)(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)methanone

Conditions
ConditionsYield
With C31H26F6N4O2 In dichloromethane at 0℃; enantioselective reaction;99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(2-fluorophenyl)prop-2-en-1-one

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(2-fluorophenyl)prop-2-en-1-one

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-2-(2-fluorophenyl)-4-hydroxythiochroman-3-yl)methanone

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-2-(2-fluorophenyl)-4-hydroxythiochroman-3-yl)methanone

Conditions
ConditionsYield
With C31H26F6N4O2 In dichloromethane at 0℃; enantioselective reaction;99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

(E)-3-(2-chlorophenyl)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)prop-2-en-1-one

(E)-3-(2-chlorophenyl)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)prop-2-en-1-one

((2R,3S,4R)-2-(2-chlorophenyl)-4-hydroxythiochroman-3-yl)(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)methanone

((2R,3S,4R)-2-(2-chlorophenyl)-4-hydroxythiochroman-3-yl)(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)methanone

Conditions
ConditionsYield
With C31H26F6N4O2 In dichloromethane at 0℃; enantioselective reaction;99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

(E)-3-(2-bromophenyl)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)prop-2-en-1-one

(E)-3-(2-bromophenyl)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)prop-2-en-1-one

((2R,3S,4R)-2-(2-bromophenyl)-4-hydroxythiochroman-3-yl)(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)methanone

((2R,3S,4R)-2-(2-bromophenyl)-4-hydroxythiochroman-3-yl)(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)methanone

Conditions
ConditionsYield
With C31H26F6N4O2 In dichloromethane at 0℃; enantioselective reaction;99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

(E)-3-(3-bromophenyl)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)prop-2-en-1-one

(E)-3-(3-bromophenyl)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)prop-2-en-1-one

((2R,3S,4R)-2-(3-bromophenyl)-4-hydroxythiochroman-3-yl)(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)methanone

((2R,3S,4R)-2-(3-bromophenyl)-4-hydroxythiochroman-3-yl)(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)methanone

Conditions
ConditionsYield
With C31H26F6N4O2 In dichloromethane at 0℃; enantioselective reaction;99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-4-hydroxy-2-(2-(trifluoromethyl)phenyl)thiochroman-3-yl)methanone

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-4-hydroxy-2-(2-(trifluoromethyl)phenyl)thiochroman-3-yl)methanone

Conditions
ConditionsYield
With C31H26F6N4O2 In dichloromethane at 0℃; enantioselective reaction;99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

(E)-2-(3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-oxoprop-1-en-1-yl) Benzonitrile

(E)-2-(3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-oxoprop-1-en-1-yl) Benzonitrile

2-((2R,3S,4R)-3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carbonyl)-4-hydroxythiochroman-2-yl)benzonitrile

2-((2R,3S,4R)-3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carbonyl)-4-hydroxythiochroman-2-yl)benzonitrile

Conditions
ConditionsYield
With C31H26F6N4O2 In dichloromethane at 0℃; enantioselective reaction;99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

(E)-4-(3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-oxoprop-1-en-1-yl)benzonitrile

(E)-4-(3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-oxoprop-1-en-1-yl)benzonitrile

4-((2R,3S,4R)-3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carbonyl)-4-hydroxythiochroman-2-yl)benzonitrile

4-((2R,3S,4R)-3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1-carbonyl)-4-hydroxythiochroman-2-yl)benzonitrile

Conditions
ConditionsYield
With C31H26F6N4O2 In dichloromethane at 0℃; enantioselective reaction;99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(4-nitrophenyl)prop-2-en-1-one

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(4-nitrophenyl)prop-2-en-1-one

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-4-hydroxy-2-(4-nitrophenyl)thiochroman-3-yl)methanone

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-4-hydroxy-2-(4-nitrophenyl)thiochroman-3-yl)methanone

Conditions
ConditionsYield
With C31H26F6N4O2 In dichloromethane at 0℃; enantioselective reaction;99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(2-methoxyphenyl)prop-2-en-1-one

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(2-methoxyphenyl)prop-2-en-1-one

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-4-hydroxy-2-(2-methoxyphenyl)thiochroman-3-yl)methanone

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-4-hydroxy-2-(2-methoxyphenyl)thiochroman-3-yl)methanone

Conditions
ConditionsYield
With C31H26F6N4O2 In dichloromethane at 0℃; enantioselective reaction;99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(3-methoxyphenyl)prop-2-en-1-one

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(3-methoxyphenyl)prop-2-en-1-one

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-4-hydroxy-2-(3-methoxyphenyl)thiochroman-3-yl)methanone

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-4-hydroxy-2-(3-methoxyphenyl)thiochroman-3-yl)methanone

Conditions
ConditionsYield
With C31H26F6N4O2 In dichloromethane at 0℃; enantioselective reaction;99%
2-formylthiophenol
29199-11-9

2-formylthiophenol

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(naphthalen-1-yl)prop-2-en-1-one

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(naphthalen-1-yl)prop-2-en-1-one

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-4-hydroxy-2-(naphthalen-1-yl)thiochroman-3-yl)methanone

(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)((2R,3S,4R)-4-hydroxy-2-(naphthalen-1-yl)thiochroman-3-yl)methanone

Conditions
ConditionsYield
With C31H26F6N4O2 In dichloromethane at 0℃; enantioselective reaction;99%

29199-11-9Relevant articles and documents

Synthesis, characterization and supramolecular building motifs of substituted salphen- and thiasalphen–metal complexes

Kumar, Nitesh,Asatkar, Ashish K.,Panda, Snigdha,Zade, Sanjio S.

, p. 718 - 728 (2016)

Two new series of substituted salphen-metal complexes and thiasalphen–metal complexes have been synthesized. The fluorine substituted salphen-metal complexes (5, 6 and 7) were prepared by the coordination of ligand 4 (obtained by the reaction of 4,5-difluorosalicylaldehyde with o-phenylenediamine) with Ni(II), Cu(II) and Zn(II) ions, respectively. The thiasalphen–metal complexes (8, 9 and 10) were prepared strategically following the unique route of the in situ reduction of bis(o-formylphenyl)disulfide to mercaptobenzaldehyde then complexation with Ni(II), Cu(II) and Zn(II) ions, followed by Schiff base coupling with o-phenylenediamine, in a single pot. The products were characterized by elemental analysis, ESI-MS, FT-IR and1H/13C NMR spectroscopy. The structures of 4, 5, 6, 9 and 10 were established by single crystal X-ray analysis. The various non-bonding interactions resulted in fascinating supramolecular building motifs. The photophysical and electrochemical properties (band gaps, HOMO?LUMO energies) of all the six complexes were studied by UV–Vis spectroscopy and cyclic voltammetry. The optical band gaps were found to be in the range 2.31–2.79?eV.

Comparative Study of Aluminum Complexes Bearing N,O- and N,S-Schiff Base in Ring-Opening Polymerization of ε-Caprolactone and l -Lactide

Chang, Meng-Chih,Lu, Wei-Yi,Chang, Heng-Yi,Lai, Yi-Chun,Chiang, Michael Y.,Chen, Hsing-Yin,Chen, Hsuan-Ying

, p. 11292 - 11298 (2015)

A series of Al complexes bearing Schiff base and thio-Schiff base ligands were synthesized, and their application for the ring-opening polymerization of ε-caprolactone (CL) and l-lactide (LA) was studied. It was found that steric effects of the ligands caused higher polymerization rate and most importantly the Al complexes with N,S-Schiff base showed significantly higher polymerization rate than Al complexes with N,O-Schiff base (5-12-fold for CL polymerization and 2-7-fold for LA polymerization). The reaction mechanism of CL polymerization was investigated by density functional theory (DFT). The calculations predicted a lower activation energy for a process involved with an Al complex bearing an N,S-Schiff base ligand (17.6 kcal/mol) than for that of an Al complex bearing an N,O-Schiff base ligand (19.0 kcal/mol), and this magnitude of activation energy reduction is comparable to the magnitude of rate enhancement observed in the experiment. The reduction of activation energy was attributed to the catalyst-substrate destabilization effect. Using a sulfur-containing ligand to decrease the activation energy in the ring-opening polymerization process may be a new strategy to design a new Al complex with high catalytic activity.

Synthesis and evaluation of antileishmanial and cytotoxic activity of benzothiopyrane derivatives

Ortiz, Cristian,Echeverri, Fernando,Robledo, Sara,Lanari, Daniela,Curini, Massimo,Qui?ones, Wiston,Vargas, Esteban

, (2020)

In continuation of our efforts to identify promising antileishmanial agents based on the chroman scaffold, we synthesized several substituted 2H-thiochroman derivatives, including thiochromenes, thichromanones and hydrazones substituted in C-2 or C-3 with carbonyl or carboxyl groups. Thirty-two compounds were thus obtained, characterized, and evaluated against intracellular amastigotes of Leishmania (V) panamensis. Twelve compounds were active, with EC50 values lower than 40 μM, but only four compounds displayed the highest antileishmanial activity, with EC50 values below 10 μM; these all compounds possess a good Selectivity Index > 2.6. Although two active compounds were thiochromenes, a clear structure-activity relationship was not detected since each active compound has a different substitution pattern.

DEPALMITOYLATING COMPOSITIONS AND THE USE THEREOF

-

Paragraph 0359; 0369; 0371, (2021/02/19)

Disclosed herein, inter alia, are depalmitoylating compounds, compositions, and methods of use thereof.

INHIBITORS OF GLUCOSE TRANSPORTERS (GLUTS)

-

Page/Page column 62, (2020/03/29)

The present invention relates to 2,6-methanobenzo[g][1]oxacin-4-onecompounds and their analog compounds and pharmaceutically acceptable salts thereof as selective inhibitor of glucose transporters 1 and 3 (GLUTs 1 and 3), to methods of preparing said compounds, and to the use thereof as pharmaceutically active agents, especially for the prophylaxis and/or treatment of metabolic diseases, immunological diseases, autoimmune diseases, inflammation, graft versus host disease, cancer, and metastasis thereof. Furthermore, the present invention is directed to pharmaceutical composition comprising at least one of 2,6-methanobenzo[g][1]oxacin-4-one compounds and their analog compounds.

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