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7311-63-9 Usage

Chemical Properties

White to light yellow crystal powder

Uses

Different sources of media describe the Uses of 7311-63-9 differently. You can refer to the following data:
1. A thiophene derivative with genotoxicity
2. 5-Bromo-2-thiophenecarboxylic acid may be used in the preparation of:5-bromo-2-thiophenecarboxylic acid butyl estersulphonyl-tetrafluorophenyl (STP) estersnew porphyrin sensitizers based on donor-Π-acceptor (D-Π-A) approach

Check Digit Verification of cas no

The CAS Registry Mumber 7311-63-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,3,1 and 1 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 7311-63:
(6*7)+(5*3)+(4*1)+(3*1)+(2*6)+(1*3)=79
79 % 10 = 9
So 7311-63-9 is a valid CAS Registry Number.
InChI:InChI=1/C5H3BrO2S/c6-4-1-3(2-9-4)5(7)8/h1-2H,(H,7,8)

7311-63-9 Well-known Company Product Price

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  • Detail
  • TCI America

  • (B2302)  5-Bromo-2-thiophenecarboxylic Acid  >98.0%(GC)(T)

  • 7311-63-9

  • 1g

  • 290.00CNY

  • Detail
  • TCI America

  • (B2302)  5-Bromo-2-thiophenecarboxylic Acid  >98.0%(GC)(T)

  • 7311-63-9

  • 5g

  • 880.00CNY

  • Detail
  • Alfa Aesar

  • (A19242)  5-Bromothiophene-2-carboxylic acid, 98%   

  • 7311-63-9

  • 1g

  • 228.0CNY

  • Detail
  • Alfa Aesar

  • (A19242)  5-Bromothiophene-2-carboxylic acid, 98%   

  • 7311-63-9

  • 5g

  • 815.0CNY

  • Detail
  • Alfa Aesar

  • (A19242)  5-Bromothiophene-2-carboxylic acid, 98%   

  • 7311-63-9

  • 25g

  • 3425.0CNY

  • Detail
  • Aldrich

  • (467944)  5-Bromo-2-thiophenecarboxylicacid  97%

  • 7311-63-9

  • 467944-1G

  • 345.15CNY

  • Detail
  • Aldrich

  • (467944)  5-Bromo-2-thiophenecarboxylicacid  97%

  • 7311-63-9

  • 467944-5G

  • 1,359.54CNY

  • Detail

7311-63-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Bromo-2-thiophenecarboxylic acid

1.2 Other means of identification

Product number -
Other names 5-bromothiophene-2-carboxylic acid

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:7311-63-9 SDS

7311-63-9Synthetic route

5-bromo-2-thiophencarboxaldehyde
4701-17-1

5-bromo-2-thiophencarboxaldehyde

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

Conditions
ConditionsYield
With chromium(III) oxide; sulfuric acid In acetone at 5 - 20℃; for 2.5h;99%
With potassium permanganate In acetone at 0 - 20℃; for 3h;85%
With potassium permanganate
5-((trimethylsilyl)ethynyl)thiophene-2-carbaldehyde
206768-50-5

5-((trimethylsilyl)ethynyl)thiophene-2-carbaldehyde

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

Conditions
ConditionsYield
With Jones reagent In acetone at 5 - 20℃; for 2.5h; Inert atmosphere;99%
2,5-dibromothiophen
3141-27-3

2,5-dibromothiophen

carbon dioxide
124-38-9

carbon dioxide

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

Conditions
ConditionsYield
With magnesium In tetrahydrofuran at -78℃; for 0.5h;88%
2-bromothiophene
1003-09-4

2-bromothiophene

carbon dioxide
124-38-9

carbon dioxide

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 2-bromothiophene With lithium diisopropyl amide at -40℃;
Stage #2: carbon dioxide at -78℃;
85%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

Conditions
ConditionsYield
With bromine; acetic acid at 0℃;47%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 75℃; for 12h; Inert atmosphere; Schlenk technique;35%
With bromine; acetic acid
With bromine In acetic acid at 20℃; for 16h;
With bromine
2,5-dibromothiophen
3141-27-3

2,5-dibromothiophen

carbon dioxide
124-38-9

carbon dioxide

A

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

B

Thiophene-2,5-dicarboxylic acid
4282-31-9

Thiophene-2,5-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: 2,5-dibromothiophen; carbon dioxide With tert.-butyl lithium In pentane at -70℃; Inert atmosphere;
Stage #2: With sulfuric acid; water In pentane at 20℃; Inert atmosphere;
A 34%
B 5%
2-bromothiophene
1003-09-4

2-bromothiophene

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

Conditions
ConditionsYield
With palladium diacetate; sodium persulfate In acetic acid for 7h; Heating;23.6%
With diethyl ether; sodium Behandeln des Reaktionsgemisches mit festem Kohlendioxid;
2-bromothiophene
1003-09-4

2-bromothiophene

carbon dioxide
124-38-9

carbon dioxide

A

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

B

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

Conditions
ConditionsYield
With ethylaluminum dichloride In hexane; chlorobenzene at 100℃; under 22502.3 Torr; for 3h; Autoclave; Inert atmosphere; regioselective reaction;A 6%
B 10%
2-bromothiophene
1003-09-4

2-bromothiophene

A

2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

B

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

Conditions
ConditionsYield
With sodium persulfate; sodium acetate; palladium In acetic acid at 70 - 80℃; for 7h;A 4.4%
B 8.8%
2,5-dibromothiophen
3141-27-3

2,5-dibromothiophen

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

Conditions
ConditionsYield
With diethyl ether; ethylmagnesium bromide Behandeln der Reaktionsloesung mit Kohlendioxid;
With methyl bromide; diethyl ether; magnesium Behandeln der Reaktionsloesung mit Kohlendioxid;
With n-butyllithium In tetrahydrofuran; hydrogenchloride liquid HCl;
2-Acetyl-5-bromothiophene
5370-25-2

2-Acetyl-5-bromothiophene

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; potassium permanganate; water
With alkaline aqueous sodium hypochlorite solution
With 1,4-dioxane; alkaline aqueous sodium hypobromite solution
With bromine; sodium hydroxide In 1,4-dioxane
5-bromo-[2]thienyl sodium

5-bromo-[2]thienyl sodium

diethyl ether
60-29-7

diethyl ether

carbon dioxide
124-38-9

carbon dioxide

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

2,5-dibromothiophen
3141-27-3

2,5-dibromothiophen

ethyl bromide
74-96-4

ethyl bromide

diethyl ether
60-29-7

diethyl ether

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

magnesium

magnesium

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

N,N'-bis-(5-bromo-thiophene-2-carbonyl)-o-phenylenediamine
859489-42-2

N,N'-bis-(5-bromo-thiophene-2-carbonyl)-o-phenylenediamine

A

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

B

2-<5-bromo-<2>thienyl>-benzimidazole

2-<5-bromo-<2>thienyl>-benzimidazole

Conditions
ConditionsYield
Erhitzen auf Temperaturen oberhalb des Schmelzpunktes;
ethyl 5-bromothiophene-2-carboxylate
5751-83-7

ethyl 5-bromothiophene-2-carboxylate

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol Heating;
(5-bromothien-2-yl)methanol
79387-71-6

(5-bromothien-2-yl)methanol

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

Conditions
ConditionsYield
With 3,5-Lutidine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; sodium persulfate; tris(2,2'‐bipyridine)ruthenium(II) hexafluorophosphate In water; acetonitrile at 20℃; for 48h; Sealed tube; Irradiation;15 %Chromat.
methanol
67-56-1

methanol

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

5-bromo-2-thiophenecarboxylic acid methyl ester
62224-19-5

5-bromo-2-thiophenecarboxylic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid for 12h; Heating;100%
With thionyl chloride for 3h;100%
With sulfuric acid for 30h; Reflux;96%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

5-bromo-2-thiophenecarboxylic acid methyl ester
62224-19-5

5-bromo-2-thiophenecarboxylic acid methyl ester

Conditions
ConditionsYield
In acetic acid100%
Multi-step reaction with 2 steps
1: SOCl2 / 0.25 h / Heating
2: 1 h / Heating
View Scheme
In acetic acid
With sulfuric acid In methanol; ethyl acetate
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo-[2,3-b]pyridine
942919-24-6

1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo-[2,3-b]pyridine

5-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]2-thiophenecarboxylic acid
943321-66-2

5-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]2-thiophenecarboxylic acid

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; for 12h; Suzuki Coupling;100%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole
1044851-76-4

5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole

5-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acid
656226-60-7

5-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; for 12h;100%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

C10H13BrN2OS

C10H13BrN2OS

Conditions
ConditionsYield
Stage #1: 5-bromothiophene-2-carboxylic acid With thionyl chloride In dichloromethane; N,N-dimethyl-formamide for 3h; Reflux;
Stage #2: With potassium carbonate In dichloromethane at 0 - 10℃; for 0.333333h;
Stage #3: 1-methyl-piperazine In dichloromethane at 20℃; for 2h;
100%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

5-bromothiophene-2-carbonyl chloride
31555-60-9

5-bromothiophene-2-carbonyl chloride

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide In chloroform for 1h; Heating / reflux;99%
With thionyl chloride
With thionyl chloride for 0.25h; Heating;
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

allyl bromide
106-95-6

allyl bromide

5-allylthiophene-2-carboxylic acid
77756-24-2

5-allylthiophene-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 5-bromothiophene-2-carboxylic acid; allyl bromide With isopropylmagnesium bromide In tetrahydrofuran at -40℃; for 3h; Solid phase reaction;
Stage #2: In dichloromethane at 20℃; for 0.25h; Hydrolysis; Further stages.;
99%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

5-bromo-2-thiophenecarboxylic acid methyl ester
62224-19-5

5-bromo-2-thiophenecarboxylic acid methyl ester

Conditions
ConditionsYield
In methanol; diethyl ether; ethyl acetate at 20℃; Cooling with ice;98%
In methanol; diethyl ether; ethyl acetate for 24.33h; Cooling with ice;98%
In methanol; diethyl ether; ethyl acetate at 20℃; Temperature; Time; Cooling with ice;98%
In methanol; diethyl ether; ethyl acetate for 24h;98%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

benzyl bromide
100-39-0

benzyl bromide

benzyl 5-bromothiophene-2-carboxylate

benzyl 5-bromothiophene-2-carboxylate

Conditions
ConditionsYield
Stage #1: 5-bromothiophene-2-carboxylic acid With tetra-(n-butyl)ammonium iodide; caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 20h;
98%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

(3‐cyanophenyl)boronic acid
150255-96-2

(3‐cyanophenyl)boronic acid

5-(3-cyanophenyl)thiophene-2-carboxylic acid
253679-30-0

5-(3-cyanophenyl)thiophene-2-carboxylic acid

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water for 12h; Inert atmosphere; Reflux;98%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

2-octyldodecan-1-ol
5333-42-6

2-octyldodecan-1-ol

2-octyl-dodecyl 5-bromothiophene-2-carboxylate
808142-41-8

2-octyl-dodecyl 5-bromothiophene-2-carboxylate

Conditions
ConditionsYield
With 4-(dimethylamino)pyridinium tosylate; diisopropyl-carbodiimide In dichloromethane at 20℃;97%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

4-(2-keto-1-benzimidazolinyl)piperidine
20662-53-7

4-(2-keto-1-benzimidazolinyl)piperidine

C17H16BrN3O2S

C17H16BrN3O2S

Conditions
ConditionsYield
With pyridine; 1,3,5-trichloro-2,4,6-triazine In acetonitrile at 140℃; for 0.0833333h; Microwave irradiation;97%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

phenylboronic acid
98-80-6

phenylboronic acid

5-phenyl-2-thiophenecarboxylic acid
19163-24-7

5-phenyl-2-thiophenecarboxylic acid

Conditions
ConditionsYield
With disodium hydrogenphosphate; Pd(OAc)2(2-amino-4,6-dihydroxypyrimidine disodium salt)2 In water at 120℃; for 0.166667h; Suzuki-Miyaura coupling; Microwave irradiation;96%
With 1-methyl-pyrrolidin-2-one; tetrakis(triphenylphosphine) palladium(0); sodium carbonate Suzuki coupling; Heating;
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

(2S)-2-methyl-1-butanol
1565-80-6

(2S)-2-methyl-1-butanol

(S)-2-methylbuthyl-5-bromothyophene-2-carboxylate

(S)-2-methylbuthyl-5-bromothyophene-2-carboxylate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform for 72h; Inert atmosphere;95.8%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

propionyl chloride
79-03-8

propionyl chloride

5-propanoylthiophene-2-carboxylic acid
4565-27-9

5-propanoylthiophene-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 5-bromothiophene-2-carboxylic acid; propionyl chloride With isopropylmagnesium bromide In tetrahydrofuran at -40 - -10℃; for 12h; Solid phase reaction;
Stage #2: In dichloromethane at 20℃; for 0.25h; Hydrolysis; Further stages.;
95%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

furan-3-boronic acid
55552-70-0

furan-3-boronic acid

5-furan-3-ylthiophene-2-carboxylic acid

5-furan-3-ylthiophene-2-carboxylic acid

Conditions
ConditionsYield
With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; palladium diacetate; potassium carbonate In water at 150℃; for 0.166667h; Suzuki-Miyaura coupling; microwave irradiation;95%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

4-Iodo-N,N-dimethylaniline
698-70-4

4-Iodo-N,N-dimethylaniline

5-[4-(dimethylamino)phenyl]thiophene-2-carboxylic acid

5-[4-(dimethylamino)phenyl]thiophene-2-carboxylic acid

Conditions
ConditionsYield
Multistep reaction.;95%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

2-(5-bromo-thiophen-2-yl)-5-phenyl-[1,3,4]oxadiazole
35403-81-7

2-(5-bromo-thiophen-2-yl)-5-phenyl-[1,3,4]oxadiazole

Conditions
ConditionsYield
Stage #1: 5-bromothiophene-2-carboxylic acid; benzoic acid hydrazide With N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 20℃; for 0.75h;
Stage #2: With Burgess Reagent In tetrahydrofuran at 20℃;
95%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

P-toluenesulfonyl cyanide
19158-51-1

P-toluenesulfonyl cyanide

5-cyanothiophene-2-carboxylic acid
59786-39-9

5-cyanothiophene-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 5-bromothiophene-2-carboxylic acid; P-toluenesulfonyl cyanide With isopropylmagnesium bromide In tetrahydrofuran at -40℃; for 2h; Solid phase reaction;
Stage #2: In dichloromethane at 20℃; for 0.25h; Hydrolysis; Further stages.;
93%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

benzoyl chloride
98-88-4

benzoyl chloride

5-(Phenylcarbonyl)thiophene-2-carboxylic acid
79505-01-4

5-(Phenylcarbonyl)thiophene-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 5-bromothiophene-2-carboxylic acid; benzoyl chloride With isopropylmagnesium bromide In tetrahydrofuran at -40 - -10℃; for 12h; Solid phase reaction;
Stage #2: In dichloromethane at 20℃; for 0.25h; Hydrolysis; Further stages.;
93%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

methanethiosulfonic acid S-methyl ester
2949-92-0

methanethiosulfonic acid S-methyl ester

5-methylsulfanyl-thiophene-2-carboxylic acid
20873-58-9

5-methylsulfanyl-thiophene-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 5-bromothiophene-2-carboxylic acid With methylmagnesium chloride; lithium chloride In tetrahydrofuran at -20℃; for 0.333333h;
Stage #2: With TurboGrignard In tetrahydrofuran at 20℃; for 0.5h;
Stage #3: methanethiosulfonic acid S-methyl ester In tetrahydrofuran at -20 - 20℃; Further stages.;
93%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

N-[2-amino-1-(3-amino-3-oxopropyl)-1H-benzimidazol-5-yl]-N-methylbenzamide
658700-12-0

N-[2-amino-1-(3-amino-3-oxopropyl)-1H-benzimidazol-5-yl]-N-methylbenzamide

C23H20BrN5O3S
1092486-06-0

C23H20BrN5O3S

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;93%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

5-bromo-thiophene-2-carboxylic acid hydrazide
98027-27-1

5-bromo-thiophene-2-carboxylic acid hydrazide

Conditions
ConditionsYield
Stage #1: 5-bromothiophene-2-carboxylic acid With dicyclohexyl-carbodiimide In acetonitrile at 0 - 20℃;
Stage #2: With benzotriazol-1-ol In acetonitrile at 0 - 20℃;
Stage #3: With hydrazine hydrate In acetonitrile at 0 - 20℃; for 5h;
93%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

1-amino-2-propene
107-11-9

1-amino-2-propene

C8H8BrNOS

C8H8BrNOS

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;93%
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;93%
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;93%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

monomethyl monopotassium malonate
38330-80-2

monomethyl monopotassium malonate

methyl 3-(5-bromothiophen-2-yl)-3-oxopropionate
137090-42-7

methyl 3-(5-bromothiophen-2-yl)-3-oxopropionate

Conditions
ConditionsYield
Stage #1: 5-bromothiophene-2-carboxylic acid With 1,1'-carbonyldiimidazole In acetonitrile at 20℃;
Stage #2: monomethyl monopotassium malonate With magnesium chloride at 20℃; for 18h;
92.3%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

ethyl 2-bromomethyl-2-propenoate
17435-72-2

ethyl 2-bromomethyl-2-propenoate

5-[2-(ethoxycarbonyl)allyl]thiophene-2-carboxylic acid

5-[2-(ethoxycarbonyl)allyl]thiophene-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 5-bromothiophene-2-carboxylic acid; ethyl 2-bromomethyl-2-propenoate With isopropylmagnesium bromide In tetrahydrofuran at -40℃; for 3h; Solid phase reaction;
Stage #2: In dichloromethane at 20℃; for 0.25h; Hydrolysis; Further stages.;
92%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

5-(4-methylphenyl)thiophene-2-carboxylic acid
40808-21-7

5-(4-methylphenyl)thiophene-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 5-bromothiophene-2-carboxylic acid; 4-methylphenylboronic acid; palladium diacetate In water at 20℃; for 0.0833333h; Suzuki-Miyaura coupling;
Stage #2: With potassium hydroxide In water at 20 - 75℃; for 3h;
92%
5-bromothiophene-2-carboxylic acid
7311-63-9

5-bromothiophene-2-carboxylic acid

2,5-dibromothiophen
3141-27-3

2,5-dibromothiophen

Conditions
ConditionsYield
With potassium phosphate; tetrabuthylammonium tribromide In acetonitrile at 100℃;92%

7311-63-9Relevant articles and documents

Combining photoredox catalysis and oxoammonium cations for the oxidation of aromatic alcohols to carboxylic acids

Nandi, Jyoti,Hutcheson, Ellen L.,Leadbeater, Nicholas E.

supporting information, (2020/12/25)

A methodology is reported for converting alcohols to the corresponding carboxylic acids. A dual catalytic system involving a merger of photoredox catalysis and 4-acetamido-TEMPO is employed to carry out this oxidation process.

Effect of alkyl chain and linking units on mesophase transitions and molecular order of rod-like thiophene mesogens: 13C NMR investigation

Santhosh Kumar Reddy,Lobo, Nitin P.,Narasimhaswamy

supporting information, p. 598 - 612 (2017/12/28)

Thermotropic liquid crystals with π-conjugated cores are increasingly witnessed due to their promising optoelectronic and optophotonic properties. As π-conjugated mesogens are often realized by direct linking of the rings of the core, the mesophase transitions are usually modulated by inserting the required alkyl/alkoxy chains either at a terminal or lateral location. In this work, five mesogens in which thiophene and two phenyl rings are common in the core unit with terminal alkyl/alkoxy chains are investigated to probe the influence of (a) a terminal alkyl chain on the mesophase characteristics, (b) the linking units on the mesophase range and (c) the disparity of thiophene orientational constraints. The mesophase properties reveal that whenever the alkyl chain is located at one end of the molecule, polymesomorphism is observed. The XRD studies reveal layer ordering typical of smectic mesophases with lower temperature and higher order phases, namely SmB and CrE phases. A detailed 13C NMR study of the mesogens in the liquid crystalline phase indicates that the order parameters are governed by the nature of the substitution of thiophene and its linkage with two phenyl rings. Importantly, the 13C NMR data of the terminal chains in the liquid crystalline phase are compared with the recently reported thiophene mesogen in which the n-hexyl chain is located at the lateral position and completely different orientation characteristics were found for the terminal versus lateral chains.

Structure–Activity Relationship of Propargylamine-Based HDAC Inhibitors

Wünsch, Matthias,Senger, Johanna,Schultheisz, Philipp,Schwarzbich, Sabrina,Schmidtkunz, Karin,Michalek, Carmela,Kla?, Michaela,Goskowitz, Stefanie,Borchert, Philipp,Praetorius, Lucas,Sippl, Wolfgang,Jung, Manfred,Sewald, Norbert

supporting information, p. 2044 - 2053 (2017/12/07)

As histone deacetylases (HDACs) play an important role in the treatment of cancer, their selective inhibition has been the subject of various studies. These continuous investigations have given rise to a large collection of pan- and selective HDAC inhibitors, containing diverse US Food and Drug Administration (FDA)-approved representatives. In previous studies, a class of alkyne-based HDAC inhibitors was presented. We modified this scaffold in two previously neglected regions and compared their cytotoxicity and affinity toward HDAC1, HDAC6, and HDAC8. We were able to show that R-configured propargylamines contribute to increased selectivity for HDAC6. Docking studies on available HDAC crystal structures were carried out to rationalize the observed selectivity of the compounds. Substitution of the aromatic portion by a thiophene derivative results in high affinity and low cytotoxicity, indicating an improved drug tolerance.

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