5-Bromothiophene-2-carboxylic acid supplier

Name
5-Bromo-2-thiophenecarboxylic acid
EINECS -0
CAS No. 7311-63-9
Article Data38
CAS DataBase
Density 1.923 g/cm³
Solubility
Melting Point 140 °C
Formula C₅H₃BrO₂S
Boiling Point 318.9 °C at 760 mmHg
Molecular Weight 207.048
Flash Point 146.7 °C
Transport Information
Appearance White to light yellow crystal powder
Safety 26-36/37/39-22-36
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms 2-Bromothiophene-5-carboxylic acid;5-bromothiophene-2-carboxylate;2-Thiophenecarboxylic acid, 5-bromo-;5-Bromo-2-Thiophenecarboxylic Acid;
PSA 65.54000
LogP 2.20880

Synthetic route

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

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

Conditions

Conditions	Yield
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

: 206768-50-5
5-((trimethylsilyl)ethynyl)thiophene-2-carbaldehyde

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

Conditions

Conditions	Yield
With Jones reagent In acetone at 5 - 20℃; for 2.5h; Inert atmosphere;	99%

: 3141-27-3
2,5-dibromothiophen

: 124-38-9
carbon dioxide

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

Conditions

Conditions	Yield
With magnesium In tetrahydrofuran at -78℃; for 0.5h;	88%

: 1003-09-4
2-bromothiophene

: 124-38-9
carbon dioxide

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

Conditions

Conditions	Yield
Stage #1: 2-bromothiophene With lithium diisopropyl amide at -40℃; Stage #2: carbon dioxide at -78℃;	85%

: 527-72-0
2-thiophenylcarboxylic acid

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

Conditions

Conditions	Yield
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

: 3141-27-3
2,5-dibromothiophen

: 124-38-9
carbon dioxide

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

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

Conditions

Conditions	Yield
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%

...Expand

: 1003-09-4
2-bromothiophene

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

Conditions

Conditions	Yield
With palladium diacetate; sodium persulfate In acetic acid for 7h; Heating;	23.6%
With diethyl ether; sodium Behandeln des Reaktionsgemisches mit festem Kohlendioxid;

: 1003-09-4
2-bromothiophene

: 124-38-9
carbon dioxide

A: 527-72-0
2-thiophenylcarboxylic acid

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

Conditions

Conditions	Yield
With ethylaluminum dichloride In hexane; chlorobenzene at 100℃; under 22502.3 Torr; for 3h; Autoclave; Inert atmosphere; regioselective reaction;	A 6% B 10%

...Expand

: 1003-09-4
2-bromothiophene

A: 527-72-0
2-thiophenylcarboxylic acid

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

Conditions

Conditions	Yield
With sodium persulfate; sodium acetate; palladium In acetic acid at 70 - 80℃; for 7h;	A 4.4% B 8.8%

: 3141-27-3
2,5-dibromothiophen

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

Conditions

Conditions	Yield
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;

: 5370-25-2
2-Acetyl-5-bromothiophene

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

Conditions

Conditions	Yield
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

: 60-29-7
diethyl ether

: 124-38-9
carbon dioxide

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

...Expand

: 3141-27-3
2,5-dibromothiophen

: 74-96-4
ethyl bromide

: 60-29-7
diethyl ether

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

magnesium: magnesium

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

...Expand

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

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

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

Conditions

Conditions	Yield
Erhitzen auf Temperaturen oberhalb des Schmelzpunktes;

: 5751-83-7
ethyl 5-bromothiophene-2-carboxylate

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

Conditions

Conditions	Yield
With potassium hydroxide In ethanol Heating;

: 79387-71-6
(5-bromothien-2-yl)methanol

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

Conditions

Conditions	Yield
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.

: 67-56-1
methanol

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

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

Conditions

Conditions	Yield
With sulfuric acid for 12h; Heating;	100%
With thionyl chloride for 3h;	100%
With sulfuric acid for 30h; Reflux;	96%

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

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

Conditions

Conditions	Yield
In acetic acid	100%
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

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

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

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

Conditions

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; for 12h; Suzuki Coupling;	100%

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

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

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

Conditions

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; for 12h;	100%

: 109-01-3
1-methyl-piperazine

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

: C10H13BrN2OS

Conditions

Conditions	Yield
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%

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

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

Conditions

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In chloroform for 1h; Heating / reflux;	99%
With thionyl chloride
With thionyl chloride for 0.25h; Heating;

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

: 106-95-6
allyl bromide

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

Conditions

Conditions	Yield
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%

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

: 18107-18-1
diazomethyl-trimethyl-silane

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

Conditions

Conditions	Yield
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%

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

: 100-39-0
benzyl bromide

: benzyl 5-bromothiophene-2-carboxylate

Conditions

Conditions	Yield
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%

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

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

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

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water for 12h; Inert atmosphere; Reflux;	98%

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

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

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

Conditions

Conditions	Yield
With 4-(dimethylamino)pyridinium tosylate; diisopropyl-carbodiimide In dichloromethane at 20℃;	97%

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

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

: C17H16BrN3O2S

Conditions

Conditions	Yield
With pyridine; 1,3,5-trichloro-2,4,6-triazine In acetonitrile at 140℃; for 0.0833333h; Microwave irradiation;	97%

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

: 98-80-6
phenylboronic acid

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

Conditions

Conditions	Yield
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;

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

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

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

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform for 72h; Inert atmosphere;	95.8%

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

: 79-03-8
propionyl chloride

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

Conditions

Conditions	Yield
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%

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

: 55552-70-0
furan-3-boronic acid

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

Conditions

Conditions	Yield
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%

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

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

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

Conditions

Conditions	Yield
Multistep reaction.;	95%

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

: 613-94-5
benzoic acid hydrazide

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

Conditions

Conditions	Yield
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%

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

: 19158-51-1
P-toluenesulfonyl cyanide

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

Conditions

Conditions	Yield
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%

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

: 98-88-4
benzoyl chloride

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

Conditions

Conditions	Yield
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%

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

: 2949-92-0
methanethiosulfonic acid S-methyl ester

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

Conditions

Conditions	Yield
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%

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

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

: 1092486-06-0
C23H20BrN5O3S

Conditions

Conditions	Yield
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;

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

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

Conditions

Conditions	Yield
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%

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

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

: C8H8BrNOS

Conditions

Conditions	Yield
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%

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

: 38330-80-2
monomethyl monopotassium malonate

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

Conditions

Conditions	Yield
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%

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

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

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

Conditions

Conditions	Yield
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%

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

: 5720-05-8
4-methylphenylboronic acid

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

Conditions

Conditions	Yield
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%

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

: 3141-27-3
2,5-dibromothiophen

Conditions

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

5-Bromothiophene-2-carboxylic acid Specification

The 5-Bromothiophene-2-carboxylic acid is an organic compound with the formula C₅H₃BrO₂S. The IUPAC name of this chemical is 5-bromothiophene-2-carboxylic acid. With the CAS registry number 7311-63-9, it is also named as 2-Thiophenecarboxylic acid, 5-bromo-. The product's categories are Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Carboxylic Acids; Thiophenes & Benzothiophenes; Thiophene & Benzothiophene; Carboxylic Acids; Thiophenes & Benzothiophenes; Halogenated Heterocycles; Heterocyclic Building Blocks; Thiophenes; Thiophenes Building Blocks. Besides, it is a white to light yellow crystal powder, which should be stored in a closed cool and dry place.

Physical properties about 5-Bromothiophene-2-carboxylic acid are: (1)ACD/LogP: 3.10 ; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 8.343; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 2; (7)#H bond donors: 1; (8)#Freely Rotating Bonds: 1; (9)Polar Surface Area: 65.54 Å²; (10)Index of Refraction: 1.65; (11)Molar Refractivity: 39.257 cm³; (12)Molar Volume: 107.627 cm³; (13)Polarizability: 15.563×10^-24cm³; (14)Surface Tension: 62.865 dyne/cm; (15)Density: 1.924 g/cm³; (16)Flash Point: 146.67 °C; (17)Enthalpy of Vaporization: 59.168 kJ/mol; (18)Boiling Point: 318.907 °C at 760 mmHg.

Preparation: this chemical can be prepared by thiophene-2-carboxylic acid. This reaction will need reagent aqueous acetic acid and bromine.

Uses of 5-Bromothiophene-2-carboxylic acid: it can be used to produce 5-bromo-thiophene-2-carboxylic acid methyl ester. It will need reagent H₂SO₄. The yield is about 95%.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(sc1C(=O)O)Br
(2)InChI: InChI=1/C5H3BrO2S/c6-4-2-1-3(9-4)5(7)8/h1-2H,(H,7,8)
(3)InChIKey: COWZPSUDTMGBAT-UHFFFAOYAP
(4)Std. InChI: InChI=1S/C5H3BrO2S/c6-4-2-1-3(9-4)5(7)8/h1-2H,(H,7,8)
(5)Std. InChIKey: COWZPSUDTMGBAT-UHFFFAOYSA-N

Product Name

5-Bromo-2-thiophenecarboxylic acid

Synthetic route

5-Bromothiophene-2-carboxylic acid Specification

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