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CAS No.: | 7311-63-9 |
---|---|
Name: | 5-Bromo-2-thiophenecarboxylic acid |
Article Data: | 38 |
Molecular Structure: | |
Formula: | C5H3BrO2S |
Molecular Weight: | 207.048 |
Synonyms: | 2-Bromothiophene-5-carboxylic acid;5-bromothiophene-2-carboxylate;2-Thiophenecarboxylic acid, 5-bromo-;5-Bromo-2-Thiophenecarboxylic Acid; |
EINECS: | -0 |
Density: | 1.923 g/cm3 |
Melting Point: | 140 °C |
Boiling Point: | 318.9 °C at 760 mmHg |
Flash Point: | 146.7 °C |
Appearance: | White to light yellow crystal powder |
Hazard Symbols: | Xi,Xn |
Risk Codes: | 36/37/38-20/21/22 |
Safety: | 26-36/37/39-22-36 |
PSA: | 65.54000 |
LogP: | 2.20880 |
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 |
5-((trimethylsilyl)ethynyl)thiophene-2-carbaldehyde
5-bromothiophene-2-carboxylic acid
Conditions | Yield |
---|---|
With Jones reagent In acetone at 5 - 20℃; for 2.5h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran at -78℃; for 0.5h; | 88% |
Conditions | Yield |
---|---|
Stage #1: 2-bromothiophene With lithium diisopropyl amide at -40℃; Stage #2: carbon dioxide at -78℃; | 85% |
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 |
2,5-dibromothiophen
carbon dioxide
A
5-bromothiophene-2-carboxylic acid
B
Thiophene-2,5-dicarboxylic acid
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% |
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; |
2-bromothiophene
carbon dioxide
A
2-thiophenylcarboxylic acid
B
5-bromothiophene-2-carboxylic acid
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% |
2-bromothiophene
A
2-thiophenylcarboxylic acid
B
5-bromothiophene-2-carboxylic acid
Conditions | Yield |
---|---|
With sodium persulfate; sodium acetate; palladium In acetic acid at 70 - 80℃; for 7h; | A 4.4% B 8.8% |
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; |
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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