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1003-09-4

Basic Information
CAS No.: 1003-09-4
Name: 2-Bromothiophene
Article Data: 78
Cas Database
Molecular Structure:
Molecular Structure of 1003-09-4 (2-Bromothiophene)
Formula: C4H3BrS
Molecular Weight: 163.038
Synonyms: 2-Thienyl bromide;Thiophene, 2-bromo-;2-Bromo Thiophene;2-Bromothiophene 96%;2-Bromothiophen;
EINECS: 213-699-4
Density: 1.714 g/cm3
Melting Point: -10 °C
Boiling Point: 149.999 °C at 760 mmHg
Flash Point: 47.052 °C
Solubility: Immiscible in water
Appearance: colorless to light yellow transparent liquid
Hazard Symbols: ToxicT,DangerousN,HarmfulXn
Risk Codes: 10-25-41-51/53-36/37/38-23/24-22-20/21/22
Safety: 26-36/37/39-45-61-16-36
Transport Information: UN 2929 6.1/PG 2
PSA: 28.24000
LogP: 2.51060
Synthetic route
188290-36-0

thiophene

1003-09-4

2-bromothiophene

Conditions
ConditionsYield
With hydrogen bromide; dihydrogen peroxide In diethyl ether at 15 - 20℃; for 0.25h;94%
With tetraethylammonium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 20℃; for 3h; chemoselective reaction;92%
With phenyltrimethylammonium tribromide In dichloromethane at -10 - 0℃; for 4h;92.6%
188290-36-0

thiophene

1003-09-4

2-bromothiophene

Conditions
ConditionsYield
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one for 0.0222222h; microwave irradiation;85%
188290-36-0

thiophene

506-68-3

bromocyane

A

1003-09-4

2-bromothiophene

B

3141-27-3

2,5-dibromothiophen

Conditions
ConditionsYield
at 45 - 50℃;
With bromine at 45 - 50℃;
at 45 - 50℃;
188290-36-0

thiophene

79-15-2

N-bromoacetamide

1003-09-4

2-bromothiophene

188290-36-0

thiophene

A

1003-09-4

2-bromothiophene

B

3141-27-3

2,5-dibromothiophen

Conditions
ConditionsYield
With bromine Behandeln des Produkts mit Wasser; anschliessend mit Natronlauge und mit alkoh. Kali;
With tetrachloromethane; bromine
With bromine; benzene
Behandlung des Reaktionsproduktes mit alkoh. Kali;
With dihydrogen peroxide; ammonium bromide; acetic acid In water for 20h; Reagent/catalyst; Time; Green chemistry; regioselective reaction;A 80 %Chromat.
B 8 %Chromat.
3141-27-3

2,5-dibromothiophen

1003-09-4

2-bromothiophene

Conditions
ConditionsYield
With magnesium Behandeln der Magnesiumverbindung mit Salzsaeure;
With quinoline; copper
With indium; 1-n-butyl-3-methylimidazolim bromide at 95℃; for 14h; Green chemistry;90 %Chromat.
With C33H30F3N2NiO2P; tert-butylmagnesium chloride In tetrahydrofuran; diethyl ether at 70℃; for 24h; Schlenk technique; Inert atmosphere; chemoselective reaction;81 %Chromat.
60-29-7

diethyl ether

506-68-3

bromocyane

[2]thienyl magnesium (1+); bromide

A

1003-09-4

2-bromothiophene

B

1003-31-2

thiophene-2-carbonitrile

60-29-7

diethyl ether

506-78-5

cyanogen iodide

[2]thienyl magnesium (1+); bromide

A

1003-09-4

2-bromothiophene

B

3437-95-4

2-Iodothiophene

60-29-7

diethyl ether

[2]thienyl magnesium (1+); bromide

506-77-4

cyanogen chloride

A

1003-09-4

2-bromothiophene

B

1003-31-2

thiophene-2-carbonitrile

188290-36-0

thiophene

128-08-5

N-Bromosuccinimide

1003-09-4

2-bromothiophene

Conditions
ConditionsYield
In acetic acid at 20℃; Rate constant; Thermodynamic data; activation energy;
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    2-Bromothiophene CAS No.:1003-09-4 Name: 2-Bromothiophene Synonyms: 2-Thienyl bromide Molecular Structure Molecular Formula: C4H3BrS Molecular Weight: 163.03 CAS Registry Number: 1003-09-4 EINECS

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Specification

The 2-Bromothiophene is an organic compound with the formula C4H3BrS. The IUPAC name of this chemical is 2-bromothiophene. With the CAS registry number 1003-09-4, it is also named as Bromothiophene. The product's categories are Thiophenes; Halides; Thiophenes & Benzothiophenes; Thiophene & Benzothiophene; Thiophenes & Benzothiophenes. Besides, it is a colorless to light yellow transparent liquid, which should be stored in a closed dark and cool place. It can be used for organic synthesis and pharmaceutical intermediates.

Physical properties about 2-Bromothiophene are: (1)ACD/LogP: 2.94; (2)ACD/LogD (pH 5.5): 2.944; (3)ACD/LogD (pH 7.4): 2.944; (4)ACD/BCF (pH 5.5): 101.742; (5)ACD/BCF (pH 7.4): 101.742; (6)ACD/KOC (pH 5.5): 951.875; (7)ACD/KOC (pH 7.4): 951.875; (8)Polar Surface Area: 28.24 Å2; (9)Index of Refraction: 1.595; (10)Molar Refractivity: 32.327 cm3; (11)Molar Volume: 95.098 cm3; (12)Polarizability: 12.816×10-24cm3; (13)Surface Tension: 41.199 dyne/cm; (14)Density: 1.714 g/cm3; (15)Flash Point: 47.052 °C; (16)Enthalpy of Vaporization: 37.095 kJ/mol; (17)Boiling Point: 149.999 °C at 760 mmHg; (18)Vapour Pressure: 4.993 mmHg at 25°C.

Preparation: this chemical can be prepared by thiophene. This reaction will need reagent PyHBrCl2 and solvent aq. methanol. The reaction time is 5 min with reaction temperature of 20 °C. The yield is about 74%.



Uses of 2-Bromothiophene: it can be used to produce 4-(5-bromo-thiophen-2-yl)-4-oxo-butyric acid at temperature of -5 - 20 °C. This reaction is a kind of Friedel-Crafts acylation. It will need reagent AlCl3 and solvent nitrobenzene. The yield is about 95%.

When you are using this chemical, please be cautious about it as the following:
It is flammable and harmful by inhalation, in contact with skin and if swallowed. Please keep away from sources of ignition - No smoking.It is toxic by inhalation, in contact with skin and if swallowed and very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 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 and risk of serious damage to eyes. When you are using it, wear suitable gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(sc1)Br
(2)InChI: InChI=1/C4H3BrS/c5-4-2-1-3-6-4/h1-3H
(3)InChIKey: TUCRZHGAIRVWTI-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C4H3BrS/c5-4-2-1-3-6-4/h1-3H
(5)Std. InChIKey: TUCRZHGAIRVWTI-UHFFFAOYSA-N