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3,4-Dibromothiophene
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  • Name 3,4-Dibromothiophene
  • EINECS221-546-8
  • CAS No. 3141-26-2
  • Density2.174 g/cm3
  • PSA28.24000
  • LogP3.27310
  • SolubilityN/A
  • Melting Point4-5 °C(lit.)
  • FormulaC4H2Br2S
  • Boiling Point221.5 °C at 760 mmHg
  • Molecular Weight241.934
  • Flash Point90.4 °C
  • Transport InformationN/A
  • Appearanceclear colorless to yellow liquid
  • Safety26-36-36/37/39
  • Risk Codes36/37/38-20/21/22
  • Molecular Structure
    Molecular Structure of 3141-26-2 (3,4-Dibromothiophene)
  • Hazard SymbolsIrritantXi,HarmfulXn
  • SynonymsIrritantXi,HarmfulXn
  • Article Data43

3,4-Dibromothiophene Synthetic route

3958-03-0

Tetrabromothiophene

3141-26-2

3,4-dibromothiophene

Conditions
ConditionsYield
With acetic acid; zinc In water at 20℃;92%
With hydrogen bromide; cadmium(II) chloride In methanol; dichloromethane at 35℃; for 5h;89%
In methanol; dichloromethane at 35℃; for 5h; Product distribution; electrolysis in presence of CdCl2 and HBr at 1 A (83 mA/cm2), 13.5-11.5 V; other conditions and other bromothiophenes investigated;89%

C4Br2Li2S

3958-03-0

Tetrabromothiophene

3141-26-2

3,4-dibromothiophene

Conditions
ConditionsYield
Stage #1: Tetrabromothiophene With n-butyllithium In diethyl ether; hexane at 0℃; for 1.66667 - 1.83333h; Argon atmosphere;
Stage #2: C4Br2Li2S With water at 0℃;		77%
3141-25-1

2,3,4-tribromothiophene

A

872-31-1

3-Bromothiophene

B

3141-26-2

3,4-dibromothiophene

Conditions
ConditionsYield
In N,N-dimethyl-formamide divided cell electrolysis at constant potential (-1.70 V); 0.1 M tetraethylammonium bromide, mercury electrode;A 74%
B 3%
1003-09-4

2-bromothiophene

A

872-31-1

3-Bromothiophene

B

3141-26-2

3,4-dibromothiophene

Conditions
ConditionsYield
With sodium amide; ferric nitrate In ammoniaA 72%
B n/a
1003-09-4

2-bromothiophene

A

3141-26-2

3,4-dibromothiophene

B

3141-24-0

2,3,5-tribromothiophene

C

3141-25-1

2,3,4-tribromothiophene

D

3958-03-0

Tetrabromothiophene

Conditions
ConditionsYield
With potassium tert-butylate; sodium amide In ammonia for 3h; Further byproducts given;A 65%
B n/a
C n/a
D n/a
3141-25-1

2,3,4-tribromothiophene

3141-26-2

3,4-dibromothiophene

Conditions
ConditionsYield
In N,N-dimethyl-formamide divided cell electrolysis at constant potential (-1.20 V); 0.1 M tetraethylammonium bromide, mercury electrode;60%
With methyl bromide; diethyl ether; magnesium Erhitzen des Reaktionsprodukts mit Wasserdampf;
188290-36-0

thiophene

A

872-31-1

3-Bromothiophene

B

3141-26-2

3,4-dibromothiophene

Conditions
ConditionsYield
Stage #1: thiophene With bromine In chloroform for 4h; Heating;
Stage #2: With acetic acid; zinc In water Heating;		A 23%
B 51%
39129-54-9

3,4-dibromo-2,5-dimethylthiophene

A

3141-26-2

3,4-dibromothiophene

B

70061-39-1

3,4-dibromo-2,5-dimethylthiophene-1,1-dioxide

C

508170-24-9

C6H2Br2O3S

D

301677-76-9

3,4-Dibromo-2,5-dimethylthiophene S-monoxide

Conditions
ConditionsYield
With aluminum oxide; ferric hydroxide; ethylenediaminetetraacetic acid; dihydrogen peroxide In methanol; water at 50 - 55℃; for 5h; Mechanism;A 36%
B 10%
C 16%
D 30%
In methanol; water at 50 - 55℃; for 5h; Mechanism;A 8%
B 10%
C 16%
D 30%
3958-03-0

Tetrabromothiophene

A

3141-26-2

3,4-dibromothiophene

B

3141-25-1

2,3,4-tribromothiophene

Conditions
ConditionsYield
With methyl bromide; diethyl ether; magnesium Behandeln des Reaktionsprodukts mit Wasser;
3141-27-3

2,5-dibromothiophen

A

188290-36-0

thiophene

B

1003-09-4

2-bromothiophene

C

872-31-1

3-Bromothiophene

D

3141-26-2

3,4-dibromothiophene

Conditions
ConditionsYield
With tetramethylammonium perchlorate In N,N-dimethyl-formamide Product distribution; Mechanism; controlled-potential electrolysis at reticulated vitreous carbon; further reagents;

3,4-Dibromothiophene Specification

The 3,4-Dibromothiophene is an organic compound with the formula C4H2Br2S. The IUPAC name of this chemical is 3,4-dibromothiophene. With the CAS registry number 3141-26-2, it is also named as Thiophene, 3,4-dibromo-. The product's categories are Thiophenes; Blocks; Thiazoles; Halides; Heterocycles; Thiophene & Benzothiophene; Miscellaneous; Halogenated; Organohalides; Thiophene; Thiophens; Halogenated Heterocycles; Heterocyclic Building Blocks; Thiophenes Building Blocks. Besides, it is a clear colorless to yellow liquid, which should be stored in a cool and dry place.

Physical properties about 3,4-Dibromothiophene are: (1)ACD/LogP: 3.21; (2)ACD/LogD (pH 5.5): 3.21; (3)ACD/LogD (pH 7.4): 3.21; (4)ACD/BCF (pH 5.5): 162.16; (5)ACD/BCF (pH 7.4): 162.16; (6)ACD/KOC (pH 5.5): 1328.88; (7)ACD/KOC (pH 7.4): 1328.88; (8)Polar Surface Area: 28.24 Å2; (9)Index of Refraction: 1.638; (10)Molar Refractivity: 40.01 cm3; (11)Molar Volume: 111.2 cm3; (12)Polarizability: 15.86×10-24cm3; (13)Surface Tension: 47 dyne/cm; (14)Density: 2.174 g/cm3; (15)Flash Point: 90.4 °C; (16)Enthalpy of Vaporization: 43.93 kJ/mol; (17)Boiling Point: 221.5 °C at 760 mmHg; (18)Vapour Pressure: 0.159 mmHg at 25°C.

Preparation: this chemical can be prepared by tetrabromo-thiophene. This reaction will need reagent Zn and AcOH.



Uses of 3,4-Dibromothiophene: it can be used to produce 4-bromo-thiophene-3-carbaldehyde. It will need reagent n-BuLi.

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and 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: Brc1cscc1Br
(2)InChI: InChI=1/C4H2Br2S/c5-3-1-7-2-4(3)6/h1-2H
(3)InChIKey: VGKLVWTVCUDISO-UHFFFAOYAN
(4)Std. InChI: InChI=1S/C4H2Br2S/c5-3-1-7-2-4(3)6/h1-2H
(5)Std. InChIKey: VGKLVWTVCUDISO-UHFFFAOYSA-N

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