| Identification | More | [Name]
2,3-Dibromothiophene | [CAS]
3140-93-0 | [Synonyms]
2,3-DIBROMOTHIOPHENE
AKOS 91257
BUTTPARK 146\50-38
2,3-Dibromothiophene, 98+% | [EINECS(EC#)]
221-542-6 | [Molecular Formula]
C4H2Br2S | [MDL Number]
MFCD00005418 | [Molecular Weight]
241.93 | [MOL File]
3140-93-0.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellowish to brownish liquid | [Melting point ]
-17.5°C | [Boiling point ]
218-219 °C (lit.) | [density ]
2.137 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.632(lit.)
| [Fp ]
125 °F
| [storage temp. ]
Flammables area | [form ]
liquid | [color ]
White to Yellow to Green | [Specific Gravity]
2.137 | [Sensitive ]
Light Sensitive | [Detection Methods]
GC,NMR | [BRN ]
107512 | [InChI]
InChI=1S/C4H2Br2S/c5-3-1-2-7-4(3)6/h1-2H | [InChIKey]
ATRJNSFQBYKFSM-UHFFFAOYSA-N | [SMILES]
C1(Br)SC=CC=1Br | [CAS DataBase Reference]
3140-93-0(CAS DataBase Reference) | [NIST Chemistry Reference]
Thiophene, 2,3-dibromo-(3140-93-0) | [Storage Precautions]
Light sensitive |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,F,Xi | [Risk Statements ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S16:Keep away from sources of ignition-No smoking .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [F ]
8 | [Hazard Note ]
Flammable/Irritant | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29349990 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Hexane-->Water-->3-Bromothiophene-->Perchloric acid-->4,5-Dibromothiophene-2-carboxylic acid-->2,4-Dibromothiophene-->Ethylmagnesium bromide-->N-Bromosuccinimide | [Preparation Products]
2-Formylthiophene-3-boronic acid-->3-Bromothiophene-2-carbaldehyde-->4,5-Dibromothiophene-2-carboxaldehyde-->4,5-Dibromothiophene-2-sulphonyl chloride-->Thiophene, 2,3-dibromo-5-methyl--->5,7-Dodecadiyne-1,12-diol-->3,5-Dibromo-2-methylthiophene-->3-Bromothiophene-2-carbonitrile-->3-(Trimethylsilylethynyl)thiophene 97-->2,3-dibromo-5-chlorothiophene |
| Hazard Information | Back Directory | [Chemical Properties]
clear yellowish to brownish liquid | [Uses]
2,3-Dibromothiophene (cas# 3140-93-0) is a compound useful in organic synthesis. | [Synthesis]
The general procedure for the synthesis of 2,3-dibromothiophene from 3-bromothiophene was as follows: 3-bromothiophene (16.3 g, 100 mmol) was added to a suspension of N-bromosuccinimide (NBS, 17.8 g, 100 mmol) in hexane (50 mL), followed by perchloric acid (70% aqueous, 0.7 mL, 5 mol%). The reaction mixture was stirred at room temperature for 24 h, after which potassium carbonate (200 mg) was added to neutralize. The reaction mixture was filtered and the solid was washed with hexane. The organic phases were combined and concentrated and the residue was purified by vacuum distillation. The final product yield was 89%. | [References]
[1] Journal of Organic Chemistry, 1993, vol. 58, # 11, p. 3072 - 3075
[2] Acta chemica Scandinavica (Copenhagen, Denmark : 1989), 1992, vol. 46, # 7, p. 654 - 660
[3] RSC Advances, 2014, vol. 4, # 96, p. 53531 - 53542
[4] Organic Electronics: physics, materials, applications, 2015, vol. 17, p. 167 - 177
[5] Organic Electronics: physics, materials, applications, 2014, vol. 17, p. 167 - 177 |
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