| Identification | More | [Name]
2-Bromothiophene | [CAS]
1003-09-4 | [Synonyms]
2-BROMOTHIOPHENE
2-THIENYL BROMIDE
ALPHA-THIENYL BROMIDE
TIMTEC-BB SBB003931
2-bromo-thiophen
Thienyl bromide
thiophene,2-bromo-
2-Bromothiophene99%
2-Bromothiophene, 98+%
forTipepidine
2-Bromothiaphene | [EINECS(EC#)]
213-699-4 | [Molecular Formula]
C4H3BrS | [MDL Number]
MFCD00005417 | [Molecular Weight]
163.04 | [MOL File]
1003-09-4.mol |
| Chemical Properties | Back Directory | [Appearance]
colorless to light yellow liqui | [Melting point ]
-10 °C
| [Boiling point ]
149-151 °C (lit.) | [density ]
1.684 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.586(lit.)
| [Fp ]
140 °F
| [storage temp. ]
2-8°C | [form ]
Liquid | [color ]
Clear colorless to slightly brownish | [Specific Gravity]
1.684 | [Water Solubility ]
IMMISCIBLE | [Sensitive ]
Light Sensitive | [BRN ]
104663 | [InChI]
1S/C4H3BrS/c5-4-2-1-3-6-4/h1-3H | [InChIKey]
TUCRZHGAIRVWTI-UHFFFAOYSA-N | [SMILES]
Brc1cccs1 | [CAS DataBase Reference]
1003-09-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Thiophene, 2-bromo-(1003-09-4) | [Storage Precautions]
Light sensitive | [EPA Substance Registry System]
1003-09-4(EPA Substance) |
| Questions And Answer | Back Directory | [General description]
2-Bromothiophene undergoes metallation-alkylation reaction with various electrophiles to generate various 5-alkylated 2-bromo products. It is coupled with 4-bromoallyl phenyl ether to produce allyl thiophene ether, which is a new type of organic thin film transistor dielectric material.
 | [Application]
In dimethylformamide containing tetramethylammonium perchlorate, 2-bromothiophene is electrochemically reduced many mono- and dihalothiophenes on a carbon cathode by cyclic voltammetry and controlled potential electrolysis.
| [Product Introduction]
The 2-Bromothiophene(casno:1003-09-4) 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, 2-Bromothiophene(casno:1003-09-4) is a colorless to light yellow transparent liquid, which should be stored in a closed dark and cool place. 2-Bromothiophene(casno:1003-09-4) can be used for organic synthesis and pharmaceutical intermediates.
|
| Safety Data | Back Directory | [Symbol(GHS) ]
  
GHS02,GHS05,GHS06 | [Signal word ]
Danger | [Hazard statements ]
H226-H300-H318 | [Precautionary statements ]
P210-P233-P240-P280-P301+P310-P305+P351+P338 | [Hazard Codes ]
T,N,Xn | [Risk Statements ]
R10:Flammable.
R25:Toxic if swallowed.
R41:Risk of serious damage to eyes.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R36/37/38:Irritating to eyes, respiratory system and skin .
R23/24:Toxic by inhalation and in contact with skin .
R22:Harmful if swallowed.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S16:Keep away from sources of ignition-No smoking .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 2929 6.1/PG 2
| [WGK Germany ]
3
| [F ]
8 | [Hazard Note ]
Irritant | [TSCA ]
T | [REACH Registrations]
Active | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29349990 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Acute Tox. 2 Oral
Eye Dam. 1
Flam. Liq. 3 |
| Hazard Information | Back Directory | [Chemical Properties]
colorless to light yellow liqui | [Uses]
2-Bromothiophene has been used in electrochemical reduction of a number of mono- and dihalothiophenes at carbon cathodes in dimethylformamide containing tetramethylammonium per chlorate by cyclic voltammetry and controlled-potential electrolysis. | [Preparation]
2-Bromothiophene is synthesized by bromination of thiophene, which is achieved through the following steps: dissolve thiophene in acetic acid, and add bromine in glacial acetic acid solution below 10°C. Water was added to the reaction mixture to precipitate an oily liquid. Extract with ether. Add potassium carbonate to the extract to remove acetic acid, dry it, distill off the ether, and then conduct vacuum distillation to collect fractions at 42-46°C (1.73kPa) to obtain 2-bromothiophene with a yield of 55%. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 79, p. 5474, 1957 DOI: 10.1021/ja01577a039
Synthesis, p. 890, 1988 DOI: 10.1055/s-1988-27740 | [General Description]
2-Bromothiophene undergoes metalation-alkylation reaction with various electrophiles to form various 5-alkylated 2-bromo products. It undergoes coupling with 4-bromo allyl phenyl ether to form allyl phenyl thiophene ether, which is a novel potential dielectric material for organic thin film transistors. | [Synthesis]
Configure a 500-mL three-neck flask with a condenser tube, stirring bar, and thermometer and place the unit in an ice bath. The condenser tube was connected to a hydrogen bromide gas absorption unit. Thiophene acetaldehyde (79 mL, 84 g, 1.0 mol) and carbon tetrachloride (160 mL, 250 g) were added to the reaction flask, and the temperature of the reaction was controlled to be in the range of 0-5°C with continuous stirring. Bromine (48 mL, 150 g, 1.15 mol) and 40% hydrobromic acid (190 mL) were added slowly dropwise for a controlled time of 80 minutes. After the dropwise addition, the reaction was continued with stirring for 60 min to ensure complete escape of hydrogen bromide gas. The reaction mixture was washed with water, dried and then distilled at atmospheric pressure to recover the solvent. The crude product was transferred to a 250 mL distillation flask for reduced pressure distillation and the fraction was collected at 58-62°C/7 kPa to give the colorless liquid 2-bromothiophene (85 mL, 143 g) in 88.1% yield and 98.4% purity. | [References]
[1] Synthesis, 1988, # 11, p. 890 - 891
[2] Synthetic Communications, 2008, vol. 38, # 16, p. 2814 - 2819
[3] Journal of Organic Chemistry, 1993, vol. 58, # 11, p. 3072 - 3075
[4] Journal of the Chemical Society, Chemical Communications, 1982, # 14, p. 778 - 779
[5] Patent: CN104447679, 2016, B. Location in patent: Paragraph 0028-0029 |
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