| Identification | More | [Name]
3-Bromothiophene | [CAS]
872-31-1 | [Synonyms]
2-BROMOTHIOPHENE
2-THIENYL BROMIDE
3-THIENYL BROMIDE
ALPHA-THIENYL BROMIDE
BROMOTHIOPHENE(3-)
TIMTEC-BB SBB003930
TIMTEC-BB SBB003931
3-bromo-thiophen
beta-Bromothiophene
thiophene,3-bromo-
β-bromothiophene
3-Bromothiophene99%
3-Bromothiophene, 96+%
3-Bromothiophene,97%
3-bromothiophene anhydrous
b-Bromothiophene | [EINECS(EC#)]
213-699-4 | [Molecular Formula]
C4H3BrS | [MDL Number]
MFCD00005417 | [Molecular Weight]
163.04 | [MOL File]
872-31-1.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colourless to slightly yellow liquid | [Melting point ]
<-10°C | [Boiling point ]
150 °C (lit.) | [density ]
1.74 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.591(lit.)
| [Fp ]
140 °F
| [storage temp. ]
0-6°C
| [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Liquid | [color ]
Clear colorless to slightly yellow | [Specific Gravity]
1.740 | [Water Solubility ]
IMMISCIBLE | [Sensitive ]
Light Sensitive/Stench | [Detection Methods]
HPLC | [BRN ]
105338 | [CAS DataBase Reference]
872-31-1(CAS DataBase Reference) | [NIST Chemistry Reference]
Thiophene, 3-bromo-(872-31-1) | [Storage Precautions]
Store under nitrogen | [EPA Substance Registry System]
872-31-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xi,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 .
R23/24/25:Toxic by inhalation, in contact with skin and 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 .
S38:In case of insufficient ventilation, wear suitable respiratory equipment .
S16:Keep away from sources of ignition-No smoking .
S24/25:Avoid contact with skin and eyes .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 2929 6.1/PG 2
| [WGK Germany ]
3
| [F ]
8 | [Hazard Note ]
Irritant | [TSCA ]
T | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colourless to slightly yellow liquid | [Uses]
3-Bromothiophene is used in the preparation of derivatives such as thienylenic alpha, μ-diformyl-alpha-oligothiophenes and 3-lithiothiophene. It is also used in the synthesis of 3-lithiothiophene by reacting with n-butyllithium. | [Preparation]
Preparation of 3-bromothiophene using 2,5-dibromothiophene
2,5-Dibromothiophene (121g, 0.5 moles), tris (3,6-dioxaheptyl) amine (1.0g, 0.003 mole), thiophene (500 cm3) and sodium amide (58.5g, 1.5 mole) were successively charged to a flask which had previously been purged with nitrogen. The reaction mixture was stirred and heated under nitrogen at 50-60°C for 6 hours. The product, after work up as described in Example 3, was found to contain 138.5g 3-bromothiophene and 2.6g 2-bromothiophene. The yield of 3-bromothiophene was 85% and the monobromothiophenes were in the ratio of 2 parts 2-bromothiophene to 98 parts 3-bromothiophene. | [Reactions]
3-Bromothiophene is an electron-rich aromatic hydrocarbon bromide. The bromine atom in it has good electrophilicity. It can perform a Suzuki coupling reaction under the catalysis of metal palladium, and react with different aryl or alkenyl borates. The corresponding substitution products are generated. This reaction is one of the very important methods in organic synthesis, which can build C-C bonds and form complex organic molecular structures. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 74, p. 2965, 1952 DOI: 10.1021/ja01132a004
Synthetic Communications, 11, p. 25, 1981 DOI: 10.1080/00397918108064278 |
|
|