Methyl 5-broMothiophene-3-carboxylate
- Product Name
- Methyl 5-broMothiophene-3-carboxylate
- CAS No.
- 88770-19-8
- Chemical Name
- Methyl 5-broMothiophene-3-carboxylate
- Synonyms
- EA458;Methyl 2-bromothiophene-4-carboxylate;Methyl 5-broMothiophene-3-carboxylate;Methyl 5-bromo-3-thiophenecarboxylate;Methyl 5-bromothiophene-3-carboxylate 98%;5-Bromothiophene-3-carboxylic acid methyl ester;3-Thiophenecarboxylic acid, 5-bromo-, methyl ester
- CBNumber
- CB72652875
- Molecular Formula
- C6H5BrO2S
- Formula Weight
- 221.07
- MOL File
- 88770-19-8.mol
Methyl 5-broMothiophene-3-carboxylate Property
- Melting point:
- 43-44 °C
- Boiling point:
- 244.6±20.0 °C(Predicted)
- Density
- 1.662±0.06 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2–8 °C
- Appearance
- Off-white to light brown Solid
Safety
- HS Code
- 2934999090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- M224648
- Product name
- Methyl5-Bromothiophene-3-carboxylate
- Packaging
- 100mg
- Price
- $65
- Updated
- 2021/12/16
- Product number
- OR17258
- Product name
- Methyl5-bromothiophene-3-carboxylate
- Purity
- 99%
- Packaging
- 1g
- Price
- $73
- Updated
- 2021/12/16
- Product number
- 6H66-9-09
- Product name
- Methyl 5-bromothiophene-3-carboxylate
- Purity
- 98%
- Packaging
- 1g
- Price
- $87
- Updated
- 2021/12/16
- Product number
- 9704AF
- Product name
- Methyl5-bromo-3-thiophenecarboxylate
- Packaging
- 250mg
- Price
- $108
- Updated
- 2021/12/16
- Product number
- OR17258
- Product name
- Methyl5-bromothiophene-3-carboxylate
- Purity
- 99%
- Packaging
- 5g
- Price
- $193
- Updated
- 2021/12/16
Methyl 5-broMothiophene-3-carboxylate Chemical Properties,Usage,Production
Synthesis
67-56-1
100523-84-0
88770-19-8
1. Add a solution of bromine (2 mL, 39.06 mmol) in glacial acetic acid (64 mL) slowly dropwise to a stirred solution of 5-bromothiophene-3-carboxylic acid (5 g, 39.06 mmol) in glacial acetic acid (37 mL) at 0 °C. Stirring was done for 20 minutes at room temperature. The reaction mixture was poured into ice water with vigorous stirring. The white solid precipitate was collected by filtration, washed with water and recrystallized from hot water to give pure 5-bromothiophene-3-carboxylic acid bromide (Int-2) as a white solid (3.68 g, 46%).1H NMR (200 MHz, DMSO-d6): δ 7.55 (s, 1H), 8.17 (s, 1H). 2. Int-2 (3.4 g, 16.42 mmol) was dissolved in methanol (40 mL), H2SO4 (321 mg, 3.28 mmol) was added, and stirred at reflux for 12 hours. Volatiles were removed by distillation under reduced pressure and the residue was extracted with DCM (75 mL). The organic phase was washed sequentially with water (40 mL), saturated aqueous NaHCO3 (40 mL), brine (40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give pure methyl 5-bromothiophene-3-carboxylate (Int-3) as a colorless viscous oil (3.3 g, 91%).1H NMR (200 MHz, DMSO-d6): δ 7.98 (s, 1H), 7.44 (s, 1H), 3.87 (s, 3H). 3. Int-3 (0.5 g, 2.26 mmol) was dissolved in dioxane (25 mL), and Int-4 (0.51 g, 2.26 mmol), Pd(OAc)2 (105 mg, 0.45 mmol), xanthic acid (265 mg, 0.497 mmol) and Cs2CO3 (1.18 g, 3.62 mmol) were added. After vacuum degassing, the reaction was stirred at reflux for 20 h under N2 protection. The reaction mixture was concentrated under reduced pressure and purified by column chromatography with the product eluting with EtOAc. The mixture was further purified by preparative HPLC (140 mg) to give pure Int-5 as a yellow solid (80 mg, 10%). Mass spectrum (m/z): 366.0 [M++1]. 1H NMR (200 MHz, DMSO-d6): δ 9.50 (d, J=7 Hz, 1H), 8.51 (d, J=7 Hz, 1H), 8.56 (d, J=5.2 Hz, 1H), 7.74 (brs, 1H), 7.66 (d, J=11.8 Hz, 1H). 7.35 (d, J=7.4 Hz, 1H), 7.11 (s, 1H), 7.02 (d, J=5.6 Hz, 1H), 6.87 (t, J=6.8 Hz, 1H), 3.86 (s, 3H), 2.73 (s, 3H). 4. Int-5 (0.7 g, 1.91 mmol) was dissolved in THF:MeOH:H2O (2:1:2, 50 mL), LiOH (0.24 g, 5.74 mmol) was added, and heated and stirred at 50 °C for 16 hours. Volatiles were removed by distillation under reduced pressure and the reaction mixture was acidified to pH 5-6 with 2N HCl. The precipitated solid was filtered and dried under vacuum to give pure Int-6 (0.51 g, 76%). Mass spectrum (m/z): 352.0 [M++1]. 1H NMR (200 MHz, DMSO-d6): δ 12.45 (brs, 1H), 10.87 (s, 1H), 9.70 (brs, 1H), 8.60 (d, J=4.68 Hz, 1H), 7.67-7.59 (m, 2H), 7.45 (t, J=8.4 Hz, 1H), 7.13 (d, J=5.2 Hz, 1H), 7.04 (s, 2H), 2.65 (s, 3H).
References
[1] Patent: US2010/29638, 2010, A1. Location in patent: Page/Page column 110
[2] Tetrahedron Letters, 2013, vol. 54, # 11, p. 1460 - 1462
[3] Journal of Materials Chemistry C, 2018, vol. 6, # 14, p. 3731 - 3742
[4] Patent: WO2005/9941, 2005, A1. Location in patent: Page 43-44
[5] Patent: WO2011/33255, 2011, A1. Location in patent: Page/Page column 72
Methyl 5-broMothiophene-3-carboxylate Preparation Products And Raw materials
Raw materials
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View Lastest Price from Methyl 5-broMothiophene-3-carboxylate manufacturers
- Product
- Methyl 5-broMothiophene-3-carboxylate 88770-19-8
- Price
- US $1.00/g
- Min. Order
- 1g
- Purity
- 99.0%
- Supply Ability
- 100kg
- Release date
- 2020-01-07