[ CAS No. 51012-64-7 ]

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Product Details

CAS No. :51012-64-7MDL No. :MFCD07364269
Formula :C9H9BrOInChI Key :BANFRNTVKCHZDE-UHFFFAOYSA-N
M.W :213.07Pubchem ID :10036129
Boiling Point :263.927°C at 760 mmHg
Synonyms :

Computed Properties

TPSA : 17.1 H-Bond Acceptor Count : 1
XLogP3 : 2.8 H-Bond Donor Count : 0
SP3 : 0.22 Rotatable Bond Count : 2

Safety

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305+P351+P338-P310UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis

[ 51012-64-7 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 33675-43-3 ]
  • [ 51012-64-7 ]
YieldReaction ConditionsOperation in experiment
94% at 40℃; for 6.00 h; Green chemistry General procedure: A mixture of haloalkyne (0.5 mmol), AgF (5molpercent) and water (1 equiv.) in TFA (1 mL) was stirred at 40°C for 6h, after which TFA was distilled out for reuse. The residue was separated by column chromatography to give the pure sample.
90% With tetrafluoroboric acid; water In 2,2,2-trifluoroethanol at 80℃; for 2.00 h; General procedure: A mixture of haloalkyne (0.2 mmol), tetrafluoroboric acid (20 molpercent, 40percent  aqueous solution ) in 2,2,2-trifluoroethanol (1 mL) was stirred at 80°C for 2 or 10 h. After the reaction was finished, water (5 mL) was added and the solution was extracted with ethyl acetate (3×5 mL), the combined extract was dried with anhydrous MgSO4. Solvent was removed, and the residue was separated by column chromatography to give the pure sample.
89% With indium(III) triflate; water In acetic acid at 100℃; Sealed tube General procedure: The reaction mixture of In(OTf)3 (16.8mg, 0.03mmol), 1-haloalkynes (0.3mmol), H2O (0.9mmol), HOAc (0.6mL), in a 5mL sealed tube was stirred at 100°C and monitored periodically by TLC. Upon completion, HOAc was removed under reduced pressure using an aspirator, and then the residue was purified by flash chromatography (PE/EA) on silica gel to afford corresponding carbonyl compounds 2a–2ad.
Reference: [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 116 - 121
[2] Tetrahedron Letters, 2014, vol. 55, # 7, p. 1373 - 1375
[3] Journal of Organic Chemistry, 2013, vol. 78, # 18, p. 9190 - 9195
[4] Tetrahedron Letters, 2016, vol. 57, # 45, p. 4983 - 4986
[5] Tetrahedron, 2016, vol. 72, # 27-28, p. 3818 - 3822
[6] Chinese Journal of Chemistry, 2016, vol. 34, # 12, p. 1251 - 1254
  • 2
  • [ 585-74-0 ]
  • [ 51012-64-7 ]
YieldReaction ConditionsOperation in experiment
96% With Oxone; ammonium bromide In methanol for 0.67 h; Reflux General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NH4Br (0.215 g, 2.2 mmol) in methanol (10 ml) and the reaction mixture was allowed to stir at room temperature (or reflux temperature). After completion of the reaction, as monitored by TLC, the reaction mixture was quenched with aqueous sodium thiosulfate, and extracted with ethyl acetate (3.x.25 ml). Finally, the combined organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and removal of solvent in vacuo yielded a crude residue, which was further purified by column chromatography over silica gel (finer than 200 mesh) to afford pure products. All the products were identified on the basis of 1H NMR and mass spectral data.
80% With bromine In 1,4-dioxane; diethyl ether at 20℃; for 5.00 h; To a solution of 1-m-tolyl-ethanone (6.Og, 44.72mmol) in dioxane (5ml), bromine (7.14g, 44.72mmol) in dioxane (10ml) and ether (15ml) was added and stirred at room temperature for 5 hr. The reaction mixture was poured into ice water and the compound was extracted using ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered and then evaporated to give crude 2- bromo- 1-m-tolyl-ethanone, 7.6g (80percent). The crude compound obtained was used in the next step without further purification.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 2, p. 191 - 195
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 19, p. 8236 - 8247,12
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 19, p. 8236 - 8247
[4] Synthetic Communications, 2013, vol. 43, # 19, p. 2603 - 2614
[5] Patent: WO2006/123145, 2006, A1. Location in patent: Page/Page column 41
[6] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 5, p. 1170 - 1176
[7] Journal of Pharmaceutical Sciences, 1982, vol. 71, # 5, p. 556 - 561
[8] Chemical & Pharmaceutical Bulletin, 1995, vol. 43, # 9, p. 1497 - 1504
[9] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1291 - 1295
[10] Patent: WO2010/29119, 2010, A1. Location in patent: Page/Page column 63
[11] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 4, p. 954 - 971
[12] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 14 - 35
[13] MedChemComm, 2015, vol. 6, # 6, p. 1036 - 1042
[14] Chemical Biology and Drug Design, 2015, vol. 86, # 4, p. 849 - 856
[15] Chemical Communications, 2016, vol. 52, # 29, p. 5152 - 5155
[16] Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 8, p. 1166 - 1173
[17] Organic Letters, 2017, vol. 19, # 11, p. 2877 - 2880
[18] Organic and Biomolecular Chemistry, 2017, vol. 15, # 38, p. 8134 - 8139
[19] Tetrahedron Letters, 2018, vol. 59, # 33, p. 3214 - 3219
[20] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 86, p. 12182 - 12185
  • 3
  • [ 100-80-1 ]
  • [ 51012-64-7 ]
YieldReaction ConditionsOperation in experiment
82% With dibromamine-T; sodium thiosulfate In water; acetone at 20℃; for 2.00 h; General procedure: To a solution of olefin (1mmol) in acetone (3mL) and water (0.1mL), TsNBr2 (2.2mmol) was added at room temperature. After completion of reaction, sodium thiosulfate (200mg approx.) was added and the reaction mixture was stirred for another 10min. The reaction mixture was extracted with ethyl acetate, dried (Na2SO4) and concentrated. Purification of the crude product by flash chromatography on silica gel (230–400 mesh) with petroleum ether–EtOAc as eluent gave the pure product.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 2, p. 356 - 358
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 48, p. 11389 - 11395
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 46, p. 9889 - 9894
  • 4
  • [ 585-74-0 ]
  • [ 875815-03-5 ]
  • [ 51012-64-7 ]
YieldReaction ConditionsOperation in experiment
93% With N-Bromosuccinimide; silica gel In methanol for 0.25 h; Reflux General procedure: The α-bromination reaction was carried out using acetophenone (1200 mg, 10 mmol), N-bromosuccinimide (2136 mg, 12 mmol), 10percent (w/w) silica gel (120mg) in 10 mL of methanol at reflux conditions until the disappearance of the substrate. (Note: 2136mg of N-bromosuccinimide was added portion wise i.e. 356 mg for each time in six portions). The progress of the reaction was monitored by TLC. The reaction mass was filtered after the completion of the reaction as per TLC and the catalyst was collected for reuse. The filtrate was concentrated under vacuum. Double distilled water was added to the reaction mixture and quenched with aqueous sodium thiosulfate and the product extracted with dichloromethane (Caution: Severe burning sensation of eyes was observed during the work-up process). The layers were separated and the organic layer was collected and washed thrice with distilled water (3×50mL). The collected organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The obtained crude product was purified by column chromatography over silica gel (60–120 mesh) using n-hexane–EtOAc (99:1 ratio). With the aim of studying the recycling of the catalyst, the isolated catalyst was washed with ethyl acetate (5mL) after its filtration from the reaction medium, collected and dried in vacuum at 70°C to a constant weight. Subsequently it was reused for the α-bromination of acetophenone and achieved 95percent, 86percent and 83percent yields of product (2a) for first, second and third reuse of catalyst respectively. All products gave spectroscopic data in agreement with the literature [15,21,27–30]. The method is also very practical for scale up in process development. We attempted large scale (100 gram scale) synthesis of 2-bromo-1-phenylethanone 2a and obtained fruitful results with isolated yields ranging from 93percent to 96percent.
Reference: [1] Chinese Chemical Letters, 2014, vol. 25, # 1, p. 179 - 182
  • 5
  • [ 875815-03-5 ]
  • [ 51012-64-7 ]
YieldReaction ConditionsOperation in experiment
170 mg With water; sodium sulfite In ethyl acetate; acetone at 20℃; General procedure: To a stirred solution of alkyne (1 mmol) in ethyl acetate(1 mL), 0.1 mL of acetone:water (1:1) and TsNBr2 (2 mmol) wasadded. After 10 min Na2SO3 (8 mmol) was added and the reaction was stirred at room temperature till completion asmonitored by TLC. The organic layer was extracted with ethylacetate, washed with water, dried with Na2SO4 and concentrated.The crude product was purified by flash chromatographyon silica gel (230-400 mesh) using petroleum ethereethyl acetateas eluent.
Reference: [1] Tetrahedron, 2016, vol. 72, # 29, p. 4151 - 4158
  • 6
  • [ 766-82-5 ]
  • [ 51012-64-7 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 8, p. 1983 - 1989
[2] Journal of Organic Chemistry, 2013, vol. 78, # 18, p. 9190 - 9195
[3] Tetrahedron, 2016, vol. 72, # 29, p. 4151 - 4158
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