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[ CAS No. 930-96-1 ] {[proInfo.proName]}

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Chemical Structure| 930-96-1
Chemical Structure| 930-96-1
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Product Details of [ 930-96-1 ]

CAS No. :930-96-1 MDL No. :MFCD00126680
Formula : C5H3BrOS Boiling Point : -
Linear Structure Formula :- InChI Key :BCZHCWCOQDRYGS-UHFFFAOYSA-N
M.W :191.05 Pubchem ID :2797079
Synonyms :

Calculated chemistry of [ 930-96-1 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 37.41
TPSA : 45.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.62
Log Po/w (XLOGP3) : 2.09
Log Po/w (WLOGP) : 2.32
Log Po/w (MLOGP) : 1.19
Log Po/w (SILICOS-IT) : 3.38
Consensus Log Po/w : 2.12

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.74
Solubility : 0.35 mg/ml ; 0.00183 mol/l
Class : Soluble
Log S (Ali) : -2.67
Solubility : 0.407 mg/ml ; 0.00213 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.47
Solubility : 0.647 mg/ml ; 0.00339 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.18

Safety of [ 930-96-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 930-96-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 930-96-1 ]
  • Downstream synthetic route of [ 930-96-1 ]

[ 930-96-1 ] Synthesis Path-Upstream   1~25

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Reference: [1] Synthetic Communications, 2009, vol. 39, # 18, p. 3315 - 3323
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YieldReaction ConditionsOperation in experiment
71%
Stage #1: With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5 h; Inert atmosphere
Stage #2: at 0℃; for 3 h; Inert atmosphere
Stage #3: With ammonium chloride In tetrahydrofuranInert atmosphere
General procedure: To the solution of 1M NaHMDS (8.8 mL, 8.8 mmol) in THF was slowly added the substrate (6.8 mmol) at 0 oC. After stirring for 30 min at 0 oC, the solution of electrophile (8.3 mmol) in anhydrous THF (2 mL) was slowly added into the reaction mixture at 0 oC and stirred for an additional 3h. The reaction was quenched with NH4Cl (sat.) solution (5 mL) and diluted with hexanes (20 mL). The organic layer was separated, washed with 15 wt.percent NaCl aqueous solution (10 mL) and concentrated to give the crude product. The product was isolated by flash chromatography using a Et3N pre-treated silca gel column and 0.1percent Et3N / 4.9percent EtOAc / 95percent hexanes as the eluent.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 2, p. 166 - 169
[2] Tetrahedron Letters, 2012, vol. 53, # 2, p. 166 - 169
  • 3
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YieldReaction ConditionsOperation in experiment
100%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at 0 - 5℃; for 0.5 h; Inert atmosphere; Large scale
Stage #2: at 0 - 5℃; for 3 h; Inert atmosphere; Large scale
Under a nitrogen atmosphere, diisopropylamine (51.6 Kg, 509.9 mol, 1 leq) and anhydrous THF (385.0 OKg) were added to a 1000 L autoclave. The temperature was lowered and maintained at 0-5 ° C. BuLi (131.4 Kg, 463.8 mol, 1.0 eq). After the addition was complete, stirring was continued for half an hour at 0-5 ° C. A solution of 3-bromothiophene (starting material 1) (75.0 Kg, 460. Omol, 1 Oeq) in THF (20.0 OKg) was added dropwise at 0-5 ° C. After the addition was complete, stirring was continued for half an hour at 0-5 ° C. A solution of DMF (35.3 kg, 473.3 mol, 1.0 eq) in THF (10Kg) was added dropwise at 0-5 ° C. After completion of the dropwise addition, the temperature was maintained at 0-5 ° C and stirring was continued for 3 hours. Aqueous 14percent NH4Cl (700.OKg) was added dropwise at 0-5 ° C. After completion of the addition, the mixture was stirred at 0 to 5 ° C for 15 minutes, allowed to stand for 15 minutes, and the organic phase was temporarily stored in a clean tetrafluoroethylene drum. The aqueous phase was pumped into the reaction kettle, methyl tert-butyl ether (150. OKg) was added, stirred for 15 minutes, allowed to stand for 15 minutes, phase separated and the upper organic phase taken. The above organic phases were combined, anhydrous sodium sulfate (85. OKg) was added, and dried for a few hours until moisture <1percent. After filtration, the filter cake was washed twice with methyl tert-butyl ether (20 mL) and concentrated under reduced pressure to remove the solvent to give 3-bromothiophene-2-carbaldehyde (Intermediate 2) (93.8 Kg, 100percent).
85%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - -30℃; for 1.5 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 6 h; Inert atmosphere
To a stirred solution of iPr2NH (5.0 mL, 3.6 g, 35.3 mmol) in THF (30 mL) in a 100-mL 2-neckedflask under dry argon nBuLi (13.7 mL, 2.35 M in hexanes, 32.2 mmol) was added dropwise during 10 minutes at 0 °C. After stirring for an additional 20 minutes at 0°C, the mixture was cooled to −78 °C and a solution of 3-bromothiophene (5.0 g, 30.6 mmol) in THF (30 mL) was added dropwise during 20 minutes. After stirring for 1 hour at −78°C, the mixture was allowed to warm to −30 °C for 30 minutes before cooling again back to −78 °C. A solution of DMF (2.9 g, 40.0 mmol) in THF (10 mL) was then added dropwise over 10 minutes the mixture was allowed to gradually warm to room temperature with stirring for 6 hours. The mixture was poured into 1M HCl (100 mL) and EtOAc (100 mL) mixture. The organic layer was separated out and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine (100 mL) then dried over Na2SO4, filtered, and concentrated in vacuo to give a brown oil. The residue was subjected to column chromatography on SiO2 (eluent EtOAc/hexane, 1/25 → 1/10) to give SI-1i (5.0 g, 26.2 mmol, 85percent) as colorless oil crystallizing in refrigerator.
68%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 1 h;
Stage #2: at 0 - 20℃; for 2 h;
EXAMPLE l.AP. Preparation of 3-bromothiophene-2-carbaldehyde (1-53). I-53 [0202] To a solution of 3-bromothiophene (25 g, 153 mmol) in tetrahydrofuran (250 mL) was added 2 M Lithium diisopropylamide in tetrahydrofuran (77 mL,154 mmol) at 0°C and the reaction mixture was stirred at 0°C for 1 h. N,N-dimethylformamide (12.2 g, 168 mmol) was added and the reaction mixture was allowed to warm to room temperature and stirred for additional 2 h. Water (100 mL) was added and extracted with ethyl acetate (500 mLx 3) was performed. The combined organic layer were dried over anhydrous magnesium sulfate, solids were removed by filtration and the filtrate was concentrated by evaporation in vacuo. The residue was purified by silica gel chromatography (petrol ether/ethyl acetate = 10/1) to provide intermediate 1-53 (20 g, 68percent). MS (ESI): m/z 190 [M + H]+.
Reference: [1] Patent: CN103172646, 2016, B, . Location in patent: Paragraph 0101-0104
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 31, p. 5263 - 5273
[3] Macromolecules, 2013, vol. 46, # 6, p. 2078 - 2091
[4] Tetrahedron Letters, 2012, vol. 53, # 2, p. 166 - 169
[5] Journal of the American Chemical Society, 2014, vol. 136, # 19, p. 7132 - 7139
[6] Tetrahedron Letters, 2016, vol. 57, # 1, p. 11 - 14
[7] Patent: WO2016/130790, 2016, A1, . Location in patent: Paragraph 0202
[8] Nippon Kagaku Zasshi, 1957, vol. 78, p. 950,962[9] Chem. Zentralbl., 1958, vol. 129, p. 13204
[10] Tetrahedron Letters, 1993, vol. 34, # 35, p. 5653 - 5656
[11] Advanced Functional Materials, 2010, vol. 20, # 10, p. 1661 - 1669
[12] Patent: US2012/116084, 2012, A1, . Location in patent: Page/Page column 16
[13] Bl. Univ. Osaka Prefect., 1958, vol. &lt;A&gt; 6, p. 127,131
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YieldReaction ConditionsOperation in experiment
85%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 0.5 h;
Stage #2: for 1 h;
A solution of 3-bromothiophene (30.0 g, 184 mmol) in THF (200 mL) cooled to 0 °C was added slowly to a 2.0 M solution of LDA in THF (92 mL, 184 mmol; Aldrich Chemicals). The orange solution was stirred at 0 °C for 30 min, then piperidine-1-carbaldehyde (20.4 mL, 184 mmol) was added. The mixture was stirred for a further1 h then diluted with Et2O (300 mL), washed with brine (100 mL), dried, and concentrated. The resulting orange oil was purifiedby chromatography (silica gel, heptane–EtOAc). Product containing fractions were combined and concentrated to give an orange liquid; 21 yield: 29.3 g (85percent).
85%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 1.5 h;
Stage #2: at 0 - 20℃; for 2 h;
Commercially available lithium diisopropylamide (LDA) solution (2 M, 27 mL, 53.4 mmol) wasdiluted in THE (100 mL)solution at0 °C. A solution of compound 6d (5.0 mL, 53.4 mmol) in THE(5 mL) was added drop wise to the dilute LDA solution at 0 °C over 60 minutes using a droppingfunnel. The reaction mixture was allowed to stir at 0 °C for 30 minutes. After 30 mins, 1-formyl-piperidine was added drop-wise to the reaction mixture. The resultant mixture was gradually warmed to room temperature and stirred at room temperature for 2 hours. The reaction mixture was quenched with NH4CI (150 mL) and extracted with Et20 (3 x 100 mL). The combined organic layers were washed with brine and concentrated to give yellow oil, which was purified by col15 umn chromatography on silica gel using DCM: hexane (v/v 1:1)to yield compound 8a as a yellow oil (8.7 g, 85percent). 1H NMR (400 MHz, CDCI3) ö 9.99 (s, 1 H), 7.71 (d, 1 H, J = 5.2 Hz), 7.15 (d, 1H, J = 5.2 Hz).
79.2%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at 0 - 2℃; for 0.5 h;
Stage #2: for 2 h;
Experimental procedure3-Bromo-thiophene (6.523 g, 40 mmol) was dissolved under N2 in THF (100 mL). After cooling to 0-2 °C it was mixed dropwise with a 2M LDA solution (20 mL, 40 mmol) and stirred for 0.5 h. Following that 1-Formylpiperidin (4.52 g, 40 mmol) was added. After 2 h the reaction was stopped by adding a surplus of a saturated solution of NH4CI. For purification it was extracted three times with Et2O (10 mL) and the pooled organic phases subsequently dried over Na2SO4. After filtration the solvent was removed under vacuum. The crude product (approx. 8.3 g) was purified using flash-chromatography (8 cm, cyclohexane:ethylacetate 9:1 , 30 mL, Rf = 0.65) and by distillation under vacuum (Bp. 62 0C, 5.6 -10"2 mbar).Colourless liquid, yield 6.05 g (79.2 percent). <n="42"/>C5H3BrOS (191.1)MS (EI): m/z = 190/192 [M+], 162 [M+ -CHO].IR (Film): v (crτT1) = 3103 (C-H)1 2843 (C-H), 1657 (C=O).1H-NMR (CDCI3):δ (ppm) = 7.15 (d, J = 5.5 Hz, 1 H, 4-H-Th), 7.71 (dd, J = 5.1/1.5 Hz, 1 H, 5-H-Th)1 9.99 (d, J = 1.5 Hz, 1 H, Th-CHO).
54%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at -78 - 0℃; for 12 h;
[00174] To a solution of lithium diisopropylamide (31.6 mmol) in 50 mL of THF at -78 °C was added 3-bromothiophene (3.0 g, 31 mmol) (1). After stirring for 1 h, formylpiperidine (3.50 g, 31.6 mmol) (2) was added and the reaction was warmed to 0 °C. After 12 h, the reaction mixture was partitioned between DCM and sat. NH4C1 and the organic layer was separated, dried over MgS04, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to afford 1.90 g (54percent) of the title compound as a yellow oil. 'H NMR (400 MHz, CDCI3) δ 9.99 (s, 1H), 7.71 (d, J= 5.2 Hz, 1H), 7.15 (d, J= 4.8 Hz, 1H).

Reference: [1] Journal of Heterocyclic Chemistry, 2009, vol. 46, # 6, p. 1132 - 1136
[2] New Journal of Chemistry, 2015, vol. 39, # 3, p. 2248 - 2255
[3] Synthesis (Germany), 2014, vol. 46, # 1, p. 96 - 100
[4] Patent: WO2015/128779, 2015, A1, . Location in patent: Page/Page column 28
[5] Advanced Functional Materials, 2012, vol. 22, # 1, p. 48 - 60
[6] Journal of Medicinal Chemistry, 2008, vol. 51, # 20, p. 6531 - 6537
[7] Patent: WO2008/155132, 2008, A1, . Location in patent: Page/Page column 40-41
[8] Heterocyclic Communications, 2016, vol. 22, # 1, p. 1 - 5
[9] Patent: WO2015/197861, 2015, A1, . Location in patent: Paragraph 00173-00174
[10] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 22, p. 3465 - 3470
[11] Molecules, 2012, vol. 17, # 10, p. 12163 - 12171
[12] Patent: KR101540066, 2015, B1, . Location in patent: Paragraph 0021; 0022; 0023
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YieldReaction ConditionsOperation in experiment
94%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at 20℃; for 12 h;
A round 500 mL flask was charged with tetrahydrofuran (200 mL) Cool to -78 ° C. Thereafter, 2.0 M LDA (55 mL, 0.11 mol) was added theretoAnd 3-bromothiophene (16.3 g, 0.1 mol) was added slowly.After stirring at the same temperature for 1 hourDimethyl formaldehyde(8.48 ml, 0.11 mol).Then, the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was fractionally distilled through ethyl acetate,The remaining water was removed with anhydrous magnesium sulfate, and the solvent was evaporated,Pure Compound A was obtained by column chromatography (18 g, 94percent).
Reference: [1] Patent: KR101822888, 2018, B1, . Location in patent: Paragraph 0102-0105
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YieldReaction ConditionsOperation in experiment
71% With n-butyllithium In water; N,N-dimethyl-formamide a)
Preparation of 3-bromothiophene-2-carboxaldehyde.
To a cold (-78° C., dry ice/acetone) solution of 2,3-dibromothiophene (10 g, 41.3 mMol) in ether (75 mL) was added n-butyllithium (19.35 mL, 48.36 mMol, 2.5M in hexanes).
The reaction was stirred for 5 min and cannul ated into a cold stirred solution of N,N-dimethylformamide (4.53 g, 61.99 mMol) in ether (25 mL).
The reaction was stirred 1 h at -78° C. and then allowed to warm to room temperature.
Water (5 mL) was added cautiously while stirring.
The reaction mixture was diluted with ether washed with water (100 mL).
The aqueous layer was washed with ether and the organic layers combined, washed with brine, dried (MgSO4), and concentrated.
Purification by flash chroma-tography (SiO2, eluted with 3percent ethylacetate/hexanes) afforded 3-bromothiophene-2-carboxaldehyde (5.6 g, 71percent) as a slightly yellow liquid that solidified upon refrigeration.
The aldehyde (1.0 g, 4.5 mMol) obtained above was dissolved in 1:1 pyridine, ethanol (15 mL).
Reference: [1] Patent: US5185363, 1993, A,
[2] Patent: US5621113, 1997, A,
[3] Patent: US6232320, 2001, B1,
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YieldReaction ConditionsOperation in experiment
71%
Stage #1: With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5 h; Inert atmosphere
Stage #2: at 0℃; for 3 h; Inert atmosphere
Stage #3: With ammonium chloride In tetrahydrofuranInert atmosphere
General procedure: To the solution of 1M NaHMDS (8.8 mL, 8.8 mmol) in THF was slowly added the substrate (6.8 mmol) at 0 oC. After stirring for 30 min at 0 oC, the solution of electrophile (8.3 mmol) in anhydrous THF (2 mL) was slowly added into the reaction mixture at 0 oC and stirred for an additional 3h. The reaction was quenched with NH4Cl (sat.) solution (5 mL) and diluted with hexanes (20 mL). The organic layer was separated, washed with 15 wt.percent NaCl aqueous solution (10 mL) and concentrated to give the crude product. The product was isolated by flash chromatography using a Et3N pre-treated silca gel column and 0.1percent Et3N / 4.9percent EtOAc / 95percent hexanes as the eluent.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 2, p. 166 - 169
[2] Tetrahedron Letters, 2012, vol. 53, # 2, p. 166 - 169
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YieldReaction ConditionsOperation in experiment
75% With acetic acid; diisopropylamine In tetrahydrofuran; water; N,N-dimethyl-formamide Thieno[3,2-b]thiophene-2-carboxamidine hydrochloride
n-Butyl lithium (2.5M in hexanes, 4.2 mL, 10.5 mmol) was added dropwise to a solution of diisopropylamine (1.112 g, 11 mmol) in THF (10 mL), stirred under N2 at 25° C.
After 10 min the solution was added dropwise over 10 min via catheter to a solution of 3-bromothiophene (1.6302 g, 10 mmol) in (THF 10 mL), stirred under N2 at -78° C. After a further 1 h, DMF (1.0 mL, 12.5 mmol) was added dropwise, followed after 10 min by a rapid addition of acetic acid (2.0 mL).
The resultant gel was quickly decomposed with water (50 mL), and the mixture was extracted with ether (3*20 mL).
The combined extracts were washed with dilute HCl (1 m, 20 mL), water (2*20 mL), saturated Na2 CO3 solution (20 mL) and dried (MgSO4).
The solvent was removed under reduced pressure, and the residue was Kugelrohr distilled at 100° C./0.2 mmHg to give 3-bromothiophene-2-carbaldehyde (1.4276 g, 75percent) as a light yellow oil.
Reference: [1] Patent: US5340833, 1994, A,
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Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 15, p. 2749 - 2752
[2] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 3, p. 670 - 684
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Reference: [1] Patent: US4876271, 1989, A,
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Reference: [1] Patent: US5880188, 1999, A,
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  • [ 68-12-2 ]
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Reference: [1] Bulletin de la Societe Chimique de France, 1967, p. 4115 - 4120
[2] Synlett, 2002, # 12, p. 2083 - 2085
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  • [ 68-12-2 ]
  • [ 1860-99-7 ]
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  • [ 930-97-2 ]
Reference: [1] Synthetic Communications, 2009, vol. 39, # 18, p. 3315 - 3323
  • 14
  • [ 3140-93-0 ]
  • [ 2591-86-8 ]
  • [ 930-96-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818
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Reference: [1] Patent: US6340759, 2002, B1, . Location in patent: Example 259
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Reference: [1] Tetrahedron, 1980, vol. 36, p. 2505 - 2512
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Reference: [1] Nippon Kagaku Zasshi, 1957, vol. 78, p. 950,962[2] Chem. Zentralbl., 1958, vol. 129, p. 13204
[3] Bulletin de la Societe Chimique de France, 1967, p. 4115 - 4120
[4] Synlett, 2002, # 12, p. 2083 - 2085
[5] Bl. Univ. Osaka Prefect., 1958, vol. &lt;A&gt; 6, p. 127,131
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 22, p. 3465 - 3470
[2] Patent: US2012/22116, 2012, A1,
[3] Advanced Functional Materials, 2012, vol. 22, # 1, p. 48 - 60
[4] Molecules, 2012, vol. 17, # 10, p. 12163 - 12171
[5] Macromolecules, 2013, vol. 46, # 6, p. 2078 - 2091
[6] New Journal of Chemistry, 2015, vol. 39, # 3, p. 2248 - 2255
[7] Patent: KR101540066, 2015, B1,
[8] Patent: CN103172646, 2016, B,
[9] Polymer, 2018, vol. 159, p. 150 - 156
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  • [ 930-96-1 ]
  • [ 25121-87-3 ]
Reference: [1] Molecules, 2012, vol. 17, # 10, p. 12163 - 12171
[2] Patent: KR101540066, 2015, B1,
  • 20
  • [ 930-96-1 ]
  • [ 124638-53-5 ]
Reference: [1] Advanced Functional Materials, 2012, vol. 22, # 1, p. 48 - 60
[2] Patent: CN103172646, 2016, B,
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  • [ 31486-86-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1805 - 1818
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 31, p. 5263 - 5273
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  • [ 40985-58-8 ]
Reference: [1] New Journal of Chemistry, 2015, vol. 39, # 3, p. 2248 - 2255
  • 23
  • [ 930-96-1 ]
  • [ 70260-17-2 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium tetrahydroborate In methanol at 0℃; for 2 h;
Stage #2: With ammonium chloride In ethyl acetate
To a solution of 3- bromothiophene-2-carbaldehyde (500 mg, 2.62 mmol) in methanol (10 mL) was added sodium borohydride (169 mg, 4.47 mmol) in small portions at 0 °C and the reaction was stirred for 2 firs. The solvent was evaporated and the residue partitioned between ethyl acetate (20 mL) and 10percent ammonium chloride solution (10 mL). The organic layer was washed with water (10 mL), dried over sodium sulfate and evaporated. The title compound (505 mg, 2.62 mmol, 100percent) was obtained as a yellow oil.
100% With sodium tetrahydroborate In methanol at 0℃; for 2 h; [00473] To a solution of 3-bromothiophene-2-carbaldehyde (6) (500 mg, 2.62 mmol) in methanol (10 mL) was added sodium borohydride (169 mg, 4.47 mmol) in small portions at 0 °C and the reaction was stirred for 2 hrs. The solvent was evaporated and the residue partitioned between ethyl acetate (20 mL) and 10percent ammonium chloride solution (10 mL). The organic layer was washed with water (10 mL), dried over sodium sulfate and evaporated. The title compound (505 mg, 2.62 mmol, 100percent) was obtained as a yellow oil.
Reference: [1] Patent: WO2011/156640, 2011, A2, . Location in patent: Page/Page column 134
[2] Patent: WO2013/86451, 2013, A2, . Location in patent: Paragraph 00473
[3] Journal of the American Chemical Society, 2014, vol. 136, # 19, p. 7132 - 7139
[4] Chemical Communications, 2015, vol. 51, # 18, p. 3842 - 3845
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Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 17, p. 2177 - 2179
  • 25
  • [ 930-96-1 ]
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Reference: [1] Patent: CN103172646, 2016, B,
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Methyl 3-bromothiophene-2-carboxylate

Similarity: 0.74

Chemical Structure| 83933-17-9

[ 83933-17-9 ]

4-Bromothiophene-2-carboxamide

Similarity: 0.72

Aldehydes

Chemical Structure| 18791-75-8

[ 18791-75-8 ]

4-Bromo-2-thiophenecarboxaldehyde

Similarity: 0.89

Chemical Structure| 98-03-3

[ 98-03-3 ]

Thiophene-2-carbaldehyde

Similarity: 0.69

Chemical Structure| 13679-70-4

[ 13679-70-4 ]

5-Methylthiophene-2-carbaldehyde

Similarity: 0.67

Chemical Structure| 4701-17-1

[ 4701-17-1 ]

5-Bromothiophene-2-carbaldehyde

Similarity: 0.66

Chemical Structure| 5834-16-2

[ 5834-16-2 ]

3-Methyl-2-thiophenecarboxaldehyde

Similarity: 0.60