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[ CAS No. 1003-31-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1003-31-2
Chemical Structure| 1003-31-2
Chemical Structure| 1003-31-2
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Product Details of [ 1003-31-2 ]

CAS No. :1003-31-2 MDL No. :MFCD00005416
Formula : C5H3NS Boiling Point : -
Linear Structure Formula :- InChI Key :CUPOOAWTRIURFT-UHFFFAOYSA-N
M.W : 109.15 Pubchem ID :66087
Synonyms :

Calculated chemistry of [ 1003-31-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 29.03
TPSA : 52.03 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.56
Log Po/w (XLOGP3) : 1.27
Log Po/w (WLOGP) : 1.62
Log Po/w (MLOGP) : 0.37
Log Po/w (SILICOS-IT) : 2.55
Consensus Log Po/w : 1.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.85
Solubility : 1.56 mg/ml ; 0.0143 mol/l
Class : Very soluble
Log S (Ali) : -1.96
Solubility : 1.19 mg/ml ; 0.0109 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.69
Solubility : 2.24 mg/ml ; 0.0205 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.07

Safety of [ 1003-31-2 ]

Signal Word:Danger Class:3,8
Precautionary Statements:P280-P303+P361+P353-P305+P351+P338-P310 UN#:2924
Hazard Statements:H225-H302-H312-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1003-31-2 ]

* 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 [ 1003-31-2 ]
  • Downstream synthetic route of [ 1003-31-2 ]

[ 1003-31-2 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 60-29-7 ]
  • [ 506-68-3 ]
  • [ 1003-09-4 ]
  • [ 1003-31-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1924, vol. 437, p. 19
  • 2
  • [ 60-29-7 ]
  • [ 506-77-4 ]
  • [ 1003-09-4 ]
  • [ 1003-31-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1924, vol. 437, p. 19
  • 3
  • [ 1003-31-2 ]
  • [ 20300-02-1 ]
YieldReaction ConditionsOperation in experiment
80% With hydrogen sulfide In dimethyl sulfoxide at 20℃; General procedure: The corresponding nitrile (100 mmol) prepared as described previously18 was dissolved in DMSO (25 mL) and H2S was slowly bubbled through the solution until no more gas was consumed. The solution was stirred at r.t. and the reaction progress was monitored by TLC (acetone). H2O was added to precipitate the product, the solid formed was collected by filtration, and recrystallized from DMF.
Reference: [1] Synthetic Communications, 2005, vol. 35, # 5, p. 761 - 764
[2] Synthesis (Germany), 2014, vol. 46, # 1, p. 126 - 134
[3] Journal of the American Chemical Society, 1955, vol. 77, p. 4062,4064
[4] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 8, p. 1167 - 1170
[5] Patent: US2005/228179, 2005, A1, . Location in patent: Page/Page column 7; 8
[6] Patent: US2005/228179, 2005, A1, . Location in patent: Page/Page column 8
[7] Patent: US2005/228179, 2005, A1, . Location in patent: Page/Page column 8
[8] Patent: US2005/228179, 2005, A1, . Location in patent: Page/Page column 8
[9] Patent: US2005/228179, 2005, A1, . Location in patent: Page/Page column 8
[10] Patent: US2005/228179, 2005, A1, . Location in patent: Page/Page column 8
[11] Synthesis, 2010, # 10, p. 1603 - 1608
[12] Chemistry of Materials, 2013, vol. 25, # 9, p. 1927 - 1934
[13] Journal of the American Chemical Society, 2015, vol. 137, # 17, p. 5670 - 5673
  • 4
  • [ 1003-31-2 ]
  • [ 68-12-2 ]
  • [ 21512-16-3 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran at -70℃; for 1 h; Inert atmosphere
Stage #2: at -78 - -70℃; for 1.5 h; Inert atmosphere
Stage #3: With water; citric acid In tetrahydrofuran
Method C5- Formylthiophene-2-carbonitrile (Intermediate compound)Under inert atmosphere BuLi (1 1 .7 ml, 29.3 mmol, 2.5 M) was added to a mixture of diisopropylamine (4.1 ml, 29.3 mmol) and THF (150 ml) at below - 70°C. When addition was finished, the mixture was allowed to reach room- temperature. The mixture was cooled back to -70°C again, where 2- thiophenecarbonitrile (3.0 g, 26.7 mmol), solved in THF (15 ml) was added drop- wise and stirred an additional hour. At -78°C. DMF (8.2 ml, 106.6 mmol) was added below -70°C. The mixture was stirred for 1 .5 h at -78°C. Citric acid (10 g) was added to the reaction-mixture. The reaction-mixture was poured out on water. The aqueous phase was extracted with diethylether. The product was dried and evaporated. The reaction mixture was purified by silica gel column chromatography using 10-50percent heptane/EtOAc as solvent. The product was isolated as a solid. Yield 2.8 g (76percent).
Reference: [1] Patent: WO2011/73298, 2011, A1, . Location in patent: Page/Page column 18
[2] Patent: US2008/200535, 2008, A1, . Location in patent: Page/Page column 169
  • 5
  • [ 1003-31-2 ]
  • [ 21512-16-3 ]
YieldReaction ConditionsOperation in experiment
84% With n-butyllithium; diisopropylamine; citric acid In tetrahydrofuran; <i>N</i>-methyl-acetamide; water; ethyl acetate EXAMPLE 65 STR100 A) Preparation of 2-cyano-5-formylthiophene
To a flame-dried 3 neck 1 L round bottom flask was added diisopropylamine (9 mL, 66 mmol) and THF (150 mL) under a nitrogen atmosphere.
The flask was cooled to an internal temperature of -78° C. (dry ice/acetone).
To this stirring solution was added n-butyllithium (1.6 M in hexanes, 41.3 mL, 66.1 mmol) via syringe and the mixture was allowed to stir for 5 min.
To this solution was added a solution of 2-thiophenecarbonitrile (6.55 g, 60 mmol) in THF (30 mL) over 10 min.
The resulting bright red solution was allowed to stir at -78° C. for 45 min, at which time dimethylformamide (23.3 mL, 300 mmol) was added via syringe.
This mixture was allowed to stir for 2 h at -78° C. and then solid citric acid (about 10 g) was added followed by water (60 mL).
Volatile solvents were removed in vacuo and the residue was partitioned between diethyl ether and brine (200 mL each).
Layers were separated and the aqueous phase was washed once with diethyl ether.
The combined organic phase was washed once with brine, dried (MgSO4), filtered and concentrated in vacuo to give a yellow solid which was purified by silica gel chromatography using an ethyl acetate/hexanes gradient (hexanes to 50percent ethyl acetate/hexanes).
Fractions containing pure product were pooled and concentrated in vacuo to give 6.9 g (84percent) of 2-cyano-5-formyl-thiophene.
84% With n-butyllithium; diisopropylamine; citric acid In tetrahydrofuran; <i>N</i>-methyl-acetamide; water; ethyl acetate EXAMPLE 65 STR95 A) Preparation of 2-cyano-5-formylthiophene
To a flame-dried 3 neck 1L round bottom flask was added diisopropylamine (9 mL, 66 mmol) and THF (150 mL) under a nitrogen atmosphere.
The flask was cooled to an internal temperature of -78° C. (dry ice/acetone).
To this stirring solution was added n-butyllithium (1.6M in hexanes, 41.3 mL, 66.1 mmol) via syringe and the mixture was allowed to stir for 5 min.
To this solution was added a solution of 2-thiophenecarbonitrile (6.55 g, 60 mmol) in THF (30 mL) over 10 min.
The resulting bright red solution was allowed to stir at -78° C. for 45 min, at which time dimethylformamide (23.3 mL, 300 mmol) was added via syringe.
This mixture was allowed to stir for 2 h at -78° C. and then solid citric acid (about 10 g) was added followed by water (60 mL).
Volatile solvents were removed in vacuo and the residue was partitioned between diethyl ether and brine (200 mL each).
Layers were separated and the aqueous phase was washed once with diethyl ether.
The combined organic phase was washed once with brine, dried (MgSO4), filtered and concentrated in vacuo to give a yellow solid which was purified by silica gel chromatography using an ethyl acetate/hexanes gradient (hexanes to 50percent ethyl acetate/hexanes).
Fractions containing pure product were pooled and concentrated in vacuo to give 6.9 g (84percent) of 2-cyano-5-formyl-thiophene.
84% With n-butyllithium; diisopropylamine; citric acid In tetrahydrofuran; <i>N</i>-methyl-acetamide; water; ethyl acetate A)
Preparation of 2-cyano-5-formylthiophene
To a flame-dried 3 neck 1L round bottom flask was added diisopropylamine (9 mL, 66 mmol) and THF (150 mL) under a nitrogen atmosphere.
The flask was cooled to an internal temperature of -78° C. (dry ice/acetone).
To this stirring solution was added n-butyllithium (1.6M in hexanes, 41.3 mL, 66.1 mmol) via syringe and the mixture was allowed to stir for 5 min.
To this solution was added a solution of 2-thiophenecarbonitrile (6.55 g, 60 mmol) in THF (30 mL) over 10 min.
The resulting bright red solution was allowed to stir at -78° C. for 45 min, at which time dimethylformamide (23.3 mL, 300 mmol) was added via syringe.
This mixture was allowed to stir for 2 h at -78° C. and then solid citric acid (about 10 g) was added followed by water (60 mL).
Volatile solvents were removed in vacuo and the residue was partitioned between diethyl ether and brine (200 mL each).
Layers were separated and the aqueous phase was washed once with diethyl ether.
The combined organic phase was washed once with brine, dried (MgSO4), filtered and concentrated in vacuo to give a yellow solid which was purified by silica gel chromatography using an ethyl acetate/hexanes gradient (hexanes to 50percent ethyl acetate/hexanes).
Fractions containing pure product were pooled and concentrated in vacuo to give 6.9 g (84percent) of 2-cyano-5-formyl-thiophene.
84% With n-butyllithium; diisopropylamine; citric acid In tetrahydrofuran; <i>N</i>-methyl-acetamide; water; ethyl acetate EXAMPLE 65 STR106 A) Preparation of 2-cyano-5-formylthiophene
To a flame-dried 3 neck 1 L round bottom flask was added diisopropylamine (9 mL, 66 mmol) and THF (150 mL) under a nitrogen atmosphere.
The flask was cooled to an internal temperature of -78° C. (dry ice/acetone).
To this stirring solution was added n-butyllithium (1.6M in hexanes, 41.3 mL, 66.1 mmol) via syringe and the mixture was allowed to stir for 5 min.
To this solution was added a solution of 2-thiophenecarbonitrile (6.55 g, 60 mmol) in THF (30 mL) over 10 min.
The resulting bright red solution was allowed to stir at -78° C. for 45 min, at which time dimethylformamide (23.3 mL, 300 mmol) was added via syringe.
This mixture was allowed to stir for 2 h at -78° C. and then solid citric acid (about 10 g) was added followed by water (60 mL).
Volatile solvents were removed in vacuo and the residue was partitioned between diethyl ether and brine (200 mL each).
Layers were separated and the aqueous phase was washed once with diethyl ether.
The combined organic phase was washed once with brine, dried (MgSO4), filtered and concentrated in vacuo to give a yellow solid which was purified by silica gel chromatography using an ethyl acetate/hexanes gradient (hexanes to 50percent ethyl acetate/hexanes).
Fractions containing pure product were pooled and concentrated in vacuo to give 6.9 g (84percent) of 2-cyano-5-formyl-thiophene.
50 %Chromat.
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.75 h;
Stage #2: With N,N-dimethyl-formamide; methylbutenedioic acid In water at -78℃; for 20 h;
A solution of diisopropylamine (35.3 ml, 0.251 moles) in tetrahydrofuran (500 ml) was cooled to -78 C. under a nitrogen blanket. To this was added 1.6M n-butyllithium in hexanes (157 ml, 0.251 moles) and allowed to stir for 5 min. Then slowly added thiopene-2-carbonitrile (21.33 ml, 0.229 moles) in tetrahydrofuran (115 ml) and allowed to stir. After 45 min. was added NN-dimethylformamide (88.66 ml, 1.145 moles) at -78 C. Citric acid (40 g) was added after 2 h. followed by water (240 ml) and stirred for 18 h. The reaction was concentrated in vacuo, transferred to a separatory funnel, diluted with brine, and extracted twice with ether. The combined ether layers were washed with brine, dried over magnesium sulfate, filtered, and the solvent removed in vacuo. Chromatography yielded 15.8 g (50percent) of 2-cyano-5-formylthiophene (EX-55A) as a brown solid: 1H NMR (300 MHZ, CDCl3) d 10.02 (s, 1H), 7.79 (m, 1H), 7.30 (m, 1H).

Reference: [1] Patent: US5914319, 1999, A,
[2] Patent: US5707966, 1998, A,
[3] Patent: US5710130, 1998, A,
[4] Patent: US5726159, 1998, A,
[5] Patent: US5705487, 1998, A,
[6] Patent: US6664255, 2003, B1, . Location in patent: Page column 117
  • 6
  • [ 1003-31-2 ]
  • [ 16689-02-4 ]
  • [ 42137-24-6 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1955, p. 1614
  • 7
  • [ 1003-31-2 ]
  • [ 16689-02-4 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1982, vol. 18, # 2, p. 127 - 130[2] Khimiya Geterotsiklicheskikh Soedinenii, 1982, vol. 18, # 2, p. 167 - 170
  • 8
  • [ 1003-31-2 ]
  • [ 7697-37-2 ]
  • [ 108-24-7 ]
  • [ 16689-02-4 ]
  • [ 42137-24-6 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1955, p. 1614
  • 9
  • [ 1003-31-2 ]
  • [ 105-36-2 ]
  • [ 13669-10-8 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 6, p. 1420 - 1424
  • 10
  • [ 1003-31-2 ]
  • [ 18945-81-8 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex In tetrahydrofuran at 25℃; for 2 h;
Stage #2: With iodine In tetrahydrofuran at 25℃; for 1 h;
General procedure: In a flame-dried flask flushed with nitrogen, the heterocyclic nitrile (1 mmol) wasdissolved in THF (1.5 mL). TMPMgCl·LiCl (1.0 M in THF, 1.8 mL, 1.8 mmol) wasadded dropwise at 25°C and the mixture was stirred for 2h (for substrate 1a, metalationwas best performed in 1 h). The completion of the metalation was checked by GC analysisof reaction aliquots quenched with a solution of I2 in dry THF. After that, a solution ofthe electrophile (2 mmol) in THF (2 mL) was added dropwise at 0°C and the reactionstirred for 1 hour at 25°C. The reaction mixture was quenched with sat. aq. NaHSO3 orNH4Cl solution (5 mL), extracted with ethyl acetate (3x15 mL) and dried over anhydrousMgSO4. After the filtration, solvent was evaporated in vacuo.
Reference: [1] Synlett, 2015, vol. 26, # 20, p. 2795 - 2800
[2] Tetrahedron Letters, 1995, vol. 36, # 27, p. 4883 - 4884
  • 11
  • [ 1003-31-2 ]
  • [ 2160-62-5 ]
YieldReaction ConditionsOperation in experiment
100% With N-Bromosuccinimide; bromine; acetic anhydride In acetic acid at 20℃; for 3 h; 5-Bromo-2-thiophenecarbonitrile To a solution of the available 2-thiophenecarbonitrile (2.22 g, 20.3 [MMOL)] in a mixture of acetic acid (1.22 g, 20.3 [MMOL)] and acetic anhydride (8.3 g, 81.3 [MMOL)] was [ADDED NBS (3.62 G, 1.0 EQ. ) AND BROMINE (1.05 ML, 1.0 EQ. ) AND THE REACTION MIXTURE] was stirred at rt for 3 hours. Water and ice were added and also a saturated sodium bisulfite solution. After extraction with DCM, the organic layer was washed with a saturated [NAHC03] solution, dried over [NA2SO4] and evaporated. The title compound was obtained as a orange liquid (3.74 g, 20 [MMOL)] in a quantitative yield ; GC/MS : [M+] C5H2BrNS 188
75% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 6 h; Darkness (1) Weighing 4 g 2-cyanothiophene (32.47 mmol) is dissolved in 30 ml DMF, taking 3.6 g NBS is slowly added to the mixture in stirring 15 min, all in the dark after adding the reaction under the room temperature condition 6 h. After the completion of the reaction methylene chloride and aqueous phase extraction purification, congeals the organic layer to dry column chromatography purification, the developing agent is the volume ratio of 1:3 of dichloromethane: petroleum ether mixed solvent, to obtain 4-bromo-2-cyanothiophene, the yield is 75percent.
Reference: [1] Patent: WO2004/6922, 2004, A1, . Location in patent: Page/Page column 53
[2] Patent: CN108530419, 2018, A, . Location in patent: Paragraph 0058; 0059
[3] Heterocycles, 1997, vol. 46, # 1, p. 489 - 501
  • 12
  • [ 1003-31-2 ]
  • [ 79-24-3 ]
  • [ 18820-82-1 ]
  • [ 2160-62-5 ]
Reference: [1] Patent: US6696110, 2004, B1,
  • 13
  • [ 1003-31-2 ]
  • [ 305832-67-1 ]
Reference: [1] Patent: US6355648, 2002, B1, . Location in patent: Page column 64
  • 14
  • [ 1003-31-2 ]
  • [ 1185885-86-2 ]
Reference: [1] Journal of Materials Chemistry, 2012, vol. 22, # 16, p. 7945 - 7953
[2] Dyes and Pigments, 2012, vol. 95, # 1, p. 126 - 133
[3] Advanced Functional Materials, 2013, vol. 23, # 28, p. 3519 - 3524
[4] European Journal of Organic Chemistry, 2013, # 23, p. 5076 - 5084
[5] RSC Advances, 2014, vol. 4, # 101, p. 58027 - 58035
[6] RSC Advances, 2015, vol. 5, # 25, p. 19520 - 19527
[7] Dyes and Pigments, 2016, vol. 127, p. 37 - 44
[8] Patent: CN103360397, 2016, B,
[9] Journal of Fluorescence, 2016, vol. 26, # 6, p. 1939 - 1949
[10] Patent: US9590187, 2017, B2,
[11] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 3, p. 1983 - 1994
  • 15
  • [ 1003-31-2 ]
  • [ 1000623-95-9 ]
Reference: [1] Dyes and Pigments, 2012, vol. 95, # 1, p. 126 - 133
[2] RSC Advances, 2014, vol. 4, # 101, p. 58027 - 58035
[3] Electrochimica Acta, 2014, vol. 144, p. 211 - 220
[4] RSC Advances, 2015, vol. 5, # 25, p. 19520 - 19527
[5] Dyes and Pigments, 2016, vol. 127, p. 37 - 44
[6] Patent: CN103360397, 2016, B,
[7] Journal of Fluorescence, 2016, vol. 26, # 6, p. 1939 - 1949
[8] Patent: US9590187, 2017, B2,
[9] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 3, p. 1983 - 1994
  • 16
  • [ 1003-31-2 ]
  • [ 1046864-83-8 ]
Reference: [1] Patent: JP6236813, 2017, B2,
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