Home Cart 0 Sign in  
X

[ CAS No. 4521-33-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 4521-33-9
Chemical Structure| 4521-33-9
Chemical Structure| 4521-33-9
Structure of 4521-33-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 4521-33-9 ]

Related Doc. of [ 4521-33-9 ]

Alternatived Products of [ 4521-33-9 ]
Product Citations

Product Details of [ 4521-33-9 ]

CAS No. :4521-33-9 MDL No. :MFCD00005433
Formula : C5H3NO3S Boiling Point : -
Linear Structure Formula :- InChI Key :CHTSWZNXEKOLPM-UHFFFAOYSA-N
M.W : 157.15 Pubchem ID :78281
Synonyms :

Calculated chemistry of [ 4521-33-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.53
TPSA : 91.13 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.72
Log Po/w (XLOGP3) : 1.56
Log Po/w (WLOGP) : 1.47
Log Po/w (MLOGP) : -0.82
Log Po/w (SILICOS-IT) : 0.57
Consensus Log Po/w : 0.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.04
Solubility : 1.45 mg/ml ; 0.00922 mol/l
Class : Soluble
Log S (Ali) : -3.08
Solubility : 0.13 mg/ml ; 0.000825 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.98
Solubility : 16.3 mg/ml ; 0.104 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.29

Safety of [ 4521-33-9 ]

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 [ 4521-33-9 ]

* 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 [ 4521-33-9 ]
  • Downstream synthetic route of [ 4521-33-9 ]

[ 4521-33-9 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 98-03-3 ]
  • [ 4521-33-9 ]
  • [ 57500-53-5 ]
YieldReaction ConditionsOperation in experiment
40% at -10℃; for 0.0833333 h; Example 1a; (S)-1-(5-((2-amιnopropanamιdo)methyl)thιophen-3-yl)-N-(2-methoxybenzyl)-3- (trιfluoromethyl)-i H-pyrazole-5-carboxamιde (9a); Step 1 4-nιtrothιophene-2-carbaldehyde (1); [0170] A mixture of fuming HNO3 (4 0 ml_) in cone H2SO4 (3 1 ml_) was added to a solution of thιophene-2-carbaldehyde (2 O g, 17 8 mmol) in cone H2SO4 (4 7 mL) cooled in an ice-salt bath according to the procedure of Pierre Foumari and Jean Paul Chane (Bull Soc Chum Fr ,1963, 479-484) After completion of addition the mixture was stirred for 5 mm, then ice was added, and the mixture was extracted with ether The ether extracts were washed with sat'dNaHCO3, then with brine, dried over MgSO4, filtered and concentrated giving brown oilProton NMR of the crude showed a mixture of the two regioisomers in a ratio of almost 40 60 for 4-nιtrothιophene-2-carbaldehyde and 5-nιtrothιophene-2-carbaldehyde respectively The mixture was separated by column chromatography eluting with 30-50percent DCM/hexanes 4-Nιtrothιophene-2-carbaldehyde was obtained in 40percent yield as a light yellow solid1H NMR (CDCI3) δ(ppm) 9 95(s, 1 H), 8 63 (s, 1 H), 8 27 (s, 1 H)
Reference: [1] Journal of Chemical Research, Miniprint, 1997, # 9, p. 2001 - 2013
[2] Patent: WO2008/104077, 2008, A1, . Location in patent: Page/Page column 46
[3] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 1, p. 162 - 165
[4] Bulletin de la Societe Chimique de France, 1963, p. 479 - 484
[5] Journal of the American Chemical Society, 1954, vol. 76, p. 1378
[6] Journal of the American Chemical Society, 1955, vol. 77, p. 577
[7] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 8088 - 8094
  • 2
  • [ 20898-85-5 ]
  • [ 4521-33-9 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 30, p. 5261 - 5264
  • 3
  • [ 14289-24-8 ]
  • [ 4521-33-9 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1963, p. 479 - 484
[2] Doklady Akademii Nauk SSSR, 1952, vol. 83, p. 85,86[3] Chem.Abstr., 1953, p. 2166
[4] Journal of the American Chemical Society, 1952, vol. 74, p. 1356
[5] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1956, vol. 243, p. 61,62[6] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 2003,2004
[7] Bulletin de la Societe Chimique de France, 1952, p. 701
[8] Journal of the American Chemical Society, 1952, vol. 74, p. 1356
[9] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1956, vol. 243, p. 61,62[10] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 2003,2004
[11] Bulletin de la Societe Chimique de France, 1952, p. 701
  • 4
  • [ 20898-86-6 ]
  • [ 4521-33-9 ]
  • [ 74786-70-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 1994, vol. 29, # 1, p. 41 - 44
  • 5
  • [ 63011-97-2 ]
  • [ 4521-33-9 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 1356
  • 6
  • [ 20898-83-3 ]
  • [ 4521-33-9 ]
Reference: [1] Australian Journal of Chemistry, 1981, vol. 34, # 9, p. 1879 - 1886
  • 7
  • [ 20409-48-7 ]
  • [ 4521-33-9 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, p. 4202 - 4205
  • 8
  • [ 87207-23-6 ]
  • [ 4521-33-9 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, p. 4202 - 4205
  • 9
  • [ 83054-95-9 ]
  • [ 4521-33-9 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, p. 4202 - 4205
  • 10
  • [ 20898-86-6 ]
  • [ 4521-33-9 ]
Reference: [1] Australian Journal of Chemistry, 1981, vol. 34, # 9, p. 1879 - 1886
  • 11
  • [ 87207-17-8 ]
  • [ 4521-33-9 ]
  • [ 87207-23-6 ]
  • [ 83054-95-9 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, p. 4202 - 4205
[2] Journal of Organic Chemistry, 1983, vol. 48, p. 4202 - 4205
  • 12
  • [ 20898-86-6 ]
  • [ 147225-22-7 ]
  • [ 4521-33-9 ]
  • [ 74786-70-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 1994, vol. 29, # 1, p. 41 - 44
  • 13
  • [ 98-03-3 ]
  • [ 4521-33-9 ]
  • [ 57500-53-5 ]
  • [ 58963-75-0 ]
Reference: [1] Synthesis, 2006, # 8, p. 1295 - 1300
  • 14
  • [ 98-03-3 ]
  • [ 4521-33-9 ]
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
  • 15
  • [ 98-03-3 ]
  • [ 7664-93-9 ]
  • [ 7697-37-2 ]
  • [ 4521-33-9 ]
  • [ 57500-53-5 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1963, p. 479 - 484
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1956, vol. 243, p. 61,62[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 2003,2004
[4] Journal of the American Chemical Society, 1954, vol. 76, p. 1378
[5] Journal of the American Chemical Society, 1955, vol. 77, p. 577
[6] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 2003[7] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 1182
  • 16
  • [ 98-03-3 ]
  • [ 7697-37-2 ]
  • [ 108-24-7 ]
  • [ 64-19-7 ]
  • [ 4521-33-9 ]
  • [ 57500-53-5 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1963, p. 479 - 484
[2] Journal of the Chemical Society, 1958, p. 1721
[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1956, vol. 243, p. 61,62[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 2003,2004
[5] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 2003[6] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 1182
  • 17
  • [ 4521-33-9 ]
  • [ 166887-84-9 ]
Reference: [1] Chemical Communications, 2013, vol. 49, # 52, p. 5859 - 5861
  • 18
  • [ 4521-33-9 ]
  • [ 16689-02-4 ]
Reference: [1] Tetrahedron, 1999, vol. 55, # 46, p. 13265 - 13268
[2] Journal of Organometallic Chemistry, 2007, vol. 692, # 14, p. 3027 - 3041
[3] Bulletin de la Societe Chimique de France, 1963, p. 479 - 484
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1956, vol. 243, p. 61,62[5] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 2003,2004
  • 19
  • [ 4521-33-9 ]
  • [ 6317-37-9 ]
YieldReaction ConditionsOperation in experiment
98.2% With hydrogenchloride; bromine In water III.
Oxidation in the presence of sodium hydroxide
Into a 250-ml flask equipped with a central stirrer, a thermometer, a condenser and a dropping-funnel, and containing 15.7 g (0.1 mol) of 5-nitro-2-formyl-thiophene, were introduced 100 ml of distilled water and then, in one operation, 16 g (0.1 mol) of bromine.
As soon as this operation was over, a solution of 8 g of sodium hydroxide in 30 ml of water was added.
During the operation of adding the sodium hydroxide solution, the temperature of the reaction medium rose to 40° C. and the colouring provoked by the bromine disappeared.
The medium was then allowed to stand for one hour at 80° C.
In the course of the oxidation reaction, the pH varied from 7 to 9.5.
The mixture was poured into water containing hydrochloric acid and then the thenoic acid so formed was extracted with ether.
The etheral phase was dried on sodium sulphate and heated to dryness in a rotatory evaporator.
The crude solid so obtained was recrystallized from a 70/30 heptane/1,2-dichloro-ethane mixture and brought to 0° C.
In this manner, 17 g of crude 5-nitro-2-thenoic acid were obtained, which represents a yield of 98.2percent.
Yield in pure product: 14 g or 81percent.
72% With potassium dichromate; sulfuric acid In water at 100℃; for 1 h; To a stirred solution of potassium dichromate (35.1 g; 143 mmol) in 5N [H2SO4] (375 ml) at [0°C,] was added solid [2-FORMYL-5-NITROTHIOPHENE] (50.0 g; 318 mmol). The resulting suspension was heated to [100°C] for 1 hour after which HPLC showed no remaining starting material. The reaction mixture was cooled to room temperature, diluted with water (300 ml) and the resulting precipitate collected by filtration, washed with water (5 x 200 ml) and dried to a constant weight in a vacuum oven at [40°C] to afford 95 (39.5 g) as a light green solid. Yield: 72percent [1H] NMR (DMSO-d6) 7.70 (d, 1H); 8.09 (d, 1H).
3.6 g With sodium chlorite; aminosulfonic acid In 1,4-dioxane; water at 0 - 20℃; A mixture of 5-nitrothiophene-2-carbaldehyde (1.685 g, 10.72 mmol) and sulfamic acid (1.249 g, 12.87 mmol) in dioxane (30 ml) was cooled to 0° C., and a solution of sodium chlorite (1.940 g, 21.44 mmol) in water (14 ml) was added drop-wise.
The mixture was allowed to warm to RT and stirred for 2 hours.
A second batch of 5-nitrothiophene-2-carbaldehyde (1.966 g, 12.51 mmol) was reacted under the same conditions using the molar ratios described above.
The two reaction mixtures were combined and portioned between ethyl acetate and water.
The organic layer was extracted twice with 5percent NaHCO3 and the organic phase was discarded.
The basic aqueous phase was acidified with 2N HCl (pH=2) and extracted twice with ethyl acetate.
The combined organic layers were washed with brine and dried over sodium sulfate; the solvent was removed affording 5-nitrothiophene-2-carboxylic acid (Int. 53) (3.6 g, 20.79 mmol, MS/ESI+173.9 [MH]+).
3.6 g With sodium chlorite; aminosulfonic acid In 1,4-dioxane; water at 0 - 20℃; for 2 h; Step 1: Preparation of 5-nitrothiophene-2-carboxylic acid (Intermediate 53) A mixture of 5-nitrothiophene-2-carbaldehyde (1.685 g, 10.72 mmol) and sulfamic acid (1.249 g, 12.87 mmol) in dioxane (30 ml) was cooled to 0°C and a solution of sodium chlorite (1.940 g, 21.44 mmol) in water (14 ml) was added drop-wise. The mixture was allowed to warm to T and stirred for 2 h. A second batch of 5-nitrothiophene-2-carbaldehyde (1.966 g, 12.51 mmol) was reacted under the same conditions using the molar ratios described above. The two reaction mixtures were combined and portioned between ethyl acetate and water. The organic layer was extracted twice with 5percent NaHCO3 and the organic phase was discarded. The basic aqueous phase was acidified with 2N HC1 (pH = 2) and extracted twice with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate; the solvent was removed affording 5-nitrothiophene-2-carboxylic acid (Int. 53) (3.6 g, 20.79 mmol, MS/ESI+ 173.9 [MH]+).

Reference: [1] Patent: US4220793, 1980, A,
[2] Patent: US4220793, 1980, A,
[3] Patent: US4220793, 1980, A,
[4] Patent: WO2004/18480, 2004, A1, . Location in patent: Page 155
[5] Helvetica Chimica Acta, 2002, vol. 85, # 12, p. 4485 - 4517
[6] Journal of Medicinal Chemistry, 1991, vol. 34, # 7, p. 2112 - 2120
[7] Doklady Akademii Nauk SSSR, 1952, vol. 83, p. 85,86[8] Chem.Abstr., 1953, p. 2166
[9] Journal of the American Chemical Society, 1952, vol. 74, p. 1356
[10] Bulletin de la Societe Chimique de France, 1952, p. 701
[11] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1980, p. 1331 - 1335
[12] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 6, p. 2067 - 2076
[13] Tetrahedron Letters, 2006, vol. 47, # 30, p. 5261 - 5264
[14] Patent: US2013/324501, 2013, A1, . Location in patent: Paragraph 0317; 0318
[15] Patent: WO2013/182451, 2013, A1, . Location in patent: Page/Page column 77-78
  • 20
  • [ 7758-19-2 ]
  • [ 4521-33-9 ]
  • [ 6317-37-9 ]
Reference: [1] Patent: US5840917, 1998, A,
  • 21
  • [ 10049-21-5 ]
  • [ 4521-33-9 ]
  • [ 7722-84-1 ]
  • [ 6317-37-9 ]
Reference: [1] Patent: US5780480, 1998, A,
  • 22
  • [ 4521-33-9 ]
  • [ 6317-37-9 ]
Reference: [1] Patent: US6201007, 2001, B1,
  • 23
  • [ 4521-33-9 ]
  • [ 1182917-82-3 ]
  • [ 1216744-19-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 11, p. 4729 - 4737
  • 24
  • [ 4521-33-9 ]
  • [ 1379686-30-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 13, p. 4413 - 4417
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 4521-33-9 ]

Aldehydes

Chemical Structure| 24372-46-1

[ 24372-46-1 ]

5-(Dimethylamino)thiophene-2-carbaldehyde

Similarity: 0.68

Chemical Structure| 98-03-3

[ 98-03-3 ]

Thiophene-2-carbaldehyde

Similarity: 0.55

Chemical Structure| 13679-70-4

[ 13679-70-4 ]

5-Methylthiophene-2-carbaldehyde

Similarity: 0.54

Chemical Structure| 207290-72-0

[ 207290-72-0 ]

5-(4-Hydroxypiperidin-1-yl)thiophene-2-carbaldehyde

Similarity: 0.54

Chemical Structure| 21512-16-3

[ 21512-16-3 ]

5-Formylthiophene-2-carbonitrile

Similarity: 0.52

Nitroes

Chemical Structure| 6317-37-9

[ 6317-37-9 ]

5-Nitrothiophene-2-carboxylic acid

Similarity: 0.86

Chemical Structure| 166887-84-9

[ 166887-84-9 ]

2-(Bromomethyl)-5-nitrothiophene

Similarity: 0.81

Chemical Structure| 16689-02-4

[ 16689-02-4 ]

5-Nitrothiophene-2-carbonitrile

Similarity: 0.81

Chemical Structure| 5832-01-9

[ 5832-01-9 ]

Methyl 5-nitrothiophene-2-carboxylate

Similarity: 0.80

Chemical Structure| 52003-20-0

[ 52003-20-0 ]

2-Nitrothiophen-3-amine

Similarity: 0.65