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Chemical Structure| 35674-27-2
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Product Details of [ 35674-27-2 ]

CAS No. :35674-27-2 MDL No. :MFCD00502399
Formula : C7H4INO4 Boiling Point : -
Linear Structure Formula :- InChI Key :DNMTZLCNLAIKQC-UHFFFAOYSA-N
M.W :293.02 Pubchem ID :11208598
Synonyms :

Calculated chemistry of [ 35674-27-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.94
TPSA : 83.12 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) : -6.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.96
Log Po/w (XLOGP3) : 1.93
Log Po/w (WLOGP) : 1.9
Log Po/w (MLOGP) : 1.43
Log Po/w (SILICOS-IT) : 0.07
Consensus Log Po/w : 1.26

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.08
Solubility : 0.243 mg/ml ; 0.000828 mol/l
Class : Soluble
Log S (Ali) : -3.3
Solubility : 0.147 mg/ml ; 0.000502 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.09
Solubility : 2.36 mg/ml ; 0.00805 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.07

Safety of [ 35674-27-2 ]

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 [ 35674-27-2 ]

* 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 [ 35674-27-2 ]
  • Downstream synthetic route of [ 35674-27-2 ]

[ 35674-27-2 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 1588-83-6 ]
  • [ 35674-27-2 ]
YieldReaction ConditionsOperation in experiment
89.7%
Stage #1: With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1 h;
Stage #2: With potassium iodide In water at 0 - 20℃; for 2 h;
Example 1
Preparation of 4-iodo-3-nitrobenzoic acid (Compound V)
45 g (0.25 mol) 4-Amino-3-nitrobenzoic acid, 400 ml water and 100 ml concentrated hydrochloric acid were added into a reaction flask.
Started to stir, and the mixture was cooled to 0 to 5° C., then 50 ml aqueous solution of 25.9 g sodium nitrite (0.38 mol) was added dropwise.
The solid was dissolved gradually.
After completing the dropwise addition, the mixture was reacted at 0 to 5° C. for 1 hour, and 200 ml aqueous solution of 88 g (0.5 mol) potassium iodide was added dropwise at this temperature.
The mixture was stirred at room temperature for 2 h after completing the dropwise addition, and solid was precipitated.
The solid was filtered, washed with water, and dried to obtain 4-iodo-3-nitrobenzoic acid (compound V) as a solid, 65 g (0.22 mol), yield 89.7percent.
Reference: [1] Patent: US2013/225810, 2013, A1, . Location in patent: Paragraph 0081; 0082
[2] Tetrahedron, 2005, vol. 61, # 42, p. 10113 - 10121
[3] Tetrahedron Letters, 1997, vol. 38, # 46, p. 7963 - 7966
[4] Patent: WO2005/40157, 2005, A2, . Location in patent: Page/Page column 67-68
[5] Patent: WO2010/62171, 2010, A2, . Location in patent: Page/Page column 140
  • 2
  • [ 619-58-9 ]
  • [ 35674-27-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 9, p. 1896 - 1904
[2] Dalton Transactions, 2015, vol. 44, # 5, p. 2047 - 2051
[3] Chemical Communications, 2017, vol. 53, # 55, p. 7808 - 7811
[4] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 1865 - 1877
[5] Chemische Berichte, 1875, vol. 8, p. 562
  • 3
  • [ 5326-39-6 ]
  • [ 35674-27-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
  • 4
  • [ 27329-27-7 ]
  • [ 35674-27-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
  • 5
  • [ 101420-88-6 ]
  • [ 35674-27-2 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 25
  • 6
  • [ 15164-44-0 ]
  • [ 35674-27-2 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 25
  • 7
  • [ 619-58-9 ]
  • [ 7697-37-2 ]
  • [ 35674-27-2 ]
Reference: [1] Chemische Berichte, 1875, vol. 8, p. 562
  • 8
  • [ 67-56-1 ]
  • [ 35674-27-2 ]
  • [ 89976-27-2 ]
YieldReaction ConditionsOperation in experiment
85% at 0 - 0.7℃; for 8 h; Example 1
Preparation of 4-iodo-3-nitrobenzoic Acid Methyl Ester Using Methanol/Sulfuric Acid
To a solution of 4-iodo-3-nitrobenzoic acid (3 g, 10 mmol) in methanol (30 ml) cooled to 0° C., sulfuric acid (3.4 g, 34.6 mmol) is added slowly.
The reaction mixture is warmed to room temperature and then refluxed (˜70° C.) for 8 hours.
After cooling, the reaction mixture is neutralized with solid NaHCO3 and the salts are filtered.
The filtrate is evaporated under reduced pressure.
To the residue obtained, water (30 ml) is added and the mixture extracted with MTBE (30 ml*2).
The combined organic phase is washed with brine, dried using anhydrous sodium sulfate and filtered.
After evaporating the solvent under reduced pressure, 4-iodo-3-nitro-benzoic acid methyl ester is obtained as a yellow solid (2.67 g, 85percent yield, 98percent HPLC).
83% at 0 - 20℃; for 16 h; Inert atmosphere [00095] To a stirred solution of 4-iodo-3-nitrobenzoic acid 46 (15 g, 51.36 mmol) in MeOH (150 mL) under inert atmosphere was added concentrated sulphuric acid (15 mL) dropwise for 10 min at 0 °C; warmed to RT at stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo. The residue was diluted with ice-cold water (500 mL) and extracted with EtOAc (3 x 100 mL). The combined organic extracts were washed saturated sodium bicarbonate solution (2 x 100 mL) dried over sodium sulfate, filtered and concentrated in vacuo to afford compound 47 (13 g, 83percent) as an off-white solid. TLC: 30percent EtOAc/ hexanes (R/. 0.8); 1H NMR (CDC13, 500 MHz) δ 8.45 (s, 1H), 8.15 (d, J = 8.4 Hz, 1H), 7.88 (dd, J = 8.2, 1.9 Hz, 1H), 3.97 (s, 3H).
77% for 6 h; Heating / reflux b) 4-Iodo-3-nitro-benzoic acid methyl ester A methanolic solution of 4-iodo-3-nitro-benzoic acid (10.0 g, 34.13 mmol, 1 eq. ) was treated with concentrated sulfuric acid (7 mL) and the reaction heated to reflux. After 6 hours, the acid was neutralized with solid sodium bicarbonate and the methanol removed in vacuo. The residual oil was diluted with water and extracted with diethyl ether. Combined the organics, washed with brine, dried, filtered, and removed the solvent in vacuo leaving an orange oil which was purified via normal phase chromatography to leave 4-iodo-3-nitro-benzoic acid methyl ester (8.08 g, 77percent yield) as a yellow solid.
Reference: [1] Dalton Transactions, 2015, vol. 44, # 5, p. 2047 - 2051
[2] Chemical Communications, 2017, vol. 53, # 55, p. 7808 - 7811
[3] Patent: US2013/172618, 2013, A1, . Location in patent: Paragraph 0025
[4] Patent: WO2017/48954, 2017, A1, . Location in patent: Paragraph 00095
[5] Patent: WO2005/40157, 2005, A2, . Location in patent: Page/Page column 68
[6] Tetrahedron Letters, 1997, vol. 38, # 46, p. 7963 - 7966
[7] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 1865 - 1877
  • 9
  • [ 35674-27-2 ]
  • [ 74-88-4 ]
  • [ 89976-27-2 ]
YieldReaction ConditionsOperation in experiment
71.5% With potassium carbonate; triethylamine In acetonitrile; Petroleum ether at 0 - 40℃; for 8 h; Example 2
Preparation of methyl 4-iodo-3-nitrobenzoate (Compound IV)
55 g (0.19 mol) 4-Iodo-3-nitrobenzoic acid (Compound V), 16.5 g (0.12 mol) potassium carbonate and 550 ml acetonitrile were added into a reaction flask, and started to stir.
The mixture was cooled to 0 to 5° C., and 52.9 ml (0.38 mol) triethylamine was added.
The temperature was controlled below 10° C., and 71 ml (1.12 mol) iodomethane was added.
The mixture was heated to about 40° C. for 8 hours, and concentrated under reduced pressure after completing the reaction until most of the acetonitrile was evaporated.
The mixture was then extracted with 500 ml ethyl acetate, washed with water for three times, and the organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to the least amount, and then 300 ml petroleum ether was added, stirred for 30 min, and then filtered.
The filter cake was washed with petroleum ether, and dried to obtain methyl 4-iodo-3-nitrobenzoate (Compound IV), about 41.2 g (0.13 mol), yield 71.5percent.
1HNMR (400 MHz, DMSO-d6): δ 3.91 (s, 3H), 7.87 (dd, 1H, J1=8.08 Hz, J2=1.88 Hz), 8.26 (d, 1H, J=8.12 Hz), 8.34 (d, 1H, J=9.12 Hz); MS (m/z): 308 [M+H].
Reference: [1] Patent: US2013/225810, 2013, A1, . Location in patent: Paragraph 0083; 0084; 0085
  • 10
  • [ 1445-45-0 ]
  • [ 35674-27-2 ]
  • [ 89976-27-2 ]
YieldReaction ConditionsOperation in experiment
99% at 0.11℃; for 15 h; Example 2
Preparation of 4-iodo-3-nitrobenzoic Acid Methyl Ester Using Trimethyl Orthoacetate
A solution of 4-iodo-3-nitrobenzoic acid (3 g, 10 mmol) in trimethyl orthoacetate (30 ml) is refluxed (˜110° C.) for 15 hours and then solvent is evaporated under reduced pressure.
The 4-iodo-3-nitrobenzoic acid methyl ester is obtained as a yellow solid (3.11 g, 99percent yield, 97.5percent HPLC).
Reference: [1] Patent: US2013/172618, 2013, A1, . Location in patent: Paragraph 0026
  • 11
  • [ 35674-27-2 ]
  • [ 51411-81-5 ]
Reference: [1] Zhurnal Organicheskoi Khimii, 1973, vol. 9, p. 2540,2541; engl. Ausg. S. 2560, 2561
[2] Tetrahedron Letters, 1997, vol. 38, # 46, p. 7963 - 7966
  • 12
  • [ 1336-21-6 ]
  • [ 35674-27-2 ]
  • [ 160003-66-7 ]
YieldReaction ConditionsOperation in experiment
40.5% With thionyl chloride In water; N,N-dimethyl-formamide; acetonitrile C.
4-Iodo-3-Nitrobenzamide
In a 100-mL flask equipped with a magnetic stirrer, thermometer and ice bath, a stirred solution of 4-Iodo-3-nitrobenzoic acid (1025 mg, 3.50 mMoles) (Chemica Alta Ltd., Edmonton, Alberta, Canada) in N,N-dimethylformamide (10 mL) is cooled to 10° C., and then thionyl chloride (0.76 mL, 10.5 mMoles) is added to it.
There is no exothermicity, the ice bath is removed, and the solution is allowed to warm to ambient temperature, and stirring is continued for a total of 1 hour.
Then the solution is poured into chilled, concentrated ammonium hydroxide (20 mL), resulting in a dark yellow mixture, which is stirred for 5 minutes.
Then chilled deionized water (50 mL) is added, causing precipitation of the light yellow product.
After allowing the precipitation mixture to stand chilled on ice for 10 minutes, the precipitate is collected on a suction filter, rinsed with cold water, and then dried by vacuum pumping.
The resultant crude product (500.4 mg) is then re-crystallized by dissolving it in acetonitrile (7.0 mL) heated to about 65° C., followed by cooling and allowing the solution to stand in the refrigerator overnight.
The yellow crystals are collected, rinsed with chilled solvent and dried by vacuum pumping, to give 415.2 mg (40.5percent yield) of 4-Iodo-3-nitrobenzamide, m.p. 152°-155° C.
1 H NMR spectrum, in DMSO-d6 δ (ppm) values relative to TMS): broad singlet (7.67) due to one nonequivalent proton of the amido NH2 group; doublet of doublets (7.84, 7.85 and 7.86, 7.87) due to H-5 split by H-6 and finely split by H-2; doublet (8.22, 8.24) due to H-6 split by H-5; broad singlet centered near 8.22, overlapping the signal of H-6, due to the second nonequivalent proton of the amido NH2 group; doublet (8.35, 8.36) due to H-2 finely split by H-5.
At higher NMR field signals due to adventitious water (2.5 ppm), deuterated-DMSO impurity protons (3.3 ppm) and crystallization solvent acetonitrile (single at 2.07 ppm) are observed.
Integration of the acetonitrile signal indicates approximately one molecule of acetonitrile per 3 molecules of 4-iodo-3-nitrobenzamide.
UV absorption spectrum in absolute ethanol, λ max (ε): 308 nm (1.59*103), 242 nm (1.31*104), 208 nm (1.45*104)
Elemental analysis (Schwarzkopf Microanalytical Laboratory):
Calculated for C7 H5 N2 O3 I: C, 28.79percent; H, 1.72; I, 43.46; N, 9.59. Found: C, 29.63; H, 1.72; I, 41.47; N, 9.99.
Deviations from calculated are believed to be due to the presence of acetonitrile (crystallization solvent) as detected in the NMR spectrum.
High resolution EI mass spectrum: calculated for C7 H5 N2 O3 I: 291.9345; Found: M+
(m/z) 291.9349 (deviation=-1.4 ppm).
Reference: [1] Patent: US5877185, 1999, A,
  • 13
  • [ 35674-27-2 ]
  • [ 160003-66-7 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 10, p. 3093 - 3097
[2] Patent: US2013/172618, 2013, A1,
  • 14
  • [ 35674-27-2 ]
  • [ 412947-54-7 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 46, p. 7963 - 7966
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