Cas no 857599-37-2 (Methyl 2-iodo-5-methoxybenzoate)

Methyl 2-iodo-5-methoxybenzoate structure
857599-37-2 structure
Product Name:Methyl 2-iodo-5-methoxybenzoate
CAS No:857599-37-2
MF:C9H9IO3
MW:292.070435285568
MDL:MFCD12923253
CID:1038783
PubChem ID:70701075
Update Time:2024-10-26

Methyl 2-iodo-5-methoxybenzoate Chemical and Physical Properties

Names and Identifiers

    • Methyl 2-iodo-5-methoxybenzoate
    • 2-Iodo-5-methoxy-benzoic acid methyl ester
    • 3345AC
    • FCH1378634
    • AK100208
    • AX8241185
    • ST24025242
    • m-Anisic acid, 6-iodo-, methyl ester (5CI)
    • CS-0131369
    • methyl 2-iodo-5-methoxy-benzoate
    • AS-44988
    • DTXSID50743854
    • DB-142885
    • AKOS016002685
    • 857599-37-2
    • AB9739
    • Methyl2-iodo-5-methoxybenzoate
    • MFCD12923253
    • SY241024
    • MDL: MFCD12923253
    • Inchi: 1S/C9H9IO3/c1-12-6-3-4-8(10)7(5-6)9(11)13-2/h3-5H,1-2H3
    • InChI Key: RDRCCNSFEFSPTO-UHFFFAOYSA-N
    • SMILES: O=C(C1C(I)=CC=C(OC)C=1)OC

Computed Properties

  • Exact Mass: 291.95964g/mol
  • Monoisotopic Mass: 291.95964g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 3
  • Complexity: 184
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.7
  • Topological Polar Surface Area: 35.5

Methyl 2-iodo-5-methoxybenzoate Pricemore >>

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Methyl 2-iodo-5-methoxybenzoate Production Method

Production Method 1

Reaction Conditions
1.1 Catalysts: Sulfuric acid ;  rt; rt → reflux; 4 h, reflux; reflux → rt
1.2 Reagents: Sodium carbonate Solvents: Water
Reference
A general method for one-step synthesis of monofluoroiodane(III) reagents using silver difluoride
Ren, Jing; et al, Chinese Chemical Letters, 2022, 33(11), 4834-4837

Production Method 2

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  12 h, rt
1.2 Reagents: Water
Reference
A Divergent Approach to the Diastereoselective Synthesis of 3,3-Disubstituted Oxindoles from Atropisomeric N-Aryl Oxindole Derivatives
Nakazaki, Atsuo ; et al, Chemistry - An Asian Journal, 2016, 11(22), 3267-3274

Production Method 3

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  12 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified, rt
Reference
2-Iodo-N-isopropyl-5-methoxybenzamide as a highly reactive and environmentally benign catalyst for alcohol oxidation
Yakura, Takayuki; et al, Beilstein Journal of Organic Chemistry, 2018, 14, 971-978

Production Method 4

Reaction Conditions
1.1 Catalysts: Dimethylformamide Solvents: Dichloromethane ;  0 °C; 2 h, rt
1.2 Solvents: Methanol ,  Dichloromethane ;  30 min, rt
Reference
Cyclopropane-Fused N-Heterocycles via Aza-Heck-Triggered C(sp3)-H Functionalization Cascades
Jing, Changcheng; et al, Journal of the American Chemical Society, 2022, 144(37), 16749-16754

Production Method 5

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Acetone ;  12 h, reflux; reflux → rt
Reference
2-Iodoxybenzenesulfonic Acid as an Extremely Active Catalyst for the Selective Oxidation of Alcohols to Aldehydes, Ketones, Carboxylic Acids, and Enones with Oxone
Uyanik, Muhammet; et al, Journal of the American Chemical Society, 2009, 131(1), 251-262

Production Method 6

Reaction Conditions
1.1 Reagents: Sodium nitrite ,  Sulfuric acid Solvents: Water ;  0 °C; 5 min, 0 °C
1.2 Reagents: Potassium iodide Solvents: Water ;  0 °C; 1 h, 100 °C; 100 °C → rt; 14 h, rt
1.3 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  12 h, rt
1.4 Reagents: Hydrochloric acid Solvents: Water ;  acidified, rt
Reference
2-Iodo-N-isopropyl-5-methoxybenzamide as a highly reactive and environmentally benign catalyst for alcohol oxidation
Yakura, Takayuki; et al, Beilstein Journal of Organic Chemistry, 2018, 14, 971-978

Production Method 7

Reaction Conditions
1.1 Reagents: Sodium nitrite ,  Sulfuric acid Solvents: Water ;  0 °C; 5 min, 0 °C
1.2 Reagents: Potassium iodide Solvents: Water ;  0 °C; 1 h, 100 °C; 100 °C → rt; 14 h, rt
2.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  12 h, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified, rt
Reference
2-Iodo-N-isopropyl-5-methoxybenzamide as a highly reactive and environmentally benign catalyst for alcohol oxidation
Yakura, Takayuki; et al, Beilstein Journal of Organic Chemistry, 2018, 14, 971-978

Production Method 8

Reaction Conditions
1.1 Reagents: Sodium nitrite ,  Sulfuric acid Solvents: Water ;  10 min, < 5 °C
1.2 Reagents: Potassium iodide Solvents: Water ;  15 min, < 5 °C; 3 h, 100 °C; 100 °C → rt; 18 h, rt
2.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  12 h, rt
2.2 Reagents: Water
Reference
A Divergent Approach to the Diastereoselective Synthesis of 3,3-Disubstituted Oxindoles from Atropisomeric N-Aryl Oxindole Derivatives
Nakazaki, Atsuo ; et al, Chemistry - An Asian Journal, 2016, 11(22), 3267-3274

Production Method 9

Reaction Conditions
1.1 Reagents: Sulfuric acid Solvents: Methanol ;  0 °C; 4 h, 75 °C
Reference
Synthesis of FeIII and FeIV Cyanide Complexes Using Hypervalent Iodine Reagents as Cyano-Transfer One-Electron Oxidants
Souilah, Charafa; et al, Angewandte Chemie, 2022, 61(22),

Production Method 10

Reaction Conditions
1.1 Reagents: Sulfuric acid ;  12 h, 80 °C; 80 °C → rt
1.2 Reagents: Potassium carbonate
Reference
2,7-Dinitrophenanthrene-9,10-dione as a photosensitizer for the dehydrogenative lactonization of 2-arylbenzoic acids
Shi, Gaochang; et al, Organic Chemistry Frontiers, 2023, 10(10), 2429-2433

Production Method 11

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Acetone ,  Dimethylformamide ;  4 h, rt
Reference
Synthesis and SAR of 4-methyl-5-pentylbenzene-1,3-diol (MPBD), produced by Dictyostelium discoideum
Murata, Chihiro; et al, Bioorganic & Medicinal Chemistry Letters, 2016, 26(5), 1428-1433

Production Method 12

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Acetone ;  24 h, rt → reflux
Reference
Direct Carbocyclizations of Benzoic Acids: Catalyst-Controlled Synthesis of Cyclic Ketones and the Development of Tandem aHH (acyl Heck-Heck) Reactions
Miles, Kelsey C.; et al, Chemistry - A European Journal, 2014, 20(36), 11336-11339

Production Method 13

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Dimethyl carbonate ;  16 h, reflux
Reference
Rapid access to a pentacyclic library core structure: A microwave assisted approach
Patterson, Stephen; et al, QSAR & Combinatorial Science, 2004, 23(10), 883-890

Production Method 14

Reaction Conditions
1.1 Reagents: Sodium nitrite ,  Sulfuric acid Solvents: Water ;  -5 °C; 30 min, -5 °C
1.2 Reagents: Potassium iodide Solvents: Water ;  -5 °C; 1 - 3 h, rt
Reference
Optimization of a Benzoylpiperidine Class Identifies a Highly Potent and Selective Reversible Monoacylglycerol Lipase (MAGL) Inhibitor
Granchi, Carlotta; et al, Journal of Medicinal Chemistry, 2019, 62(4), 1932-1958

Production Method 15

Reaction Conditions
1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Water ;  0 °C; 20 min, 0 °C
1.2 Reagents: Potassium iodide Solvents: Water ;  cooled; 70 °C
1.3 Reagents: Thionyl chloride Solvents: Methanol ;  0 °C; 0 °C → reflux; 2 h, reflux
Reference
A facile synthesis of dibenzopyrroloazepinones as tetracyclic allocolchicinoids - an unusual 1,2-phenyl shift
Wu, Liang; et al, Chemical Communications (Cambridge, 2010, 46(2), 318-320

Production Method 16

Reaction Conditions
Reference
Pd-Catalyzed/Iodide-Promoted α-Arylation of Ketones for the Regioselective Synthesis of Isocoumarins
Casnati, Alessandra; et al, Journal of Organic Chemistry, 2017, 82(15), 8296-8303

Production Method 17

Reaction Conditions
1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Water ;  30 min, 0 °C
1.2 Reagents: Potassium iodide Solvents: Water ;  0 °C; 20 min, 0 °C; 30 min, 90 °C
2.1 Reagents: Potassium carbonate Solvents: Acetone ,  Dimethylformamide ;  4 h, rt
Reference
Synthesis and SAR of 4-methyl-5-pentylbenzene-1,3-diol (MPBD), produced by Dictyostelium discoideum
Murata, Chihiro; et al, Bioorganic & Medicinal Chemistry Letters, 2016, 26(5), 1428-1433

Methyl 2-iodo-5-methoxybenzoate Raw materials

Methyl 2-iodo-5-methoxybenzoate Preparation Products

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