Cas no 943595-13-9 (2-Bromomethyl-6-methoxy-benzoic Acid Methyl Ester)

2-Bromomethyl-6-methoxy-benzoic acid methyl ester is a versatile intermediate in organic synthesis, particularly valued for its reactive bromomethyl group and ester functionality. The compound serves as a key building block in the preparation of pharmaceuticals, agrochemicals, and fine chemicals, enabling efficient derivatization through nucleophilic substitution or further functionalization. Its methoxy and ester groups enhance solubility and stability, facilitating controlled reactions in multi-step syntheses. The bromomethyl moiety allows for selective alkylation or cross-coupling reactions, making it useful in constructing complex molecular frameworks. This compound is typically handled under inert conditions due to its sensitivity to moisture and light, ensuring optimal reactivity in synthetic applications.
2-Bromomethyl-6-methoxy-benzoic Acid Methyl Ester structure
943595-13-9 structure
Product Name:2-Bromomethyl-6-methoxy-benzoic Acid Methyl Ester
CAS No:943595-13-9
MF:C10H11BrO3
MW:259.096542596817
MDL:MFCD15474833
CID:1092606
PubChem ID:16723776
Update Time:2025-06-08

2-Bromomethyl-6-methoxy-benzoic Acid Methyl Ester Chemical and Physical Properties

Names and Identifiers

    • Methyl 2-(bromomethoxy)-6-methoxybenzoate
    • methyl 2-(bromomethyl)-6-methoxybenzoate
    • 2-Bromomethyl-6-methoxy-benzoic acid methyl ester
    • AKOS024259187
    • AS-48094
    • Benzoic acid, 2-(bromomethyl)-6-methoxy-, methyl ester
    • MFCD15474833
    • DA-33125
    • SCHEMBL14352049
    • methyl2-(bromomethyl)-6-methoxybenzoate
    • F17793
    • SB40127
    • KJLOXBFOHKOSBO-UHFFFAOYSA-N
    • 943595-13-9
    • 2-(Bromomethyl)-6-methoxy-benzoic acid methyl ester
    • 2-Bromomethyl-6-methoxy-benzoic Acid Methyl Ester
    • MDL: MFCD15474833
    • Inchi: 1S/C10H11BrO3/c1-13-8-5-3-4-7(6-11)9(8)10(12)14-2/h3-5H,6H2,1-2H3
    • InChI Key: KJLOXBFOHKOSBO-UHFFFAOYSA-N
    • SMILES: O=C(C1C(CBr)=CC=CC=1OC)OC

Computed Properties

  • Exact Mass: 257.98916g/mol
  • Monoisotopic Mass: 257.98916g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 4
  • Complexity: 196
  • 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: 2.3
  • Topological Polar Surface Area: 35.5?2

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2-Bromomethyl-6-methoxy-benzoic Acid Methyl Ester Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride ;  4 h, reflux
Reference
Copper-Catalyzed One-Pot Synthesis of Dibenzofurans, Xanthenes, and Xanthones from Cyclic Diphenyl Iodoniums
Zhu, Daqian ; Li, Min; Wu, Zhouming; Du, Yongliang; Luo, Bingling; et al, European Journal of Organic Chemistry, 2019, 2019(28), 4566-4571

Production Method 2

Reaction Conditions
1.1 Reagents: Benzoyl peroxide ,  N-Bromosuccinimide Solvents: Carbon tetrachloride ;  1.5 h, reflux; reflux → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt
Reference
The synthesis of (-)-varitriol and (-)-3'-epi-varitriol via a Ramberg-Baecklund route
McAllister, Graeme D.; Robinson, James E.; Taylor, Richard J. K., Tetrahedron, 2007, 63(49), 12123-12130

Production Method 3

Reaction Conditions
1.1 Reagents: Azobisisobutyronitrile ,  N-Bromosuccinimide Solvents: Acetonitrile
Reference
Isosteric analogs of lenalidomide and pomalidomide: Synthesis and biological activity
Ruchelman, Alexander L.; Man, Hon-Wah; Zhang, Weihong; Chen, Roger; Capone, Lori; et al, Bioorganic & Medicinal Chemistry Letters, 2013, 23(1), 360-365

Production Method 4

Reaction Conditions
1.1 Reagents: Azobisisobutyronitrile ,  N-Bromosuccinimide Solvents: Carbon tetrachloride ;  72 °C; 3 h, reflux
Reference
Metabolically Stable Dibenzo[b,e]oxepin-11(6H)-ones as Highly Selective p38 MAP Kinase Inhibitors: Optimizing Anti-Cytokine Activity in Human Whole Blood
Baur, Benjamin; Storch, Kirsten; Martz, Kathrin E.; Goettert, Marcia I.; Richters, Andre; et al, Journal of Medicinal Chemistry, 2013, 56(21), 8561-8578

Production Method 5

Reaction Conditions
Reference
Treating long QT syndrome
, World Intellectual Property Organization, , ,

Production Method 6

Reaction Conditions
Reference
Radical-mediated synthesis of 3,4-dihydroisocoumarins. Total synthesis of hydrangenol. [Erratum to document cited in CA147:143153]
Mandal, Samir Kumar; Roy, Subhas Chandra, Tetrahedron Letters, 2007, 48(35),

Production Method 7

Reaction Conditions
1.1 Reagents: N-Bromosuccinimide Solvents: Carbon tetrachloride ;  reflux
1.2 Catalysts: Azobisisobutyronitrile ;  2 h, reflux; reflux → rt
Reference
Titanocene(III) chloride mediated radical-induced synthesis of 3,4-dihydroisocoumarins: synthesis of (±)-hydrangenol, (±)-phyllodulcin, (±)-macrophyllol and (±)-thunberginol G
Mandal, Samir Kumar; Roy, Subhas Chandra, Tetrahedron, 2008, 64(49), 11050-11057

Production Method 8

Reaction Conditions
1.1 Reagents: Azobisisobutyronitrile ,  N-Bromosuccinimide Solvents: Carbon tetrachloride
Reference
Radical-mediated synthesis of 3,4-dihydroisocoumarins. Total synthesis of hydrangenol
Mandal, Samir Kumar; Roy, Subhas Chandra, Tetrahedron Letters, 2007, 48(23), 4131-4134

Production Method 9

Reaction Conditions
1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride ;  15 min, 25 °C; 12 h, 60 °C
Reference
Compounds modulating protein recruitment and/or degradation
, World Intellectual Property Organization, , ,

Production Method 10

Reaction Conditions
1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride ;  6 h, rt → reflux
Reference
Histone acetyltransferase activators and compositions and uses thereof
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Production Method 11

Reaction Conditions
1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride ;  6 h, reflux
Reference
Preparation of isoindolinone and benzamide derivatives as histone acetyltransferase activators useful in disease therapy
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Production Method 12

Reaction Conditions
1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride ;  2 h, reflux
Reference
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D'Hollander, Agathe C. A.; Westwood, Nicholas J., Tetrahedron, 2018, 74(2), 224-239

Production Method 13

Reaction Conditions
1.1 Reagents: Thionyl chloride ;  3 h, 80 °C
1.2 cooled; 30 min, 80 °C
1.3 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride ;  overnight, reflux
Reference
Preparation of isoindole carboxamides, pyrrolopyridine carboxamides, and similar compounds as inhibitors of phosphodiesterase type 10A for treating neurological and psychiatric disorders
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2-Bromomethyl-6-methoxy-benzoic Acid Methyl Ester Raw materials

2-Bromomethyl-6-methoxy-benzoic Acid Methyl Ester Preparation Products

2-Bromomethyl-6-methoxy-benzoic Acid Methyl Ester Suppliers

Amadis Chemical Company Limited
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(CAS:943595-13-9)2-Bromomethyl-6-methoxy-benzoic Acid Methyl Ester
Order Number:A1045985
Stock Status:in Stock
Quantity:100mg/250mg/1g
Purity:99%
Pricing Information Last Updated:Thursday, 29 August 2024 17:21
Price ($):173.0/292.0/788.0
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Amadis Chemical Company Limited
(CAS:943595-13-9)2-Bromomethyl-6-methoxy-benzoic Acid Methyl Ester
A1045985
Purity:99%/99%/99%
Quantity:100mg/250mg/1g
Price ($):173.0/292.0/788.0
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