Methyl 2-(bromomethyl)-4-nitrobenzoate

Base Information

• Chemical Name: Methyl 2-(bromomethyl)-4-nitrobenzoate
• CAS No.: 133446-99-8
• Molecular Formula: C9H8BrNO4
• Molecular Weight: 274.071
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID30568027
• Wikidata: Q82454147
• Mol file: 133446-99-8.mol

Synonyms:Methyl 2-(bromomethyl)-4-nitrobenzoate;133446-99-8;2-BROMOMETHYL-4-NITRO-BENZOIC ACID METHYL ESTER;MFCD11505948;Benzoic acid, 2-(bromomethyl)-4-nitro-, methyl ester;methyl 2-bromomethyl-4-nitrobenzoate;Methyl2-(bromomethyl)-4-nitrobenzoate;SCHEMBL33884;DTXSID30568027;PGNKFDOPHHNVNF-UHFFFAOYSA-N;AKOS016004573;SB32872;methyl 2-(bromomethyl)-4-nitro-benzoate;AS-53240;SY260593;CS-0049201;methyl 2-bromomethyl-4-nitrobenzenecarboxylate;2-Bromomethyl-4-nitrobenzoic acid methyl ester;EN300-299918;P16236;A930426;Methyl 2-(bromomethyl)-4-nitrobenzoate, AldrichCPR

Chemical Property of Methyl 2-(bromomethyl)-4-nitrobenzoate

Chemical Property:

• Boiling Point: 398.4±37.0 °C(Predicted)
• PSA: 72.12000
• Density: 1.624±0.06 g/cm3(Predicted)
• LogP: 2.79950
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 272.96367
• Heavy Atom Count: 15
• Complexity: 253

Purity/Quality:

99% ^*data from raw suppliers

Methyl2-(Bromomethyl)-4-nitrobenzoate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C=C(C=C1)[N+](=O)[O-])CBr
• Uses: Methyl 2-(Bromomethyl)-4-nitrobenzoate is used in the synthetic preparation of cyclic hydroxamic acid derivatives as histone deacetylase inhibitors with antitumor activity.

Technology Process of Methyl 2-(bromomethyl)-4-nitrobenzoate

There total 6 articles about Methyl 2-(bromomethyl)-4-nitrobenzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methyl 2-methyl-4-nitrobenzoate (62621-09-4) → 2-bromomethyl-4-nitro-benzoic acid methyl ester (133446-99-8)

Guidance literature:

With N-Bromosuccinimide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In tetrachloromethane; at 85 ℃; for 12h;

Reference yield: 55.0%

4-bromo-2-methyl-benzoic acid methyl ester (99548-55-7) → 2-bromomethyl-4-nitro-benzoic acid methyl ester (133446-99-8)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In chlorobenzene; at 80 ℃; for 16h;

Reference yield:

2-cyano-5-nitrotoluene (89001-53-6) → 2-bromomethyl-4-nitro-benzoic acid methyl ester (133446-99-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / 80 percent aq. H₂SO₄ / 1.25 h / 100 °C

2: 88 percent / 6 N aq. HCl / 20 h / Heating

3: 99 percent / thionyl chloride / 21 h / 20 °C

4: N-bromosuccinimide; benzoyl peroxide / 1,2-dichloro-ethane / 48 h / Heating

With hydrogenchloride; N-Bromosuccinimide; thionyl chloride; sulfuric acid; dibenzoyl peroxide; In 1,2-dichloro-ethane; 1: Hydrolysis / 2: Hydrolysis / 3: Esterification / 4: Bromination;

DOI:10.1021/jm9807205

upstream raw materials:

methyl 2-methyl-4-nitrobenzoate

2-methyl-4-nitrobenzoic acid

2-methyl-4-nitro-benzoic acid amide

2-cyano-5-nitrotoluene

Downstream raw materials:

methyl 2-L-(2,3-dihydro-5-nitro-1-oxo-2(1H)-isoindolyl)-5-[N-(benzyloxycarbonyl)amino]pentanoate

2-benzyl-5-nitroisoindolin-1-one

4-nitro-2-phenoxymethyl-benzoic acid methyl ester

4-nitro-2-(phenoxymethyl)benzoic acid