Methyl 4-amino-5-iodo-2-methylbenzoate

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Methyl 4-amino-5-iodo-2-methylbenzoate Basic information
Product Name:Methyl 4-amino-5-iodo-2-methylbenzoate
Synonyms:Methyl 4-amino-5-iodo-2-methylbenzoate;4-Amino-5-iodo-2-methyl-benzoic acid methyl ester;187484;Benzoic acid, 4-amino-5-iodo-2-methyl-, methyl ester
CAS:672293-33-3
MF:C9H10INO2
MW:291.09
EINECS:
Product Categories:
Mol File:672293-33-3.mol
Methyl 4-amino-5-iodo-2-methylbenzoate Structure
Methyl 4-amino-5-iodo-2-methylbenzoate Chemical Properties
Boiling point 367.0±42.0 °C(Predicted)
density 1.733±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
pka0.53±0.10(Predicted)
AppearanceLight yellow to yellow Solid
Safety Information
MSDS Information
Methyl 4-amino-5-iodo-2-methylbenzoate Usage And Synthesis
Synthesis
Methyl4-amino-2-methylbenzoate

6933-47-7

Methyl 4-amino-5-iodo-2-methylbenzoate

672293-33-3

Methyl 2-methyl-4-aminobenzoate (Intermediate 7) (2.9 g, 16.6 mmol) was used as raw material and dissolved in DMF (15 ml), sodium periodate (1.45 g, 6.6 mmol) and iodine (3.4 g, 13.3 mmol) were added sequentially. The reaction mixture was stirred at a constant temperature at 50°C for 2 hours. After the reaction was completed, the mixture was slowly poured into cold water containing NaHSO3 (0.5 g). After stirring and mixing, the mixture was allowed to stand overnight. On the following day, the precipitate was collected by filtration, washed with water and subsequently dissolved with dichloromethane. The resulting solution was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the target product methyl 4-amino-5-iodo-2-methylbenzoate as an orange solid (4.1 g, 85% yield). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 8.20 (s, 1H), 6.47 (s, 1H), 3.75 (s, 3H), 2.42 (s, 3H).

References[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 942 - 945
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 946 - 949
[3] Patent: WO2009/47240, 2009, A1. Location in patent: Page/Page column 30
[4] Patent: US2018/291002, 2018, A1. Location in patent: Paragraph 0462; 0463
[5] Patent: US2004/142940, 2004, A1. Location in patent: Page/Page column 42
Methyl 4-amino-5-iodo-2-methylbenzoate Preparation Products And Raw materials
Raw materialsMethyl4-amino-2-methylbenzoate-->iodine-->N,N-Dimethylformamide-->Sodium periodate
Tag:Methyl 4-amino-5-iodo-2-methylbenzoate(672293-33-3) Related Product Information
Benzoic acid, 3-amino-5-iodo-2-methyl-, methyl ester Methyl 4-amino-3-iodobenzoate 4-Amino-3,5-diiodobenzoic acid methyl ester Methyl 4-Amino-3-iodo-5-methylbenzoate 4-Amino-5-iodo-2-methyl-benzoic acid 5-Amino-4-iodo-2-methyl-benzoic acid methyl ester