| Identification | More | [Name]
Methyl 4-amino-3-iodobenzoate | [CAS]
19718-49-1 | [Synonyms]
METHYL 4-AMINO-3-IODOBENZOATE
Methyl 4-amino-3-iodobenzozte | [Molecular Formula]
C8H8INO2 | [MDL Number]
MFCD00090423 | [Molecular Weight]
277.06 | [MOL File]
19718-49-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
86-91 °C (lit.) | [Boiling point ]
369.6±32.0 °C(Predicted) | [density ]
1.826±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Crystalline Powder | [pka]
0.41±0.10(Predicted) | [color ]
Beige | [InChI]
InChI=1S/C8H8INO2/c1-12-8(11)5-2-3-7(10)6(9)4-5/h2-4H,10H2,1H3 | [InChIKey]
MRLVFVTVXSKAMX-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C1=CC=C(N)C(I)=C1 | [CAS DataBase Reference]
19718-49-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29224985 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Definition]
ChEBI: Methyl 4-amino-3-iodobenzoate is a benzoate ester. | [Synthesis]
General procedure for the synthesis of methyl 4-amino-3-iodobenzoate from methyl 4-aminobenzoate: dissolve methyl 4-aminobenzoate (5.0 g, 0.033 mol), benzyltrimethylammonium dichloroiodonate (22.1 g, 0.056 mol), and calcium carbonate (5.0 g, 0.050 mol) in a solvent mixture of dichloromethane (200 ml) and methanol (100 g). . The reaction mixture was heated to reflux overnight with stirring. Upon completion of the reaction, the solution was cooled to room temperature, washed with saturated sodium bisulfate solution, and the organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product methyl 4-amino-3-iodobenzoate (9.6 g, quantitative yield), which was used in the subsequent reaction without further purification. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 3.75 (s, 3H), 6.09 (s, 2H), 6.75 (d, J = 8.59 Hz, 1H), 7.66 (dd, J = 8.59, 2.02 Hz, 1H), 8.11 (d, J = 2.02 Hz, 1H). | [References]
[1] Patent: WO2007/38331, 2007, A2. Location in patent: Page/Page column 30-31
[2] Patent: WO2007/103759, 2007, A2. Location in patent: Page/Page column 48
[3] European Journal of Medicinal Chemistry, 2019, p. 234 - 248
[4] European Journal of Organic Chemistry, 2001, # 24, p. 4607 - 4613
[5] Synlett, 2014, vol. 25, # 3, p. 399 - 402 |
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