| Identification | More | [Name]
Methyl 3,4-diaminobenzoate | [CAS]
36692-49-6 | [Synonyms]
3,4-DIAMINOBENZOIC ACID METHYL ESTER
BUTTPARK 96\50-24
METHYL 3,4-DIAMINOBENZENECARBOXYLATE
METHYL 3,4-DIAMINOBENZOATE
Methyldibromobenzoate
3,4-DIAMINOBENZOIC ACID METHYL ESTER 97%
3 5-DIAMINO-2-METHYL BENZOIC ACID 97%
BENZOICACID,3,4-DIAMINO-,METHYLESTER | [EINECS(EC#)]
628-323-8 | [Molecular Formula]
C8H10N2O2 | [MDL Number]
MFCD00017098 | [Molecular Weight]
166.18 | [MOL File]
36692-49-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
105-110 °C | [Boiling point ]
376.9±22.0 °C(Predicted) | [density ]
1.260±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
3.02±0.10(Predicted) | [color ]
White to Gray to Red | [BRN ]
2091675 | [InChI]
InChI=1S/C8H10N2O2/c1-12-8(11)5-2-3-6(9)7(10)4-5/h2-4H,9-10H2,1H3 | [InChIKey]
IOPLHGOSNCJOOO-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C1=CC=C(N)C(N)=C1 | [CAS DataBase Reference]
36692-49-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
2811 | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [PackingGroup ]
Ⅲ | [HS Code ]
29224999 |
| Hazard Information | Back Directory | [Chemical Properties]
White to light brown to light yellow powder or crystals | [Synthesis]
Thionyl chloride (0.72 mL, 9.80 mmol) was slowly added dropwise to a solution of 3,4-diaminobenzoic acid (1.00 g, 6.58 mmol) in methanol (15.0 mL) for a controlled time of 10 minutes. The reaction mixture was stirred at room temperature for 4 hours before the solvent was removed by evaporation under reduced pressure. The residue was partitioned between water and ethyl acetate (EtOAc) to separate the organic layer. The organic layer was diluted with ethyl acetate and washed sequentially with saturated aqueous sodium bicarbonate, saturated brine and water and then dried with anhydrous magnesium sulfate. The desiccant was removed by filtration and the solvent was evaporated under reduced pressure to afford methyl 3,4-diaminobenzoate (993 mg, 95.0% yield) as a brown solid. The product characterization data were as follows: 1H NMR (CDCl3, 500 MHz) δ 7.49 (d, 1H, J = 7.01 Hz, Ar-H), 7.47 (s, 1H, Ar-H), 6.68 (d, 1H, J = 7.01 Hz, Ar-H), 3.87 (s, 3H, -COOCH3), 3.80 (br s, 2H, -NH2 ), 3.35 (br s, 2H, -NH2); 13C NMR (CDCl3, 125 MHz) δ 166.56, 140.89, 138.16, 120.87, 118.23, 118.16, 52.11; LCMS m/z calculated value (MNa)+ 189.06, measured value 189.00. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7456 - 7460
[2] Patent: US2016/33489, 2016, A1. Location in patent: Paragraph 0204
[3] Medicinal Chemistry Research, 2015, vol. 24, # 8, p. 3143 - 3156
[4] Patent: WO2005/113489, 2005, A1. Location in patent: Page/Page column 75-76
[5] Patent: EP1502916, 2005, A1. Location in patent: Page 440 |
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