| Identification | More | [Name]
2-Amino-5-methoxybenzoic acid | [CAS]
6705-03-9 | [Synonyms]
2-AMINO-5-METHOXYBENZOIC ACID
5-METHOXYANTHRANILIC ACID
5-Methoxyanththranillic Acid
2-AMINO-5-METHOXYLBENZOIC ACID
2-Amino-5-MethoxybenzoicAcid98%
2-Amino-5-Methoxybenzoic | [Molecular Formula]
C8H9NO3 | [MDL Number]
MFCD00016509 | [Molecular Weight]
167.16 | [MOL File]
6705-03-9.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
148-152 °C | [Boiling point ]
349.9±27.0 °C(Predicted) | [density ]
1.303±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Methanol (Slightly) | [form ]
Crystalline Powder | [pka]
2.08±0.10(Predicted) | [color ]
White to yellow to pale orange | [BRN ]
777690 | [Major Application]
peptide synthesis | [InChI]
InChI=1S/C8H9NO3/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4H,9H2,1H3,(H,10,11) | [InChIKey]
UMKSAURFQFUULT-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=CC(OC)=CC=C1N | [CAS DataBase Reference]
6705-03-9(CAS DataBase Reference) | [NIST Chemistry Reference]
5-Methoxyanthranilic acid(6705-03-9) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
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:Wear suitable protective clothing . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HS Code ]
29225090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
2-Amino-5-methoxybenzoic Acid is used in the synthesis of quinazolinone class of histamine H3 receptor inverse agonists. It is also used in the synthesis of Alogliptin, a selective inhibitor of the s
erine protease dipeptidyl peptidase IV. | [Definition]
ChEBI: 2-Amino-5-methoxybenzoic acid is a methoxybenzoic acid. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
Using 5-methoxy-2-nitrobenzoic acid (1) as starting material, its nitro group was reduced by catalytic hydrogenation using H2 and Pd/C to afford 2-amino-5-methoxybenzoic acid (2) in quantitative yield. Subsequently, compound (2) was subjected to diazotization reaction with NaNO2 followed by treatment with Na2S2 to obtain stable disulfide compound (3) in 80% yield. This disulfide (3) was directly reacted with SOCl2 without further purification, followed by reaction with 2-chloroethylamine in the presence of Et3N to produce amide (4) in 90% yield. The compound (4) was converted to the cyclized product (5) by a one-pot method with trimethylphosphine and Et3N co-refluxed in THF. Finally, reduction of the cyclized amide (5) using LiAlH4 afforded 7-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (6). | [References]
[1] Patent: US2007/49572, 2007, A1. Location in patent: Page/Page column 34
[2] Patent: US2005/215540, 2005, A1. Location in patent: Page/Page column 37
[3] Patent: WO2016/23826, 2016, A1. Location in patent: Page/Page column 40
[4] Synthesis (Germany), 2017, vol. 49, # 1, p. 135 - 144
[5] Medicinal Chemistry Research, 2002, vol. 11, # 9, p. 504 - 537 |
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