Methyl 4-aminobenzoate
Basic information
- CAS
619-45-4- Standard SMILES
COC(=O)c1ccc(N)cc1- InChIKey
LZXXNPOYQCLXRS-UHFFFAOYSA-N- Molecular formula
- C8H9NO2
- Average molar mass
- 151.16 g/mol
- Monoisotopic mass
- 151.06332853
Overview
RN given refers to parent cpd
Names & identifiers
- Preferred name
- Methyl 4-aminobenzoate
- IUPAC
- methyl 4-aminobenzoate
- English name
- Methyl 4-aminobenzoate
- Molecular formula
- C8H9NO2
- Molecular weight
- 151.16
Names & synonyms
Methyl 4-aminobenzoate619-45-4METHYL P-AMINOBENZOATEBenzoic acid, 4-amino-, methyl ester4-Carbomethoxyaniline4-(Methoxycarbonyl)anilinep-Aminobenzoic acid methyl ester4-(Carbomethoxyl)anilineBenzoic acid, p-amino-, methyl esterAI3-02437GC4GA4E73ENSC-3783
Show more names
Tetracaine Impurity 1benzoicacid,4-amino-,methylesterh-4-abz-omeTIMTEC-BB SBB004063Benzocaine impurity HTetracaine Impurity 4
DTXSID7060704RefChem:816182DTXCID1043176210-598-74-Aminobenzoic acid methyl esterMethyl4-aminobenzoateMFCD00007891Methyl aniline-4-carboxylate
Database identifiers
- CAS
619-45-4- PubChem CID
- 12082
- DTXSID
DTXSID7060704- ChEMBL
CHEMBL1927048- UNII
- GC4GA4E73E
- EC Number
- 210-598-7
- Nikkaji
- J45.061H
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 52.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 139
Experimental & physicochemical properties
LogP1.48
Physicochemical properties
- Melting point
- 110 · 110-111 °C (lit.)
- Boiling point
- 273.17 °C · 273.17°C (rough estimate)
- Density
- 1.2023 · 1.2023 (rough estimate)
- refractive index
- 1.581 · 1.5810 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- 3.82 g/l · 3.82g/l
- form
- Crystals or Crystalline Powder
- pka
- 1 · pK1:2.38(+1) (25°C)
- color
- White to beige
- Water Solubility
- Soluble in alcohol and ether. Slightly soluble in water.
- BRN
- 775913 · 775913
- InChI
- 1S/C8H9NO2/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5H,9H2,1H3
- InChIKey
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationChemical: Benzoic acid, 4-amino-, methyl ester
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- DG2900000
- hs_code
- 29224995
- risk_code
- 36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- safety_code
- 26-37/39-36/37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H335-H315-H319
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationBenzoic acid, 4-amino-, methyl ester: ACTIVE
Applications
UsesMethyl 4-aminobenzoate is used in the synthesis of guanidine alkaloids, (±)-martinelline and (±)-martinellic acid by a protic acid catalyzed hetero Diels-Alder coupling reaction with N-Cbz 2-pyrroline. It is also used in organic synthesis and acts as a dye intermediate. Further, it is used to prepare 4-(2-methyl-4-oxo-4H-quinazolin-3-yl)-benzoic acid methyl ester by reacting with 2-acetylamino-benzoic acid.
UsesMethyl 4-aminobenzoate was used in the syntheses of guanidine alkaloids, (±)-martinelline and (±)-martinellic acid by a protic acid catalyzed hetero Diels-Alder coupling reaction with N-Cbz 2-pyrroline.
General DescriptionThe catalytic oxidation of methyl 4-aminobenzoate by hydrogen peroxide was studied.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
759 records
Compound notes
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