Basic information
- Standard SMILES
CC(=O)Nc1ccccc1C(=O)O- InChIKey
QSACCXVHEVWNMX-UHFFFAOYSA-N- Molecular formula
- C9H9NO3
- Average molar mass
- 179.17 g/mol
- Monoisotopic mass
- 179.05824315
Overview
N-acetylanthranilic acid is an amidobenzoic acid consisting of anthranilic acid carrying an N-acetyl group. It is functionally related to an anthranilic acid. It is a conjugate acid of a N-acetylanthranilate.
Names & identifiers
- Preferred name
- N-acetylanthranilic acid
- IUPAC
- 2-acetamidobenzoic acid
- English name
- N-Acetylanthranilic acid
- Molecular formula
- C9H9NO3
- Molecular weight
- 179.17
Names & synonyms
N-ACETYLANTHRANILIC ACID2-Acetamidobenzoic acid89-52-12-(Acetylamino)benzoic acid2-Carboxyacetanilideo-Acetamidobenzoic acidBenzoic acid, 2-(acetylamino)-o-Acetoaminobenzoic acidN-Acetylanthranilate2-(Acetylamino)-benzoic acidP1IE9J75C2NSC-4000
Show more names
AKOS 92175Lappaconiticacid2-acetamidobenzoateN-Acetylantranilzuuracetylanthranilicacid2-ACETAMIDOBENOIC ACIDo-acetamidoanthranilicn-acetyl-anthranilicaci
NSC-17831DTXSID9058991CHEBI:36555DEA NO. 8522CHEBI:16803RefChem:927025DTXCID3048659201-914-4
Database identifiers
- CAS
89-52-1- PubChem CID
- 6971
- DTXSID
DTXSID9058991- ChEBI
CHEBI:36555- UNII
- P1IE9J75C2
- EC Number
- 201-914-4
- Nikkaji
- J60.455K
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 66.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 215
Physicochemical properties
- Melting point
- 184 · 184-187 °C(lit.)
- Boiling point
- 311.69 °C · 311.69°C (rough estimate)
- Density
- 1.2822 · 1.2822 (rough estimate)
- refractive index
- 1.56 · 1.5600 (estimate)
- solubility
- 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml; PBS (pH 7.2): 0.5 mg/ml
- form
- A crystalline solid
- pka
- 1 · pK1: 3.63 (25°C)
- Water Solubility
- slightly soluble
- BRN
- 880371 · 880371
- Stability
- Stable. Combustible. Incompatible with strong oxidizing agents.
- CAS DataBase Reference
- 89 · 89-52-1(CAS DataBase Reference)
- FDA UNII
- 1 IE9J75C2 · P1IE9J75C2
- EPA Substance Registry System
- 2 · Benzoic acid, 2-(acetylamino)- (89-52-1)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312+P330-P501
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 36 · 36-37/39-26
- WGK Germany
- 3 · 3
- RTECS
- 2455000 · CB2455000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29242300 · 29242300
- Toxicity
- 50 orl-mus: · LD50 orl-mus: 1114 mg/kg FRPSAX 38,847,83
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (98.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 72 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
List I Chemical: A chemical specified by regulation that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act and is important to the manufacture of a controlled substance. (21 eCFR 1310.02)
Hazard Classes and CategoriesAcute Tox. 4 (98.6%)
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- CB2455000
- hs_code
- 29242300
- Toxicity
- LD50 orl-mus: 1114 mg/kg FRPSAX 38,847,83
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 36-37/39-26
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312+P330-P501
Chemistry & industry
Uses & manufacturing
DEA Listed Chemicals
N-Acetylanthranilic acid, its esters, and its salts
A chemical specified by regulation that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act and is important to the manufacture of a controlled substance. (21 eCFR 1310.02)
General Manufacturing InformationBenzoic acid, 2-(acetylamino)-: ACTIVE
Applications
DescriptionN-Acetylanthranilic acid (Item No. 18707) is an analytical reference standard categorized as a precursor in the synthesis of methaqualone (Item Nos. 20283 | 9000636).1 N-Acetylanthranilic Acid is regulated as a List I chemical in the United States. This product is intended for research and forensic applications.WARNING This product is not for human or veterinary use.
UsesN-Acetylanthranilic acid is a pharmaceutical intermediate used in the production of the non-barbiturate hypnotic drug methaqualone.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: An amidobenzoic acid consisting of anthranilic acid carrying an N-acetyl group.
Related reactions
7 records
Linked notes
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