Basic information
- CAS
556-08-1- Standard SMILES
CC(=O)Nc1ccc(C(=O)O)cc1- InChIKey
QCXJEYYXVJIFCE-UHFFFAOYSA-N- Molecular formula
- C9H9NO3
- Average molar mass
- 179.17 g/mol
- Monoisotopic mass
- 179.05824315
Overview
P-acetamidobenzoic acid appears as needles or off-white powder. (NTP, 1992)
Names & identifiers
- Preferred name
- p-Acetamidobenzoic acid
- IUPAC
- 4-acetamidobenzoic acid
- English name
- 4-acetamidobenzoic acid
- Molecular formula
- C9H9NO3
- Molecular weight
- 179.17
Names & synonyms
4-Acetamidobenzoic acid556-08-1Acedobenp-Acetamidobenzoic acid4-(Acetylamino)benzoic acid4-Acetylaminobenzoic acid4-CarboxyacetanilideBenzoic acid, 4-(acetylamino)-p-Acetylaminobenzoic acidp-Acetoaminobenzoic acidN-Acetyl-p-aminobenzoic acidPAAB
Show more names
p-acetamidobenzoic4-ACETAMIDOBENZOIC ACID FOR SYNTHESISp-Acetylamino benzoic acido benzoic acidLR-64PAABA
Acedobenep-Acetaminobenzoic acidN-Acetyl-PABAPara Acetamido Benzoic AcidAcedobenumBenzoic acid, p-acetamido-DTXSID5024392NSC-4002
Database identifiers
- CAS
556-08-1- PubChem CID
- 19266
- DTXSID
DTXSID5024392- ChEMBL
CHEMBL112687- ChEBI
CHEBI:46171- UNII
- 04Z20NMK31
- EC Number
- 209-114-7
- Nikkaji
- J95.026B
Properties
Computed structural properties
- XLogP
- 1.3
- 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
- 207
Experimental & physicochemical properties
Chemical Classes
Nitrogen Compounds -> Aminobenzoic Acids
Industrial compound
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP1.27
Solubility
less than 1 mg/mL at 70 °F (NTP, 1992)
>26.9 [ug/mL] (The mean of the results at pH 7.4)
Melting Point493.7 °F (NTP, 1992)
Vapor Pressure0.00000071 [mmHg]
Physical Description
P-acetamidobenzoic acid appears as needles or off-white powder. (NTP, 1992)
Off-white solid; [CAMEO] White powder, insoluble in water; [MSDSonline]
Physicochemical properties
- Melting point
- 259 · 259-262 °C (dec.)(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)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 1 · pK1: 4.28 (25°C)
- form
- Powder
- color
- Off-white to slightly beige
- Water Solubility
- 0.1 g/100 · <0.1 g/100 mL at 21 ºC
- BRN
- 390602 · 390602
- Stability
- Stable. Combustible. Incompatible with strong oxidizing agents.
- Major Application
- peptide synthesis
- InChI
- 1S/C9H9NO3/c1-6(11)10-8-4-2-7(3-5-8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13)
- InChIKey
- QCXJEYYXVJIFCE-UHFFFAOYSA-N
- SMILES
- CC(=O)Nc1ccc(cc1)C(O)=O
- CAS DataBase Reference
- 556 · 556-08-1(CAS DataBase Reference)
- FDA UNII
- 4 Z20NMK31 · 04Z20NMK31
- NIST Chemistry Reference
- N-(4-Carboxyphenyl)acetic acid amide(556-08-1)
- EPA Substance Registry System
- 4 · Benzoic acid, 4-(acetylamino)- (556-08-1)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- TSCA
- TSCA listed
- HS Code
- 29242995 · 29242995
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 53.3% (8 of 15) of all reports.
Warning
H315 (46.7%): 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 15 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 24-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21117
Benzoic acid, 4-(acetylamino)-: Does not have an individual approval but may be used under an appropriate group standard
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Hazards SummaryAn irritant to the skin, eyes, and respiratory tract; Stable under recommended storage conditions. [MSDSonline]
Reactive GroupAcids, Carboxylic
Reactivity ProfileSimultaneously an amide and a carboxylic acid.
Air and Water ReactionsWater insoluble.
Hazard Classes and CategoriesSkin Irrit. 2 (46.7%)
Safety & protection
Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29242995
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationBenzoic acid, 4-(acetylamino)-: ACTIVE
Applications
Description4-Acetamidobenzoic acid (PAcBA) is a naturally occurring acetylated metabolite of 4-aminobenzoic acid and is a component of the antiviral and immunostimulatory drug inosine pranobex (Inosiplex; Isoprinosine; Methisoprinol).
Usesimmune stimulant (component)
UsesAcedoben is the acetylated derivative of p-aminobenzoic acid (PABA). Acedoben is a metabolite of the anesthetic Benzocaine (B202970).
General DescriptionNeedles or off-white powder.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
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Additional notes
DefinitionChEBI: 4-acetamidobenzoic acid is a amidobenzoic acid that consists of benzoic acid bearing an acetamido substituent at position 4. It is functionally related to a 4-aminobenzoic acid. It is a conjugate acid of a 4-acetamidobenzoate.
Related reactions
81 records
Compound notes
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