Basic information
- Standard SMILES
O=C(O)c1ccc[nH]1- InChIKey
WRHZVMBBRYBTKZ-UHFFFAOYSA-N- Molecular formula
- C5H5NO2
- Average molar mass
- 111.1 g/mol
- Monoisotopic mass
- 111.0320284
Overview
Pyrrole-2-carboxylic acid is a pyrrolecarboxylic acid that is 1H-pyrrole carrying a carboxy substituent at position 2. It has a role as a plant metabolite. It is a conjugate acid of a pyrrole-2-carboxylate.
Names & identifiers
- Preferred name
- Pyrrole-2-Carboxylic Acid
- IUPAC
- 1H-pyrrole-2-carboxylic acid
- English name
- Pyrrole-2-carboxylic acid
- Molecular formula
- C5H5NO2
- Molecular weight
- 111.1
Names & synonyms
PYRROLE-2-CARBOXYLIC ACID634-97-91H-Pyrrole-2-carboxylic acidMinaline2-Pyrrolecarboxylic acidMinalin2NNB85QQT9NSC-48130CHEBI:36751DTXSID50212813RefChem:483441DTXCID80135304
Show more names
2-MialineH-PYL(2)-OHH-PYLE(2)-OH2-CARBOXYPYRROLETIMTEC-BB SBB004332RARECHEM AL BO 11902-Carboxy-1H-pyrrole
211-221-9Pyrrole-2-carboxylicacidMFCD00005219CHEMBL5090271H-Pyrrolecarboxylic acidPYC2-minalin2-Minaline
Database identifiers
- CAS
634-97-9- PubChem CID
- 12473
- DTXSID
DTXSID50212813- ChEMBL
CHEMBL509027- ChEBI
CHEBI:36751- UNII
- 2NNB85QQT9
- EC Number
- 211-221-9
- Nikkaji
- J1.713B
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 53.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 103
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesBoiling point
LogP0.85
Physical DescriptionSolid
Collision Cross Section
113.8 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
114.3 Ų [M-H]-
Physicochemical properties
- Melting point
- 204 · 204-208 °C (dec.) (lit.)
- Boiling point
- 340.3 · 340.3±15.0 °C(Predicted)
- Density
- 0.862 · 0.862
- refractive index
- 1.441 · 1.441-1.445
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Soluble in methanol.
- form
- Powder
- pka
- 4.45 · 4.45(at 20℃)
- color
- White to off-white to pale pink
- BRN
- 80825 · 80825
- InChI
- InChI=1S/C5H5NO2/c7-5(8)4-2-1-3-6-4/h1-3,6H,(H,7,8)
- InChIKey
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N
- SMILES
- N1C=CC=C1C(O)=O
- CAS DataBase Reference
- 634 · 634-97-9(CAS DataBase Reference)
- FDA UNII
- 2 NNB85QQT9 · 2NNB85QQT9
- NIST Chemistry Reference
- -2 · Pyrrole-2-carboxylic acid(634-97-9)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-37/39
- WGK Germany
- 3 · 3
- Hazard Note
- Irritant
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
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 47 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information1H-Pyrrole-2-carboxylic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29339900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36-37/39
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
UsesPyrrole-2-carboxylic acid is small amphoteric polar metabolite produced by many Streptomyces species, often co-produced with its dimer, pyrocoll. Pyrrole-2-carboxylic acid is an important dereplication standard in discovery, displaying a distinctive UV spectrum and a broad range of biological activities, albeit weak. More recently, pyrrole-2-carboxylic has demonstrated antiparasitic activity against Trypanosomes by selective proline racemase inhibition and has potent antifungal activity against Phytophthora.
UsesPyrrole-2-carboxylic Acid is a reagent used in the synthesis of potent small molecule inhibitors of severe acute respiratory syndrome (SARS) coronavirus. Also used in the synthesis of [2,3-c]pyridine-7-one scaffolds.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: A pyrrolecarboxylic acid that is 1H-pyrrole carrying a carboxy substituent at position 2.
Related reactions
184 records
Linked notes
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