Basic information
- Standard SMILES
O=C(O)c1cccc(C(=O)O)n1- InChIKey
WJJMNDUMQPNECX-UHFFFAOYSA-N- Molecular formula
- C7H5NO4
- Average molar mass
- 167.12 g/mol
- Monoisotopic mass
- 167.02185764
Names & identifiers
- Preferred name
- 2,6-Pyridinedicarboxylic acid
- IUPAC
- pyridine-2,6-dicarboxylic acid
- English name
- Pyridine-2,6-dicarboxylic acid
- Molecular formula
- C7H5NO4
- Molecular weight
- 167.12
Names & synonyms
2,6-Pyridinedicarboxylic acid499-83-2Dipicolinic acidPYRIDINE-2,6-DICARBOXYLIC ACID2,6-Dipicolinic acid2,6-DicarboxypyridineDTXSID7022043UE81S5CQ0GNSC-176DTXCID602043CHEBI:46837RefChem:134748
Show more names
dipicolinic2,6-PYRIDINECARBOXYLIC ACIDPyridine-2,6-dicarboxylate26DPAL-042134
207-894-3DipicolinateMFCD00006299DPACpydcH2EINECS 207-894-3Oprea1_533632SCHEMBL34595
Database identifiers
- CAS
499-83-2- PubChem CID
- 10367
- DTXSID
DTXSID7022043- ChEMBL
CHEMBL284104- ChEBI
CHEBI:46837- UNII
- UE81S5CQ0G
- EC Number
- 207-894-3
- Nikkaji
- J6.184K
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 87.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 184
Experimental & physicochemical properties
Solubility5 mg/mL at 25 °C
Melting Point252 °C
Vapor Pressure0.0000061 [mmHg]
Physical Description
White crystalline powder; [Alfa Aesar MSDS]
Solid
Physicochemical properties
- Melting point
- 248 · 248-250 °C (dec.)(lit.)
- Boiling point
- 295.67 °C · 295.67°C (rough estimate)
- Density
- 1.5216 · 1.5216 (rough estimate)
- bulk density
- 700 kg/m3 · 700kg/m3
- vapor pressure
- 0.01 hPa · <0.01 hPa (20 °C)
- refractive index
- 1.628 · 1.6280 (estimate)
- Flash point
- 188 °C · 188 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 2 O: · H2O: 1%, clear
- pka
- 2.16 · 2.16(at 25℃)
- form
- Crystalline Powder
- color
- White
- PH
- 2 · 2.0 (5g/l, H2O, 20℃)
- Water Solubility
- 5 g/L · 5 g/L (20 ºC)
- BRN
- 131629 · 131629
- Cosmetics Ingredients Functions
- CHELATING
- InChI
- 1S/C7H5NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-3H,(H,9,10)(H,11,12)
- InChIKey
- WJJMNDUMQPNECX-UHFFFAOYSA-N
- SMILES
- OC(=O)c1cccc(n1)C(O)=O
- LogP
- 0.3 at · 0.3 at 25℃ and pH1.8
- CAS DataBase Reference
- 499 · 499-83-2(CAS DataBase Reference)
- Indirect Additives used in Food Contact Substances
- 2 · 2,6-PYRIDINEDICARBOXYLIC ACID
- FDA 21 CFR
- 178.101 · 178.1010
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 81 S5CQ0G · UE81S5CQ0G
- NIST Chemistry Reference
- 2 · 2,6-Pyridinedicarboxylic acid(499-83-2)
- EPA Substance Registry System
- 2 · 2,6-Pyridinedicarboxylic acid (499-83-2)
- UNSPSC Code
- 41116105 · 41116105
- NACRES
- 21 · NB.21
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 302 · P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38-37/38-36
- Safety Statements
- 26 · 26-36-24/25-37
- WGK Germany
- 3 · 3
- Autoignition Temperature
- 620 °C · 620 °C
- TSCA
- TSCA listed
- HazardClass
- IRRITANT
- HS Code
- 29333999 · 29333999
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 1 Skin · Eye Dam. 1Skin Corr. 1BSTOT SE 3
- Toxicity
- 50 orally · LD50 orally in Rabbit: 10500 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H314 (42.9%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]；H315 (57.1%): Causes skin irritation [Warning Skin corrosion/irritation]；H318 (48.4%): Causes serious eye damage [Danger Serious eye damage/eye irritation]；H319 (52.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (99.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 273 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Chemical: 2,6-Pyridinedicarboxylic acid
Status: Active Update: 02-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/24614
Dipicolinic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS] See Pyridine and Picolinic acid.
Hazard Classes and CategoriesSkin Corr. 1B (42.9%)；Skin Irrit. 2 (57.1%)；Eye Dam. 1 (48.4%)；Eye Irrit. 2A (52.4%)；STOT SE 3 (99.6%)
Safety & protection
Protective Action Criteria (PAC)
12 [mg/m3]
130 [mg/m3]
790 [mg/m3]
Regulatory information
Regulatory Information
Chemical: 2,6-Pyridinedicarboxylic acid
Status: Active Update: 02-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/24614
Dipicolinic acid: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29333999
- Toxicity
- LD50 orally in Rabbit: 10500 mg/kg
- risk_code
- 36/37/38-37/38-36
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-24/25-37
- hazard_class
- IRRITANT
- Storage Class
- 8A - Combustible corrosive hazardous materials
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Dam. 1Skin Corr. 1BSTOT SE 3
- Autoignition Temperature
- 620 °C
- Precautionary statements
- P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Cellular LocationsCytoplasm；Extracellular
Uses & manufacturing
UsesPermitted for use as an inert ingredient in non-food pesticide products; [EPA]
Use ClassificationCosmetics -> Chelating
General Manufacturing Information2,6-Pyridinedicarboxylic acid: ACTIVE
Applications
Description2,6-Pyridinedicarboxylic acid (PDCA) contains two carboxylic groups on each side of the pyridine ring. Both groups form rigid 120° angles with the pyridine. Carboxylic functionality could be complex and bind with metals under certain conditions. Numerous metalorganic frameworks, metal complexes, drugs, and CPs based on PDCA were developed for applications related to gas storage, separation, catalysis, magnetism, and sensing[1]. Shao et al. researched the solubility of PDCA in methanol, ethanol, n-propanol, isopropanol, THF, 1,4-dioxane, acetic acid, formic acid, acetonitrile, ethyl acetate, and toluene. They found that PDCA solubility was the highest in methanol but the lowest in acetonitrile.
UsesPyridine-2,6-dicarboxylic acid is used in the preparation of dipicolinato ligated lanthanide and transition metal complexes. It acts as a chelating agent for chromium, zinc, manganese, copper, iron and molybdenum. Its calcium-dipcolinic acid complex is used to protect deoxyribonucleic acid (DNA) from heat denaturation which enhances the DNA stability. It plays an important role as a marker for the effectiveness of sterilization.
General DescriptionThis certified eluent concentrate for ion chromatography is traceable by potentiometric titration to NIST Standard Reference Material. It is certified in accordance with ISO Guide 31. All details about exact content, uncertainty, traceability and expiry date are described in the certificate.
Preparation methods
Preparationpyridine-2,6-dicarboxylic acid was synthesized by hydrolyzing of ester prepared by coupling of diethyl 4-hydroxypyridine-2,6-dicarboxylate to bis-halohydrocarbon or bis-halide.Synthesis of Novel Derivatives of Pyridine‐2,6‐dicarboxylic Acid
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: Pyridine-2,6-dicarboxylic acid is a pyridinedicarboxylic acid carrying two carboxy groups at positions 2 and 6. It has a role as a bacterial metabolite. It is a conjugate acid of a dipicolinate(1-).
Related reactions
45 records
Linked notes
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