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2-Chloronicotinic acid

HCID 76258
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
2942-59-8
Standard SMILES
O=C(O)c1cccnc1Cl
InChIKey
IBRSSZOHCGUTHI-UHFFFAOYSA-N
Molecular formula
C6H4ClNO2
Average molar mass
157.55 g/mol
Monoisotopic mass
156.99305605

Overview

2-Chloronicotinic acid is a member of pyridines and an aromatic carboxylic acid.

Names & identifiers

Preferred name
2-Chloronicotinic acid
IUPAC
2-chloropyridine-3-carboxylic acid
English name
2-Chloronicotinic acid
Molecular formula
C6H4ClNO2
Molecular weight
157.55

Names & synonyms

2-Chloronicotinic acid2-Chloropyridine-3-carboxylic acid2-Chloro-3-pyridinecarboxylic acid3-Pyridinecarboxylic acid, 2-chloro-2-Chloro-nicotinic acidNicotinic acid, 2-chloro-3-Carboxy-2-chloropyridineNSC 378NSC-378UNII-93G386213FEINECS 220-937-093G386213F
Show more names
CHLORONICOTINIC ACID2CLNA2-ChloronicotiAKOS BBS-000042312 - chloro niacinoronicotinic acidRARECHEM AL BO 0287TIMTEC-BB SBB004002
DTXSID9062726EC 220-937-03-PYRIDINECARBOXYLIC ACID,2-CHLOROFLUNIXIN MEGLUMINE IMPURITY A [EP IMPURITY]FLUNIXIN MEGLUMINE IMPURITY A (EP IMPURITY)RefChem:86514DTXCID6037984220-937-0

Database identifiers

CAS
2942-59-8
PubChem CID
76258
DTXSID
DTXSID9062726
ChEMBL
CHEMBL1505789
ChEBI
CHEBI:194658
UNII
93G386213F
EC Number
220-937-0
Nikkaji
J164C

Properties

Computed structural propertiesFilling in

XLogP
1.3
Topological polar surface area
50.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
10
Formal charge
0
Complexity
140

Experimental & physicochemical properties

SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
PesticidesEnvironmental transformation -> Pesticide transformation products (metabolite, successor)

Physicochemical properties

Melting point
176 · 176-178 °C (dec.)(lit.)
Boiling point
316.8 · 316.8±22.0 °C(Predicted)
Density
1.47 · 1.470±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
DMSO, Ethyl Acetate (Slightly)
pka
2.07 · 2.07±0.25(Predicted)
form
Powder
color
White to cream
Odor
Pungent odor
BRN
119023 · 119023
InChI
InChI=1S/C6H4ClNO2/c7-5-4(6(9)10)2-1-3-8-5/h1-3H,(H,9,10)

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 · 5 items

This chemical does not meet GHS hazard criteria for 8.1% (11 of 136) of reports.

Warning

H315 (14.7%): 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 136 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 13-04-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/7352
Hazard Classes and CategoriesSkin Irrit. 2 (14.7%)

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
hs_code
29333999
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
22-24/25-37/39-26-36
hazard_class
IRRITANT
Storage Class
11 - Combustible Solids
target organs
Respiratory system

Chemistry & industry

Uses & manufacturing

Use ClassificationEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
General Manufacturing Information3-Pyridinecarboxylic acid, 2-chloro-: ACTIVE

Applications

Uses2-Chloronicotinic Acid is used in the preparation of 4-thiazolidinone derivatives and Schiff bases displaying antimicrobial activity.

Preparation methods · 1 item

PreparationChloronicotinic acid was synthesized from nicotinic acid by oxidation by H2O2 and then chlorinationby POCl3 and PCl5 in a yield of 87.5%.Synthesis of 2-chloronicotinic acid: Pour chlorine gas into the mixed solution of phosphorus oxychloride and phosphorus trichloride, control the temperature at about 60°C, until the remaining chlorine gas escapes, cool and add nicotinic acid N-oxide in batches, and heat the mixed solution. The reaction was carried out at 100-105°C for 1-1.5 h, and the reaction mixture was stirred for 30 min after the reaction mixture was transparent, and phosphorus oxychloride was removed under reduced pressure. The obtained residue was cooled to room temperature, and water was added to obtain the finished product of 2-chloronicotinic acid.

Upstream & downstream products

Upstream raw materials

2-Chloro-3-methylpyridine3-PicolineDiisopropylamine2-chloro-3-trichloromethylpyridine2-Chloro-5-methylpyridine

Related reactions

434 records
New reaction record
HRID 4780 reaction equation
HRID 4780As reactantuspto-grants-1988_02
HRID 4783 reaction equation
HRID 4783As reactantuspto-grants-1988_02
HRID 4784 reaction equation
HRID 4784As reactantuspto-grants-1988_02
HRID 4819 reaction equation
HRID 4819As reactantuspto-grants-1988_02
HRID 4822 reaction equation
HRID 4822As reactantuspto-grants-1988_02
HRID 4823 reaction equation
HRID 4823As reactantuspto-grants-1988_02
HRID 11704 reaction equation
HRID 11704As reactantuspto-grants-2006_08
HRID 12186 reaction equation
HRID 12186As reactantuspto-grants-2010_06
Page 1 of 55

Compound notes

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InChIKey
IBRSSZOHCGUTHI-UHFFFAOYSA-N
SMILES
C1(Cl)=NC=CC=C1C(O)=O
LogP
0.988 · 0.988
CAS DataBase Reference
2942 · 2942-59-8(CAS DataBase Reference)
FDA UNII
93 G386213F · 93G386213F
EPA Substance Registry System
2 · 2-Chloronicotinic acid (2942-59-8)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
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 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
22 · 22-24/25-37/39-26-36
WGK Germany
3 · 3
TSCA
TSCA listed
HazardClass
IRRITANT
HS Code
29333999 · 29333999
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
REACH Registrations
Active
Hazard statements
H315-H319-H335
REACH Registrations
Active
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements
P261-P264-P271-P280-P302+P352-P305+P351+P338
Nicotinic acid N-oxide

Downstream products

Diflufenican2-Chloropyridine-3,4-dicarboxylic acid2-(Ethylthio)nicotinic acid2-Hydroxynicotinic acid2-Aminonicotinic acidMethyl 2-chloronicotinate2-Methoxynicotinic acid2-(2,3-dihydro-1,4-benzodioxin-6-yl)aminonicotinic acid

Additional notes

DefinitionChEBI: 2-Chloronicotinic acid is an aromatic carboxylic acid and a member of pyridines.