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2,4-Dichlorobenzoic Acid

HCID 5787
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Basic information

CAS
50-84-0
Standard SMILES
O=C(O)c1ccc(Cl)cc1Cl
InChIKey
ATCRIUVQKHMXSH-UHFFFAOYSA-N
Molecular formula
C7H4Cl2O2
Average molar mass
191.01 g/mol
Monoisotopic mass
189.95883473

Overview

2,4-dichlorobenzoic acid is a white to slightly yellowish powder. (NTP, 1992)

Names & identifiers

Preferred name
2,4-Dichlorobenzoic Acid
IUPAC
2,4-dichlorobenzoic acid
English name
2,4-Dichlorobenzoic acid
Molecular formula
C7H4Cl2O2
Molecular weight
191.01

Names & synonyms

2,4-DICHLOROBENZOIC ACID50-84-0Benzoic acid, 2,4-dichloro-DTXSID0024977NSC-5780SR0320D45DTXCID104977CHEBI:307482,4-DCBARefChem:82379200-067-8Furosemide EP impurity E
Show more names
2,4-Dichlorobenzoic2,4-Dichlolrobenzoic Acid2,4-Dichlorobenzoicacid,98%'LGC' (1305)2.4-Dichlorobeorbenzoic acidAKOS BBS-00003747Dichlorbenzoic aci
MFCD000024142,4 dichlorobenzoic acidBRN 1868192CCRIS 94722,4-Dichlorobenzoesyre2,4-Dichlorbenzoic acid2,4-DichlorobenzoicacidAKOS000119754

Database identifiers

CAS
50-84-0
PubChem CID
5787
DTXSID
DTXSID0024977
ChEMBL
CHEMBL1492029
ChEBI
CHEBI:30748
UNII
0SR0320D45
EC Number
200-067-8
Nikkaji
J55.459F

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
11
Formal charge
0
Complexity
161

Experimental & physicochemical properties

SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
PesticidesEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
LogP2.76
Solubilityless than 1 mg/mL at 66 °F (NTP, 1992)
Boiling PointSublimes (NTP, 1992)
Melting Point315 to 320 °F (NTP, 1992)
Physical Description2,4-dichlorobenzoic acid is a white to slightly yellowish powder. (NTP, 1992)

Physicochemical properties

Melting point
157 · 157-160 °C (lit.)
Boiling point
200 °C · 200 °C
Density
1.441 · 1.4410 (rough estimate)

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 · 4 items

Warning

H302 (96.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 117 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Benzoic acid, 2,4-dichloro-

2,4-Dichlorobenzoic acid: 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)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation.
Reactive GroupAcids, Carboxylic
Reactivity Profile · 1 item

2,4-DICHLOROBENZOIC ACID is a halogenated carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Chemistry & industry

Uses & manufacturing

Use ClassificationEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
General Manufacturing InformationBenzoic acid, 2,4-dichloro-: ACTIVE
Applications · 3 items

Uses2,4-Dichlorobenzoic Acid is a di-halogenated benzoic acid derivative and an intermediate in the synthesis of spirodiclofen (S682990), a tetronic acid acaricide fungicide used in controlling red mites.

Uses2,4-Dichlorobenzoic acid is used as reagent during the synthesis of pyrimido[2,1:2,3]thiazolo[4,5-b]quinoxaline derivatives. It is also used as starting reagent during the synthesis of 1-(substituted)-1,4-dihydro-6-nitro-4-oxo-7-(sub-secondary amino)-quinoline-3-carboxylic acids.

General DescriptionWhite to slightly yellowish powder.

Upstream & downstream products

Upstream raw materials

2,4-Dichlorotoluene2,3,4,5,6-Pentachlorotoluene2,4-DiaminotoluenePhosgeneCopper(I) chloridePotassium formatePotassium permanganate2,4-Dichlorobenzoyl chloride3,4-Dichlorobenzoic acid

Related reactions

91 records
New reaction record
HRID 46225 reaction equation
HRID 46225As reactantuspto-grants-2013_09
HRID 93348 reaction equation
HRID 93348As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 189832 reaction equation
HRID 189832As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 196022 reaction equation
HRID 196022As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 209647 reaction equation
HRID 209647As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 210693 reaction equation
HRID 210693As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 213417 reaction equation
HRID 213417As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 217283 reaction equation
HRID 217283As reactantuspto-grants-2012_06
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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refractive index
1.459 · 1.4590 (estimate)
Flash point
80 ° · 80°
storage temp.
Sealed in dry,Room Temperature
solubility
1 g/10 · ethanol: soluble1g/10 mL, clear, colorless
pka
2.68 · 2.68±0.25(Predicted)
form
Powder
color
White to almost white
PH
2.8 · 2.8 (0.36g/l, H2O, 15℃)
Water Solubility
0.36 g/L · 0.36 g/L (15 ºC)
BRN
1868192 · 1868192
Stability
Stable. Incompatible with strong oxidizing agents.
InChI
1S/C7H4Cl2O2/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3H,(H,10,11)
InChIKey
ATCRIUVQKHMXSH-UHFFFAOYSA-N
SMILES
OC(=O)c1ccc(Cl)cc1Cl
CAS DataBase Reference
50 · 50-84-0(CAS DataBase Reference)
EWG's Food Scores
2 · 2
FDA UNII
0 SR0320D45 · 0SR0320D45
NIST Chemistry Reference
2 · 2,4-Dichlorobenzoic acid(50-84-0)
EPA Substance Registry System
2 · Benzoic acid, 2,4-dichloro- (50-84-0)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
target organs
Respiratory system
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn,Xi
Risk Statements
22 · 22-36/37/38
Safety Statements
26 · 26-36-37/39-22
WGK Germany
3 · 3
RTECS
6650000 · DG6650000
Hazard Note
Irritant
TSCA
TSCA listed
HS Code
29163900 · 29163900
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesAcute Tox. 4 (96.6%)

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

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 · 1 item

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) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is stored, weighed and diluted, wear an 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
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
DG6650000
hs_code
29163900
risk_code
22-36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn,Xi
hazard_note
Irritant
safety_code
26-36-37/39-22
Storage Class
11 - Combustible Solids
target organs
Respiratory system
Hazard statements
H302-H315-H319-H335
Hazard Classifications
Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements
P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
2,4-Dichlorobenzaldehyde

Downstream products

LobenzaritEthyl 2,4-dichlorobenzoateFurosemide2,4-Dichlorobenzonitrile2,4-Dichloro-5-sulfamoylbenzoic acid7-Chloro-10-(4-hydroxyanilino)-2-methoxy benzo(b)-1,5-naphthy ridine2,4-Dichloro-3,5-dinitrobenzoic acid6-chloro-1H-indazol-3-amine4-Chloro-2-(4-methoxy-phenylamino)-benzoic acid2,4-Dichlorobenzoyl chloride2,4-Dichlorobenzyl chloride2,4-Dichlorophenylacetonitrile2,4-Dichlorobiphenyl2,4,5-Trichlorobenzoic acid5-broMo-2,4-dichloro benzoic acidethyl N-(2,4-dichlorobenzoyl)glycinate

Additional notes

DefinitionChEBI: A chlorobenzoic acid that is benzoic acid in which the ring hydrogens at positions 2 and 4 are substituted by chloro groups.