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50-30-6

Basic Information
CAS No.: 50-30-6
Name: 2,6-Dichlorobenzoic acid
Molecular Structure:
Molecular Structure of 50-30-6 (2,6-Dichlorobenzoic acid)
Formula: C7H4Cl2O2
Molecular Weight: 191.01
Synonyms: Benzoic acid, 2,6-dichloro-;4-09-00-01005 (Beilstein Handbook Reference);2,6-Dichloro benzoic acid;
EINECS: 200-025-9
Density: 1.517 g/cm3
Melting Point: 139-142 ºC (lit.)
Boiling Point: 298.7 ºC at 760 mmHg
Flash Point: 134.5 ºC
Solubility: water: 0.1-1 g/100 mL at 19 ºC
Appearance: white to off-white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-24/25
Transport Information:
PSA: 37.30000
LogP: 2.69160
Synthetic route
4659-45-4

2,6-Dichlorobenzoyl chloride

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With water; triethylamine In acetone at 20℃; for 18h;99%
With NaH; acetic acid In dichloromethane; water; N,N-dimethyl-formamide
With NaH; acetic acid In dichloromethane; water; N,N-dimethyl-formamide
15258-73-8

2,6-dichlorobenzyl alcohol

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
Stage #1: 2,6-dichlorobenzyl alcohol With sodium t-butanolate In tetrahydrofuran at 25℃; for 1h; Schlenk technique;
Stage #2: With hydrogenchloride In water Reagent/catalyst;
99%
With tert.-butylhydroperoxide; sodium chloride; sodium hydroxide In water at 70℃; Sealed tube; Green chemistry;85%
With tert.-butylhydroperoxide; water; iodine; sodium hydroxide at 70℃; pH=10; Green chemistry;83%
124-38-9

carbon dioxide

541-73-1

1,3-Dichlorobenzene

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide With AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); potassium hydroxide In tetrahydrofuran at 20℃; under 1125.11 Torr; for 0.25h;
Stage #2: 1,3-Dichlorobenzene In tetrahydrofuran at 20℃; under 1125.11 Torr; for 12h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water regioselective reaction;
96%
With n-butyllithium In tetrahydrofuran; hexane for 0.75h; cooling;95%
Stage #1: 1,3-Dichlorobenzene With n-butyllithium In tetrahydrofuran at -75℃; for 2h;
Stage #2: carbon dioxide In tetrahydrofuran
95%
Stage #1: 1,3-Dichlorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Inert atmosphere;
Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere;
437 mg
118-69-4

2,6-dichlorotoluene

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
95%
With potassium permanganate; water
With nitric acid at 140℃; im Druckrohr;
1194-65-6

2,6-dichloro-benzonitrile

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 2.5h; Green chemistry;95%
With pro-nitro010; water Reagent/catalyst; Enzymatic reaction;
37532-04-0

N'-(2,6-dichlorobenzylidene)-4-methylbenzene-1-sulfonohydrazide

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 144h; Heating;94%
83-38-5

2,6-dichlorobenzaldehyde

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide for 0.0333333h; Microwave irradiation;92%
With tert.-butylhydroperoxide; water; iodine; sodium hydroxide at 70℃; pH=10; Green chemistry;92%
With air; octadecafluorodecahydronaphthalene (cis+trans); isobutyraldehyde; [Co{TPP(C8F17)4}] In acetonitrile under 760 Torr; for 16h;91%
25185-95-9

2,6-dichlorobenzaldoxime

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 240h; Heating;92%
83-38-5

2,6-dichlorobenzaldehyde

A

87-65-0

2,6-Dichlorophenol

B

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With selenium(IV) oxide; dihydrogen peroxide In tetrahydrofuran for 52h; Heating;A 4 % Chromat.
B 86%
6575-28-6

(1E)-2,6-dichlorobenzaldehyde oxime

75-05-8

acetonitrile

A

1194-65-6

2,6-dichloro-benzonitrile

B

55151-92-3

3-(2,6-dichlorophenyl)-5-methyl-1,2,4-oxadiazole

C

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate at 70℃; for 1h; Yields of byproduct given;A n/a
B 30%
C 11%
2148-56-3

2-chloro-6-aminobenzoic acid

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
Diazotization.Einw. von CuCl und HCl auf das Diazotierungsprodukt;
20443-98-5

2,6-Dichlorobenzyl bromide

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide; potassium permanganate
With ethanol; potassium acetate Erwaermen des Reaktionsprodukts mit wss. Natronlauge und Behandeln des Reaktionsgemisches mit Kaliumpermanganat;
With sodium periodate; 2>(6-); sulfuric acid 1) aq. KOH, rt, 4 h; Yield given. Multistep reaction;
90281-00-8, 90364-83-3

1,1-dichloro-t-2-<((E)-2'-(2,6-dichlorophenyl)-ethen-1'-yl)>-r-3-phenylcyclopropane

A

34266-21-2

1,1-dichloro-t-3-phenylcyclopropane-r-2-carboxylic acid

B

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With formic acid; dihydrogen peroxide; oxygen; ozone 1.) CHCl3, 30 min, -10 deg C; 2.) water, 30 min; 3.) reflux, 1 h; Yield given. Multistep reaction. Yields of byproduct given;
124-38-9

carbon dioxide

87-61-6

1,2,3-trichlorobenzene

A

50-45-3

2,3-dichlorbenzoic acid

B

535-80-8

3-chlorobenzoate

C

118-91-2

ortho-chlorobenzoic acid

D

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 5℃; electrolysis (I=0.4 A); Yield given. Further byproducts given. Yields of byproduct given;

2,6-Dichloro-benzoic acid 2-methyl-2-nitro-propyl ester

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol for 12h; Heating; Yield given;
118-69-4

2,6-dichlorotoluene

7726-95-6

bromine

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
at 170℃; Eintragen von KMnO4 in das mit wss. NaOH versetzte Reaktionsgemisch bei Siedetemperatur;
118-69-4

2,6-dichlorotoluene

7697-37-2

nitric acid

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
im Rohr;
7446-70-0

aluminium trichloride

81055-73-4

ethyl 2,6-dichlorobenzoate

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
at 120 - 130℃;
124-38-9

carbon dioxide

87-61-6

1,2,3-trichlorobenzene

A

50-75-9

2,3,4-trichlorobenzoic acid

B

50-45-3

2,3-dichlorbenzoic acid

C

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
Stage #1: 1,2,3-trichlorobenzene With sec.-butyllithium In tetrahydrofuran; cyclohexane at -75℃; for 0.75h;
Stage #2: carbon dioxide In tetrahydrofuran; cyclohexane Title compound not separated from byproducts;
A 13 % Chromat.
B 5.7 % Chromat.
C 67 % Chromat.

2-(2,6-Dichloro-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Oxone, NaHCO3, 1,1,1-trifluoroacetone / acetonitrile; H2O / Ambient temperature; Na2*EDTA, pH 7-7.5
2: 5percent NaOH / methanol / 12 h / Heating
View Scheme
7463-35-6

N-(3-chloro-2-methylphenyl)acetamide

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium permanganate; magnesium sulfate
2: concentrated hydrochloric acid / Zers. des entstandenen Hydrochlorids mit Natriumdicarbonat
3: Diazotization.Einw. von CuCl und HCl auf das Diazotierungsprodukt
View Scheme
19407-42-2

2-(acetylamino)-6-chlorobenzoic acid

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated hydrochloric acid / Zers. des entstandenen Hydrochlorids mit Natriumdicarbonat
2: Diazotization.Einw. von CuCl und HCl auf das Diazotierungsprodukt
View Scheme
95-49-8

2-methylchlorobenzene

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iron / durch Chlorierung
2: bei der Oxydation
View Scheme
603-83-8

3-nitro-o-tolylamine

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Austausch der Aminogruppe gegen Chlor, Reduktion und Ersatz der neuentstandenen Aminogruppe durch Chlor
2: bei der Oxydation
View Scheme
108-88-3

toluene

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: MoCl5 / durch Chlorierung
2: bei der Oxydation
View Scheme

C7H3Cl2O2(1-)*C25H30N3(1+)

A

467-63-0

crystal violet carbinol base

B

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With water In chlorobenzene at 28℃; Equilibrium constant;

C22H18Cl2O4

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
In ethanol; dichloromethane at 25℃; Kinetics;
15258-73-8

2,6-dichlorobenzyl alcohol

A

83-38-5

2,6-dichlorobenzaldehyde

B

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide at 70℃; Catalytic behavior; Reagent/catalyst; Temperature;

C13H20Cl2OSi

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetra-N-butylammonium tribromide / acetonitrile / 15 h / 20 °C / Irradiation
2: tetra-N-butylammonium tribromide / acetonitrile / 24 h / 20 °C / Irradiation
View Scheme
616-38-6

carbonic acid dimethyl ester

50-30-6

2,6-dichlorobenzoic acid

14920-87-7

2,6-dichlorobenzoic acid methyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene for 24h; Heating;99%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 160℃; under 15001.2 Torr; for 0.4h; microwave irradiation;98%
With 1,8-diazabicyclo[5.4.0]undec-7-ene for 48h; Heating / reflux;86%
68641-49-6

bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride

50-30-6

2,6-dichlorobenzoic acid

77331-22-7

C13H11Cl2N2O7P

Conditions
ConditionsYield
With 1-ethyl-piperidine In dichloromethane at 15℃; for 1.5h;98%
50-30-6

2,6-dichlorobenzoic acid

57193-24-5

<2,6-2H2>benzoic acid

Conditions
ConditionsYield
With deuterated hypophosphorous acid; palladium 10% on activated carbon; sodium carbonate In water-d2 at 50℃; regioselective reaction;98%
39217-08-8

2-chloropyridine-3,4-diamine

50-30-6

2,6-dichlorobenzoic acid

1334411-80-1

2-(2,6-dichlorophenyl)-1H-imidazo[4,5-c]pyridin-4-ol

Conditions
ConditionsYield
Stage #1: 2-chloropyridine-3,4-diamine; 2,6-dichlorobenzoic acid at 190℃; for 3h;
Stage #2: With sodium carbonate In water at 20℃; Cooling with ice;
97%
With polyphosphoric acid at 190℃; for 3h;97%
611239-90-8

C17H28N2O

50-30-6

2,6-dichlorobenzoic acid

A

4128-37-4

1,3-diisopropylurea

B

1160842-96-5

4-phenylbutan-2-yl 2,6-dichlorobenzoate

Conditions
ConditionsYield
In acetonitrile at 130℃; for 0.0833333h; Microwave irradiation;A n/a
B 96%
50-30-6

2,6-dichlorobenzoic acid

55775-97-8

2,6-dichloro-3-nitrobenzoic acid

Conditions
ConditionsYield
With sulfuric acid; nitric acid for 1h; Heating;95%
With sulfuric acid; nitric acid at 30℃; Temperature; Inert atmosphere;95.2%
With sulfuric acid; nitric acid at 70℃; for 5h;95%
1160843-02-6

C17H28N2O

50-30-6

2,6-dichlorobenzoic acid

A

4128-37-4

1,3-diisopropylurea

B

1160843-05-9

(R)-4-phenylbutan-2-yl 2,6-dichlorobenzoate

Conditions
ConditionsYield
In acetonitrile at 130℃; for 0.0833333h; Microwave irradiation; optical yield given as %ee;A n/a
B 95%
78-39-7

Triethyl orthoacetate

50-30-6

2,6-dichlorobenzoic acid

81055-73-4

ethyl 2,6-dichlorobenzoate

Conditions
ConditionsYield
In various solvent(s) at 80℃; for 2h;94%
108-98-5

thiophenol

50-30-6

2,6-dichlorobenzoic acid

68504-48-3

phenyl 2,6-dichlorothiolbenzoate

Conditions
ConditionsYield
With pyridine; O-phenyl phosphorodichloridate In dichloromethane for 24h; Ambient temperature;92%
With PPE for 15h; Ambient temperature;83%
74-88-4

methyl iodide

50-30-6

2,6-dichlorobenzoic acid

2,6-dichloro-3-methylbenzoic acid

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tetrahydrofuran 1.) -90 deg C, 30 min, 2.) -78 deg C;92%
50-30-6

2,6-dichlorobenzoic acid

16442-10-7

2,6-dichlorobenzoic anhydride

Conditions
ConditionsYield
With 1-ethyl-piperidine; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride In acetonitrile at 20℃; for 4h;91%
5292-43-3

bromoacetic acid tert-butyl ester

50-30-6

2,6-dichlorobenzoic acid

81055-78-9

C13H14Cl2O4

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 16h;91%
26049-94-5

(S)-benzyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate

50-30-6

2,6-dichlorobenzoic acid

2,6-Dichloro-benzoic acid (S)-3-benzyloxycarbonylamino-2-oxo-4-phenyl-butyl ester

Conditions
ConditionsYield
Multistep reaction;90%
113984-36-4

C15H32N2O

50-30-6

2,6-dichlorobenzoic acid

A

4128-37-4

1,3-diisopropylurea

B

1160843-00-4

octan-2-yl-2,6-dichlorobenzoate

Conditions
ConditionsYield
In acetonitrile at 130℃; for 0.0833333h; Microwave irradiation;A n/a
B 90%
18881-04-4

(S)-cis-Verbenol

50-30-6

2,6-dichlorobenzoic acid

144681-51-6

(+)-(1S)-<(1α,2β,5α)-4,6,6-trimethylbicyclo<3.1.1>hept-3-en-2-yl> 2,6-dichlorobenzoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In diethyl ether; acetonitrile for 0.5h; Ambient temperature;89%
7305-71-7

5-methyl-2-thiazol-2-amine

50-30-6

2,6-dichlorobenzoic acid

6-chloro-2-methyl-5H-[1,3]-thiazolo[2,3-b]quinazolin-5-one

Conditions
ConditionsYield
With copper; potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.25h; sonication;88%
With copper Ullmann condensation; Sonication;
75-66-1

2-methylpropan-2-thiol

50-30-6

2,6-dichlorobenzoic acid

68504-44-9

t-butyl 2,6-dichlorothiolbenzoate

Conditions
ConditionsYield
With PPE at 45℃; for 15h;85%
50-30-6

2,6-dichlorobenzoic acid

5-(piperazin-1-yl)benzofuran-2-carboxylic acid ethyl ester

ethyl 5-[4-(2,6-dichlorobenzoyl)piperazin-1-yl]benzofuran-2-carboxylate

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane85%
114-33-0

N-Methylnicotinamide

6046-93-1

copper(II) acetate monohydrate

50-30-6

2,6-dichlorobenzoic acid

C28H24Cl4CuN4O7*2H2O

Conditions
ConditionsYield
In acetonitrile for 24h;85%
67-64-1

acetone

50-30-6

2,6-dichlorobenzoic acid

2-oxopropyl 2,6-dichlorobenzoate

Conditions
ConditionsYield
With sodium chlorite; potassium iodide at 100℃; for 24h; Schlenk technique;85%
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    CAS: 50-30-6 MF: C7H4Cl2O2 MW: 191.01 EINECS: 200-025-9 Properties Melting point: 139-142 °C(lit.) Boiling point: 273.68°C (rough estimate)

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Specification

The 2,6-Dichlorobenzoic acid, with the CAS registry number 50-30-6, is also known as Benzoic acid, 2,6-dichloro-. It belongs to the product categories of Fine Chemical & Intermediates; C7; Carbonyl Compounds; Carboxylic Acids; Alpha Sort; D; DAlphabetic; DIA - DIC; Pesticides & Metabolites. Its EINECS registry number is 200-025-9. This chemical's molecular formula is C7H4Cl2O2 and molecular weight is 191.01. What's more, its IUPAC name is the same with its product name.

Physical properties about 2,6-Dichlorobenzoic acid are: (1)ACD/LogP: 2.20; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.87; (4)ACD/LogD (pH 7.4): -0.95; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.598; (14)Molar Refractivity: 42.97 cm3; (15)Molar Volume: 125.8 cm3; (16)Surface Tension: 53.9 dyne/cm; (17)Density: 1.517 g/cm3; (18)Flash Point: 134.5 °C; (19)Enthalpy of Vaporization: 56.88 kJ/mol; (20)Boiling Point: 298.7 °C at 760 mmHg; (21)Vapour Pressure: 0.000557 mmHg at 25 °C.

Preparation of 2,6-Dichlorobenzoic acid: this chemical can be prepared by 2,6-Dichloro-benzaldehyde. This reaction needs reagent Jones and solvent acetone at temperature of 0 °C. The reaction time is 20 min. The yield is 70 %.

2,6-Dichlorobenzoic acid can be prepared by 2,6-Dichloro-benzaldehyde.

Uses of 2,6-Dichlorobenzoic acid: (1) it is used to synthetize pharmaceutical and pesticide; (2) it is used to produce other chemicals. For example, it can produce 2,6-Dichloro-3-nitro-benzoic acid. The reaction occurs with reagents H2SO4, HNO3 and other condition of heating for 1 hour. The yield is 65 %.

2,6-Dichlorobenzoic acid can produce 2,6-Dichloro-3-nitro-benzoic acid.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable protective clothing and avoid contacting with skin, eyes. And in case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O)c1c(Cl)cccc1Cl
(2) InChI: InChI=1S/C7H4Cl2O2/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3H,(H,10,11)
(3) InChIKey: MRUDNSFOFOQZDA-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 316mg/kg (316mg/kg) BEHAVIORAL: REGIDITY

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Journal of Medicinal Chemistry. Vol. 11, Pg. 1020, 1968.
mouse LD50 subcutaneous 1500mg/kg (1500mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Biochemical Pharmacology. Vol. 13, Pg. 1538, 1964.