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Chlorothalonil

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Identification
Molecular formula
C8H4Cl3NO2S
CAS number
1897-45-6
IUPAC name
2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione
State
State

At room temperature, Chlorothalonil is typically in a solid state. It exists as a white powder or crystalline solid.

Melting point (Celsius)
250.00
Melting point (Kelvin)
523.00
Boiling point (Celsius)
350.00
Boiling point (Kelvin)
623.00
General information
Molecular weight
265.92g/mol
Molar mass
265.9200g/mol
Density
1.6150g/cm3
Appearence

Chlorothalonil is a white crystalline solid. Its appearance is often characterized by a fine, powdery texture. Due to its physical characteristics, it can be easily dispersed in air when handled without care.

Comment on solubility

Solubility of 2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione

The solubility of 2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione can be quite complex due to its structure and functional groups. This compound is characterized by the presence of a trichloromethyl group and a sulfanophore, both of which significantly influence its solubility properties. Below are key points to consider:

  • Solvent Type: Generally, compounds with polar functional groups tend to be soluble in polar solvents such as water, while non-polar or weakly polar compounds show better solubility in organic solvents like dichloromethane or ethyl acetate.
  • Influence of Chlorine Atoms: The presence of three chlorine atoms can enhance solubility in organic solvents but may reduce water solubility due to the increased hydrophobic character.
  • Hydrogen Bonding: If the compound can participate in hydrogen bonding, this may increase solubility in suitable polar solvents.
  • Structural Considerations: The fused isoindole structure may impose steric hindrance affecting solubility because of spatial bulk, potentially making the compound less accessible to solvent molecules.

In summary, while it is challenging to generalize the solubility behavior without empirical data, one can hypothesize that 2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione is more likely to be soluble in organic solvents than in water. This emphasizes the notion that the solubility of a compound is intricately linked to its chemical structure and the nature of the solvent used.

Interesting facts

Interesting Facts about 2-(Trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione

This complex compound is a fascinating member of the isoindole family, which is known for its unique bicyclic structure that often lends itself to diverse biological activities. Here are some notable highlights:

  • Diverse Applications: Compounds like this one have drawn interest in medicinal chemistry due to their potential roles as pharmacophores, which can interact with biological targets.
  • Trichloromethyl Group: The presence of a trichloromethyl group is particularly intriguing. This functional group is known for its reactivity and can influence the compound's properties significantly.
  • Sulfur Chemistry: The incorporation of the sulfanyl group introduces unique reactivity patterns and can affect the compound's biological interactions, making it a target for synthesis in pharmaceuticals.
  • Isoindole Structure: The isoindole ring system is not only structurally interesting but has also been shown to possess a range of bioactivities, including antitumor and anti-inflammatory effects.
  • Natural Product Inspiration: Many compounds with isoindole frameworks are inspired by natural products, indicating that studying such synthetic variations can lead to discovering vital therapeutic agents.

In summary, 2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione is more than just a chemical compound; it exemplifies the intricate relationship between chemistry and biological systems, showcasing the importance of structural features in the design of new drugs. As noted by researchers, "Understanding the subtle changes in structure can lead to significant variations in biological activity." This statement encapsulates the essence of medicinal chemistry, where the possibilities for discovery are limitless.

Synonyms
CAPTAN
133-06-2
Aacaptan
Vondcaptan
Amercide
Captane
Malipur
Neracid
Orthocide
Captaf
Captex
Kaptan
Merpan
Trimegol
Vancide 89
Vanicide
Bangton
Captab
Hexacap
Osocide
Ugecap
Stauffer captan
Le captane
Vangard K
Orthocide 50
Orthocide 83
Orthocide 406
Orthocide 7.5
Ortocid 50
Vancide 89RE
Captaf 85W
Captan 50W
Captadin
Captanex
Fungus Ban Type II
Kaptazor
Venturin
Zenecal
Esso fungicide 406
Granox pfm
Glyodex 37-22
Agrosol S
Flit 406
Orthocide 75
Micro-check 12
Bean Seed Protectant
Vancide P-75
SR 406
Sr406
N-[(Trichloromethyl)thio]tetrahydrophthalimide
ENT 26,538
DTXSID9020243
Gustafson captan 30-dd
Agrox 2-way and 3-way
Vanguard K
Captancapteneet 26,538
NCI-C00077
Orthocide S 50
CHEBI:34608
2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione
N-Trichloromethylthio-3a,4,7,7a-tetrahydrophthalimide
N-(Trichlor-methylthio)-phthalimid
1H-Isoindole-1,3(2H)-dione,3a,4,7,7a-tetrahydro-2-[(trichloromethyl)thio]-
Trichloromethylthio-1,2,5,6-tetrahydrophthalamide
DTXCID90243
Buvisild K
3a,4,7,7a-Tetrahydro-N-(trichloromethanesulphenyl)phthalimide
Captan 100 microg/mL in Acetone
Captan 1000 microg/mL in Acetone
1H-Isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-[(trichloromethyl)thio]-
2-((Trichloromethyl)thio)-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione
3a,4,7,7a-Tetrahydro-2-[(trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione
Captaf 50W
Captan [ISO]
Ugecap 83
NSC-36726
N-Trichloromethylthiocyclohex-4-ene-1,2-dicarboximide
Captan 100 microg/mL in Acetonitrile
Caswell No. 159
Glyodex 3722
Captan [BSI:ISO]
LE Captane [French]
Captan-streptomycin 7.5-0.1 potato seed piece protectant
Isotox Seed Treater D
Isotox Seed Treater F
N-[(Trichloromethyl)thio]-4-cyclohexene-1,2-dicarboximide
N-Trichloromethylmercapto-4-cyclohexene-1,2-dicarboximide
Trichlormethylthioamid kyseliny 1,2,3,6-tetrahydroftalove
NCGC00091034-02
4-Cyclohexene-1,2-dicarboximide, N-[(trichloromethyl)thio]-
Captane [ISO-French]
NSC 36726
N-((Trichloromethyl)thio)tetrahydrophthalimide
UNII-EOL5G26Q9F
1H-Isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-((trichloromethyl)thio)-
3a,4,7,7a-Tetrahydro-2-((trichloromethyl)thio)-1H-isoindole-1,3(2H)-dione
2-[(Trichloromethyl)sulfanyl]-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione
1,2,3,6-Tetrahydro-N-(trichloromethylthio)phthalimide
CCRIS 120
HSDB 951
N-((Trichloromethyl)thio)-4-cyclohexene-1,2-dicarboximide
N-(trichloromethylmercapto)-Delta(4)-tetrahydrophthalimide
Bangtan
Meteoro
Phytocape
Sepicap
Captol
Sorene
Orthocide-406
EINECS 205-087-0
EPA Pesticide Chemical Code 081301
BRN 0023177
LE Captane (French)
Captane (ISO-French)
CAS-133-06-2
AI3-26538
CAPTAN (IARC)
CAPTAN [HSDB]
CAPTAN [IARC]
CAPTAN (II)
CAPTAN [II]
CAPTAN [MI]
N-(Trichlor-methylthio)-phthalimid [German]
EC 205-087-0
N-[(Trichloromethyl)thio]-Delta4-tetrahydrophthalimide
4-Cyclohexene-1,2-dicarboximide, N-(trichloromethyl)thio-
N-((Trichloromethyl)thio)cyclohex-4-ene-1,2-dicarboximide
N-[(Trichloromethyl)thio]cyclohex-4-ene-1,2-dicarboximide
Captonex
Clomitane
Dangard
N-(Trichloromethylmercapto)-delta(sup 4)-tetrahydrophthalimide
Pillarcap
Captal
N-((Trichloromethyl)mercapto)-4-cyclohexene-1,2-dicarboximide
N-((TRICHLOROMETHYL)THIO)-DELTA4-TETRAHYDROPHTHALIMIDE
N-[(Trichloromethyl)mercapto]-4-cyclohexene-1,2-dicarboximide
N-(Trichloromethylthio)-4-cyclohexene-1,2-dicarboximide
Trichlormethylthioamid kyseliny 1,2,3,6-tetrahydroftalove [Czech]
4-CYCLOHEXENE-1,2-DICARBOXIMIDE, N-((TRICHLOROMETHYL)THIO)-
N-((TRICHLOROMETHYL)THIO)-4-CYCLOHEXENE-1,2,-DICARBODIMIDE
N-[(TRICHLOROMETHYL)THIO]-4-CYCLOHEXENE-1,2,-DICARBODIMIDE
4-Cyclohexene-1,2-dicarboxylic acid, imide, N(trichloromethylthio)-
ENT-26538
N-Trichloromethylthio-cis-delta(sup 4)-cyclohexene-1,2-dicarboximide
SR-406
2-((trichloromethyl)sulfanyl)-2,3,3a,4,7,7a-hexahydro-1H-isoindole-1,3-dione
2-((trichloromethyl)sulfanyl)-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione
2-[(trichloromethyl)sulfanyl]-2,3,3a,4,7,7a-hexahydro-1H-isoindole-1,3-dione
2-[(trichloromethyl)thio]-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione
Granox PPM
Orthocide-83
Orthocide406
Orthocid-83
Captan (Standard)
essofungicide 406
Fungicide 406
Captan (ACGIH)
MFCD00041811
RADOCAPTAN
N-(Trichlor-methylthio)-phthalimid (German)
RALLIS CAPTAF
ORTHOCIDE 83RP
CAPTAN [INCI]
ORTHOCIDE 75W
N-Trichloromethylthio-4-cyclohexene-1,2-dicarboximide
n-(trichloromethylthio)cyclohex-4-ene-1,2-dicarboximide
SCHEMBL21047
MLS002222339
Trichlormethylthioamid kyseliny 1,2,3,6-tetrahydroftalove (Czech)
CHEMBL388676
N Trichloromethylthio 4 cyclohexane 1,2 dicarboximide
N-Trichloromethylthio-4-cyclohexane-1,2-dicarboximide
4-CYCLOHEXENE-1,2-DICARBOXIMIDE, N-((TRICHLOROMETHYL)THIO)-, CIS-
HY-B1584R
LDVVMCZRFWMZSG-UHFFFAOYSA-
Isotox Seed Treater "D" and "F
1H-ISOINDOLE-1,3(2H)-DIONE, 3A,4,7,7A-TETRAHYDRO-2-((TRICHLOROMETHYL)THIO)-, (3AR,7AS)-REL-
1H-ISOINDOLE-1,3(2H)-DIONE, 3A,4,7,7A-TETRAHYDRO-2-((TRICHLOROMETHYL)THIO)-, CIS-
HY-B1584
NSC36726
WLN: T56 BVNV GUTJ CSXGGG
Tox21_111065
Tox21_201276
Tox21_300772
4-Cyclohexene-1,2-dicarboximide,n-
(4-Ethoxybenzyl)furan-2-ylmethylamine
AKOS015895773
CCG-231621
FC19674
USEPA/OPP Pesticide Code: 081301
1H-ISOINDOLE-1,3(2H)-DIONE,
NCGC00091034-01
NCGC00091034-03
NCGC00091034-04
NCGC00091034-05
NCGC00091034-06
NCGC00091034-07
NCGC00091034-08
NCGC00091034-09
NCGC00091034-10
NCGC00254676-01
NCGC00258828-01
AS-13811
SMR001307282
Captan, PESTANAL(R), analytical standard
4-Cyclohexene-1, N-(trichloromethylthio)-
C2059
CS-0013481
NS00008419
4-Cyclohexene-1, N-[(trichloromethyl)thio]-
D89482
NTrichloromethylthio4cyclohexane1,2dicarboximide
SBI-0654030.0001
Captan, certified reference material, TraceCERT(R)
N-Trichloromethylthio-3a,7,7a-tetrahydrophthalimide
Q2194382
Trichloromethyl thio-1,2,5,6-tetrahydrophthalamide
BRD-A79857384-001-03-6
N-Trichloromethyl-thio-3a,4,7,7a-tetrahydropthalimide
N-(trichloromethylthio)-4-cyclohexane-1,2-dicarboximide
N-trichloro methylthio-3a,4,7,7a-tetrahydrophthalimide
1H-isoindole-1,3-(2H)-dione, 3a,4,7,7a-tetrahydro-2-
N-((trichloromethyl)thio-4-cyclohexene-1,2-dicarboximide
N-[(Trichloromethyl)thio]-.DELTA.4-tetrahydrophthalimide
N-((Trichloromethyl)mercapto)-.DELTA.4-tetrahydrophthalimide
N-(TRICHLOROMETHYL)THIO-4-CYCLOHEXENE-1,2-DICARBOXIMIDE
1H-Isoindole-1, 3a,4,7,7a-tetrahydro-2-[(trichloromethyl)thio]-
N-(trichloro methylmercapto)-delta(sup 4)-tetrahydro phthalimide
N-(TRICHLOROMETHYLMERCAPTO)-DELTA(SUP 4)TETRAHYDROPHTHALIMIDE
N-[(Trichloromethyl)mercapto]-.delta.(sup 4)-tetrahydrophthalimide
3a,4,7,7a-Tetrahydro-2-[(trichloromethyl)thio]-1H-isoindole-1,3(2H)dione
N-[(Trichloromethyl)thio]-cis-.delta.(sup 4)-cyclohexene-1,2-dicarboximide
2-[(Trichloromethyl)sulfanyl]-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione #
205-087-0
3a,4,7,7a-Tetrahydro-2-[(trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione;N-[(Trichloromethyl)thio]tetrahydrophthalimide
InChI=1/C9H8Cl3NO2S/c10-9(11,12)16-13-7(14)5-3-1-2-4-6(5)8(13)15/h1-2,5-6H,3-4H2