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133221

Sigma-Aldrich

Bis(5-chloro-2-hydroxyphenyl)methane

95%

Synonym(s):

Dichlorophen, Dichlorophene

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About This Item

Linear Formula:
CH2[C6H3(Cl)OH]2
CAS Number:
97-23-4
Molecular Weight:
269.12
Beilstein:
1884514
EC Number:
202-567-1
MDL number:
MFCD00002322
UNSPSC Code:
12352100
PubChem Substance ID:
24848095

Quality Level

100

Assay

95%

form

powder

mp

168-172 °C (lit.)

solubility

95% ethanol: soluble 1g/g
methanol: soluble
petroleum ether: soluble
toluene: very slightly soluble
water: insoluble

SMILES string

Oc1ccc(Cl)cc1Cc2cc(Cl)ccc2O

InChI

1S/C13H10Cl2O2/c14-10-1-3-12(16)8(6-10)5-9-7-11(15)2-4-13(9)17/h1-4,6-7,16-17H,5H2

InChI key

MDNWOSOZYLHTCG-UHFFFAOYSA-N

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General description

Bis(5-chloro-2-hydroxyphenyl)methane is a fungicide and is very effective against many celluloytic fungi, such as Penicillium, Aspergillus,Cladosporium and Trichoderma sp. It is a phenolic pesticide and undergoes photodegradation in the presence of visible-light absorber photosensitizer riboflavin.

Application

Bis(5-chloro-2-hydroxyphenyl)methane can be used as a starting material to synthesize methyl aluminium-(2,2′-methylene-p-chloro-bisphenoxide), which is used as a catalyst for the ring opening polymerization (ROP) of cyclic esters. It can also be used as an organic building block to prepare phosphomides substituted with aminoacid esters for various biological studies.

Disclaimer

The product is not intended for use as a biocide under global biocide regulations, including but not limited to US EPA′s Federal Insecticide Fungicide and Rodenticide Act, European Biocidal Products Regulation, Canada’s Pest Management Regulatory Agency, Turkey’s Biocidal Products Regulation, Korea’s Consumer Chemical Products and Biocide Safety Management Act (K-BPR) and others.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302 - H319 - H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Reaction of methyl aluminium-(2, 2?-methylene-p-chloro-bisphenoxide) with 2, 2?-di (hydroxymethyl) biphenyl: A new aluminium complex bearing two kinds of diolate ligands
Ziemkowska W, et al.
Journal of Organometallic Chemistry, 693(3), 369-373 (2008)
Synthesis and antimicrobial activity of 2,10-dichloro-6-substituted amino acid ester12H-dibenzo[d,g][1,3,2]dioxaphosphocin-6-oxides
BS Kumar, et al.
Bulgarian Chemical Communications, 41(4), 422-426 (2009)
F J Verhagen et al.
Applied and environmental microbiology, 64(9), 3225-3231 (1998-09-03)
Higher fungi have a widespread capacity for biosynthesis of organohalogens. Commonly occurring chloroaromatic fungal metabolites can end up in anaerobic microniches at the boundary of fungal colonies and wetland soils. The aim of this study was to investigate the environmental
Antoine Ghauch et al.
Journal of hazardous materials, 164(2-3), 665-674 (2008-09-30)
Palladium, ruthenium and silver were investigated as catalysts for the dechlorination of dichlorophen (DCP, 2,2'-methylenebis(4-chlorophenol)), an antimicrobial and anthelmintic agent largely used as algicide, fungicide and bactericide. Experiments were undertaken under oxic and anoxic conditions for experimental durations up to
J Langrand et al.
Clinical toxicology (Philadelphia, Pa.), 51(3), 178-181 (2013-03-12)
Human dichlorophen poisoning is rare. We aim to report a case of dichlorophen poisoning resulting in complete recovery despite life-threatening multiorgan failure and huge serum dichlorophen concentrations. Description of features and management in one dichlorophen-poisoned patient. After liquid-liquid extraction, dichlorophen
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