3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenol

• ChemBase ID: 636
• Molecular Formular: C13H6Cl6O2
• Molecular Mass: 406.90354
• Monoisotopic Mass: 403.84989551
• SMILES: Clc1c(Cc2c(O)c(Cl)cc(Cl)c2Cl)c(O)c(Cl)cc1Cl
• Canonical SMILES: Clc1cc(Cl)c(c(c1O)Cc1c(O)c(Cl)cc(c1Cl)Cl)Cl
• InChI: InChI=1S/C13H6Cl6O2/c14-6-2-8(16)12(20)4(10(6)18)1-5-11(19)7(15)3-9(17)13(5)21/h2-3,20-21H,1H2
• InChIKey: ACGUYXCXAPNIKK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenol
• IUPAC Traditional name: pre-OP; hexachlorophene
• Brand Name: AT-7; Acigena; Almederm; Bilevon; Bivelon; Compound G-11; Cotofilm; Dermadex; Dial; Distodin; E-Z Scrub; Eleven; Exofene; Fascol; Fesia-Sin; Fomac; Fostril; G-Eleven; G-II; Gamophen; Gamophene; Germa-Medica; HCP; Hexa-Germ; Hexabalm; Hexachlorofen; Hexachlorophane; Hexachlorophen; Hexachlorophene, Pharma; Hexafen; Hexascrub; Hexazinone; Hexide; Hexophene; Hexosan; Isobac; Isobac 20; Nabac; Nabac 25 Ec; Neosept V; Phiso-Scrub; Phisodan; Phisohex; Pre-Op; Rcra Waste Number U132; Ritosept; Scrubteam Surgical Spongebrush; Septi-Soft; Septisol; Septofen; Soy-Dome; Ster-Zac; Steral; Steraskin; Surgi-Cen; Surgi-Cin; Surofene; Tersaseptic; Trichlorophene; Turgex
• Synonyms: Hexachlorophene; Hexachlorophene; 2,2'-Methylene-bis-[3,4,6-trichlorophenol]; 2,2′-Methylenebis(3,4,6-trichlorophenol); 2,2’-Methylenebis-[3,4,6-trichlorophenol]; 2,2',3,3',5,5'-Hexachloro-6,6'-dihydroxydiphenylmethane; Acigena; Almederm; B 32; Bilevon; Bis(2-hydroxy-3,5,6-trichlorophenyl)methane; Gamophene; Germa-Medica; Hexabalm; Hexachlorofen; Hexachlorophen; NSC 49115; NSC 9887; 6,6'-Methylenebis(2,4,5-trichlorophenol); 2,2′-亚甲基双(3,4,6-三氯苯酚); 六氯酚

Database IDs

• CAS Number: 70-30-4
• EC Number: 200-733-8
• MDL Number: MFCD00002171
• Beilstein Number: 2064407
• PubChem SID: 160964099; 24869046; 46505858; 24895645
• PubChem CID: 3598

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.153373
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 6.580989
• LogD (pH = 7.4): 5.1763735
• Log P: 7.082177
• Molar Refractivity: 88.5858 cm^3
• Polarizability: 34.521233 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.77
• LOG S: -5.97
• Solubility (Water): 4.33e-04 g/l

PROPERTIES

Physical Property

• Solubility: 140 mg/L; Chloroform; DMSO; Methanol
• Apperance: Off-White Solid; off-white to tan crystalline
• Melting Point: 159-161°C; 161-164 °C; 163-165 °C(lit.); 166 - 167 deg. C.
• Hydrophobicity(logP): 6.3

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: SM0700000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2875
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 24/25-50/53; R:24/25-50/53
• Safety Statements: 20-37-45-60-61; S:20-37-45-60-61
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 151
• GHS Pictograms: GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H410
• GHS Precautionary statements: P273-P280-P301 + P310-P312-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2875 6.1/PG 3

Product Information

• Purity: ≥98.0% (T); 95+%; 98%; 99%
• Grade: PESTANAL®, analytical standard; purum
• Linear Formula: CH2[C6H(Cl)3OH]2

DETAILS

MP Biomedicals - 02190213

Crystalline
Off-white to tan crystals

DrugBank - DB00756

• Drug Groups: approved
• Description: A chlorinated bisphenol antiseptic with a bacteriostatic action against Gram-positive organisms, but much less effective against Gram-negative organisms. It is mainly used in soaps and creams and is an ingredient of various preparations used for skin disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p797)
• Indication: For use as a surgical scrub and a bacteriostatic skin cleanser. It may also be used to control an outbreak of gram-positive infection where other infection control procedures have been unsuccessful.
• Pharmacology: Hexachlorophene, a detergent cleanser, is an antibacterial sudsing emulsion for topical administration. It is a bacteriostatic cleansing agent. It cleanses the skin thoroughly and has bacteriostatic action against staphylococci and other gram-positive bacteria. Cumulative antibacterial action develops with repeated use. Cleansing with alcohol or soaps containing alcohol removes the antibacterial residue.
• Toxicity: Oral, rat LD₅₀: 66 mg/kg. Signs of overdose include anorexia, vomiting, abdominal cramps, diarrhea, dehydration, convulsions, hypotension, and shock, and in several reported instances, fatalities.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Detectable blood levels of hexachlorophene following absorption through intact skin have been found in subjects who regularly scrubbed with hexachlorophene.
• Protein Binding: 92%
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - H4625

包装
500 g in poly bottle

Sigma Aldrich - 45526

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Toronto Research Chemicals - H290810

Used as an antiseptic.

REFERENCES

• Gaines, T.B. and Linder, R.E.: Fundam. Appl. Toxicol., 7, 299 (1986)