Basic information
- Standard SMILES
c1ccc2c(c1)Oc1ccccc1[As]2O[As]1c2ccccc2Oc2ccccc21- InChIKey
VCRZAKVGPJFABU-UHFFFAOYSA-N- Molecular formula
- C24H16As2O3
- Average molar mass
- 502.2 g/mol
- Monoisotopic mass
- 501.95313737
Overview
Phenoxarsine, 10,10'-oxydi- appears as a clear light yellow liquid with a mild odor. Insoluble in water and slightly denser than water. Contact may severely irritate skin, eyes, and mucous membranes.
Names & identifiers
- Preferred name
- 10,10'-Oxybisphenoxarsine
- IUPAC
- 10-phenoxarsinin-10-yloxyphenoxarsinine
- English name
- 10,10-Oxybisphenoxarsine
- Molecular formula
- C24H16As2O3
- Molecular weight
- 502.23
Names & synonyms
Show more names
Database identifiers
- CAS
58-36-6- PubChem CID
- 6017
- DTXSID
DTXSID0032443- UNII
- 1R0GEE9L5Z
- EC Number
- 200-377-3
- Nikkaji
- J9.323H
Properties
Computed structural properties
- Topological polar surface area
- 27.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 482
Experimental & physicochemical properties
Physical Description
Phenoxarsine, 10,10'-oxydi- appears as a clear light yellow liquid with a mild odor. Insoluble in water and slightly denser than water. Contact may severely irritate skin, eyes, and mucous membranes.
Colorless solid; [Merck Index] White crystalline solid; [MSDSonline]
Physicochemical properties
- Melting point
- 180 · 180-184°C
- Boiling point
- 232.5 °C · 232.5°C
- Density
- 1.4 · 1.40-1.42
- storage temp.
- Sealed in dry,Room Temperature
- form
- solid
- color
- 2 · Colorless or white crystals, monoclinic prisms from EtOH or 2-propanol
- Water Solubility
- insoluble
- InChI
- InChI=1S/C24H16As2O3/c1-5-13-21-17(9-1)25(18-10-2-6-14-22(18)27-21)29-26-19-11-3-7-15-23(19)28-24-16-8-4-12-20(24)26/h1-16H
- InChIKey
- VCRZAKVGPJFABU-UHFFFAOYSA-N
- SMILES
- O([As]1C2=CC=CC=C2OC2=C1C=CC=C2)[As]1C2=CC=CC=C2OC2=C1C=CC=C2
- REACH Annex XVII Substances List
- -10 · Diphenoxarsin-10-yl oxide (58-36-6)
- CAS DataBase Reference
- 58 · 58-36-6(CAS DataBase Reference)
- FDA UNII
- 1 R0GEE9L5Z · 1R0GEE9L5Z
- Pesticides Freedom of Information Act (FOIA)
- OBPA
- EPA Substance Registry System
- 10 · 10,10'-Oxybisphenoxarsine (58-36-6)
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 410 · H410-H400-H300-H314-H372-H330-H311
- Precautionary statements
- 264 · P264-P270-P280-P260-P271-P284-P273-P301+P316-P321-P330-P302+P352-P316-P361+P364-P301+P330+P331-P363-P304+P340-P305+P351+P338-P320-P319-P391-P405-P403+P233-P501
- RIDADR
- 1557 · 1557
- HazardClass
- 6.1 · 6.1(a)
- PackingGroup
- II
- Hazardous Substances Data
- 58 · 58-36-6(Hazardous Substances Data)
- Toxicity
- 50 orl-rat: · LD50 orl-rat: 40 mg/kg TXCYAC 10,341,78
Safety & regulation
GHS classification
GHS Classification
Danger
H300 (73.4%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P361+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 94 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 10H-Phenoxarsine, 10,10'-oxybis-
Restricted substance: Diphenoxarsin-10-yl oxide
10H-Phenoxarsine, 10,10'-oxybis-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Hazards Summary
Severely irritating to skin; Toxic by ingestion and inhalation; Oral LD50 (rat) = 40 mg/kg; [Sax] Retards growth and causes liver effects in high-dose feeding studies; No developmental, reproductive, or mutagenic effects; Arsenic accumulates in liver and kidneys of exposed animals with clearing 2 weeks after last exposure; The potential for occupational exposure to OBPA is minimal provided that OBPA is used in a closed system and that appropriate Personal Protective Equipment (PPE) is worn. [EPA REDs] An irritant that can cause skin burns; May be lethal if ingested or inhaled; May cause liver and kidney damage; [MSDSonline] Almost nothing is known regarding health effects of organic arsenic compounds in humans. Studies in animals show that some simple organic arsenic compounds are less toxic than inorganic forms. Ingestion of methyl and dimethyl compounds can cause diarrhea and damage to the kidneys. [ATSDR ToxProfiles]
Safety & protection
Protective Action Criteria (PAC)
1.3 [mg/m3]
14 [mg/m3]
84 [mg/m3]
Personal Protective Equipment (PPE)
For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)
Toxicology
Treatment
Arsenic poisoning can be treated by chelation therapy, using chelating agents such as dimercaprol, EDTA or DMSA. Charcoal tablets may also be used for less severe cases. In addition, maintaining a diet high in sulfur helps eliminate arsenic from the body. (L20)
Toxicity Summary
Arsenic and its metabolites disrupt ATP production through several mechanisms. At the level of the citric acid cycle, arsenic inhibits pyruvate dehydrogenase and by competing with phosphate it uncouples oxidative phosphorylation, thus inhibiting energy-linked reduction of NAD+, mitochondrial respiration, and ATP synthesis. Hydrogen peroxide production is also increased, which might form reactive oxygen species and oxidative stress. Arsenic's carginogenicity is influenced by the arsenical binding of tubulin, which results in aneuploidy, polyploidy and mitotic arrests. The binding of other arsenic protein targets may also cause altered DNA repair enzyme activity, altered DNA methylation patterns and cell proliferation. (T1, A17)
Toxicity Data
LCLo (guinea pigs) = 141 mg/m3/2h
LD50: 40 mg/kg (Oral, Rat) (T14)
Safety data
- ridadr
- 1557
- Toxicity
- LD50 orl-rat: 40 mg/kg TXCYAC 10,341,78
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- hazard_class
- 6.1(a)
- packing_group
- II
- Hazard statements
- H410-H400-H300-H314-H372-H330-H311
- Precautionary statements
- P264-P270-P280-P260-P271-P284-P273-P301+P316-P321-P330-P302+P352-P316-P361+P364-P301+P330+P331-P363-P304+P340-P305+P351+P338-P320-P319-P391-P405-P403+P233-P501
- Hazardous Substances Data
- 58-36-6(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Arsenic is absorbed mainly by inhalation or ingestion, as to a lesser extent, dermal exposure. It is then distributed throughout the body, where it is reduced into arsenite if necessary, then methylated into monomethylarsenic (MMA) and dimethylarsenic acid (DMA) by arsenite methyltransferase. Arsenic and its metabolites are primarily excreted in the urine. Arsenic is known to induce the metal-binding protein metallothionein, which decreases the toxic effects of arsenic and other metals by binding them and making them biologically inactive, as well as acting as an antioxidant. (L20)
Uses & manufacturing
Uses
Used to protect plastics and textiles from fungi and bacteria; [HSDB] Used as a bacteriocide/germicide and fungicide in shower curtains, floor and wall coverings, coated fabrics, marine upholstery, vinyl moldings, awnings, weather stripping, and swimming pool liners; Also used as a preservative in adhesives, coatings, carpets, and other products (paper, plastic, and textile); [EPA REDs]
Pulp and Paper Processing [Category: Industry]
Applications
Description0-100-Oxidiphenoxarsine is a colorless crystalline, organometallic solid or a dense yellow liquid. Molecularweight 5 502.23; Boiling point =233℃; Freezing/Meltingpoint =185℃. Decomposition temperature =380℃. Flashpoint =
Uses10,10-Oxybisphenoxarsine prevents mold, bacteria, and algae growth, making it one of the most effective antibacterial agents in the industrial field. It can be added to PVC products, plastic products, PVC flooring materials, wall coatings, paints, inks, paper, etc.
General DescriptionA clear light yellow liquid with a mild odor. Insoluble in water and slightly denser than water. Contact may severely irritate skin, eyes, and mucous membranes. Flash point 98°F.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
Loading…