58-36-6

Basic information

• Product Name: 10,10-Oxybisphenoxarsine
• Synonyms: 10,10’-bis(Phenoxyarsinyl)oxide;10,10’-Oxidiphenoxarsine;10,10’-oxybis-10h-phenoxarsin;10,10’-oxybis-phenoxyarsin;10,10’-oxybisphenoxyarsine;10,10’-oxybis-Phenoxyarsine;10,10’-oxybisphenoxy-arsine;10,10’-oxydi-phenoxarsin
• CAS NO: 58-36-6
• Molecular Formula: C₂₄H₁₆As₂O₃
• Molecular Weight: 502.23
• EINECS: 200-377-3
• Product Categories: Industrial/Fine Chemicals
• Mol File: 58-36-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 180-184°C
• Boiling Point: 232.5°C
• Flash Point: 214.1 °C
• Appearance: /solid
• Density: 1.40-1.42
• Vapor Pressure: 7.77E-11mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: insoluble
• CAS DataBase Reference: 10,10-Oxybisphenoxarsine(CAS DataBase Reference)
• NIST Chemistry Reference: 10,10-Oxybisphenoxarsine(58-36-6)
• EPA Substance Registry System: 10,10-Oxybisphenoxarsine(58-36-6)

Safety Data

• RIDADR: 1557
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 58-36-6(Hazardous Substances Data)

Usage

Chemical Properties

10-10′-Oxidiphenoxarsine is a colorless crystalline, organometallic solid or a dense yellow liquid. Odorless.

General Description

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. Flash point 98°F.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Organometallics, such as 10,10-Oxybisphenoxarsine, are reactive with many other groups. Incompatible with acids and bases. Organometallics are good reducing agents and therefore incompatible with oxidizing agents.

Health Hazard

(Non-Specific -- Arsenic Compounds) Arsenic compounds are acutely poisonous by ingestion. Ingestion or inhalation may result in chronic poisoning. Arsenic compounds are recognized carcinogens of the skin, lungs, and liver.

Fire Hazard

(Non-Specific -- Arsenic Compounds) When heated to decomposition, 10,10-Oxybisphenoxarsine emits highly toxic fumes of arsenic.

Safety Profile

Poison by ingestion and inhalation. A severe skin irritant. When heated to decomposition it emits toxic fumes of As.

Potential Exposure

This material is used primarily for fungicidal and bactericidal protection of plastics. It is an organoarsenic and a heavy metal compound.

Shipping

UN1760 Corrosive liquids, n.o.s., Hazard class: 8; Labels: 8-Corrosive material, Technical Name Required. UN3465 Organoarsenic compound, solid, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Incompatibilities

A reducing agent; reacts violently with strong oxidizers. Keep away from strong acids and strong bases.

InChI:InChI=1/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

Synthetic route

10-<2-chloro-1-(chloromethyl)ethoxy>phenoxarsine → 1,3-Dichloro-2-propanol (96-23-1) + 10,10,oxybisphenoxarsine (58-36-6)

Conditions	Yield
With water In acetone	A 83.8% B 93.9%

10-sec-butyl-10H-phenoxarsine (55369-40-9) → 10,10,oxybisphenoxarsine (58-36-6)

Conditions	Yield
With oxygen

diphenylether (101-84-8) → 10,10,oxybisphenoxarsine (58-36-6)

Conditions	Yield
(i) AsCl3, (ii) O2; Multistep reaction;

10-allylphenoxarsine (39548-42-0) → 10,10,oxybisphenoxarsine (58-36-6)

Conditions	Yield
With oxygen

10-tert-butylphenoxarsine (39548-35-1) → 10,10,oxybisphenoxarsine (58-36-6)

Conditions	Yield
With ethanol

phenoxarsine chloride → 10,10,oxybisphenoxarsine (58-36-6)

Conditions	Yield
With ethanol; ammonia

10-chloro-10H-phenoxarsine (2865-70-5) → 10,10,oxybisphenoxarsine (58-36-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene; diethyl ether 2: O2 View Scheme
Multi-step reaction with 2 steps 1: benzene; diethyl ether 2: O2 View Scheme
Multi-step reaction with 2 steps 1: toluene; diethyl ether 2: aq. EtOH View Scheme

Elaidic Acid (112-79-8) + 10,10,oxybisphenoxarsine (58-36-6) → (E)-Octadec-9-enoic acid phenoxarsin-10-yl ester

Conditions	Yield
In toluene Heating;	80.8%

10,10,oxybisphenoxarsine (58-36-6) + acrylic acid (79-10-7) → Acrylic acid phenoxarsin-10-yl ester

Conditions	Yield
In toluene Heating;	71.5%

succinic acid anhydride (108-30-5) + 10,10,oxybisphenoxarsine (58-36-6) → Succinic acid diphenoxarsin-10-yl ester

Conditions	Yield
In toluene for 5h; Heating;	66%

2-butenoic acid (3724-65-0) + 10,10,oxybisphenoxarsine (58-36-6) → (E)-But-2-enoic acid phenoxarsin-10-yl ester

Conditions	Yield
In toluene Heating;	62.8%

succinic acid (110-15-6) + 10,10,oxybisphenoxarsine (58-36-6) → succinic acid mono(10-phenoxyarsinyl) ester

Conditions	Yield
In toluene for 5h; Heating;	61.2%

succinic acid (110-15-6) + 10,10,oxybisphenoxarsine (58-36-6) → Succinic acid diphenoxarsin-10-yl ester

Conditions	Yield
In toluene for 8h; Heating;	59%

10,10,oxybisphenoxarsine (58-36-6) → 10-oxo-10H-10λ5-phenoxarsin-10-ol (4846-20-2)

Conditions	Yield
With ethanol; iodine

ethanol (64-17-5) + phosphoric acid (86119-84-8, 7664-38-2) + 10,10,oxybisphenoxarsine (58-36-6) → bis-phenoxarsinyl-(10)

hydrogen bromide (10035-10-6, 12258-64-9) + 10,10,oxybisphenoxarsine (58-36-6) → phenoxarsine bromide

10,10,oxybisphenoxarsine (58-36-6) → 10,10'bis(phenoxarsine) selenide

Conditions	Yield
Multi-step reaction with 2 steps 1: conc. HI / benzene / 2 h 2: H2Se, pyridine / ethanol / 2 h View Scheme

Upstream product

• 55369-40-9 10-sec-butyl-10H-phenoxarsine 
• 39548-42-0 10-allylphenoxarsine 
• 39548-35-1 10-tert-butylphenoxarsine 
• 2865-70-5 10-chloro-10H-phenoxarsine 
• 101-84-8 diphenylether 

Downstream Products

• 4227-32-1 10-iodophenoxarsine 
• 4846-20-2 10-oxo-10H-10λ⁵-phenoxarsin-10-ol 

Relevant articles and documents

KINETICS OF THE REACTION OF 10-CHLOROPHENOXARSINE WITH 1-CHLORO-2,3-EPOXYPROPANE

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