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4,4'-Oxydianiline
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Name

4,4'-Oxydianiline

 EINECS 202-977-0
CAS No. 101-80-4 Density 1.216 g/cm3
PSA 61.27000 LogP 3.80570
Solubility Insoluble in water Melting Point 188-192 °C(lit.)
Formula C12H12N2O Boiling Point 389.4 °C at 760 mmHg
Molecular Weight 200.24 Flash Point 218.9 °C
Transport Information UN 3077 9/PG 3 Appearance odorless colorless crystals or an odorless fine, beige powder
Safety 53-45-61-36/37-26-20 Risk Codes 45-46-23/24/25-51/53-62-36/37/38-22
Molecular Structure Molecular Structure of 101-80-4 (4,4'-Oxydianiline) Hazard Symbols ToxicT,DangerousN
Synonyms

4,4'-Diaminobiphenyl oxide;4,4'-Diaminodiphenyl ether;4,4'-Diaminodiphenyl oxide;4,4'-Diaminophenylether;4,4'-Oxybis(aniline);4,4'-Oxybis[benzenamine];Aniline,4,4'-oxydi- (6CI,8CI);4,4'-Diaminobiphenyl ether;

Article Data 60

4,4'-Oxydianiline Synthetic route

101-63-3

bis(4-nitrophenyl)ether

101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With hydrogen; triethylamine In ethanol; water at 110℃; under 30003 Torr; for 48h; Autoclave;99%
Stage #1: bis(4-nitrophenyl)ether With pyrographite In N,N-dimethyl-formamide at 140℃; for 2h;
Stage #2: With 5%-palladium/activated carbon; hydrogen In N,N-dimethyl-formamide at 140℃; under 7500.75 Torr; for 5h; Temperature;		99.5%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 2h;98%
28896-49-3

bis(4-iodophenyl) ether

101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With ammonium hydroxide; caesium carbonate98%

4,4'-dinitrosodiphenyl ether

101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With hydrogen In ethanol at 75 - 80℃; under 22502.3 Torr; Autoclave;90.8%
76263-55-3

2-Iodo-4-nitro-1-(4-nitro-phenoxy)-benzene

101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With copper(I) chloride; potassium borohydride In methanol for 0.5h; Ambient temperature;82%
350-46-9

4-Fluoronitrobenzene

101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With aluminum (III) chloride; caesium carbonate; 1,2-bis-(diphenylphosphino)ethane; bis(pinacol)diborane In N,N-dimethyl-formamide at 152℃; for 6h;80%
Multi-step reaction with 2 steps
1.1: sodium hydride / dimethyl sulfoxide / 0.17 h / 20 °C
1.2: 80 °C
2.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide / dimethyl sulfoxide / 12 h / 80 °C
2: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C
View Scheme
98-95-3

nitrobenzene

A

123-30-8

4-amino-phenol

B

101-80-4

4,4'-oxydiphenylene diamine

C

62-53-3

aniline

D

95-55-6

2-amino-phenol

Conditions
ConditionsYield
With hypophosphorous acid; palladium on activated charcoal In water at 80℃; for 4h; Product distribution; var. of temp., ratio, degree of conversion, solvent, catalyst;A 47%
B n/a
C n/a
D n/a
101-84-8

diphenylether

A

101-80-4

4,4'-oxydiphenylene diamine

B

139-59-3

4-phenoxyanilin

C

2688-84-8

2-phenoxyaniline

Conditions
ConditionsYield
With O-(4-nitrobenzoyl)hydroxylammonium trifluoromethanesulfonate; iron(II) bromide; silver(I) triflimide In 2,2,2-trifluoroethanol; water at 30℃; for 2h;A 19.8%
B 19.8%
C 39.5%
2444-89-5

4,4'-dichlorodiphenyl ether

101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With copper(I) oxide; ammonia; water at 170℃;
2050-47-7

4,4'-dibromodiphenyl ether

101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With copper(I) oxide; ammonia; water at 170℃;
With ammonium hydroxide; caesium carbonate In ethanol; water at 130℃; for 24h; Inert atmosphere; Sealed tube;
100-65-2

N-Phenylhydroxylamine

101-80-4

4,4'-oxydiphenylene diamine

Conditions
ConditionsYield
With sulfuric acid

4,4'-Oxydianiline Chemical Properties

Molecular structure of 4,4'-Oxydianiline (CAS NO.101-80-4) is:

Product Name: 4,4'-Oxydianiline
CAS Registry Number: 101-80-4
IUPAC Name: 4-(4-Aminophenoxy)aniline
Molecular Weight: 200.23648 [g/mol]
Molecular Formula: C12H12N2O
XLogP3: 1.4
H-Bond Donor: 2
H-Bond Acceptor: 3 
EINECS: 202-977-0
Melting Point: 188-192 °C(lit.)
Surface Tension: 55.9 dyne/cm
Density: 1.216 g/cm3
Flash Point: 218.9 °C
Enthalpy of Vaporization: 63.87 kJ/mol
Boiling Point: 389.4 °C at 760 mmHg
Vapour Pressure: 2.87E-06 mmHg at 25 °C
Water Solubility: Insoluble. <0.01 g/100 mL at 15 °C
Stability: Stable. Combustible. Incompatible with strong oxidizing agents. Hygroscopic.
Product Categories: Intermediates of Dyes and Pigments; Biphenyl & Diphenyl ether; Diphenyl Ethers (for High-Performance Polymer Research); Functional Materials; Reagent for High-Performance Polymer Research; Monomer for Polyimide film

4,4'-Oxydianiline Uses

4,4'-Oxydianiline (CAS NO.101-80-4) is used as the monomer of polyimide,which is high temperature resistant polymer material. It can be used in the production of a wide variety of polymer resins. It is also used in the production of a wide variety of polymer resins and plastic industry.

4,4'-Oxydianiline Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 650mg/kg (650mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 43, 1982.
mouse LD50 intraperitoneal 300mg/kg (300mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Hygiene and Sanitation Vol. 33(10-12), Pg. 137, 1968.
mouse LD50 oral 685mg/kg (685mg/kg)   Hygiene and Sanitation Vol. 33(10-12), Pg. 137, 1968.
rabbit LD50 intraperitoneal 650mg/kg (650mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Hygiene and Sanitation Vol. 33(10-12), Pg. 137, 1968.
rabbit LD50 oral 700mg/kg (700mg/kg)   Hygiene and Sanitation Vol. 33(10-12), Pg. 137, 1968.
rat LD50 intraperitoneal 365mg/kg (365mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Hygiene and Sanitation Vol. 33(10-12), Pg. 137, 1968.
rat LD50 oral 725mg/kg (725mg/kg)   Hygiene and Sanitation Vol. 33(10-12), Pg. 137, 1968.

4,4'-Oxydianiline Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 29 ,1982,p. 203.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 16 ,1978,p. 301.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-205 ,1980. . Reported in EPA TSCA Inventory.

4,4'-Oxydianiline Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by intraperitoneal route. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: ToxicT, DangerousN
Risk Statements: 45-46-23/24/25-51/53-62-36/37/38-22 
R45:May cause cancer. 
R46:May cause heritable genetic damage. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R62:Risk of impaired fertility. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R22:Harmful if swallowed.
Safety Statements: 53-45-61-36/37-26-20 
S53:Avoid exposure - obtain special instructions before use. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets. 
S36/37:Wear suitable protective clothing and gloves. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S20:When using, do not eat or drink.
RIDADR: UN 3077 9/PG 3
WGK Germany: 3
RTECS: BY7900000
HazardClass: 6.1
PackingGroup: III
HS Code: 29222900

4,4'-Oxydianiline Standards and Recommendations

DFG MAK: Animal Carcinogen, Suspected Human Carcinogen

4,4'-Oxydianiline Specification

 4,4'-Oxydianiline , its cas register number is 101-80-4. It also can be called Bis(4-aminophenyl) ether ; Di-(4-aminophenyl)ether ; 4,4'-Diaminobiphenyl oxide ; 4,4'-Diaminodiphenyl ether ; 4,4'-Diaminodiphenyl oxide ; 4,4'-Diaminophenyl ether ; 4,4'-Diaminophenyl oxide ; 4,4'-Oxybisaniline ; 4,4'-Oxybisbenzenamine ; 4,4'-Oxydiphenylamine ; 4,4-Diaminodiphenyl ether ; 4-13-00-01038 (Beilstein Handbook Reference) ; 4-Aminophenyl ether ; AI3-18375 ; Aniline, 4,4'-oxydi- ; BRN 0475735 ; Bis(4-aminophenyl) ether ; Bis(4-aminophenyl)ether ; Bis(p-aminophenyl) ether ; Bis(p-aminophenyl)ether ; CCRIS 491 ; Dadpe ; Diaminodiphenyl ether ; Ether, 4,4'-diaminodiphenyl ; HSDB 1316 ; NCI-C50146 ; NSC 37075 ; Oxybis(4-aminobenzene) ; Oxydi-p-phenylenediamine ; Oxydianiline ; p,p'-Diaminodiphenyl ether ; p,p'-Oxybis(aniline) ; p,p'-Oxydianiline ; p-Aminophenyl ether ; Aniline, 4,4'-oxydi- ; Benzenamine, 4,4'-oxybis- . It is a odorless colorless crystals or an odorless fine, beige powder.  It is an ether derivative of aniline. also it is a useful monomer and cross-linking agent for polymers.

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