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4,4'-Methylenedianiline
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Name

4,4'-Methylenedianiline

 EINECS 202-974-4
CAS No. 101-77-9 Density 1.143 g/cm3
PSA 52.04000 LogP 3.60420
Solubility Slightly soluble. <0.1 g/100 mL at 19 oC Melting Point 89-91 °C(lit.)
Formula C13H14N2 Boiling Point 398 °C at 760 mmHg
Molecular Weight 198.268 Flash Point 226.3 °C
Transport Information UN 2651 6.1/PG 3 Appearance white to yellow or beige flakes or crystals
Safety 53-45-61 Risk Codes 45-39/23/24/25-43-48/20/21/22-51/53-68
Molecular Structure Molecular Structure of 101-77-9 (4,4'-Methylenedianiline) Hazard Symbols ToxicT,DangerousN
Synonyms

Aniline,4,4'-methylenedi- (8CI);Aniline, p,p'-methylenebis- (3CI);4,4'-Diaminobiphenyl methane;4,4'-Diaminodiphenylenemethane;4,4'-Diaminodiphenylmethane;4,4'-Diphenylmethanediamine;4,4'-Methylenebis(aniline);4,4'-Methylenebis(benzenamine);Benzenamine,4,4'-methylenebis-;4,4'-Methylenedibenzenamine;4,4'-Methylenediphenylamine;4-(4-Aminobenzyl)aniline;4-(p-Aminobenzyl)aniline;Acmex H 84BM;Ancamine 1692;AralditeR 972;Bis(4-aminophenyl)methane;Bis(aminophenyl)methane;Bis(p-aminophenyl)methane;DEH 50;Di-(4-aminophenyl)methane;Diaminodiphenylmethane;Dianilinemethane;Dianilinomethane;

Article Data 116

4,4'-Methylenedianiline Synthetic route

1817-74-9

bis(4-nitrophenyl)methane

101-77-9

4,4'-diamino diphenyl methane

Conditions
ConditionsYield
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran; water at 20℃; for 0.5h;93%
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h;93%
With hydrazine In methanol at 50℃;93%
71840-36-3

chloromethylmercurioacetaldehyde

A

24007-66-7

N-(4-aminobenzyl)aniline

B

101-77-9

4,4'-diamino diphenyl methane

C

75-07-0

acetaldehyde

Conditions
ConditionsYield
With aniline at 20℃; for 0.333333h;A 1%
B 88%
C 41%
71840-36-3

chloromethylmercurioacetaldehyde

62-53-3

aniline

A

24007-66-7

N-(4-aminobenzyl)aniline

B

101-77-9

4,4'-diamino diphenyl methane

C

75-07-0

acetaldehyde

Conditions
ConditionsYield
at 20℃; for 0.333333h;A 1%
B 88%
C 41%
at 20℃; for 0.333333h; Product distribution; reactions of aromatic amines with monochloroalkylmercury(II) compounds;A 1%
B 88%
C 41%
2719-05-3

N,N’-(methylenebis(4,1-phenylene))diacetamide

101-77-9

4,4'-diamino diphenyl methane

Conditions
ConditionsYield
With Iron(III) nitrate nonahydrate In methanol at 20℃; for 24h;88%
73269-48-4

C9H9ClHgO

62-53-3

aniline

A

101-77-9

4,4'-diamino diphenyl methane

B

98-86-2

acetophenone

Conditions
ConditionsYield
at 20℃; for 1h;A 39%
B 87%
5293-94-7

bis(chloromethyl)mercury

62-53-3

aniline

A

101-77-9

4,4'-diamino diphenyl methane

B

121-69-7

N,N-dimethyl-aniline

C

100-61-8

N-methylaniline

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 12h;A 84%
B 14%
C 18%
1817-74-9

bis(4-nitrophenyl)methane

A

726-17-0

4-(4-nitrophenyl)methylaniline

B

101-77-9

4,4'-diamino diphenyl methane

Conditions
ConditionsYield
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h;A 17%
B 83%
622-14-0

N,N'-diphenylmethylenediamine

A

1208-52-2

2,4'-diaminodiphenylmethane

B

101-77-9

4,4'-diamino diphenyl methane

Conditions
ConditionsYield
With zeolite H-CBV 760 at 80℃; Activation energy; Reagent/catalyst; Concentration; Temperature;A n/a
B 82%
Reaxys ID: 11378101

Reaxys ID: 11378101

101-77-9

4,4'-diamino diphenyl methane

Conditions
ConditionsYield
With sodium hydroxide; water In butan-1-ol at 230℃; under 41254.1 Torr; for 4h;81%
142-04-1

aniline hydrochloride

129075-89-4

4-[(benzotriazol-1-yl)methyl]phenylamine

101-77-9

4,4'-diamino diphenyl methane

Conditions
ConditionsYield
In methanol; water for 72h; Heating;80%

4,4'-Methylenedianiline Chemical Properties

Structure of 4,4'-Methylenedianiline (CAS NO.101-77-9):

IUPAC Name: 4-[(4-aminophenyl)methyl]aniline 
Empirical Formula: C13H14N2
Molecular Weight: 198.2637 
EINECS: 202-974-4 
Index of Refraction: 1.66
Molar Refractivity: 64.03 cm3
Molar Volume: 173.3 cm3
Polarizability: 25.38×10-24cm3
Surface Tension: 53.9 dyne/cm
Density: 1.143 g/cm3
Flash Point: 226.3 °C
Enthalpy of Vaporization: 64.85 kJ/mol 
Melting Point: 89-91 °C(lit.)
Boiling Point: 398 °C at 760 mmHg
Vapour Pressure: 1.52E-06 mmHg at 25°C 
Water Solubility: Slightly soluble. <0.1 g/100 mL at 19 ºC 
Physical Appearance: white to yellow or beige flakes or crystals
Product Categories: Industrial/Fine Chemicals;Aromatic Hydrocarbons (substituted) & Derivatives;Diphenylmethanes (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research

4,4'-Methylenedianiline Uses

 4,4'-Methylenedianiline (CAS NO.101-77-9) is used in the production of insulating materials, dyes and diisocyanate, polyurethane rubber, class H adhesives, epoxy resin curing agent, etc.

4,4'-Methylenedianiline Toxicity Data With Reference

1.    

eye-rbt 100 mg/24H MOD

     85JCAE    Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,481.
2.    

mmo-sat 250 μg/plate

     MUREAV    Mutation Research. 67 (1979),123.
3.    

mma-sat 50 μg/plate

     MUREAV    Mutation Research. 67 (1979),123.
4.    

dnd-rat-ipr 370 μmol/kg

     CRNGDP    Carcinogenesis. 2 (1981),1317.
5.    

sce-mus-ipr 9 mg/kg

     MUREAV    Mutation Research. 108 (1983),225.
6.    

orl-man TDLo:8420 μg/kg:CNS,LIV

     BMJOAE    British Medical Journal. 1 (1966),514.
7.    

orl-man TDLo:8420 μg/kg

     BMJOAE    British Medical Journal. 1 (1966),514.
8.    

orl-rat LD50:347 mg/kg

     28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,71.
9.    

ipr-rat LD50:193 mg/kg

     ZHYGAM    Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. 20 (1974),393.
10.    

scu-rat LD50:200 mg/kg

     NATWAY    Naturwissenschaften.

4,4'-Methylenedianiline 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 . 39 ,1986,p. 347.(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 . 4 ,1974,p. 79.(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) . Community Right-To-Know List. Reported in EPA TSCA Inventory.

4,4'-Methylenedianiline Safety Profile

Confirmed carcinogen with experimental tumorigenic data. Human poison by ingestion. Poison by subcutaneous and intraperitoneal routes. Human systemic effects by ingestion: rigidity, jaundice, other liver changes. An eye irritant. Mutation data reported. It is not rapidly absorbed through the skin. Combustible when exposed to heat or flame. When heated to decomposition it emits highly toxic fumes of aniline and NOx.
Hazard Codes: ToxicT,DangerousN
Risk Statements: 45-39/23/24/25-43-48/20/21/22-51/53-68 
R45:May cause cancer. 
R39:Danger of very serious irreversible effects. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R48:Danger of serious damage to health by prolonged exposure. 
R20/21/22:Harmful 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. 
R68:Possible risk of irreversible effects.
Safety Statements: 53-45-61 
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.
RIDADR: UN 2651 6.1/PG 3
WGK Germany: 3
RTECS: BY5425000
HazardClass: 6.1
PackingGroup: III

4,4'-Methylenedianiline Standards and Recommendations

ACGIH TLV: TWA 0.1 ppm (skin); Animal Carcinogen
DFG MAK: Animal Carcinogen, Suspected Human Carcinogen
DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD

4,4'-Methylenedianiline Analytical Methods

For occupational chemical analysis use OSHA: #ID-57 or NIOSH: 4,4′-Methylenedianiline (MDA), 5029.

4,4'-Methylenedianiline Specification

  4,4'-Methylenedianiline , its cas register number is 101-77-9. It also can be called 4,4'-Diaminodiphenylmethan ; 4,4'-Methylenebis(benzeneamine) ; 4-(4-Aminobenzyl)aniline ; Ancamine TL ; Aniline, 4,4'-methylenedi- ; Benzenamine, 4,4'-methylenebis- ; Bis(4-aminophenyl)methane ; Bis-p-aminofenylmethan ; Curithane ; Dadpm ; Di-(4-aminophenyl)methane ;
 Diaminodiphenylmethane ; Methylenebis(aniline) ; Sumicure M ; p,p'-Diaminodifenylmethan ; p,p'-Methylenedianiline ; p-Toluidine, alpha-(p-aminophenyl)- .

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