4,4'-Methylenedianiline supplier

Name
4,4'-Methylenedianiline
EINECS 202-974-4
CAS No. 101-77-9
Article Data116
CAS DataBase
Density 1.143 g/cm³
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
Hazard Symbols T,N
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;
PSA 52.04000
LogP 3.60420

Synthetic route

: 1817-74-9
bis(4-nitrophenyl)methane

: 101-77-9
4,4'-diamino diphenyl methane

Conditions

Conditions	Yield
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

Conditions	Yield
With aniline at 20℃; for 0.333333h;	A 1% B 88% C 41%

...Expand

: 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

Conditions	Yield
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%

...Expand

: 2719-05-3
N,N’-(methylenebis(4,1-phenylene))diacetamide

: 101-77-9
4,4'-diamino diphenyl methane

Conditions

Conditions	Yield
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

Conditions	Yield
at 20℃; for 1h;	A 39% B 87%

...Expand

: 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

Conditions	Yield
In tetrahydrofuran at 20℃; for 12h;	A 84% B 14% C 18%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: 71893-15-7
C4H7ClHgO

: 62-53-3
aniline

A: 101-77-9
4,4'-diamino diphenyl methane

B: 67-64-1
acetone

Conditions

Conditions	Yield
at 20℃; for 0.333333h;	A 79% B 79%

...Expand

: 142-04-1
aniline hydrochloride

: 88933-19-1
methoxymethylphenylamine

: 101-77-9
4,4'-diamino diphenyl methane

Conditions

Conditions	Yield
In methanol; water for 3h; Heating;	76%
In methanol; water for 3h; Heating; further N,O-aminals and amine hydrochlorides; procedure for the preparation of bis(4-aminoaryl)methanes;	76%

: 73269-50-8
α-chloromethylmercuriopropiophenone

A: 101-77-9
4,4'-diamino diphenyl methane

B: 93-55-0
1-phenyl-propan-1-one

Conditions

Conditions	Yield
With aniline at 20℃; for 1h;	A 42% B 73%

: 73269-50-8
α-chloromethylmercuriopropiophenone

: 62-53-3
aniline

A: 101-77-9
4,4'-diamino diphenyl methane

B: 93-55-0
1-phenyl-propan-1-one

Conditions

Conditions	Yield
at 20℃; for 1h;	A 42% B 73%

...Expand

: 73269-52-0
NN-diethyl-4-chloromethylmercurioaniline

: 62-53-3
aniline

A: 135-91-1
4-(4-(diethylamino)benzyl)-N,N-diethylbenzenamine

B: 101-77-9
4,4'-diamino diphenyl methane

C: 75815-90-6
NN-diethylbis-(4-aminophenyl)methane

Conditions

Conditions	Yield
In tetrahydrofuran for 12h; Ambient temperature;	A n/a B n/a C 73%

...Expand

: 73269-50-8
α-chloromethylmercuriopropiophenone

A: 76973-09-6
propiophenone-α-d1

B: 101-77-9
4,4'-diamino diphenyl methane

Conditions

Conditions	Yield
With aniline-N,N-d2 for 1h; Ambient temperature;	A 69% B 41%

: 91-66-7
N,N-diethylaniline

A: 135-91-1
4-(4-(diethylamino)benzyl)-N,N-diethylbenzenamine

B: 101-77-9
4,4'-diamino diphenyl methane

C: 73269-52-0
NN-diethyl-4-chloromethylmercurioaniline

Conditions

Conditions	Yield
In tetrahydrofuran for 12h; Ambient temperature;	A 63% B n/a C n/a

...Expand

: 2915-44-8
4,4'-diazidodiphenylmethane

: 101-77-9
4,4'-diamino diphenyl methane

Conditions

Conditions	Yield
With hydrogenchloride; indium In tetrahydrofuran at 20℃; for 24h;	60%

: 142-04-1
aniline hydrochloride

: 74205-82-6
1-(hydroxymethyl)-1,2,4-triazole

A: 101-77-9
4,4'-diamino diphenyl methane

B: 119192-10-8
4-(1H-1,2,4-triazol-1-ylmethyl)aniline

Conditions

Conditions	Yield
With acetic acid for 0.0833333h; Heating;	A 10% B 59%

...Expand

: 62001-29-0
N-phenyl-1H-benzotriazolyl-1-methanamine

: 142-04-1
aniline hydrochloride

: 101-77-9
4,4'-diamino diphenyl methane

Conditions

Conditions	Yield
In methanol; water for 3h; Heating;	58%

: 50-00-0
formaldehyd

: 62-53-3
aniline

A polyamines: polyamines

B: 1208-52-2
2,4'-diaminodiphenylmethane

C: 6582-52-1
2,2'-methylenedianiline

D: 101-77-9
4,4'-diamino diphenyl methane

Conditions

Conditions	Yield
Stage #1: formaldehyd; aniline In water at 25 - 80℃; Stage #2: hydrogenchloride In water at 45 - 140℃; under 750.075 - 3750.38 Torr; for 2.5 - 2.83333h; Stage #3: With sodium hydroxide In water at 100℃; Product distribution / selectivity;	A 33.7% B 6% C 0.2% D 44.5%

...Expand

: 83215-16-1
4-(4-anilinomethylanilinomethyl)aniline

A: 1208-52-2
2,4'-diaminodiphenylmethane

B: 101-77-9
4,4'-diamino diphenyl methane

C: 54243-53-7
4-<4-(4-aminobenzyl)anilinomethyl>aniline

Conditions

Conditions	Yield
With hydrogenchloride at 90℃; for 2h; Product distribution; other time, other temperature, other reagent, other solvent;	A n/a B 38% C n/a

...Expand

: 109-87-5
Dimethoxymethane

: 142-04-1
aniline hydrochloride

: 101-77-9
4,4'-diamino diphenyl methane

Conditions

Conditions	Yield
With water at 60 - 90℃;

: 623-04-1
4-aminobenzenemethanol

: 142-04-1
aniline hydrochloride

: 101-77-9
4,4'-diamino diphenyl methane

Conditions

Conditions	Yield
With water at 80℃;

: 622-14-0
N,N'-diphenylmethylenediamine

: 101-77-9
4,4'-diamino diphenyl methane

Conditions

Conditions	Yield
With aniline hydrochloride; aniline

: 611-98-3
4,4'-diaminobenzophenone

: 101-77-9
4,4'-diamino diphenyl methane

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

: 7330-46-3
4,4'-diamino-3,3'-dicarboxydiphenylmethane

: 101-77-9
4,4'-diamino diphenyl methane

Conditions

Conditions	Yield
With hydrogenchloride at 200℃;

: 24007-66-7
N-(4-aminobenzyl)aniline

: 101-77-9
4,4'-diamino diphenyl methane

Conditions

Conditions	Yield
With hydrogenchloride
With aniline hydrochloride; aniline

: 146509-65-1
bis-(4-amino-phenyl)-acetic acid

: 101-77-9
4,4'-diamino diphenyl methane

Conditions

Conditions	Yield
With hydrogenchloride at 180 - 200℃;

: 2375-30-6
pentafluorosulfanyl isocyanate

: 101-77-9
4,4'-diamino diphenyl methane

: 90598-06-4
1,1'-(Methylenedi-4,1-phenylene)bis<3-(pentafluorosulfanyl)urea>

Conditions

Conditions	Yield
In chloroform for 4h; -196 deg C to r.t.;	100%

: 24424-99-5
di-tert-butyl dicarbonate

: 101-77-9
4,4'-diamino diphenyl methane

: 59255-81-1
O,O'-di-tert-butyl 4,4'-methylenebis(4,1-phenylene)dicarbamate

Conditions

Conditions	Yield
With 1,4-disulfopiperazine-1,4-diium chloride In neat (no solvent) at 20℃; for 0.0833333h; Green chemistry; chemoselective reaction;	100%
With triethylamine In acetonitrile at 20℃; for 1h;	81%
With iron oxide In ethanol at 20℃; for 1h; Green chemistry; chemoselective reaction;	80%
Stage #1: di-tert-butyl dicarbonate With C12H24KO6(1+)*Br3H(1-) In ethanol at 20℃; for 0.0166667h; Stage #2: 4,4'-diamino diphenyl methane In ethanol at 20℃; for 3.5h;	70%
With [H2-cryptand 222](Br3)2 In acetonitrile at 20℃; for 4.5h; chemoselective reaction;	65%

: 102-09-0
bis(phenyl) carbonate

: 101-77-9
4,4'-diamino diphenyl methane

: 4,4'-methylenediphenylene biscarbamate

Conditions

Conditions	Yield
With 4-nitro-benzoic acid In toluene at 80℃; for 16h; Reagent/catalyst; Inert atmosphere;	100%

: 101-77-9
4,4'-diamino diphenyl methane

: 1761-71-3
4,4'-diaminodicyclohexylmethane

Conditions

Conditions	Yield
With potassium aluminum sulfate; ruthenium on aluminium oxide; hydrogen In tetrahydrofuran at 140℃; under 60006 Torr; for 4h; Temperature; Autoclave; Large scale;	99.6%
Stage #1: With lithium hydroxide; hydrogen In tetrahydrofuran at 190℃; under 44718.8 Torr; for 0 - 0.1h; Stage #2: 4,4'-diamino diphenyl methane With hydrogen at 185℃; under 42133 Torr; for 2.66667 - 3.15h; Product distribution / selectivity;	75.2%
With lithium hydroxide; hydrogen In tetrahydrofuran at 185℃; under 42133 Torr; for 2 - 3.96667h; Product distribution / selectivity;	71.1%

: 91-56-5
indole-2,3-dione

: 101-77-9
4,4'-diamino diphenyl methane

: 41307-83-9
3,3'-[methylenebis(4,1-phenylenenitrilo)]bis[1,3-dihydro-2H-indol-2-one]

Conditions

Conditions	Yield
With acetic acid In ethanol for 0.5h; Heating;	99%
In water at 20℃; for 22h;	98%

: 101-77-9
4,4'-diamino diphenyl methane

: 57-13-6
urea

: 4,4'-diphenylmethanediurea

Conditions

Conditions	Yield
With phenol at 100 - 120℃; for 3.5h; Reagent/catalyst; Temperature; Inert atmosphere;	99%
With p-cumylphenol at 50 - 200℃; for 0.025h; Inert atmosphere;	95%
at 100℃; Product distribution / selectivity; Industry scale;

: 286-20-4
cyclohexane-1,2-epoxide

: 101-77-9
4,4'-diamino diphenyl methane

: 2-(4-(4-(2-hydroxycyclohexylamino)benzyl)phenylamino)cyclohexanol

Conditions

Conditions	Yield
With iron oxide In neat (no solvent) at 20℃; for 20h; Green chemistry; regioselective reaction;	99%

: 285-67-6
Cyclopentene oxide

: 101-77-9
4,4'-diamino diphenyl methane

: 2-(4-(4-(2-hydroxycyclopentylamino)benzyl)phenylamino)cyclopentanol

Conditions

Conditions	Yield
With iron oxide In neat (no solvent) at 20℃; for 20h; Green chemistry; regioselective reaction;	99%

: 98-54-4
para-tert-butylphenol

: 4461-52-3
methoxymethanol

: 101-77-9
4,4'-diamino diphenyl methane

: C37H42N2O2

Conditions

Conditions	Yield
Stage #1: methoxymethanol; 4,4'-diamino diphenyl methane With 4-methyl-2-pentanone at 50℃; for 10h; Dean-Stark; Inert atmosphere; Stage #2: para-tert-butylphenol for 6h; Inert atmosphere; Dean-Stark; Reflux;	99%

...Expand

: 50-00-0
formaldehyd

: 1078574-77-2
bis[2-(2-methoxyethoxy)ethyl]acetylenedicarboxylate

: 104-94-9
4-methoxy-aniline

: 101-77-9
4,4'-diamino diphenyl methane

: C59H76N4O18

Conditions

Conditions	Yield
Stage #1: bis[2-(2-methoxyethoxy)ethyl]acetylenedicarboxylate; 4,4'-diamino diphenyl methane In methanol at 20℃; for 0.5h; Stage #2: formaldehyd; 4-methoxy-aniline With acetic acid In methanol; water at 20℃; for 4h;	99%

...Expand

: 102-09-0
bis(phenyl) carbonate

: 101-77-9
4,4'-diamino diphenyl methane

: 101-65-5
N,N'-(4,4'-methanediyl-di-phenyl)-bis-carbamic acid diphenyl ester

Conditions

Conditions	Yield
With zinc(II) acetate dihydrate at 50℃; Product distribution / selectivity; Industry scale;	98.8%
With phenol; zinc(II) acetate dihydrate at 50℃; Product distribution / selectivity; Industry scale;	98.8%
With isobutyric Acid; 1,3,5-tris(N,N-dimethylaminopropyl)-hexahydro-s-triazine In toluene at 55℃; for 48h;	96.4%
With diphenyl-phosphinic acid at 89.85℃; for 7h; Acylation;	91%

: 101-77-9
4,4'-diamino diphenyl methane

: 1079-66-9
chloro-diphenylphosphine

: 261735-49-3
N,N'-bis(diphenylphosphino)-4,4'-diaminodiphenylmethane

Conditions

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at -10℃; Substitution;	98%

: 101-77-9
4,4'-diamino diphenyl methane

: 616-38-6
carbonic acid dimethyl ester

: 7450-63-7
dimethyl 4,4'-methylenebis(1,4-phenylene)diurethane

Conditions

Conditions	Yield
zinc(II) acetate dihydrate at 180℃; under 6000.6 Torr; for 2.66667h; Product distribution / selectivity; Autoclave; Inert atmosphere;	98%
With aluminum oxide for 24h; Acylation; Heating;	95%
With microcrystalline Zr-metal-organic framework-808(6-connected)(at)mesoporous silica material MCM-41 at 160℃; for 3h; Reagent/catalyst; Temperature; Green chemistry;	95%

: 89-95-2
2-methyl-benzyl alcohol

: 101-77-9
4,4'-diamino diphenyl methane

: 4434-23-5
2,2'[methylenebis(4,1-phenylenenitrilomethylylidene)]diphenol

Conditions

Conditions	Yield
In methanol; acetonitrile	98%
In methanol for 2h; Heating;

: 101-77-9
4,4'-diamino diphenyl methane

: 474003-17-3
2,2'-bis(4''-trimethylsilylphenyl)-4,4',5,5'-biphenyltetracarboxylic acid dianhydride

polyimide; monomer(s): 2,2\-bis(4\'\-trimethylsilylphenyl)-4,4\,,5,5\-biphenyltetracarboxylic acid dianhydride; 4,4\-methylenedianiline: polyimide; monomer(s): 2,2\-bis(4\'\-trimethylsilylphenyl)-4,4\,,5,5\-biphenyltetracarboxylic acid dianhydride; 4,4\-methylenedianiline

Conditions

Conditions	Yield
In various solvent(s) at 20 - 200℃;	98%

: (2,5-di-tert-butyl-phenylamino)-acetic acid

: 101-77-9
4,4'-diamino diphenyl methane

: 917254-04-7
C45H60N4O2

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃;	98%

: 1217-89-6
1-benzylisatin

: 101-77-9
4,4'-diamino diphenyl methane

: 955949-99-2
4,4'-[methylenebis(4,1-phenylenenitrilo)]bis[1,3-dihydro]-1-phenylmethylene-2H-indol-2-one

Conditions

Conditions	Yield
With acetic acid In ethanol for 8h; Heating;	98%
With acetic acid In ethanol Heating;
In ethanol Heating;

: 24623-65-2
3-tert-butyl-2-hydroxybenzaldehyde

: 101-77-9
4,4'-diamino diphenyl methane

: 937721-11-4
[(HO-(3-tert-butyl)C6H3-o-C(H)=N-C6H4)2-4-CH2]

Conditions

Conditions	Yield
With formic acid In methanol at 20℃; for 25h; Reflux;	98%
toluene-4-sulfonic acid In methanol for 12h; Heating / reflux;	95%

: 37942-07-7
3,5-di-tert-butyl-2-hydroxybenzaldehyde

: 101-77-9
4,4'-diamino diphenyl methane

: 6,6'-{methylenebis[(p-phenylene)iminomethyl]}-bis(2,4-di-tert-butylphenol)

Conditions

Conditions	Yield
With formic acid In methanol Reflux;	98%

: 101-77-9
4,4'-diamino diphenyl methane

: naphthalen-2-ylmethyl pyridine-2-carbimidothioate hydrobromide

: N,N'-(methylenebis(1,4-phenylene))dipicolinimidamide dihydrochloride

Conditions

Conditions	Yield
Stage #1: 4,4'-diamino diphenyl methane; naphthalen-2-ylmethyl pyridine-2-carbimidothioate hydrobromide In ethanol; acetonitrile at 20℃; Cooling with ice; Stage #2: With sodium hydroxide In ethanol at 0℃; pH=Ca. 10; Stage #3: With hydrogenchloride In ethanol at 0 - 20℃;	98%

: 50-00-0
formaldehyd

: 1078574-77-2
bis[2-(2-methoxyethoxy)ethyl]acetylenedicarboxylate

: 104-94-9
4-methoxy-aniline

: 101-77-9
4,4'-diamino diphenyl methane

: C59H76N4O18

Conditions

Conditions	Yield
Stage #1: bis[2-(2-methoxyethoxy)ethyl]acetylenedicarboxylate; 4-methoxy-aniline In methanol at 20℃; for 0.5h; Stage #2: formaldehyd; 4,4'-diamino diphenyl methane With acetic acid In methanol; water at 20℃; for 4h;	98%

...Expand

: 900189-14-2
1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylic acid methyl ester

: 101-77-9
4,4'-diamino diphenyl methane

: C39H32N4O8

Conditions

Conditions	Yield
With cerium(III) chloride heptahydrate In ethanol at 20℃; for 40h; regiospecific reaction;	98%
With cerium(III) chloride heptahydrate In water Sonication; Green chemistry;	70%

: 101-77-9
4,4'-diamino diphenyl methane

: 616-38-6
carbonic acid dimethyl ester

: 101-61-1
4,4'-methylene-bis(N,N-dimethylaniline)

Conditions

Conditions	Yield
With NaY Zeolite at 190℃; for 6h; Reagent/catalyst; Temperature;	97.4%

: 101-77-9
4,4'-diamino diphenyl methane

: 4-(4'-aminobenzyl)cyclohexylamine

Conditions

Conditions	Yield
Stage #1: 4,4'-diamino diphenyl methane In tetrahydrofuran at 90℃; under 3750.38 - 7500.75 Torr; for 5h; Autoclave; Inert atmosphere; Stage #2: With hydrogen In tetrahydrofuran at 170℃; under 45004.5 Torr; for 2h; Temperature; Reagent/catalyst; Pressure;	97.03%
With hydrogen; nickel at 100 - 180℃; under 6750.68 Torr; for 12h; Temperature; Reagent/catalyst; Pressure; Autoclave;

: 101-77-9
4,4'-diamino diphenyl methane

: 105-58-8
Diethyl carbonate

: 10097-16-2
(methylenedi-4,1-phenylene)bis-carbamic acid diethyl ester

Conditions

Conditions	Yield
Zn4O(OAc)6 at 180℃; for 2.5h; Inert atmosphere; Autoclave;	97%

: 539-92-4
diisobutyl carbonate

: 101-77-9
4,4'-diamino diphenyl methane

: 76788-39-1
C23H30N2O4

Conditions

Conditions	Yield
With sodium isobutoxide at 120℃; for 0.5h; Inert atmosphere;	97%

: 131520-88-2
2-(1-carboxy-2-methylpropyl)-1,3-dioxoisoindoline-5-carboxylic acid

: 101-77-9
4,4'-diamino diphenyl methane

: C28H27N3O5

Conditions

Conditions	Yield
With 5,15,10,20-tetraphenylporphyrin; calcium chloride In pyridine; 1-methyl-pyrrolidin-2-one at 60 - 130℃; for 10.5h;	97%

: 101-77-9
4,4'-diamino diphenyl methane

: 532-55-8
Benzoyl isothiocyanate

: 4,4'-di(benzoylthiocarbamoylamino)diphenylmethane

Conditions

Conditions	Yield
In ethyl acetate	96.1%

: 101-77-9
4,4'-diamino diphenyl methane

: 474003-15-1
2,2'-bis(4''-tert-butylphenyl)-4,4',5,5'-biphenyltetracarboxylic acid dianhydride

polyimide, Mw 141500 Da, PDI 2.33; monomer(s): 2,2\-bis(4\'\-tert-butylphenyl)-4,4\,,5,5\-biphenyltetracarboxylic acid dianhydride; 4,4\-methylenedianiline: polyimide, Mw 141500 Da, PDI 2.33; monomer(s): 2,2\-bis(4\'\-tert-butylphenyl)-4,4\,,5,5\-biphenyltetracarboxylic acid dianhydride; 4,4\-methylenedianiline

Conditions

Conditions	Yield
In various solvent(s) at 20 - 200℃;	96%

: 101-77-9
4,4'-diamino diphenyl methane

: 108-90-7
chlorobenzene

: 2698-09-1
N,N'-diphenyl-4,4'-diaminodiphenylmethane

Conditions

Conditions	Yield
With sodium t-butanolate; Ni(0)*2IPr In 1,4-dioxane at 100℃;	96%

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 NO_x.
Hazard Codes: Toxic T, Dangerous N
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)- .

Product Name

4,4'-Methylenedianiline

Synthetic route

4,4'-Methylenedianiline Chemical Properties

4,4'-Methylenedianiline Uses

4,4'-Methylenedianiline Toxicity Data With Reference

4,4'-Methylenedianiline Consensus Reports

4,4'-Methylenedianiline Safety Profile

4,4'-Methylenedianiline Standards and Recommendations

4,4'-Methylenedianiline Analytical Methods

4,4'-Methylenedianiline Specification

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