Conditions | Yield |
---|---|
With sodium tetrahydroborate In water at 20℃; for 1h; | 100% |
With hydrogen; sodium fluoride In methanol at 39.84℃; for 2.17h; | 100% |
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 3h; chemoselective reaction; | 100% |
Conditions | Yield |
---|---|
With C37H23Cl2N7Pd2(2+)*2F6P(1-); hydrogen; sodium cyanoborohydride In methanol at 50℃; under 760.051 Torr; for 6h; | 100% |
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran; water at 20℃; for 0.5h; | 99% |
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h; | 99% |
Conditions | Yield |
---|---|
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h; | 99% |
With {(o-C6H4(NCHC6H4O)2)cobalt(II)}2; ammonia at 150℃; under 1500.15 Torr; for 10h; Autoclave; Inert atmosphere; Large scale; | 73% |
With ammonia; water; copper(II) sulfate at 175 - 180℃; |
Conditions | Yield |
---|---|
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 120℃; for 16h; Sealed tube; chemoselective reaction; | 99% |
With copper(l) iodide; 1,2,4,5-tetramethylbenzene; ammonia at 20℃; for 15h; Reagent/catalyst; | 94% |
Conditions | Yield |
---|---|
With sodium hypochlorite; water at -5 - 50℃; for 2h; Temperature; Inert atmosphere; | 97% |
With sodium hypochlorite In water at -5 - 50℃; for 4h; Temperature; Hofmann Rearrangement; Inert atmosphere; | 84.2% |
With sodium hypochlorite at 45℃; for 6h; Green chemistry; | 92 g |
With sodium hypochlorite; potassium hydroxide at 0 - 80℃; Hofmann Rearrangement; Inert atmosphere; | 7.1 g |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrazine hydrate In methanol at 120℃; for 0.25h; Microwave irradiation; | 96% |
Conditions | Yield |
---|---|
With ammonium hydroxide In water at 20℃; for 9h; Green chemistry; | 96% |
m-aminophenyl azide
m-phenylenediamine
Conditions | Yield |
---|---|
With hydrazinium monoformate; zinc In methanol at 20℃; for 0.15h; | 95% |
m-phenylenediamine
Conditions | Yield |
---|---|
In water; acetonitrile at 110℃; for 2h; | 95% |
Conditions | Yield |
---|---|
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; | 94% |
With copper(l) iodide; tetra(n-butyl)ammonium hydroxide; ammonia In water at 80℃; for 48h; Inert atmosphere; Sealed tube; chemoselective reaction; | 75% |
Conditions | Yield |
---|---|
Stage #1: 1,3-diacetylbenzene With hydroxylamine hydrochloride at 80℃; for 3h; Stage #2: With hydrogenchloride In water at 100℃; for 2h; Temperature; Concentration; | 92% |
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; N-((1-oxy-pyridin-2-yl)methyl)oxalamic acid; ammonia In water; dimethyl sulfoxide at 25℃; Schlenk technique; Inert atmosphere; Sealed tube; chemoselective reaction; | 91% |
Stage #1: 3-Iodoaniline With copper(l) iodide; L-valine; caesium carbonate In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere; Stage #2: With oxygen In dimethyl sulfoxide at 90℃; for 24h; Stage #3: With hydrogenchloride In dichloromethane; water; dimethyl sulfoxide at 20℃; for 0.333333h; pH=1; | 28% |
Conditions | Yield |
---|---|
With hydrogen; PdCl2-anthranilic acid catalyst In ethanol at 60℃; under 77572.2 Torr; for 1h; | A 90% B 1% |
With hydrogen; trans-Pdpy2Cl2 In ethanol at 30℃; for 6h; | A 90% B 4.5% |
With hydrogen In methanesulfonic acid at 150℃; under 22502.3 Torr; for 1h; Autoclave; | A 25% B 75% |
3-Aminophenylboronic acid
m-phenylenediamine
Conditions | Yield |
---|---|
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h; | 90% |
With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 12h; | 89% |
Conditions | Yield |
---|---|
With sodium azide; trifluoroacetic acid In hexane at 40℃; for 4h; Sealed tube; | 87% |
With sodium azide; methanesulfonic acid; trifluoroacetic acid In hexane at 40℃; for 12h; | 87% |
Conditions | Yield |
---|---|
With ammonia; 0.8Ni*0.2Cu*C20H16N2O2 at 160℃; under 1500.15 Torr; for 11h; Reagent/catalyst; Autoclave; Inert atmosphere; | 84% |
With ammonium hydroxide; potassium phosphate; Cu0.18Bi0.88O0.88I1.06 In ethanol; water at 80℃; for 20h; Inert atmosphere; Green chemistry; | 98 %Chromat. |
Conditions | Yield |
---|---|
With carbon monoxide; hydrogen sulfide; iron(III) oxide at 325℃; for 1.05h; Product distribution; Mechanism; var. time; | A 80.2% B 4.5% C n/a |
Conditions | Yield |
---|---|
With hydrogenchloride; indium In tetrahydrofuran at 20℃; for 8h; | 76% |
3-nitro-aniline
A
3,3'-diaminoazobenzene
B
m-phenylenediamine
Conditions | Yield |
---|---|
With ethylenediamine at 150℃; | A 24% B 75% |
2,4-dinitrotoluene
A
4-methylbenzene-1,3-diamine
B
4,6-dimethyl-1,3-benzenediamine
C
m-phenylenediamine
Conditions | Yield |
---|---|
With carbon monoxide; hydrogen sulfide; iron(III) oxide at 325℃; for 1.73333h; Product distribution; Mechanism; var. time, further catalyst: 5percent Co on γ-Al2O3; | A 61% B 29.6% C 9.3% |
3-(prop-1-en-2-yl)aniline
m-phenylenediamine
Conditions | Yield |
---|---|
Stage #1: 3-(prop-1-en-2-yl)aniline With sodium azide; trifluoroacetic acid In hexane; water at 20 - 40℃; for 4h; Stage #2: With sodium hydroxide In water at 0℃; for 0.333333h; Reagent/catalyst; | 55% |
Conditions | Yield |
---|---|
With copper(l) iodide In water at 200℃; for 2h; Autoclave; | 54% |
Conditions | Yield |
---|---|
With titanium; sulfuric acid; hydroxylamine Mechanism; other aromatic compounds electrochemical amination, dropping mercury electrode; var. solvents; | 0.1% |
Conditions | Yield |
---|---|
With hydrogenchloride; tin |
Conditions | Yield |
---|---|
With methanol; sodium hydroxide; nickel Hydrogenation; | |
With sodium hydroxide; nickel; isopropyl alcohol Hydrogenation; |
Conditions | Yield |
---|---|
With barytes bei Destillation; |
Conditions | Yield |
---|---|
With hydrogenchloride; tin |
2,4,6-tribromo-1,3-dinitrobenzene
m-phenylenediamine
Conditions | Yield |
---|---|
With hydrogenchloride; tin |
2,4,6-tribromo-1,3-dinitrobenzene
A
2,4,6-tribromo-1,3-phenylenediamine
B
m-phenylenediamine
Conditions | Yield |
---|---|
With acetic acid; zinc |
carbon disulfide
2-[2-(vinyloxy)ethoxymethyl]oxirane
m-phenylenediamine
1,3-di<9-vinyloxy-5-hydroxy-2-thioxo-7-oxa-3-thia-1-azanonyl>benzene
Conditions | Yield |
---|---|
for 6h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
In benzene Heating; | A 92.3% B 100% |
2-(vinyloxy)ethyl isothiocyanate
m-phenylenediamine
1-(2-Vinyloxy-ethyl)-3-{3-[3-(2-vinyloxy-ethyl)-thioureido]-phenyl}-thiourea
Conditions | Yield |
---|---|
for 0.0833333h; | 100% |
m-phenylenediamine
4-methoxy-aniline
(E)-4-(2-(4-methoxyphenyl)diazenyl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Stage #1: 4-methoxy-aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.666667h; Stage #2: m-phenylenediamine With hydrogenchloride In water at 0℃; for 0.5h; | 100% |
With hydrogenchloride; sodium nitrite 1. H2O, 0 deg C; 2. 0 deg C, 2 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
Stage #1: aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.666667h; Stage #2: m-phenylenediamine With hydrogenchloride In water at 0℃; for 0.5h; | 100% |
m-phenylenediamine
sulfanilamide
(E)-4-(2-(4-sulfonamido)diazenyl)benzene-1,3-diamine
Conditions | Yield |
---|---|
Stage #1: sulfanilamide With hydrogenchloride; sodium nitrite In water at 0℃; for 0.666667h; Stage #2: m-phenylenediamine With hydrogenchloride In water at 0℃; for 0.5h; | 100% |
4-iodo-2-methylaniline
m-phenylenediamine
Conditions | Yield |
---|---|
Stage #1: 4-iodo-2-methylaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.666667h; Stage #2: m-phenylenediamine With hydrogenchloride In water at 0℃; for 0.5h; | 100% |
3-iodo-4-methylaniline
m-phenylenediamine
Conditions | Yield |
---|---|
Stage #1: 3-iodo-4-methylaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.666667h; Stage #2: m-phenylenediamine With hydrogenchloride In water at 0℃; for 0.5h; | 100% |
Conditions | Yield |
---|---|
Stage #1: 4-methoxy-2-nitroaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.666667h; Stage #2: m-phenylenediamine With hydrogenchloride In water at 0℃; for 0.5h; | 100% |
m-phenylenediamine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one Heating; | 100% |
m-phenylenediamine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 20 - 90℃; for 1h; | 100% |
4-chlorophthalic anhydride
m-phenylenediamine
1,3-bis[N-(4-chlorophthalimidio)]benzene
Conditions | Yield |
---|---|
Sodium phenylphosphinate In methoxybenzene at 200℃; under 760.051 - 1824.12 Torr; for 2 - 7h; Conversion of starting material; | 99.44% |
In glycerol at 150℃; for 15h; | 55.3% |
In 1,2-dichloro-benzene at 20 - 180℃; for 32h; |
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol; trifluoroacetic acid at 80℃; for 24h; | 99.2% |
2-diethylaminoethylisothiocyanate
m-phenylenediamine
1,3-bis-1-<(N,N-diethylamino)ethyl>thioureido>benzene
Conditions | Yield |
---|---|
In 1,4-dioxane for 3h; Heating; | 99% |
di-tert-butyl dicarbonate
m-phenylenediamine
(3-aminophenyl)carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 18h; Cooling with ice; | 99% |
Stage #1: di-tert-butyl dicarbonate; m-phenylenediamine In dichloromethane at 20℃; for 18h; Stage #2: With sodium carbonate In water; ethyl acetate | 93% |
In tetrahydrofuran at 20℃; for 24h; | 92% |
Conditions | Yield |
---|---|
In acetone at 20℃; for 12h; | 99% |
Conditions | Yield |
---|---|
In acetone | 99% |
Conditions | Yield |
---|---|
With zeolite NaY for 2h; Heating; | 99% |
Conditions | Yield |
---|---|
With [Li(THF)(DME)]3La[μ-η2η1(iPrN)2C(NC6H4p-Cl)]3 at 25℃; for 2h; Inert atmosphere; | 99% |
With C36H52N5O4Si2Yb In neat at 60℃; for 0.5h; Inert atmosphere; | 93% |
[{Me2Si(C5Me4)(NPh)}Y(CH2SiMe3)(thf)2] In benzene at 80℃; for 1h; |
Conditions | Yield |
---|---|
With pyridine for 5h; Reflux; | 99% |
m-phenylenediamine
N-3-aminophenyl-N',N"-bis(4-pyrazol-1-ylphenyl)-1,3,5-triazine-2,4,6-triamine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 140℃; under 760.051 Torr; for 0.166667h; Inert atmosphere; Microwave irradiation; | 99% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In dichloromethane at 0 - 20℃; | 99% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide | 99% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; Inert atmosphere; | 99% |
3-hydroxy-2-naphthoyl chloride
m-phenylenediamine
N,N'-bis-(3-hydroxy-[2]naphthoylamino)-benzene
Conditions | Yield |
---|---|
With thionyl chloride In 1-methyl-pyrrolidin-2-one at 10 - 20℃; for 2h; | 98.5% |
With thionyl chloride In 1-methyl-pyrrolidin-2-one at 10 - 20℃; for 2.5h; |
m-phenylenediamine
methanesulfonyl chloride
3-(methylsulfonamido)aniline
Conditions | Yield |
---|---|
With calcium bicarbonate; magnesium hydrogencarbonate; sodium dodecyl-sulfate; sodium carbonate; calcium chloride; magnesium chloride In water at -8 - 30℃; for 13.5h; Reagent/catalyst; Temperature; | 98.5% |
IARC Cancer Review: Group 3 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 Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 16 ,1978,p. 111.(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) . EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.
ACGIH TLV: TWA 0.1 mg/m3; Not Classifiable as a Human Carcinogen
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans
DOT Classification: 6.1; Label: KEEP AWAY FROM FOOD
1,3-Benzenediamine, its cas register number is 108-45-2. It also can be call 1,3-Phenylenediamine; 3-Aminoaniline;
Benzene, 1,3-diamino-; Metaphenylenediamine; m-Aminoaniline; m-Benzenediamine; m-Diaminobenzene; m-Fenylendiamin; m-Phenylenediamine. 1,3-diaminobenzene, is an organic compound with the formula C6H4(NH2)2. It is an isomer of o-phenylenediamine and p-phenylenediamine. It is a colourless solid. m-Phenylenediamine is produced by hydrogenation of 1,3-dinitrobenzene. The dinitrobenzene is prepared by dinitration of benzene.
Physical properties about 1,3-Benzenediamine are: (1)ACD/LogP: -0.306; (2)ACD/LogD (pH 5.5): -0.40; (3)ACD/LogD (pH 7.4): -0.31; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 13.08; (7)ACD/KOC (pH 7.4): 16.19; (8)#H bond acceptors: 2 ; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.66 ; (12)Molar Refractivity: 34.725 cm3; (13)Molar Volume: 93.994 cm3; (14)Polarizability: 13.766 10-24cm3; (15)Surface Tension: 57.5979995727539 dyne/cm; (16)Density: 1.15 g/cm3; (17)Flash Point: 147.572 °C; (18)Enthalpy of Vaporization: 52.208 kJ/mol; (19)Boiling Point: 283.179 °C at 760 mmHg; (20)Vapour Pressure: 0.00300000002607703 mmHg at 25°C
Uses of 1,3-Benzenediamine: 1,3-Benzenediamine is used in the preparation various polymers including aramid fibers, epoxy resins, wire enamel coatings and polyurea elastomers. Other uses for m-phenylenediamine include as an accelerator for adhesive resins, and as a component of dyes for leather and textiles.
When you are using this chemical, please be cautious about it as the following:
1. After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer);
2. Wear suitable protective clothing and gloves;
3. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
4. This material and/or its container must be disposed of as hazardous waste;
5. Avoid release to the environment. Refer to special instructions safety data sheet;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2;
(2)InChIKey=WZCQRUWWHSTZEM-UHFFFAOYSA-N;
(3)Smilesc1c(cccc1N)N;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
bird - wild | LD50 | oral | 562mg/kg (562mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
cat | LDLo | oral | 300mg/kg (300mg/kg) | LUNGS, THORAX, OR RESPIRATION: CYANOSIS BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Journal of Industrial Hygiene. Vol. 4, Pg. 386, 1923. |
dog | LDLo | intravenous | 17mg/kg (17mg/kg) | Journal of Industrial Hygiene. Vol. 4, Pg. 386, 1923. | |
dog | LDLo | subcutaneous | 100mg/kg (100mg/kg) | National Technical Information Service. Vol. OTS0555804, | |
guinea pig | LD50 | oral | 450mg/kg (450mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(7), Pg. 62, 1988. | |
guinea pig | LD50 | unreported | 450mg/kg (450mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(8), Pg. 46, 1987. | |
mouse | LD50 | oral | 67700ug/kg (67.7mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(7), Pg. 62, 1988. | |
mouse | LD50 | subcutaneous | 90mg/kg (90mg/kg) | Kyushu Journal of Medical Science. Vol. 13, Pg. 175, 1962. | |
mouse | LD50 | unreported | 65300ug/kg (65.3mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(8), Pg. 46, 1987. | |
mouse | LDLo | intraperitoneal | 400mg/kg (400mg/kg) | Revue Belge de Pathologie et de Medecine Experimentale. Vol. 22, Pg. 1, 1952. | |
rabbit | LD50 | oral | 437mg/kg (437mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(7), Pg. 62, 1988. | |
rabbit | LD50 | unreported | 438mg/kg (438mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(8), Pg. 46, 1987. | |
rabbit | LDLo | skin | 1500mg/kg (1500mg/kg) | LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION | National Technical Information Service. Vol. OTS0555804, |
rabbit | LDLo | subcutaneous | 200mg/kg (200mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Journal of Industrial Hygiene. Vol. 4, Pg. 386, 1923. |
rat | LD50 | intraperitoneal | 283mg/kg (283mg/kg) | Journal of Toxicology and Environmental Health. Vol. 2, Pg. 657, 1977. | |
rat | LD50 | oral | 280mg/kg (280mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(7), Pg. 62, 1988. | |
rat | LD50 | unreported | 351mg/kg (351mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(8), Pg. 46, 1987. | |
rat | LDLo | subcutaneous | 80mg/kg (80mg/kg) | National Technical Information Service. Vol. OTS0555804, |
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