Conditions | Yield |
---|---|
With pyridine; pyridine hydrochloride at 100℃; for 23h; Inert atmosphere; | 98% |
C14H17NO2
N-benzyl-N-phenylhydrazine hydrochloride
5-(1-benzyl-1H-indol-3-yl)-2-(benzyloxy)pentanenitrile
Conditions | Yield |
---|---|
With acetic acid at 100℃; for 1h; Fischer indole synthesis; Inert atmosphere; | 89% |
1-phenyl-2-(2-propenyloxy)ethanone
N-benzyl-N-phenylhydrazine hydrochloride
Conditions | Yield |
---|---|
With L-Tartaric acid at 70℃; for 4h; | 87% |
N-benzyl-N-phenylhydrazine hydrochloride
α-dimethylaminomethylene-N-phenyl-γ-butyrolactam
A
2,3,4,9-Tetrahydro-2-phenyl-1H-pyrido<3,4-b>indol-1-one
B
9-benzyl-2-phenyl-1-oxo-1,2,3,4-tetrahydro-β-carboline
Conditions | Yield |
---|---|
In hydrogenchloride; isopropyl alcohol for 3h; Heating; | A 3% B 86% |
N-benzyl-N-phenylhydrazine hydrochloride
α-dimethylaminomethylene-γ-butyrolactam
A
1,2,3,4-tetrahydronorharman-1-one
B
9-benzyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-one
Conditions | Yield |
---|---|
With hydrogenchloride In isopropyl alcohol for 3h; Heating; | A 5% B 82% |
N-benzyl-N-phenylhydrazine hydrochloride
3-<(N,N-dimethylamino)methylene>-1-methyl-2-pyrrolidinone
A
Strychnocarpine
B
2,3,4,9-Tetrahydro-2-methyl-9-(phenylmethyl)-1H-pyrido<3,4-b>indol-1-one
Conditions | Yield |
---|---|
With hydrogenchloride In water; isopropyl alcohol for 3h; Heating; | A n/a B 80% |
3,4-dihydro-2H-thiopyran
N-benzyl-N-phenylhydrazine hydrochloride
1-(2-tetrahydrothiopyranylthio)-3-(1-benzyl-3-indolyl)propane
Conditions | Yield |
---|---|
With water In 1,4-dioxane for 4h; Heating; | 79% |
hexyl 6-methoxy-2-naphthyl ketone
N-benzyl-N-phenylhydrazine hydrochloride
1-benzyl-2-(6-methoxynaphthalen-2-yl)-3-pentyl-1H-indole
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water at 70 - 80℃; for 7h; Fischer Indole Synthesis; Heating / reflux; | 78% |
N-benzyl-N-phenylhydrazine hydrochloride
3-[1-Dimethylamino-meth-(Z)-ylidene]-dihydro-thiophen-2-one
Conditions | Yield |
---|---|
With trifluoroacetic acid In 1,4-dioxane for 8h; Heating; | 77% |
Conditions | Yield |
---|---|
With hydrogenchloride In water; isopropyl alcohol for 3h; Reflux; | 76% |
With hydrogenchloride In water; isopropyl alcohol for 3h; Reflux; | 76% |
ethyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate
N-benzyl-N-phenylhydrazine hydrochloride
2,4-dimethyl-3-acetyl-5-ethoxycarbonylpyrrole N-benzyl-N-phenylhydrazone hydrochloride
Conditions | Yield |
---|---|
In ethanol for 5h; Heating; | 75% |
diethyl (3-oxopropyl)phosphonate
N-benzyl-N-phenylhydrazine hydrochloride
(1-Benzyl-1H-indol-3-ylmethyl)-phosphonic acid diethyl ester
Conditions | Yield |
---|---|
In ethanol Heating; | 72% |
N-benzyl-N-phenylhydrazine hydrochloride
α,α'-hydroxybis(1-methyl-3-methylene-2-piperidone)
10-benzyl-2-methyl-3,4,5,10-tetrahydroazepino[3,4-b]indol-1(2H)-one
Conditions | Yield |
---|---|
With sulfuric acid In ethanol; water for 4h; Heating; | 70% |
1-benzylpyrrolidine-2,3-dione
N-benzyl-N-phenylhydrazine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 1-benzylpyrrolidine-2,3-dione; N-benzyl-N-phenylhydrazine hydrochloride With acetic acid at 80℃; for 0.333333h; Stage #2: With hydrogenchloride In water at 80℃; for 2.5h; | 66% |
N-benzyl-N-phenylhydrazine hydrochloride
1-Methyl-3-formyl-2-pyrrolidone
2,3,4,9-Tetrahydro-2-methyl-9-(phenylmethyl)-1H-pyrido<3,4-b>indol-1-one
Conditions | Yield |
---|---|
With hydrogenchloride In water; isopropyl alcohol for 3h; Heating; | 62% |
N-benzyl-N-phenylhydrazine hydrochloride
N-methyl-α-dimethylaminomethylenesuccinimide
A
2-Methyl-4,9-dihydro-β-carboline-1,3-dione
B
9-Benzyl-2-methyl-4,9-dihydro-β-carboline-1,3-dione
Conditions | Yield |
---|---|
With hydrogenchloride In acetic acid for 3h; Heating; | A 13% B 61% |
N-benzyl-N-phenylhydrazine hydrochloride
N-methyl-α-dimethylaminomethyleneglutarimide
A
2-methyl-1,3-dioxo-1,2,3,4,5,10-hexahydroazepino<3,4-b>indole
B
2-methyl-10-benzyl-1,3-dioxo-1,2,3,4,5,10-hexahydroazepino<3,4-b>indole
Conditions | Yield |
---|---|
With hydrogenchloride In acetic acid for 3h; Heating; | A 7% B 61% |
N-benzyl-N-phenylhydrazine hydrochloride
α-dimethylaminomethylene-N-butyl-γ-butyrolactam
A
9-Benzyl-2-butyl-2,3,4,9-tetrahydro-β-carbolin-1-one
B
2-n-butyl-1-oxo-1,2,3,4-tetrahydro-β-carboline
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; isopropyl alcohol for 3h; Heating; | A 60% B n/a |
1-methylpiperidin-2-one
N-benzyl-N-phenylhydrazine hydrochloride
N,N-dimethyl-formamide
10-benzyl-2-methyl-3,4,5,10-tetrahydroazepino[3,4-b]indol-1(2H)-one
Conditions | Yield |
---|---|
Stage #1: 1-methylpiperidin-2-one; N,N-dimethyl-formamide With trichlorophosphate In benzene for 5.5h; Vilsmeier Reaction; Reflux; Stage #2: N-benzyl-N-phenylhydrazine hydrochloride In ethanol for 2h; Reflux; | 60% |
Stage #1: 1-methylpiperidin-2-one; N,N-dimethyl-formamide With trichlorophosphate In benzene for 5.5h; Vilsmeier Reaction; Reflux; Stage #2: N-benzyl-N-phenylhydrazine hydrochloride In ethanol for 2h; Reflux; | 60% |
N-benzyl-N-phenylhydrazine hydrochloride
Ethyl β-(2,4-dimethyl-5-carboethoxypyrrolyl-3)-β-ketopropionate
2,4-dimethyl-3-acetyl-5-ethoxycarbonylpyrrole N-benzyl-N-phenylhydrazone hydrochloride
Conditions | Yield |
---|---|
In ethanol for 11h; Heating; than standing for 2 days; | 59% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; for 2h; | 59% |
Diphenyliodonium triflate
N-benzyl-N-phenylhydrazine hydrochloride
N′-benzyl-N′-phenylbenzenesulfonohydrazide
Conditions | Yield |
---|---|
With potassium pyrosulfite; C34H30N2O4 In dimethyl sulfoxide; acetonitrile at 20℃; for 2h; Inert atmosphere; Schlenk technique; Irradiation; | 59% |
α-hydroxymethylene-N-methyl-δ-valerolactam
N-benzyl-N-phenylhydrazine hydrochloride
A
10-benzyl-2-methyl-3,4,5,10-tetrahydroazepino[3,4-b]indol-1(2H)-one
B
2-methyl-3,4,5,10-tetrahydroazepino[3,4-b]indol-1(2H)-one
Conditions | Yield |
---|---|
With sulfuric acid In ethanol; water for 4h; Heating; | A 57% B 8% |
3-oxopentanedioic acid dimethyl ester
N-benzyl-N-phenylhydrazine hydrochloride
methyl 1-benzyl-2-(2-methoxy-2-oxoethyl)-1H-indole-3-carboxylate
Conditions | Yield |
---|---|
In methanol Fischer Indole Synthesis; Heating; | 57% |
In methanol for 12h; Fischer Indole Synthesis; Heating; | 57% |
N-benzyl-N-phenylhydrazine hydrochloride
diethyl 1,3-acetonedicarboxylate
1-benzyl-2-ethoxycarbonylmethyl-indole-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
In ethanol Fischer Indole Synthesis; Reflux; | 54% |
N-benzyl-N-phenylhydrazine hydrochloride
4a′-methyl-4′,4a′,7′,8′-tetrahydro-3′H-spiro[[1,3]dithiolane-2,2′-naphthalen]-5′(6′H)-one
Conditions | Yield |
---|---|
With acetic acid at 100℃; for 2h; Inert atmosphere; | 53% |
Conditions | Yield |
---|---|
In acetic acid for 1h; Fiacher indole synthesis; Heating; | 52% |
N-benzyl-N-phenylhydrazine hydrochloride
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 130℃; for 0.5h; Fischer Indole Synthesis; Microwave irradiation; | 51% |
3,4-dihydro-2H-thiopyran
N-benzyl-N-phenylhydrazine hydrochloride
5-(2-tetrahydrothiopyranylthio)pentanal α-benzylphenylhydrazone
Conditions | Yield |
---|---|
In 1,4-dioxane; water for 24h; Ambient temperature; | 50% |
N-benzyl-N-phenylhydrazine hydrochloride
3-[1-Dimethylamino-meth-(Z)-ylidene]-1-methyl-azepan-2-one
A
2-methyl-2,3,4,5,6,11-hexahydro-1H-azocino<3,4-b>indol-1-one
B
2-methyl-11-benzyl-2,3,4,5,6,11-hexahydro-1H-azocino<3,4-b>indol-1-one
Conditions | Yield |
---|---|
With sulfuric acid In ethanol; water for 4h; Heating; | A 17% B 45% |
The N-Benzyl-N-phenylhydrazine hydrochloride, with the CAS registry number 5705-15-7 and EINECS registry number 227-195-7, has the systematic name of 1-benzyl-1-phenylhydrazine hydrochloride (1:1). And the molecular formula of the chemical is C13H14N2.HCl.
The characteristics of N-Benzyl-N-phenylhydrazine hydrochloride are as followings: (1)ACD/LogP: 2.63; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.4; (4)ACD/LogD (pH 7.4): 2.63; (5)ACD/BCF (pH 5.5): 34.44; (6)ACD/BCF (pH 7.4): 58.44; (7)ACD/KOC (pH 5.5): 376.3; (8)ACD/KOC (pH 7.4): 638.41; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 6.48 Å2; (13)Flash Point: 186.3 °C; (14)Enthalpy of Vaporization: 59.08 kJ/mol; (15)Boiling Point: 346.6 °C at 760 mmHg; (16)Vapour Pressure: 5.7E-05 mmHg at 25°C.
Uses of N-Benzyl-N-phenylhydrazine hydrochloride: It can be used to produce 1-(2-tetrahydrothiopyranylthio)-3-(1-benzyl-3-indolyl)propane. This reaction will need reagent H2O, and the menstruum dioxane. The reaction time is 4 hours with heating, and the yield is about 79%.
You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: Cl.NN(c1ccccc1)Cc2ccccc2
(2)InChI: InChI=1/C13H14N2.ClH/c14-15(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12;/h1-10H,11,14H2;1H
(3)InChIKey: JTYLHYOCBGPMNO-UHFFFAOYAE
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 300mg/kg (300mg/kg) | National Technical Information Service. Vol. AD277-689, | |
mouse | LD50 | intravenous | 106mg/kg (106mg/kg) | Acta Biologica et Medica Germanica. Vol. 17, Pg. 614, 1966. | |
rat | LD50 | intraperitoneal | 404mg/kg (404mg/kg) | Acta Biologica et Medica Germanica. Vol. 18, Pg. 617, 1967. |
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