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1073-69-4

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1073-69-4 Usage

Definition

ChEBI: Phenylhydrazine substituted at the para position by a chloro group.

Check Digit Verification of cas no

The CAS Registry Mumber 1073-69-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,7 and 3 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1073-69:
(6*1)+(5*0)+(4*7)+(3*3)+(2*6)+(1*9)=64
64 % 10 = 4
So 1073-69-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H7ClN2.H2O4S/c7-5-1-3-6(9-8)4-2-5;1-5(2,3)4/h1-4,9H,8H2;(H2,1,2,3,4)

1073-69-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-chlorophenylhydrazine

1.2 Other means of identification

Product number -
Other names (4-chlorophenyl)hydrazine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1073-69-4 SDS

1073-69-4Synthetic route

4-chloro-aniline
106-47-8

4-chloro-aniline

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

Conditions
ConditionsYield
With hydrazine hydro-chloride In ethylene glycol at 110℃; for 5h; Temperature; Reflux;92%
Stage #1: 4-chloro-aniline With hydrogenchloride; sodium nitrite In water for 2h;
Stage #2: With hydrogenchloride; sodium sulfite In water at 0 - 100℃; for 4h;
70.67%
Stage #1: 4-chloro-aniline With hydrogenchloride; acetic acid; sodium nitrite In water at 0 - 20℃;
Stage #2: With hydrogenchloride; tin(II) dichloride dihydrate In water
60%
4-chloro-aniline
106-47-8

4-chloro-aniline

butan-1-ol
71-36-3

butan-1-ol

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sodium hydrogen sulfate; sodium nitrite78%
p-chlorobenzenediazonium tetrafluoroborate
673-41-6

p-chlorobenzenediazonium tetrafluoroborate

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

Conditions
ConditionsYield
With borohydride exchange resin In methanol at 0℃;63%
With sodium perchlorate In water at 4℃; for 2h; electrolysis, pH=2.2;60%
N-chloro-N'-phenyl-urea
113546-44-4

N-chloro-N'-phenyl-urea

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

A

phenyl carbamate
64-10-8

phenyl carbamate

B

chlorobenzene
108-90-7

chlorobenzene

C

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

D

N-(4-chlorophenyl)urea
140-38-5

N-(4-chlorophenyl)urea

p-chlorobenzenediazonium chloride
2028-74-2

p-chlorobenzenediazonium chloride

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

Conditions
ConditionsYield
With sodium sulfite nachf. Erhitzen mit Salzsaeure;
at 70℃; Zufuegen von Zinkstaub, Eisessig und konz. Salzsaeure;
With tin(ll) chloride
[N'-(4-chloro-phenyl)-hydrazino]-triphenyl-phosphonium; chloride

[N'-(4-chloro-phenyl)-hydrazino]-triphenyl-phosphonium; chloride

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

Conditions
ConditionsYield
With hydrogenchloride
hydrogenchloride
7647-01-0

hydrogenchloride

N’-(4-chlorophenyl)acetohydrazide
6947-29-1

N’-(4-chlorophenyl)acetohydrazide

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

potassium-4-chloro-benzene isodiazotate-(1)

potassium-4-chloro-benzene isodiazotate-(1)

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

Conditions
ConditionsYield
With sodium hydroxide; sodium amalgam
sodium-<4-chloro-benzene-trans-diazoate>

sodium-<4-chloro-benzene-trans-diazoate>

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

Conditions
ConditionsYield
With water Electrolysis;
methyl 2-(4-chlorophenyl)hydrazinecarboxylate
51317-82-9

methyl 2-(4-chlorophenyl)hydrazinecarboxylate

A

methanol
67-56-1

methanol

B

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

C

CO2

CO2

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 25℃; Rate constant;
ethyl 2-(4-chlorophenyl)hydrazinecarboxylate
13124-13-5

ethyl 2-(4-chlorophenyl)hydrazinecarboxylate

A

ethanol
64-17-5

ethanol

B

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

C

CO2

CO2

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 25℃; Rate constant;
hydrogenchloride
7647-01-0

hydrogenchloride

p-chlorobenzenediazonium chloride
2028-74-2

p-chlorobenzenediazonium chloride

tin dichloride

tin dichloride

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

hydrogenchloride
7647-01-0

hydrogenchloride

4-chloro-benzenediazonium; tribromoide

4-chloro-benzenediazonium; tribromoide

tin dichloride

tin dichloride

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

hydrogenchloride
7647-01-0

hydrogenchloride

4-chloro-benzenediazonium; dichloride iodide

4-chloro-benzenediazonium; dichloride iodide

tin dichloride

tin dichloride

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

hydrogenchloride
7647-01-0

hydrogenchloride

4-chloro-benzenediazonium; thiocyanate

4-chloro-benzenediazonium; thiocyanate

tin dichloride

tin dichloride

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

hydrogenchloride
7647-01-0

hydrogenchloride

4-chloro-benzenediazonium; tetrachloride

4-chloro-benzenediazonium; tetrachloride

tin dichloride

tin dichloride

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

hydrogenchloride
7647-01-0

hydrogenchloride

4-chlorophenyldiazonium nitrate

4-chlorophenyldiazonium nitrate

tin dichloride

tin dichloride

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

hydrogenchloride
7647-01-0

hydrogenchloride

4-chloro-benzenediazonium; β-naphthalenethiosulfonate

4-chloro-benzenediazonium; β-naphthalenethiosulfonate

tin dichloride

tin dichloride

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

hydrogenchloride
7647-01-0

hydrogenchloride

4-chloro-benzenediazonium; hexachloroplatinate (IV)

4-chloro-benzenediazonium; hexachloroplatinate (IV)

tin dichloride

tin dichloride

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

hydrogenchloride
7647-01-0

hydrogenchloride

N-acetyl-N-(4-chloro-phenyl)-N'-(4-nitro-benzoyl)-hydrazine
861323-92-4

N-acetyl-N-(4-chloro-phenyl)-N'-(4-nitro-benzoyl)-hydrazine

A

acetic acid
64-19-7

acetic acid

B

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

C

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-chlorobenzenediazonium sulfate
53486-30-9

4-chlorobenzenediazonium sulfate

tin dichloride

tin dichloride

hydrochloric acid

hydrochloric acid

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

4-chloro-benzenediazonium; trichloromercurate(II), compound with mercury chloride

4-chloro-benzenediazonium; trichloromercurate(II), compound with mercury chloride

tin dichloride

tin dichloride

hydrochloric acid

hydrochloric acid

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

N'-(4-Chloro-phenyl)-hydrazinecarboxylic acid propyl ester

N'-(4-Chloro-phenyl)-hydrazinecarboxylic acid propyl ester

A

propan-1-ol
71-23-8

propan-1-ol

B

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

C

CO2

CO2

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 25℃; Rate constant;
N'-(4-Chloro-phenyl)-hydrazinecarboxylic acid 2,2,2-trichloro-ethyl ester
137273-07-5

N'-(4-Chloro-phenyl)-hydrazinecarboxylic acid 2,2,2-trichloro-ethyl ester

A

1,1,1-trichloroethanol
115-20-8

1,1,1-trichloroethanol

B

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

C

CO2

CO2

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 25℃; Rate constant;
4-chlorophenylhydrazine hydrochloride
1073-70-7

4-chlorophenylhydrazine hydrochloride

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; diethyl ether; water
With potassium carbonate In water at 20℃; for 0.25h;
With potassium carbonate In water at 20℃; for 0.25h; Inert atmosphere;
1-Chloro-4-iodobenzene
637-87-6

1-Chloro-4-iodobenzene

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; hydrazine hydrate at 120℃; for 10h; Sealed tube; Inert atmosphere;
4-chlorophenylhydrazine halfsulfate

4-chlorophenylhydrazine halfsulfate

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water
p-chlorophenyl chloramine
57311-92-9

p-chlorophenyl chloramine

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

Conditions
ConditionsYield
With ammonia In water at 45℃; Temperature;132.6 g
para-dichlorobenzene
106-46-7

para-dichlorobenzene

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

Conditions
ConditionsYield
With bis(tri-ortho-tolylphosphine)palladium(0); (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)ferrocene; hydrazine hydrate; sodium t-butanolate In 1,4-dioxane; dodecane at 110℃; for 24h; Catalytic behavior; Temperature; Reagent/catalyst; Solvent; Time; Inert atmosphere; Sealed tube;
With bis(tri-ortho-tolylphosphine)palladium(0); (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)ferrocene; hydrazine hydrate; potassium hydroxide In 1,4-dioxane at 100℃; Inert atmosphere; Sealed tube;
1-methyl-4-methylene-1-azacyclohexane
13669-28-8

1-methyl-4-methylene-1-azacyclohexane

carbon monoxide
201230-82-2

carbon monoxide

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

5-chloro-3-(1-methylpiperidin-4-yl)-1H-indole

5-chloro-3-(1-methylpiperidin-4-yl)-1H-indole

Conditions
ConditionsYield
With sulfuric acid; hydrogen; Rh(acac)2(CO)2 at 100℃; under 45003.6 Torr; for 72h;100%
Stage #1: 1-methyl-4-methylene-1-azacyclohexane; carbon monoxide; N-4-chlorophenylhydrazine With hydrogen; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; Rh(acac)2(CO)2 In tetrahydrofuran at 100℃; under 45003.6 Torr; for 72h;
Stage #2: With sulfuric acid for 2h; Heating;
85%
6-bromoindan-1-one
14548-39-1

6-bromoindan-1-one

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

N-(6-Bromo-indan-1-ylidene)-N'-(4-chloro-phenyl)-hydrazine

N-(6-Bromo-indan-1-ylidene)-N'-(4-chloro-phenyl)-hydrazine

Conditions
ConditionsYield
With acetic acid In ethanol for 0.5h; Heating / reflux;100%
N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

(E)-1-(4-chlorophenyl)-2-(3-methyl-4-phenylbutan-2-ylidene)hydrazine
1381772-29-7

(E)-1-(4-chlorophenyl)-2-(3-methyl-4-phenylbutan-2-ylidene)hydrazine

Conditions
ConditionsYield
In dichloromethane for 17h; Molecular sieve; Inert atmosphere; Reflux;100%
1-methyl-3-phenyl-butanal
17913-10-9

1-methyl-3-phenyl-butanal

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

A

(Z)-1-(4-chlorophenyl)-2-(4-phenylpentan-2-ylidene)hydrazine
1381772-31-1

(Z)-1-(4-chlorophenyl)-2-(4-phenylpentan-2-ylidene)hydrazine

B

(E)-1-(4-chlorophenyl)-2-(4-phenylpentan-2-ylidene)hydrazine
1381772-27-5

(E)-1-(4-chlorophenyl)-2-(4-phenylpentan-2-ylidene)hydrazine

Conditions
ConditionsYield
In dichloromethane for 17h; Molecular sieve; Inert atmosphere; Reflux;A n/a
B 100%
4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

A

(Z)-1-(4-chlorophenyl)-2-(4-methylpentan-2-ylidene)hydrazine
1381772-41-3

(Z)-1-(4-chlorophenyl)-2-(4-methylpentan-2-ylidene)hydrazine

B

(E)-1-(4-chlorophenyl)-2-(4-methylpentan-2-ylidene)hydrazine
1381772-37-7

(E)-1-(4-chlorophenyl)-2-(4-methylpentan-2-ylidene)hydrazine

Conditions
ConditionsYield
In dichloromethane for 17h; Molecular sieve; Inert atmosphere; Reflux;A n/a
B 100%
methallyl acetate
820-71-3

methallyl acetate

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

A

3-(4-chlorophenyl)-2-hydroperoxy-2-methylpropyl acetate
1621652-06-9

3-(4-chlorophenyl)-2-hydroperoxy-2-methylpropyl acetate

B

1-(4-chlorophenyl)propan-2-one
5586-88-9

1-(4-chlorophenyl)propan-2-one

Conditions
ConditionsYield
With manganese(IV) oxide; acetic acid In acetonitrile at 23℃; for 1h;A n/a
B 100%
N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

methacrylonitrile
126-98-7

methacrylonitrile

A

3-(4-chlorophenyl)-2-hydroperoxy-2-methylpropanenitrile
1621652-17-2

3-(4-chlorophenyl)-2-hydroperoxy-2-methylpropanenitrile

B

1-(4-chlorophenyl)propan-2-one
5586-88-9

1-(4-chlorophenyl)propan-2-one

Conditions
ConditionsYield
With manganese(IV) oxide; acetic acid In acetonitrile at 23℃; for 1h;A n/a
B 100%
4-(4-methylphenyl)butan-2-one
7774-79-0

4-(4-methylphenyl)butan-2-one

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

A

(Z)-1-(4-chlorophenyl)-2-(4-p-tolylbutan-2-ylidene)hydrazine
1381772-17-3

(Z)-1-(4-chlorophenyl)-2-(4-p-tolylbutan-2-ylidene)hydrazine

B

(E)-1-(4-chlorophenyl)-2-(4-p-tolylbutan-2-ylidene)hydrazine
1381772-14-0

(E)-1-(4-chlorophenyl)-2-(4-p-tolylbutan-2-ylidene)hydrazine

Conditions
ConditionsYield
In dichloromethane for 17h; Molecular sieve; Inert atmosphere; Reflux;A n/a
B 99%
(E)-ethyl 5-(3-(dimethylamino)acryloyl)-4-methyl-2-(phenylamino)thiophene-3-carboxylate

(E)-ethyl 5-(3-(dimethylamino)acryloyl)-4-methyl-2-(phenylamino)thiophene-3-carboxylate

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

ethyl 5-(1-(4-chlorophenyl)-1H-pyrazol-3-yl)-4-methyl-2-(phenylamino)thiophene-3-carboxylate

ethyl 5-(1-(4-chlorophenyl)-1H-pyrazol-3-yl)-4-methyl-2-(phenylamino)thiophene-3-carboxylate

Conditions
ConditionsYield
In ethanol for 6h; Reflux;99%
N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

acetylacetone
123-54-6

acetylacetone

1-(4-chlorophenyl)-3, 5-dimethyl-1H-pyrazole
51560-55-5

1-(4-chlorophenyl)-3, 5-dimethyl-1H-pyrazole

Conditions
ConditionsYield
In neat (no solvent) at 120℃; for 0.166667h; Microwave irradiation;98%
In water; glycerol at 90℃; for 0.533333h; Green chemistry;96%
With Fe3O4(at)SiO2-bonded N-propyl-diethylenetetrasulfamic acid In water at 20℃; for 0.0833333h; Catalytic behavior; Green chemistry;95%
2-cyano-3-methylthio-3-p-toluenesulfonylaminopropenamide
131169-00-1

2-cyano-3-methylthio-3-p-toluenesulfonylaminopropenamide

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

5-amino-1-p-chlorophenyl-3-p-toluenesulfonylaminopyrazole-4-carboxamide
131168-95-1

5-amino-1-p-chlorophenyl-3-p-toluenesulfonylaminopyrazole-4-carboxamide

Conditions
ConditionsYield
at 100℃;98%
3-ethyl-2,4-pentanedione
1540-34-7

3-ethyl-2,4-pentanedione

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

1-(4-chlorophenyl)-4-ethyl-3,5-dimethyl-1H-pyrazole
1006613-71-3

1-(4-chlorophenyl)-4-ethyl-3,5-dimethyl-1H-pyrazole

Conditions
ConditionsYield
In neat (no solvent) at 120℃; for 0.25h; Microwave irradiation;98%
With glutathione-modified ferrite nanoparticles In water at 140℃; under 2585.81 - 9308.91 Torr; for 0.333333h; Microwave irradiation;84%
polystyrene supported sulfonic acid In water at 20℃; for 0.0333333h;80%
N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

1-butyn-4-ol
927-74-2

1-butyn-4-ol

1-(4-chlorophenyl)-3-methyl-4,5-dihydropyrazole
27301-76-4

1-(4-chlorophenyl)-3-methyl-4,5-dihydropyrazole

Conditions
ConditionsYield
With zinc trifluoromethanesulfonate In tetrahydrofuran at 100℃; for 24h; Inert atmosphere;98%
4-(4-methoxyphenyl)-2-butanone
104-20-1

4-(4-methoxyphenyl)-2-butanone

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

A

(Z)-1-(4-chlorophenyl)-2-(4-(4-methoxyphenyl)butan-2-ylidene)hydrazine
1381772-16-2

(Z)-1-(4-chlorophenyl)-2-(4-(4-methoxyphenyl)butan-2-ylidene)hydrazine

B

(E)-1-(4-chlorophenyl)-2-(4-(4-methoxyphenyl)butan-2-ylidene)hydrazine
1381772-13-9

(E)-1-(4-chlorophenyl)-2-(4-(4-methoxyphenyl)butan-2-ylidene)hydrazine

Conditions
ConditionsYield
In dichloromethane for 17h; Molecular sieve; Inert atmosphere; Reflux;A n/a
B 98%
N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

2-Benzoylcyclohexanone
3580-38-9

2-Benzoylcyclohexanone

2-(4-chlorophenyl)-3-phenyl-4,5,6,7-tetrahydro-2H-indazole

2-(4-chlorophenyl)-3-phenyl-4,5,6,7-tetrahydro-2H-indazole

Conditions
ConditionsYield
In neat (no solvent) at 150℃; for 0.166667h; Microwave irradiation; regioselective reaction;98%
allyl bromide
106-95-6

allyl bromide

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

2-ethyl-3-methyl-6-chloroquinoline
80609-90-1

2-ethyl-3-methyl-6-chloroquinoline

Conditions
ConditionsYield
With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II); cis-dichlorobis(triphenylphosphine)platinum(II); tris(o-methoxyphenyl)phosphine; N-ethyl-N,N-diisopropylamine In ethylene glycol at 20 - 75℃; for 8h; Reagent/catalyst; Solvent; Inert atmosphere;97.3%
cyclohexanone
108-94-1

cyclohexanone

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

6-chloro-1,2,3,4-tetrahydrocarbazole
36684-65-8

6-chloro-1,2,3,4-tetrahydrocarbazole

Conditions
ConditionsYield
With L-(+)-tartaric acid-urea melt at 70℃; for 0.5h; Fischer Indole Synthesis;97%
With aluminium trichloride; n-butylpyridinium chloride for 0.583333h; Fischer indole synthesis; Heating;92%
With 1,3-bis(3-sulfopropyl)-1H-imidazol-3-ium hydrogensulfate In water at 100℃; for 1h; Fischer indole synthesis;92%
3-chloropentane-2,4-dione
1694-29-7

3-chloropentane-2,4-dione

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

4-chloro-1-(4-chlorophenyl)-3,5-dimethyl-1H-pyrazole
1006613-70-2

4-chloro-1-(4-chlorophenyl)-3,5-dimethyl-1H-pyrazole

Conditions
ConditionsYield
In neat (no solvent) at 120℃; for 0.166667h; Microwave irradiation;97%
With tetrafluoroboric acid; water In acetonitrile at 20℃; for 4h;90%
With glutathione-modified ferrite nanoparticles In water at 140℃; under 2585.81 - 9308.91 Torr; for 0.333333h; Microwave irradiation;78%
n-octyne
629-05-0

n-octyne

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

5-chloro-2-methyl-3-pentylindole
1026711-57-8

5-chloro-2-methyl-3-pentylindole

Conditions
ConditionsYield
With zinc trifluoromethanesulfonate In tetrahydrofuran at 120℃; for 24h;97%
bromostyrene
103-64-0

bromostyrene

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

1-chloro-4-(2-phenylethynyl)benzene
5172-02-1

1-chloro-4-(2-phenylethynyl)benzene

Conditions
ConditionsYield
With dmap; zirconocene dichloride; dichloro(1,2-bis(diphenylphosphino)ethane)cobalt(II); 1-(1-ferrocenylethyl)-3-isopropyl-imidazolium iodide salt In 1,4-dioxane at 60℃; for 4h; Reagent/catalyst; Solvent; Inert atmosphere;96.5%
ethyl 5-oxohexanoate
13984-57-1

ethyl 5-oxohexanoate

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

Ethyl 5-chloro-2-methyl-1H-indole-3-propanoate
117752-80-4

Ethyl 5-chloro-2-methyl-1H-indole-3-propanoate

Conditions
ConditionsYield
96%
N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

acetylacetone
123-54-6

acetylacetone

1-(1-(4-chlorophenyl)-5-methyl-1H-pyrazol-4-yl)ethan-1-one
667866-04-8

1-(1-(4-chlorophenyl)-5-methyl-1H-pyrazol-4-yl)ethan-1-one

Conditions
ConditionsYield
at 70℃; for 0.0166667h; Neat (no solvent); regioselective reaction;96%
With 2,2,2-trifluoroethanol at 20℃; for 0.166667h; regioselective reaction;95%
3-acetyl-4-chloro-6-methyl-2H-pyran-2-one
83516-81-8

3-acetyl-4-chloro-6-methyl-2H-pyran-2-one

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

4-[2-(4-chlorophenyl)hydrazinyl]-3-acetyl-6-methyl-2H-pyran-2-one
1370350-15-4

4-[2-(4-chlorophenyl)hydrazinyl]-3-acetyl-6-methyl-2H-pyran-2-one

Conditions
ConditionsYield
In ethanol at 20℃;96%
benzyl acetoacetate
5396-89-4

benzyl acetoacetate

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

1-(4-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid benzyl ester
1379475-40-7

1-(4-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid benzyl ester

Conditions
ConditionsYield
at 70℃; for 0.0166667h; Neat (no solvent); regioselective reaction;96%
4-(4-chlorophenyl)butan-2-one
3506-75-0

4-(4-chlorophenyl)butan-2-one

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

A

(Z)-1-(4-chlorophenyl)-2-(4-(4-chlorophenyl)butan-2-ylidene)hydrazine
1381772-22-0

(Z)-1-(4-chlorophenyl)-2-(4-(4-chlorophenyl)butan-2-ylidene)hydrazine

B

(E)-1-(4-chlorophenyl)-2-(4-(4-chlorophenyl)butan-2-ylidene)hydrazine
1381772-18-4

(E)-1-(4-chlorophenyl)-2-(4-(4-chlorophenyl)butan-2-ylidene)hydrazine

Conditions
ConditionsYield
In dichloromethane for 17h; Molecular sieve; Inert atmosphere; Reflux;A n/a
B 96%
2-benzylcyclohexan-1-one
946-33-8

2-benzylcyclohexan-1-one

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

A

(Z)-1-(2-benzylcyclohexylidene)-2-(4-chlorophenyl)hydrazine
1381772-38-8

(Z)-1-(2-benzylcyclohexylidene)-2-(4-chlorophenyl)hydrazine

B

(E)-1-(2-benzylcyclohexylidene)-2-(4-chlorophenyl)hydrazine
1381772-34-4

(E)-1-(2-benzylcyclohexylidene)-2-(4-chlorophenyl)hydrazine

Conditions
ConditionsYield
In dichloromethane for 17h; Molecular sieve; Inert atmosphere; Reflux;A n/a
B 96%
(Z)-3-(furan-2-yl)-3-hydroxy-1-(thiophen-2-yl)prop-2-ene-1-thione
1432595-93-1

(Z)-3-(furan-2-yl)-3-hydroxy-1-(thiophen-2-yl)prop-2-ene-1-thione

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

1-(4-chlorophenyl)-5-(furan-2-yl)-3-(thiophen-2-yl)-1H-pyrazole
86201-92-5

1-(4-chlorophenyl)-5-(furan-2-yl)-3-(thiophen-2-yl)-1H-pyrazole

Conditions
ConditionsYield
In ethanol for 4h; Reflux; regioselective reaction;96%
N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

rimonabant acid
162758-35-2

rimonabant acid

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid N’-(4-chlorophenyl)-hydrazide

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid N’-(4-chlorophenyl)-hydrazide

Conditions
ConditionsYield
Stage #1: rimonabant acid With isobutyl chloroformate In tetrahydrofuran at -20 - -10℃; for 0.333333h;
Stage #2: N-4-chlorophenylhydrazine In tetrahydrofuran at -20 - -10℃; for 1h;
96%
BOC-glycine
4530-20-5

BOC-glycine

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

tert-butyl (2-(2-(4-chlorophenyl)hydrazineyl)-2-oxoethyl)carbamate

tert-butyl (2-(2-(4-chlorophenyl)hydrazineyl)-2-oxoethyl)carbamate

Conditions
ConditionsYield
Stage #1: BOC-glycine With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.25h;
Stage #2: N-4-chlorophenylhydrazine In tetrahydrofuran at 0 - 20℃; for 1.5h;
96%
4-Chlorophenyl isothiocyanate
2131-55-7

4-Chlorophenyl isothiocyanate

N-4-chlorophenylhydrazine
1073-69-4

N-4-chlorophenylhydrazine

1,4-bis-(4-chloro-phenyl)-thiosemicarbazide
119379-84-9

1,4-bis-(4-chloro-phenyl)-thiosemicarbazide

Conditions
ConditionsYield
With agar at 20℃; for 0.25h;95%
at 50℃; microwave irradiation;95.5%

1073-69-4Relevant articles and documents

Solid-supported sulfonylhydroxylamine as an effective N-animating agent of anilines

Ohno, Hiroshi,Tanaka, Hiroshi,Takahashi, Takashi

, p. 1191 - 1194 (2005)

An effective method for the synthesis of aryl hydrazines by amination of anilines using the solid-supported phenylsulfonylhydroxylamine was described. Treatment of aniline with the solid-supported aminating agent, followed by removal of the resin, provided the corresponding hydrazine in 21% yield. The resulting hydrazines were directly adapted to the solid-phase synthesis of indoles, providing nine naltrindole derivatives varying the substituents on the aromatic rings.

Cross-Coupling between Hydrazine and Aryl Halides with Hydroxide Base at Low Loadings of Palladium by Rate-Determining Deprotonation of Bound Hydrazine

Borate, Kailaskumar,Choi, Kyoungmin,Goetz, Roland,Hartwig, John F.,Shinde, Harish,Wang, Justin Y.,Zuend, Stephan J.

supporting information, p. 399 - 408 (2020/10/29)

Reported here is the Pd-catalyzed C–N coupling of hydrazine with (hetero)aryl chlorides and bromides to form aryl hydrazines with catalyst loadings as low as 100 ppm of Pd and KOH as base. Mechanistic studies revealed two catalyst resting states: an arylpalladium(II) hydroxide and arylpalladium(II) chloride. These compounds are present in two interconnected catalytic cycles and react with hydrazine and base or hydrazine alone to give the product. The selectivity of the hydroxide complex with hydrazine to form aryl over diaryl hydrazine was lower than that of the chloride complex, as well as the catalytic reaction. In contrast, the selectivity of the chloride complex closely matched that of the catalytic reaction, indicating that the aryl hydrazine is derived from this complex. Kinetic studies showed that the coupling process occurs by rate-limiting deprotonation of a hydrazine-bound arylpalladium(II) chloride complex to give an arylpalladium(II) hydrazido complex.

PROCESS FOR THE SYNTHESIS OF ARYL HYDRAZINES

-

Page/Page column 21-23; 25; 26; 30; 31; 34; 35, (2020/06/01)

The invention relates to a process for the synthesis of aryl hydrazinesof formula I or a salt thereof, which process comprises subjecting an arene of formula II to a coupling reaction with hydrazine or a derivative thereof, wherein the coupling reaction is conducted in the presence of a catalyst comprising palladium and a diphosphine ligand, wherein the phosphorus atoms are connected through two, three, four, or five atoms selected from car- bon, nitrogen, oxygen or iron, and in which the non-connecting phosphorus substituents are C1- C 10-alkyl or C3-C10-cycloalkyl, wherein the amount of Pd used is up to 0.5 mol-% relative to the amount of arene of formula II; and a base.

Method for synthesizing 1-(2,4-dichlorophenyl)-3-methyl-4-difluoromethyl-1,2,4-triazole-5-ketone

-

Paragraph 0056; 0057, (2018/03/28)

The invention discloses a method for synthesizing 1-(2,4-dichlorophenyl)-3-methyl-4-difluoromethyl-1,2,4-triazole-5-ketone. The method takes p-chloroaniline as a raw material, through diazotization, reduction, and salt forming, p-chlorophenylhydrazine hydrochloride is synthesized, p-chlorophenylhydrazine is obtained through alkali neutralization, under condition that tert-butyl alcohol is taken asa solvent, chlorophenylhydrazine, acetaldehyde, sodium cyanate and sodium hypochlorite are subjected to condensation, cyclisation and an oxidation reaction to generate 1-p-chlorophenyl-3-methyl-1H-1,2,4-triazole-5-ketone, and the 1-p-chlorophenyl-3-methyl-1H-1,2,4-triazole-5-ketone is subjected to salt forming, reaction with chlorodifluoromethane, and chlorination to obtain the 1-(2,4-dichlorophenyl)-3-methyl-4-difluoromethyl-1,2,4-triazole-5-ketone (a sulfentrazone intermediate). The synthetic method takes p-chloroanniline as the raw material, the synthetic method is realized by only one-time chlorination, steric hindrance for intermediate synthesis is small, and the impurity is low, so that the yield is increased; in addition, the raw materials required by the synthesis route are easilyacquired, the cost is low, the condition is mild, operation is simple, security is high, and the synthesis method is in favor of realizing industrial production.

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