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4752-10-7

4752-10-7

Identification

Synonyms:Phthalazine,1,4-dichloro-;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:1,4-Dichlorophthalazine
  • Packaging:1g
  • Price:$ 55
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:1,4-Dichlorophthalazine >98.0%(GC)
  • Packaging:1g
  • Price:$ 42
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  • Manufacture/Brand:TCI Chemical
  • Product Description:1,4-Dichlorophthalazine >98.0%(GC)
  • Packaging:5g
  • Price:$ 126
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1,4-Dichlorophthalazine 95%
  • Packaging:5g
  • Price:$ 109
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1,4-Dichlorophthalazine 95%
  • Packaging:1g
  • Price:$ 55.4
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:1,4-Dichlorophthalazine
  • Packaging:10 g
  • Price:$ 2200
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:1,4-Dichlorophthalazine 95%
  • Packaging:5g
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:1,4-Dichlorophthalazine 95%
  • Packaging:25g
  • Price:$ 286
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  • Manufacture/Brand:Heterocyclics
  • Product Description:1,4-Dichlorophthalazine 97%
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  • Manufacture/Brand:Heterocyclics
  • Product Description:1,4-Dichlorophthalazine 97%
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Relevant articles and documentsAll total 42 Articles be found

Synthesis and anti-inflammatory activity evaluation of a novel series of 6-phenoxy-[1,2,4]triazolo[3,4-a]phthalazine-3-carboxamide derivatives

Liu, Da-Chuan,Gong, Guo-Hua,Wei, Cheng-Xi,Jin, Xue-Jun,Quan, Zhe-Shan

, p. 1576 - 1579 (2016)

The transcription factor nuclear factor-κB (NF-κB) controls many physiological processes including inflammation, immunity, and apoptosis. In this study, a novel series of 6-phenoxy-[1,2,4]triazolo[3,4-a]phthalazine-3-carboxamide derivatives were synthesized as potent anti-inflammatory agents, which acted on tumor necrosis factor (TNF-α) as inhibitors of NF-κB activation. We showed that compounds 6h (6-(2,4-dichlorophenoxy)-[1,2,4]triazolo[3,4-a]phthalazine-3-carboxamide) and 6i (6-(3-tolyloxy)-[1,2,4]triazolo[3,4-a]phthalazine-3-carboxamide) showed more prominent anti-inflammatory activity than other compounds, with similar activities as the reference drug dihydrotanshinone; compound 6i showed the lowest cellular toxicity among the tested compounds. In vivo evaluation of the anti-inflammatory activity showed that compound 6i exhibited excellent anti-inflammatory activity with 58.19% inhibition at 50?mg/kg intraperitoneal (i.p.), with equal efficacy as the positive control indomethacin (100?mg/kg i.p.; 59.21% inhibition).

Discovery of novel triazolophthalazine derivatives as DNA intercalators and topoisomerase II inhibitors

Sakr, Helmy,Ayyad, Rezk R.,El-Helby, Ali A.,Khalifa, Mohamed M.,Mahdy, Hazem A.

, (2021/02/16)

A new series of triazolophthalazine derivatives was designed and synthesized as topoisomerase II (Topo II) inhibitors and DNA intercalators. The synthesized derivatives were evaluated in vitro for their cytotoxic activities against three human cancer cell lines: HepG2, MCF-7, and HCT-116 cells. Compound IXb was the most potent counterpart with IC50 values of 5.39 ± 0.4, 3.81 ± 0.2, and 4.38 ± 0.3 μM, as it was about 1.47, 1.77, and 1.19 times more active than doxorubicin (IC50 = 7.94 ± 0.6, 6.75 ± 0.4, and 5.23 ± 0.3 μM) against HepG2, MCF-7, and HCT-116 cells, respectively. Additionally, the binding affinity of the synthesized compounds toward the DNA molecule was assessed using the DNA/methyl green assay. Compound?IXb showed an excellent DNA binding affinity with an IC50 value of 27.16 ± 1.2 μM, which was better than that of the reference drug doxorubicin (IC50 = 31.02 ± 1.80 μM). Moreover, compound IXb was the most potent member among the tested compounds when investigated for their Topo II inhibitory activity. Furthermore, compound IXb induced apoptosis in HepG2 cells and arrested the cell cycle at the G2/M phase. Additionally, compound IXb showed Topo II poisoning effects at 2.5 μM and Topo II catalytic inhibitory effects at 5 and 10 μM. Finally, molecular docking studies were carried out against the DNA–Topo II complex and DNA, to investigate the binding patterns of the designed compounds.

Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis

Wang, Jian,Li, Yan-Hui,Pan, Song-Cheng,Li, Ming-Fang,Du, Wenting,Yin, Hong,Li, Jing-Hua

supporting information, p. 146 - 153 (2020/03/10)

The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.

Process route upstream and downstream products

Process route

PHTHALAZINE
253-52-1

PHTHALAZINE

1-chlorophthalazine
5784-45-2

1-chlorophthalazine

1,4-dichlorophthalazine
4752-10-7

1,4-dichlorophthalazine

Conditions
Conditions Yield
With trichloroisocyanuric acid; In N,N-dimethyl-formamide; at 40 - 50 ℃;
2,3-dihydrophthalazine-1,4-dione
1445-69-8

2,3-dihydrophthalazine-1,4-dione

1,4-dichlorophthalazine
4752-10-7

1,4-dichlorophthalazine

Conditions
Conditions Yield
With chlorine; phosphorus trichloride; In chloroform; at 105 ℃; under 7500.75 Torr; Reagent/catalyst; Temperature;
97.9%
With pyridine; trichlorophosphate; for 1h; Reflux;
93%
With trichlorophosphate; at 110 ℃; for 1h;
90.1%
With trichlorophosphate; at 110 ℃; for 1h;
90%
With trichlorophosphate; at 110 ℃;
90%
With trichlorophosphate; at 106 ℃;
90%
With N,N-dimethyl-formamide; trichlorophosphate; Heating;
90%
With trichlorophosphate; In ethanol; for 4h; Reflux;
85%
With trichlorophosphate; Reflux;
84%
With trichlorophosphate; at 110 ℃; for 1h;
83%
With trichlorophosphate; for 4h; Reflux;
83.5%
With phosphorus pentachloride; N,N-dimethyl-formamide; for 7h; Heating; Inert atmosphere;
81%
With trichlorophosphate; for 4h; Reflux;
81.2%
With trichlorophosphate; for 4h; Reflux;
81.99%
With phosphorus pentachloride; N,N-dimethyl-formamide; at 145 ℃; for 8h; Inert atmosphere;
81%
With trichlorophosphate; Reflux;
81%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; phosphorus trichloride; In acetonitrile; at 50 - 72 ℃; for 10h; Reagent/catalyst; Temperature; Autoclave; Large scale;
80%
With phosphorus pentachloride; N,N-dimethyl-formamide; 1.) r.t. -> 145 deg C, 60 min, 2.) 145 deg C, 4 h;
78%
With trichlorophosphate; In N,N-dimethyl-formamide; for 2h; Heating / reflux;
39%
With N,N-dimethyl-formamide; trichlorophosphate; for 2h; Inert atmosphere; Reflux;
22.8%
With trichlorophosphate; In N,N-dimethyl-formamide; for 2h; Reflux;
22.8%
With phosphorus pentachloride;
With trichlorophosphate;
With trichlorophosphate; Reflux;
With trichlorophosphate; at 110 ℃; for 4h;
With trichlorophosphate; for 4h; Reflux;
9 g
With triethylamine; trichlorophosphate; for 4h; Reflux;
With trichlorophosphate; at 110 ℃; for 3h;
With trichlorophosphate; at 80 - 110 ℃; for 1h;
With trichlorophosphate; at 80 - 110 ℃; for 1h;
With trichlorophosphate;
With trichlorophosphate; at 110 ℃; for 1h;
With trichlorophosphate; for 3h; Inert atmosphere; Reflux;
With trichlorophosphate; for 1h; Heating;
phthalic anhydride
85-44-9

phthalic anhydride

1,4-dichlorophthalazine
4752-10-7

1,4-dichlorophthalazine

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 140 °C
2: N2H4+H2O; acetic acid
3: PCl5
With phosphorus pentachloride; hydrazine hydrate; acetic acid;
Multi-step reaction with 3 steps
1: acetic acid
2: N2H4+H2O; acetic acid
3: PCl5
With phosphorus pentachloride; hydrazine hydrate; acetic acid;
Multi-step reaction with 3 steps
1: 140 °C
2: N2H4+H2O; acetic acid
3: PCl5
With phosphorus pentachloride; hydrazine hydrate; acetic acid;
Multi-step reaction with 3 steps
1: acetic acid; hydrazine hydrate / in geringer Menge
2: 200 °C
3: PCl5
With phosphorus pentachloride; hydrazine hydrate; acetic acid;
Multi-step reaction with 4 steps
1: acetic acid; hydrazine hydrate / in geringer Menge
2: acetic acid
3: N2H4+H2O; acetic acid
4: PCl5
With phosphorus pentachloride; hydrazine hydrate; acetic acid;
Multi-step reaction with 2 steps
1: hydrazine hydrate / ethanol / 1 h / 85 °C / Inert atmosphere
2: phosphorus pentachloride; N,N-dimethyl-formamide / 4 h / 145 °C / Inert atmosphere
With phosphorus pentachloride; hydrazine hydrate; N,N-dimethyl-formamide; In ethanol;
Multi-step reaction with 2 steps
1: hydrazine hydrate / acetic acid / 4 h / 120 °C
2: trichlorophosphate / 1 h / 110 °C
With hydrazine hydrate; trichlorophosphate; In acetic acid;
Multi-step reaction with 2 steps
1: hydrazine hydrate / ethanol / 12 h / Reflux
2: trichlorophosphate; triethylamine / 4 h / Reflux
With hydrazine hydrate; triethylamine; trichlorophosphate; In ethanol;
Multi-step reaction with 2 steps
1: hydrazine hydrate; acetic acid / 4 h / 120 °C
2: trichlorophosphate / 1 h / 110 °C
With hydrazine hydrate; acetic acid; trichlorophosphate;
Multi-step reaction with 2 steps
1: hydrazine hydrate; acetic acid / 2 h / 0 - 125 °C / Inert atmosphere
2: trichlorophosphate; N,N-dimethyl-formamide / 2 h / Inert atmosphere; Reflux
With hydrazine hydrate; acetic acid; N,N-dimethyl-formamide; trichlorophosphate;
Multi-step reaction with 2 steps
1: hydrazine hydrate; acetic acid / acetic acid / 2 h / 0 - 125 °C
2: trichlorophosphate / N,N-dimethyl-formamide / 2 h / Reflux
With hydrazine hydrate; acetic acid; trichlorophosphate; In acetic acid; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: acetic acid; hydrazine hydrate / 4 h / 120 °C
2: trichlorophosphate / 1 h / 110 °C
With hydrazine hydrate; acetic acid; trichlorophosphate;
Multi-step reaction with 2 steps
1: acetic acid; hydrazine hydrate / 4 h / 120 °C / Reflux
2: trichlorophosphate / 1 h / 80 - 110 °C
With hydrazine hydrate; acetic acid; trichlorophosphate;
Multi-step reaction with 2 steps
1: hydrazine hydrate; acetic acid / water / 4 h / Reflux
2: trichlorophosphate / 1 h / 80 - 110 °C
With hydrazine hydrate; acetic acid; trichlorophosphate; In water;
Multi-step reaction with 2 steps
1: hydrazine hydrate; acetic acid
2: trichlorophosphate
With hydrazine hydrate; acetic acid; trichlorophosphate;
Multi-step reaction with 2 steps
1: hydrazine hydrate; acetic acid / Reflux
2: trichlorophosphate / Reflux
With hydrazine hydrate; acetic acid; trichlorophosphate;
Multi-step reaction with 2 steps
1: hydrazine hydrate; acetic acid / 3 h / Reflux
2: trichlorophosphate / 1 h / 110 °C
With hydrazine hydrate; acetic acid; trichlorophosphate;
Multi-step reaction with 2 steps
1: hydrogenchloride; hydrazine hydrate / quinoline / 24 h / Reflux
2: trichlorophosphate / 3 h / Inert atmosphere; Reflux
With hydrogenchloride; hydrazine hydrate; trichlorophosphate; In quinoline;
Multi-step reaction with 2 steps
1: hydrazine hydrate; acetic acid / 120 °C
2: trichlorophosphate / 110 °C
With hydrazine hydrate; acetic acid; trichlorophosphate;
Multi-step reaction with 2 steps
1: hydrazine hydrate; acetic acid / 120 °C
2: trichlorophosphate / 106 °C
With hydrazine hydrate; acetic acid; trichlorophosphate;
Multi-step reaction with 2 steps
1: hydrazine hydrate / ethanol / 5 h / Reflux
2: trichlorophosphate / 1 h / Heating
With hydrazine hydrate; trichlorophosphate; In ethanol;
phthalic anhydride; With hydrazine hydrate; In ethanol; at 70 ℃; for 3h;
With N,N-dimethyl-formamide; trichlorophosphate; for 3h; Reflux;
1,4-dihydroxyphthalazine
1445-69-8

1,4-dihydroxyphthalazine

1,4-dichlorophthalazine
4752-10-7

1,4-dichlorophthalazine

Conditions
Conditions Yield
With dmap; thionyl chloride; bis(trichloromethyl) carbonate; for 8h; Reflux; Green chemistry;
97%
With phosphorus pentachloride; N,N-dimethyl-formamide; at 145 ℃; for 4h; Inert atmosphere;
75%
With phosphorus pentachloride; trichlorophosphate; for 5h; Heating;
6.3 g
With trichlorophosphate; In 1,2-dichloro-ethane;
1,4-dichlorophthalazine
4752-10-7

1,4-dichlorophthalazine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: alcohol; hydrazine hydrate
2: PCl5
With ethanol; phosphorus pentachloride; hydrazine hydrate;
Multi-step reaction with 3 steps
1: ethanol; hydrazine hydrate / anschliessenden Erwaermen
2: 200 °C
3: PCl5
With ethanol; phosphorus pentachloride; hydrazine hydrate;
Multi-step reaction with 4 steps
1: ethanol; hydrazine hydrate / anschliessenden Erwaermen
2: acetic acid
3: N2H4+H2O; acetic acid
4: PCl5
With ethanol; phosphorus pentachloride; hydrazine hydrate; acetic acid;
Multi-step reaction with 2 steps
1: hydrazine hydrate / ethanol / 70 °C / Cooling with ice
2: trichlorophosphate / ethanol / 4 h / Reflux
With hydrazine hydrate; trichlorophosphate; In ethanol;
Multi-step reaction with 2 steps
1: hydrazine hydrate / neat (no solvent) / 4 h / Reflux
2: trichlorophosphate; N,N-dimethyl-formamide / Heating
With hydrazine hydrate; N,N-dimethyl-formamide; trichlorophosphate; In neat (no solvent);
N-aminophthalamide
1875-48-5

N-aminophthalamide

1,4-dichlorophthalazine
4752-10-7

1,4-dichlorophthalazine

Conditions
Conditions Yield
With trichlorophosphate; at 200 ℃; im Autoklaven;
Multi-step reaction with 2 steps
1: 200 °C
2: PCl5
With phosphorus pentachloride;
Multi-step reaction with 3 steps
1: acetic acid
2: N2H4+H2O; acetic acid
3: PCl5
With phosphorus pentachloride; hydrazine hydrate; acetic acid;
With trichlorophosphate; at 200 ℃; im Autoklaven;
PHTHALAZINE
253-52-1

PHTHALAZINE

1,4-dichlorophthalazine
4752-10-7

1,4-dichlorophthalazine

Conditions
Conditions Yield
With phosphorus pentachloride; at 210 - 230 ℃; for 30h;
<i>N</i>,<i>N</i>'-bis-(2-methoxycarbonyl-benzoyl)-hydrazine

N,N'-bis-(2-methoxycarbonyl-benzoyl)-hydrazine

1,4-dichlorophthalazine
4752-10-7

1,4-dichlorophthalazine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: aqueous H2SO4
2: PCl5
With phosphorus pentachloride; sulfuric acid;
Multi-step reaction with 3 steps
1: acetic acid
2: N2H4+H2O; acetic acid
3: PCl5
With phosphorus pentachloride; hydrazine hydrate; acetic acid;
phthalic monoacid monomethyl ester chloride
4397-55-1

phthalic monoacid monomethyl ester chloride

1,4-dichlorophthalazine
4752-10-7

1,4-dichlorophthalazine

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: pyridine; hydrazine hydrate
2: aqueous H2SO4
3: PCl5
With pyridine; phosphorus pentachloride; sulfuric acid; hydrazine hydrate;
Multi-step reaction with 4 steps
1: pyridine; hydrazine hydrate
2: acetic acid
3: N2H4+H2O; acetic acid
4: PCl5
With pyridine; phosphorus pentachloride; hydrazine hydrate; acetic acid;
benzene-1,2-dicarboxylic acid
88-99-3,73607-73-5

benzene-1,2-dicarboxylic acid

1,4-dichlorophthalazine
4752-10-7

1,4-dichlorophthalazine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: NH2NH2*H2SO4
2: POCl3
With hydrazinium sulfate; trichlorophosphate;

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