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Cas Database

42135-76-2

42135-76-2

Identification

  • Product Name:Hydrazinecarbothioamide,N-(3-chlorophenyl)-

  • CAS Number: 42135-76-2

  • EINECS:

  • Molecular Weight:201.68

  • Molecular Formula: C7H8ClN3S

  • HS Code:2930909090

  • Mol File:42135-76-2.mol

Synonyms:Semicarbazide,4-(m-chlorophenyl)-3-thio- (6CI);4-(3-Chlorophenyl)thiosemicarbazide;4-(m-Chlorophenyl)-3-thiosemicarbazide;NSC 132373;

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Safety information and MSDS view more

  • Pictogram(s):R25:Toxic if swallowed.;

  • Hazard Codes:R25:Toxic if swallowed.;

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowed

  • 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

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:4-(3-Chlorophenyl)-3-thiosemicarbazide
  • Packaging:500mg
  • Price:$ 60
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-(3-Chlorophenyl)-3-thiosemicarbazide
  • Packaging:5 g
  • Price:$ 134
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-(3-Chlorophenyl)-3-thiosemicarbazide
  • Packaging:1 g
  • Price:$ 55
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:4-(3-Chlorophenyl)-3-thiosemicarbazide
  • Packaging:5g
  • Price:$ 82
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  • Manufacture/Brand:Crysdot
  • Product Description:N-(3-Chlorophenyl)hydrazinecarbothioamide 95+%
  • Packaging:100g
  • Price:$ 638
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:4-(3-CHLOROPHENYL)-3-THIOSEMICARBAZIDE 95.00%
  • Packaging:5G
  • Price:$ 840.84
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:4-(3-CHLOROPHENYL)-3-THIOSEMICARBAZIDE 95.00%
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:4-(3-Chlorophenyl)-3-thiosemicarbazide, 98+%
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:4-(3-Chlorophenyl)-3-thiosemicarbazide, 98+%
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  • Manufacture/Brand:AK Scientific
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Relevant articles and documentsAll total 16 Articles be found

Synthesis, characterization, and antioxidant activity of some new N 4-arylsubstituted-5-methoxyisatin-β-thiosemicarbazone derivatives

Mu?lu, Halit

, p. 2083 - 2098 (2020/01/13)

Abstract: Firstly, thiosemicarbazides were prepared by the reaction of hydrazine monohydrate with isothiocyanates in cold dry ethanol at 0?°C for 1?h. After that, new isatin-β-thiosemicarbazones were synthesized by treatment of 5-methoxyisatin with thiose

Synthesis and antitumor activity of novel pyridazinone derivatives containing 1,3,4-thiadiazole moiety

Qin, Junhu,Zhu, Mei,Zhu, Hongmei,Zhang, Liqiong,Fu, Yihong,Liu, Jiamin,Wang, Zhenchao,OuYang, Guiping

, p. 592 - 599 (2020/03/16)

A series of novel pyridazinone derivatives containing the 1,3,4-thiadiazole moiety were synthesized and characterized by 1H NMR, 13C NMR, spectroscopies HRMS and IR. Among them, the structure of compound 5c (2-(Tert-butyl)?4-chloro-5-((5-((2-ethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was unambiguously confirmed via single crystal X-ray diffraction analysis. The inhibitory activity of all the target compounds against MGC-803 and Bcap-37 was determined by MTT assay, with doxorubicin (the inhibition rates were 95.5 ± 0.4% and 95.7 ± 1.0% respectively) as a control. The preliminary results showed that the inhibitory activity of compound 5n (2-(Tert-butyl)?4-chloro-5-((5-((3-fluorophenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was superior to the others. The inhibition rates of MGC-803 and Bcap-37 cells were 86.3 ± 2.2% and 92.3 ± 0.6% at a concentration of 10 μmol/L, respectively. The preliminary structure-activity relationship showed that when the 2-position of the benzene ring was substituted by a methyl group, such as compound 5j (2-(Tert-butyl)?4-chloro-5-((5-((2,3-dimethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), it exhibited good anticancer activity on MGC-803 cells. Besides, introducing fluorine, chlorine, or trifluoromethyl group onto the benzene ring, such as compound 5 m (2-(Tert-butyl)?4-chloro-5-((5-((4-(trifluoromethoxy)phenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), displayed good anticancer activity on MGC-803 and Bcap-37 cells.

Synthesis, molecular modeling and antiviral activity of novel 5-fluoro-1H-indole-2,3-dione 3-thiosemicarbazones

?zbil, Mehmet,Duran, Gizem Nur,Karal?, Nilgün,Sevin?li, Zekiye ?eyma

, (2020/09/07)

In this work, novel 5-fluoro-1-methyl/ethyl-1H-indole-2,3-dione 3-[4-(substituted phenyl)-thiosemicarbazones] 6a-n and 7a-n were synthesized. The antiviral effects of the compounds were tested against HSV-1 (KOS), HSV-2 (G) HSV-1 TK- KOS ACVr and VV in HEL cell cultures using acyclovir and ganciclovir as standards, and Coxsackie B4 virus in Vero cell cultures using ribavirin and mycophenolic acid as standards. R2 ethyl substituted 7 derivatives were found effective against viruses tested. R1 4-CF3 substituted 7d, R1 4-OCH3 substituted 7 g and R1 3-Cl substituted 7 l showed activity against HSV-1 (KOS), HSV-2 (G) HSV-1 TK- KOS ACVr and VV. Whereas only R1 4-Br substituted 7n has selective activity against coxsackie B4 virus. Molecular modeling studies of 7d and 7l were performed to determine binding side on HSV-1 glycoprotein B and D, HSV-2 glycoprotein B structures.

Preparation, structure elucidation, and antioxidant activity of new bis(thiosemicarbazone) derivatives

Yakan, Hasan

, p. 1085 - 1099 (2020/09/16)

Schiff-base–bearing new bis(thiosemicarbazone) derivatives were prepared from terephthalaldehyde and various thiosemicarbazides. FT–IR, 1 H NMR, 13 C NMR, and UV–Vis spectroscopic methods and elemental analysis were used to elucidate

Functionalized Oxoindolin Hydrazine Carbothioamide Derivatives as Highly Potent Inhibitors of Nucleoside Triphosphate Diphosphohydrolases

Afzal, Saira,Hameed, Abdul,Iqbal, Jamshed,Pelletier, Julie,Sévigny, Jean,al-Rashida, Mariya

, (2020/12/18)

Ectonucleoside triphosphate diphosphohydrolases (NTPDases) are ectoenzymes that play an important role in the hydrolysis of nucleoside triphosphate and diphosphate to nucleoside monophosphate. NTPDase1, -2, -3 and -8 are the membrane bound members of this enzyme family that are responsible for regulating the levels of nucleotides in extracellular environment. However, the pathophysiological functions of these enzymes are not fully understood due to lack of potent and selective NTPDase inhibitors. Herein, a series of oxoindolin hydrazine carbothioamide derivatives is synthesized and screened for NTPDase inhibitory activity. Four compounds were identified as selective inhibitors of h-NTPDase1 having IC50 values in lower micromolar range, these include compounds 8b (IC50 = 0.29 ± 0.02 μM), 8e (IC50 = 0.15 ± 0.009 μM), 8f (IC50 = 0.24 ± 0.01 μM) and 8l (IC50 = 0.30 ± 0.03 μM). Similarly, compound 8k (IC50 = 0.16 ± 0.01 μM) was found to be a selective h-NTPDase2 inhibitor. In case of h-NTPDase3, most potent inhibitors were compounds 8c (IC50 = 0.19 ± 0.02 μM) and 8m (IC50 = 0.38 ± 0.03 μM). Since NTPDase3 has been reported to be associated with the regulation of insulin secretion, we evaluated our synthesized NTPDase3 inhibitors for their ability to stimulate insulin secretion in isolated mice islets. Promising results were obtained showing that compound 8m potently stimulated insulin secretion without affecting the NTPDase3 gene expression. Molecular docking studies of the most potent compounds were also carried out to rationalize binding site interactions. Hence, these compounds are useful tools to study the role of NTPDase3 in insulin secretion.

Process route upstream and downstream products

Process route

3-chlorophenyl-isothiocyanate
2392-68-9

3-chlorophenyl-isothiocyanate

4-(3-chlorophenyl)-3-thiosemicarbazide
42135-76-2

4-(3-chlorophenyl)-3-thiosemicarbazide

Conditions
Conditions Yield
With hydrazine; In water; isopropyl alcohol; at 20 ℃; for 0.5h;
85%
With hydrazine hydrate; In isopropyl alcohol; at 20 ℃; for 3h; Inert atmosphere;
66%
With ethanol; hydrazine hydrate; unter Kuehlung;
With sodium monochloroacetic acid; hydrazine; In ethanol; for 4h; Yield given; Ambient temperature;
With hydrazine; In dichloromethane; water; for 1h;
With hydrazine hydrate; In dichloromethane; at 20 ℃; for 4h;
With hydrazine hydrate; In methanol; at 20 ℃; for 24.25h; Cooling with ice;
With hydrazine hydrate; In ethanol; Cooling with ice;
With hydrazine hydrate; In isopropyl alcohol; at 25 ℃; for 2h;
With hydrazine hydrate; In ethanol; Cooling with ice;
With hydrazine hydrate; In ethanol; Cooling with ice;
With hydrazine hydrate; In ethanol; for 0.5h; Cooling with ice;
C<sub>7</sub>H<sub>6</sub>ClNS<sub>2</sub>

C7H6ClNS2

4-(3-chlorophenyl)-3-thiosemicarbazide
42135-76-2

4-(3-chlorophenyl)-3-thiosemicarbazide

Conditions
Conditions Yield
With sodium monochloroacetic acid; hydrazine hydrate; In water;
With sodium monochloroacetic acid; hydrazine hydrate; at 60 ℃; for 4h;
3-chloro-aniline
108-42-9

3-chloro-aniline

4-(3-chlorophenyl)-3-thiosemicarbazide
42135-76-2

4-(3-chlorophenyl)-3-thiosemicarbazide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: liq. NH3 / -30 °C
2: hydrazine hydrate, sodium chloroacetate / aq. ethanol
With ammonia; sodium monochloroacetic acid; hydrazine hydrate; In ethanol;
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / chloroform; water / 1 h / 20 °C
2: hydrazine / dichloromethane; water / 1 h
With sodium hydrogencarbonate; hydrazine; In dichloromethane; chloroform; water;
Multi-step reaction with 2 steps
1: ammonia / ethanol / Cooling with ice
2: sodium monochloroacetic acid; hydrazine hydrate / water
With ammonia; sodium monochloroacetic acid; hydrazine hydrate; In ethanol; water;
Multi-step reaction with 2 steps
1: ammonia / ethanol / 15 - 20 °C
2: sodium monochloroacetic acid; hydrazine hydrate / 4 h / 60 °C
With ammonia; sodium monochloroacetic acid; hydrazine hydrate; In ethanol;
Multi-step reaction with 2 steps
1.1: triethylamine / 12 h / Cooling with ice
1.2: 6 h / 25 °C
2.1: hydrazine hydrate / isopropyl alcohol / 2 h / 25 °C
With hydrazine hydrate; triethylamine; In isopropyl alcohol;
C<sub>7</sub>H<sub>6</sub>ClNS<sub>2</sub>

C7H6ClNS2

sodium monochloroacetic acid
3926-62-3

sodium monochloroacetic acid

4-(3-chlorophenyl)-3-thiosemicarbazide
42135-76-2

4-(3-chlorophenyl)-3-thiosemicarbazide

Conditions
Conditions Yield
C7H6ClNS2; sodium monochloroacetic acid; In ethanol;
With hydrazine hydrate; In ethanol; at 60 ℃; for 4h;
ammonium salt of N-m-chlorophenylamino dithiocarbamic acid

ammonium salt of N-m-chlorophenylamino dithiocarbamic acid

4-(3-chlorophenyl)-3-thiosemicarbazide
42135-76-2

4-(3-chlorophenyl)-3-thiosemicarbazide

Conditions
Conditions Yield
With sodium monochloroacetic acid; hydrazine hydrate; In ethanol;
3-chloro-aniline
108-42-9

3-chloro-aniline

4-(3-chlorophenyl)-3-thiosemicarbazide
42135-76-2

4-(3-chlorophenyl)-3-thiosemicarbazide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: aq. ammonia / ethanol / 4 h / Ambient temperature
2: aq. sodium chloroacetate, hydrazine / ethanol / 4 h / Ambient temperature
With ammonium hydroxide; sodium monochloroacetic acid; hydrazine; In ethanol;
C<sub>9</sub>H<sub>7</sub>ClNO<sub>2</sub>S<sub>2</sub><sup>(1-)</sup>*Na<sup>(1+)</sup>

C9H7ClNO2S2(1-)*Na(1+)

4-(3-chlorophenyl)-3-thiosemicarbazide
42135-76-2

4-(3-chlorophenyl)-3-thiosemicarbazide

Conditions
Conditions Yield
With hydrazine hydrate;
3-chlorophenyl-isothiocyanate
2392-68-9

3-chlorophenyl-isothiocyanate

4-(3-chlorophenyl)-3-thiosemicarbazide
42135-76-2

4-(3-chlorophenyl)-3-thiosemicarbazide

Conditions
Conditions Yield
With hydrazine; In water; isopropyl alcohol; at 20 ℃; for 0.5h;
85%
With hydrazine hydrate; In isopropyl alcohol; at 20 ℃; for 3h; Inert atmosphere;
66%
With ethanol; hydrazine hydrate; unter Kuehlung;
With sodium monochloroacetic acid; hydrazine; In ethanol; for 4h; Yield given; Ambient temperature;
With hydrazine; In dichloromethane; water; for 1h;
With hydrazine hydrate; In dichloromethane; at 20 ℃; for 4h;
With hydrazine hydrate; In methanol; at 20 ℃; for 24.25h; Cooling with ice;
With hydrazine hydrate; In ethanol; Cooling with ice;
With hydrazine hydrate; In isopropyl alcohol; at 25 ℃; for 2h;
With hydrazine hydrate; In ethanol; Cooling with ice;
With hydrazine hydrate; In ethanol; Cooling with ice;
With hydrazine hydrate; In ethanol; for 0.5h; Cooling with ice;
C<sub>7</sub>H<sub>6</sub>ClNS<sub>2</sub>

C7H6ClNS2

4-(3-chlorophenyl)-3-thiosemicarbazide
42135-76-2

4-(3-chlorophenyl)-3-thiosemicarbazide

Conditions
Conditions Yield
With sodium monochloroacetic acid; hydrazine hydrate; In water;
With sodium monochloroacetic acid; hydrazine hydrate; at 60 ℃; for 4h;
3-chloro-aniline
108-42-9

3-chloro-aniline

4-(3-chlorophenyl)-3-thiosemicarbazide
42135-76-2

4-(3-chlorophenyl)-3-thiosemicarbazide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: liq. NH3 / -30 °C
2: hydrazine hydrate, sodium chloroacetate / aq. ethanol
With ammonia; sodium monochloroacetic acid; hydrazine hydrate; In ethanol;
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / chloroform; water / 1 h / 20 °C
2: hydrazine / dichloromethane; water / 1 h
With sodium hydrogencarbonate; hydrazine; In dichloromethane; chloroform; water;
Multi-step reaction with 2 steps
1: ammonia / ethanol / Cooling with ice
2: sodium monochloroacetic acid; hydrazine hydrate / water
With ammonia; sodium monochloroacetic acid; hydrazine hydrate; In ethanol; water;
Multi-step reaction with 2 steps
1: ammonia / ethanol / 15 - 20 °C
2: sodium monochloroacetic acid; hydrazine hydrate / 4 h / 60 °C
With ammonia; sodium monochloroacetic acid; hydrazine hydrate; In ethanol;
Multi-step reaction with 2 steps
1.1: triethylamine / 12 h / Cooling with ice
1.2: 6 h / 25 °C
2.1: hydrazine hydrate / isopropyl alcohol / 2 h / 25 °C
With hydrazine hydrate; triethylamine; In isopropyl alcohol;

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