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Cas Database

1603-91-4

1603-91-4

Identification

  • Product Name:2-Thiazolamine,4-methyl-

  • CAS Number: 1603-91-4

  • EINECS:216-505-6

  • Molecular Weight:114.171

  • Molecular Formula: C4H6N2S

  • HS Code:2934.10

  • Mol File:1603-91-4.mol

Synonyms:Thiazole,2-amino-4-methyl- (6CI,7CI,8CI);2-Amino-4-methyl-1,3-thiazole;4-Methyl-1,3-thiazol-2-amine;4-Methyl-2-aminothiazole;Aminomethiazole bitartrate;NSC 40462;Nomortiroide;Normotiroide;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn,IrritantXi

  • Hazard Codes:Xi,Xn

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • 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

  • Manufacture/Brand
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  • Manufacture/Brand:TRC
  • Product Description:4-Methylthiazol-2-amine
  • Packaging:250mg
  • Price:$ 45
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Amino-4-methylthiazole >99.0%(GC)
  • Packaging:250g
  • Price:$ 155
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Amino-4-methylthiazole >99.0%(GC)
  • Packaging:25g
  • Price:$ 32
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Amino-4-methylthiazole
  • Packaging:5 g
  • Price:$ 16
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Amino-4-methylthiazole 98%
  • Packaging:5g
  • Price:$ 31
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Amino-4-methylthiazole 98%
  • Packaging:25g
  • Price:$ 51
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:2-Amino-4-methylthiazole >99%
  • Packaging:25 g
  • Price:$ 585
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2-Amino-4-methyl-1,3-thiazole 97%
  • Packaging:50g
  • Price:$ 135
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2-Amino-4-methyl-1,3-thiazole 97%
  • Packaging:10g
  • Price:$ 59
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2-Amino-4-methyl-1,3-thiazole 97%
  • Packaging:1g
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Relevant articles and documentsAll total 34 Articles be found

-

King,Ryden

, p. 1813 (1947)

-

Synthesis and properties of a series of iridium complexes with imidazolo[2,1-b]thiazole derivatives as primary ligands

Yin, Xin-ying,Yang, Zhi-yu,Huang, Guo-li,Bian, Jian-jian,Wang, Deng-qiang,Wang, Qin,Teng, Ming-yu,Wang, Zheng-liang,Zhang, Jie

, p. 5849 - 5856 (2019)

3-Methyl-6-phenylimidazo[2,1-b]thiazole (mpmt) and 3-methyl-6-(4-(trifluoromethyl)phenyl)imidazo[2,1-b]thiazole (mtfpmt) were easily prepared from thiourea, acetone (or trifluoroacetone), and α-bromoacetophenone as novel primary ligands. These were used to synthesize ten phosphorescent iridium complexes with picolinate (pic), isoquinoline-5-carboxylic acid (3-IQA), quinoline-2-carboxylic acid (2-QA), phenyl isoquinoline (piq), and 1,4-difluorophenyl pyrimidine (dfppy) as ancillary ligands. Their structures, photoluminescence, and electrochemistry were investigated. The introduction of trifluoromethyl groups at the phenyl ring of mpmt and to mtfpmt blue shifts the emission spectra of Ir3+ complexes by about 50 nm, and the corresponding emission peaks in CH2Cl2, which shifted from 545 to 613 nm, were observed at room temperature with an increase in the corresponding internal quantum efficiencies (IQEs) from 5.8% to 31.6%. Constructed with title complexes as emitters, LED chips based on InGaN chip excitation show good performances. Particularly, a device based on (mpmt)2Ir(2-QA) showed the best red light emission with a CIE (0.64, 0.30), a CRI of 72.0, and a color purity that was over 80%. Also, a device based on (mpmt)2Ir(3-IQA) provided a maximum luminescence efficiency of 3.01 lm W?1. These results suggest that the title complexes have potential applications in LED chips and OLEDs.

Inhibitory effect of 2-aminothiazole derivatives in oxidation reactions

Karpov,Pekarevskii,Potekhin

, p. 1484 - 1486 (2001)

The kinetics and mechanism of inhibitory effect of 2-aminothiazole derivatives in the radical-initiated oxidation of cumene were studied.

Nanochitosan: A biopolymer catalytic system for the synthesis of 2-aminothiazoles

Safari, Javad,Abedi-Jazini, Zahra,Zarnegar, Zohre,Sadeghi, Masoud

, p. 108 - 112 (2016)

A convenient and efficient method is described for the synthesis of 2-aminothiazoles by one-pot reaction of ketone and thiourea using chitosan nanoparticles under mild condition. Nanochitosan was used as a biodegradable and green catalyst for this reaction in satisfactory yields. The attractive advantages of the present process include easy isolation of products, milder and cleaner conditions, higher purity and yields and easier work-up procedure.

-

Markees et al.

, p. 304 (1947)

-

N,O π-Conjugated 4-Substituted 1,3-Thiazole BF2 Complexes: Synthesis and Photophysical Properties

Potopnyk, Mykhaylo A.,Lytvyn, Roman,Danyliv, Yan,Ceborska, Magdalena,Bezvikonnyi, Oleksandr,Volyniuk, Dmytro,Gra?ulevi?ius, Juozas Vidas

, p. 1095 - 1105 (2018)

A series of 1,3-thiazole-based organoboron complexes has been designed and synthesized by acylation of 2-amino 4-subsituted 1,3-thiazoles with (4-dimethylamino)benzoyl chloride and the subsequent BF2 complexation reaction. The influence of substituents in position 4 of the thiazole ring on photophysical properties of the complexes has been investigated. Synthesized thiazolo[3,2-c][1,3,5,2]oxadiazaborinines mainly showed intensive fluorescence in solutions. Complex with a 4,5-unsubstituted thiazole unit demonstrated an aggregation induced emission (AIE) effect and a very high fluorescent quantum yield (94%) in the solid state because of the inhibition of π-π/π-n interactions in the molecular packing.

Biocidal and anticorrosive effect of 2-aminothiazole derivatives used as additives to jet fuels

Karpov,Nazarenko,Pekarevskii,Potekhin

, p. 998 - 1001 (2001)

The effect of 2-aminothiazole derivatives on the biological resistance and corrosion activity of jet fuels was studied under conditions of water condensation.

Design and synthesis of new 4-methylthiazole derivatives: In vitro and in silico studies of antimicrobial activity

DAWBAA, Sam,EVREN, Asaf Evrim,GüL, ülküye Dudu,NUHA, Demokrat,YAVUZ, ?ule Aybüke,YURTTA?, Leyla

, (2021)

The development of resistance against antimicrobial drugs has become a world-wide issue. It is predicted that some or perhaps all the antimicrobial drugs used in clinics will be out of the treatment protocols soon. Therefore, researchers pay more attention to the development of new antimicrobial drugs. For this purpose, we designed and synthesized new 4-methylthiazole-(benz)azole derivatives. The structural elucidation of the compounds was performed by 1H-NMR, 13C-NMR, HSQC, NOESY, HMBC and LC/MS-IT-TOF spectral and elemental analyses. Then, their antimicrobial activity against bacteria and fungi strains was tested. The antibacterial effect of the compounds was found valuable as compared with their anticandidal activity. By combining the findings with molecular docking results, structure-activity relationship (SAR) was explained. Thus, in the development of new antimicrobial agents which can be used as DNA gyrase inhibitors, SAR showed that the products might be used in the discovery of new antimicrobials where their activity is owed to the allosteric effect. Although the effect of compound 3f was modest compared to the reference compound, it was better than the other synthesized compounds. Also, compound 3f has a better allosteric effect and might be a good lead candidate to synthesize new and better active hits. In addition, it was observed that all the synthesized compounds showed half potency against P. aeruginosa compared to the reference drug. On the other hand, no significant difference was seen between compounds against gram-positive or gram-negative bacteria. Briefly, meaningful data to correlate the SAR with thiazole-(benz)azole hybridized compounds were presented in this study. In future projects, the mentioned ideas can be used to synthesize new compounds having better antibacterial activity, particularly against resistant organisms.

-

Dodson,King

, (1946)

-

Aiding the versatility of simple ammonium ionic liquids by the synthesis of bioactive 1,2,3,4-tetrahydropyrimidine, 2-aminothiazole and quinazolinone derivatives

Kakati, Praachi,Singh, Preeti,Yadav, Priyanka,Awasthi, Satish Kumar

, p. 6724 - 6738 (2021/04/22)

Simple ammonium ionic liquids [ILs] are efficient, green, environmentally friendly catalysts in promoting the Biginelli condensation reaction, Hantzsch reaction and Niementowski reaction to afford 1,2,3,4-tetrahydropyrimidine, 2-aminothiazole and quinazolinone derivatives respectively by eliminating the need for harmful volatile organic solvents. These [ILs] are air and water stable, easy to prepare and cost-effective. The effects of the anions and cations present in [IL] on reactions were investigated. The results clearly indicated that the Biginelli condensation reaction, Hantzsch reaction and Niementowski reaction were heavily influenced by the acidity of [IL], and among various ammonium ionic liquids, [Et3NH][HSO4] showed the best catalytic activity. Furthermore, [IL] could be easily separated and reused with a slight loss of its activity. This technique provided a good alternative way for the industrial synthesis of 1,2,3,4-tetrahydropyrimidinones, 2-aminothiazoles and quinazolinones. The present processes are eco-friendly methods for the synthesis of these derivatives authenticated by several green parameters, namely,E-factor, process mass intensity, reaction mass efficiency, atom economy, and carbon efficiency.

Synthesis and photoelectric properties of IrIIIcomplexes using fluorobenzylimidazole[2,1-b]thiazole derivatives as primary ligands

Liu, Xiao-Qing,Rong, Mei-Zhu,Si, Peng-Bin,Teng, Ming-Yu,Wang, Qin,Wang, Yu-Fei,Wang, Zheng-Liang,Zhang, Jie,Zhe, Hai-Feng,Zhou, Ai-Hui

, p. 18796 - 18804 (2021/10/26)

3-Methyl-6-(3,5-difluorophenyl)imidazo[2,1-b]thiazole (mdfpit) and 3-methyl-6-(3,4,5-trifluorophenyl)imidazo[2,1-b]thiazole (mtfpit) were easily prepared from thiourea, acetone, and 3,5-difluorobenzoyl bromide or 3,4,5-trifluorobenzoyl bromide. These were used as primary ligands to synthesize twelve phosphorescent IrIIIcomplexes with picolinic acid (pic), isoquinoline-3-carboxylic acid (3-IQA), quinoline-2-carboxylic acid (2-QA), 2-(pyridin-2-yl)phenol (2-ylppy), 2-(2,4-difluorophenyl)pyridine (dfppy), and pyridine-2-sulfonic acid (2-sappy) as auxiliary ligands. Their structures, photoluminescence, and electrochemical properties were investigated. Upon introducing more fluorine atoms into the benzene ring of the primary ligand, the thermal stability, photoluminescence quantum yield (PLQY), LUMO energy level, and luminous efficiency of the resulting IrIIIcomplexes are significantly improved, and the photoluminescence emission spectra are blue-shifted. Their maximum emission wavelengths are present in the range of 517-618 nm, and the luminous colors span from the green to red light region. Using the synthesized IrIIIcomplexes as emitters, LED chips based on InGaN chip excitation were developed, which showed good performances. Among all LEDs, the PLQY of the (mtfpmt)2Ir(pic) based LED is 58.4%, and the luminous efficiency is as high as 17.11 lm W?1; the luminous efficiency of the (mdfpmt)2Ir(2-QA) based LED is 3.41 lm W?1with CIE coordinates of 0.60 and 0.38, which are very similar to the saturated standard red light emission. The results demonstrate the potential of the studied IrIIIcomplexes as candidates for LED materials.

Synthesis of 6-membered-ring fused thiazine-dicarboxylates and thiazole-pyrimidines via one-pot three-component reactions

Bode, Moira L.,Coyanis, Elena Mabel,Fernandes, Manuel A.,Fish, Muhammad Q.,Mohlala, Reagan L.

, (2021/09/18)

A facile and efficient one-pot three-component reaction method for the synthesis of thiazine-dicarboxylates is reported. Reaction of an isocyanide and dialkyl acetylenedicarboxylate with 2-amino-4H-1,3-thiazin-4-one derivatives containing both an acidic proton and an internal nucleophile gave the products in good yields of 76–85%. The reactivity of dialkyl acetylenedicarboxylates was further tested in the synthesis of thiazole-pyrimidines where a two-component reaction of 2-aminothiazole with dialkyl acetylenedicarboxylates was successfully converted to a more efficient three-component reaction of a thiourea, α-haloketone and dialkyl acetylenedicarboxylate (DMAD/DEtAD) to give thiazole-pyrimidines in good yields of 70–91%.

Iridium complex with 3-methyl-6-phenylimidazole[2, 1-b]thiazole derivative as main ligand

-

Paragraph 0029-0031, (2020/03/12)

The invention discloses ten iridium (III) complexes, which are characterized in that: the main ligands of the complexes are 3-methyl-6-phenylimidazole[2, 1-b]thiazole (mpmt) and 3-methyl-6-(4-(trifluoromethyl)phenyl)imidazo[2, 1-b]thiazole (mtfpmt) respectively, and the auxiliary ligands are 2-picolinic acid (pic), isoquinoline-3-formic acid (3-IQA), quinoline-2-carboxylic acid (2-QA), 1-phenylisoquinoline (piq) and 2-(2, 4-difluorophenyl)pyridine (dfppy) respectively, and the structures are shown as the specification, wherein the definition of X substituent group is selected from one of twogroups of complexes. Light-emitting diodes prepared from the complexes have a maximum emission wavelength of 540.3-627.8nm and light-emitting efficiency of 0.18-3.01 lm.W, wherein (mtfpmt)2Ir(pic)emits pure green light, and (mpmt)2Ir(2-QA) emits pure red light, and the color purity is high. near white light can be obtained after mixing of the light emitted by (mtfpmt)2Ir(dfppy) and a galliumnitride chip, therefore the complexes can be used for making of white light LED. Excellent performance of the devices indicates that the complexes have application value in preparation of organic photoluminescent and electroluminescent devices. The invention discloses a structure and a synthesis method of the complexes, and a structure and a preparation method of organic photoluminescent devices.

Process route upstream and downstream products

Process route

thiourea
17356-08-0

thiourea

acetone
67-64-1

acetone

4-methylthiazol-2-ylamine
1603-91-4

4-methylthiazol-2-ylamine

Conditions
Conditions Yield
With N-iodo-succinimide; In ethanol; at 20 ℃; for 1h;
90%
With iodine; triethylamine sulfate; In neat (no solvent); at 40 ℃;
89%
With iodine; In ethanol; for 3h; Reflux;
87%
With carbon tetrabromide; triethylamine; In acetonitrile; at 20 ℃; for 3h;
86%
With iodine; for 4h; Reflux; Inert atmosphere;
74%
With iodine; at 70 ℃; for 4h;
74.3%
With sodium iodine dichloride; In tetrahydrofuran; water; for 12h; Reflux;
70%
With iodine; for 4h; Reflux;
70.1%
With iodine;
60%
With iodine;
60%
With iodine; for 4h; Reflux;
37%
With iodine; In acetone; for 8.5h; Reflux;
20.4%
With hydrogenchloride; dimethyl sulfoxide; In water;
15%
With bromine;
With iodine;
With chlorine;
With iodine;
thiourea; acetone; With iodine; for 4h; Heating;
With sodium hydroxide; at 20 ℃;
With iodine; at 100 ℃;
With iodine; at 65 ℃; for 4h;
acetaldehyde
75-07-0,9002-91-9

acetaldehyde

thiourea
17356-08-0

thiourea

4-methylthiazol-2-ylamine
1603-91-4

4-methylthiazol-2-ylamine

Conditions
Conditions Yield
With N-iodo-succinimide; In ethanol; at 20 ℃; for 1h;
90%
thiourea
17356-08-0

thiourea

chloroacetone
78-95-5

chloroacetone

4-methylthiazol-2-ylamine
1603-91-4

4-methylthiazol-2-ylamine

Conditions
Conditions Yield
thiourea; chloroacetone; In water; Reflux;
With sodium hydroxide; In water; Cooling with ice;
73%
In water; for 4h; Inert atmosphere; Reflux;
66%
for 5h; Reflux;
60%
With water;
In ethanol; at 49.84 ℃; Further Variations:; reactant conc.; Activation energy; Kinetics;
In ethanol; at 49.84 ℃;
In ethanol; at 20 ℃;
In tetrahydrofuran; ethanol; at 20 ℃; for 0.25h;
potassium thioacyanate
333-20-0

potassium thioacyanate

chloroacetone
78-95-5

chloroacetone

4-methylthiazol-2-ylamine
1603-91-4

4-methylthiazol-2-ylamine

Conditions
Conditions Yield
With ammonium acetate on neutral alumina; silica gel; In benzene; at 80 ℃; for 6h;
83%
propargyl bromide
106-96-7

propargyl bromide

thiourea
17356-08-0

thiourea

4-methylthiazol-2-ylamine
1603-91-4

4-methylthiazol-2-ylamine

Conditions
Conditions Yield
With potassium carbonate; In N,N-dimethyl-formamide; at 130 ℃; for 0.166667h; Microwave irradiation;
90%
2,5-dimethyl-1-(4-methylthiazol-2-yl)pyrrole
83756-28-9

2,5-dimethyl-1-(4-methylthiazol-2-yl)pyrrole

4-methylthiazol-2-ylamine
1603-91-4

4-methylthiazol-2-ylamine

Conditions
Conditions Yield
With hydroxylamine hydrochloride; In ethanol; water; for 24h; Heating;
65%
With hydroxylamine hydrochloride; In ethanol; Yield given; Heating;
thiourea
17356-08-0

thiourea

1-bromoacetone
598-31-2

1-bromoacetone

4-methylthiazol-2-ylamine
1603-91-4

4-methylthiazol-2-ylamine

Conditions
Conditions Yield
In ethanol; for 2h; Heating;
52%
4-(chloromethyl)thiazol-2-amine hydrochloride
59608-97-8

4-(chloromethyl)thiazol-2-amine hydrochloride

4-methylthiazol-2-ylamine
1603-91-4

4-methylthiazol-2-ylamine

Conditions
Conditions Yield
With palladium on activated charcoal; ethanol; Hydrogenation;
thiourea
17356-08-0

thiourea

4-methylthiazol-2-ylamine
1603-91-4

4-methylthiazol-2-ylamine

Conditions
Conditions Yield
With ethanol;
Dimethyl ether
115-10-6,157621-61-9

Dimethyl ether

thiourea
17356-08-0

thiourea

4-methylthiazol-2-ylamine
1603-91-4

4-methylthiazol-2-ylamine

Conditions
Conditions Yield
With bromine; for 2h; Heating;
78%

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