| Identification | More | [Name]
4-Methoxy-2-aminobenzothiazole | [CAS]
5464-79-9 | [Synonyms]
2-AMINO-4-METHOXYBENZOTHIAZOLE
4-METHOXY-1,3-BENZOTHIAZOL-2-AMINE
4-methoxy-2-aminobenzothiazole
4-METHOXY-BENZOTHIAZOL-2-YLAMINE
AKOS BBS-00007984
TIMTEC-BB SBB000220
2-amino-4-methoxy-benzothiazol
2-Amino-5-methoxy-1,3-benzothiazole
2-Amino-4-methoxy-1,3-benzothiazole
Benzothiazole, 2-amino-4-methoxy.
2-Benzothiazolamine,4-methoxy-(9CI)
2-AMINO-4-METTHOXYBENZOTHIAZOLE
4-methoxybenzo[d]thiazol-2-amine
4-Methoxybenzothiazol-2-amine | [EINECS(EC#)]
226-763-1 | [Molecular Formula]
C8H8N2OS | [MDL Number]
MFCD00005792 | [Molecular Weight]
180.23 | [MOL File]
5464-79-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Beige crystalline powder | [Melting point ]
153-155 °C (lit.) | [Boiling point ]
240°C (rough estimate) | [density ]
1.2425 (rough estimate) | [refractive index ]
1.5690 (estimate) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
Crystalline Powder | [pka]
4.09±0.10(Predicted) | [color ]
Beige | [Water Solubility ]
<0.1 g/100 mL at 19.5 ºC | [BRN ]
141363 | [InChI]
InChI=1S/C8H8N2OS/c1-11-5-3-2-4-6-7(5)10-8(9)12-6/h2-4H,1H3,(H2,9,10) | [InChIKey]
YEBCRAVYUWNFQT-UHFFFAOYSA-N | [SMILES]
S1C2=CC=CC(OC)=C2N=C1N | [CAS DataBase Reference]
5464-79-9(CAS DataBase Reference) | [EPA Substance Registry System]
5464-79-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
DL2000000
| [Hazard Note ]
Harmful | [HS Code ]
29342000 |
| Hazard Information | Back Directory | [General Description]
Beige chunky solid. | [Reactivity Profile]
An amine, organosulfide. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. | [Air & Water Reactions]
Insoluble in water. | [Health Hazard]
ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits very toxic fumes of NOx and SOx. | [Fire Hazard]
Flash point data for this chemical are not available. 2-AMINO-4-METHOXYBENZOTHIAZOLE(5464-79-9) is probably combustible. | [Chemical Properties]
Beige crystalline powder | [Uses]
2-Amino-4-methoxybenzothiazole is a useful research intermediate for the synthesis of various benzothiazole and aminobenzothiazoles derivatives with antibacterial and antifungal activity. | [Biochem/physiol Actions]
2-Amino-4-methoxybenzothiazole on condensation reaction with 4-acetamidobenzaldehyde affords tridentate Schiff bases. It reacts with 2,4,6-trichloro 1,3,5-triazine to give 2-(4-methoxybenzothiazol-2′-ylamino)-4-(phenylthioureido)-6-(substitutedthioureido)-1,3,5-triazines. | [Synthesis]
General procedure for the synthesis of 2-amino-4-methoxybenzothiazole from 1-(2-methoxyphenyl)thiourea: 1-(2-methoxyphenyl)thiourea (3.76 g, 0.02 mol) was dissolved in acetic acid (36 ml). To this solution, lithium bromide (2.6 g, 0.03 mol) was added at room temperature, followed by slow dropwise addition of bromine (1 ml, 0.02 mol) under ice bath conditions. The reaction mixture was heated to 40°C and the reaction was stirred at this temperature for 17 hours. After completion of the reaction, the system was cooled to room temperature and allowed to stand for 2 hours. The reaction product was collected by filtration and washed with acetic acid. Finally, the resulting white solid was dried in a vacuum oven to afford the target product 2-amino-4-methoxybenzothiazole (3.5 g, 94.08% yield). | [References]
[1] Patent: US2016/102066, 2016, A1. Location in patent: Paragraph 0021; 0025; 0027
[2] Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1136 - 1148
[3] Helvetica Chimica Acta, 1942, vol. 25, p. 515,519
[4] Yakugaku Zasshi, 1940, vol. 60, p. 462,473; dtsch. Ref. S. 184, 189
[5] Chem.Abstr., 1941, p. 452 |
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