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| CAS No.: | 105827-91-6 |
|---|---|
| Name: | 2-Chloro-5-chloromethylthiazole |
| Article Data: | 43 |
| Molecular Structure: | |
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| Formula: | C4H3Cl2NS |
| Molecular Weight: | 168.047 |
| Synonyms: | 2-Chloro-5-(chloromethyl)thiazole;2-Chloro-5-chloromethyl-1,3-thiazole;2-Chloro-5-thiazolylmethyl chloride;5-Chloromethyl-2-chloro-1,3-thiazole; |
| EINECS: | 429-830-5 |
| Density: | 1.503 g/cm3 |
| Melting Point: | 31 °C |
| Boiling Point: | 268.6 °C at 760 mmHg |
| Flash Point: | 116.3 °C |
| Solubility: | insoluble in water, soluble in dichloromethane, chloroform, carbon tetrachloride and other solvents |
| Appearance: | white to pale yellow crystal or colorless liquid |
| Hazard Symbols: |
 Xi
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| Risk Codes: | 36/37/38 |
| Safety: | 26-37 |
| PSA: | 41.13000 |
| LogP: | 2.53530 |
2-chloro-3-isothiocyanato-1-propene
α-Cl-β-thiazolyl chloride
| Conditions | Yield |
|---|---|
| With hydrogenchloride; chlorine In 1,2-dichloro-ethane at 0 - 60℃; for 1h; Temperature; | 98% |
| With chlorine In dichloromethane at 20 - 30℃; | 96% |
| With sulfuryl dichloride In chloroform at 36℃; for 3h; | 94.6% |
3-chloro-1-isothiocyanato-1-propene
α-Cl-β-thiazolyl chloride
| Conditions | Yield |
|---|---|
| With sulfuryl dichloride; sodium hydrogencarbonate | 91.2% |
| With sulfuryl dichloride; sodium carbonate In chloroform | 69.2% |
| With sulfuryl dichloride; sodium carbonate | 68.3% |
| With sodium carbonate In chloroform | 62.4% |
| With sulfuryl dichloride; sodium carbonate | 45.3% |
α-Cl-β-thiazolyl chloride
| Conditions | Yield |
|---|---|
| With hydrogenchloride; chlorine In water; chlorobenzene at 20 - 25℃; for 6h; | 90% |
5-methylene-1,3-thiazolidine-2-thione
α-Cl-β-thiazolyl chloride
| Conditions | Yield |
|---|---|
| With sulfuryl dichloride In dichloromethane; water for 1h; Chlorination; | 80% |
| With sulfuryl dichloride In dichloromethane; water at 0 - 20℃; for 1h; | 70% |
| With sodium hydroxide; chlorine In water; acetic acid at 10 - 15℃; for 2 - 3h; | 56% |
| With sodium hydroxide; sulfuryl dichloride In dichloromethane; water at -5℃; for 0.0833333h; | 31% |
| In chloroform; ethyl acetate |
2-chloro-5-methyl-thiazole
α-Cl-β-thiazolyl chloride
| Conditions | Yield |
|---|---|
| With N-chloro-succinimide In chloroform at 50℃; for 5h; | 65% |
| With N-chloro-succinimide In chloroform at 50℃; for 5h; Time; | 65% |
| With N-chloro-succinimide; dibenzoyl peroxide In tetrachloromethane Chlorination; Heating; | 50% |
| With N-chloro-succinimide; dibenzoyl peroxide In tetrachloromethane at 20℃; for 72h; Heating / reflux; |
(E)-3,3'-(diazene-1,2-diyl)bis(2-methylpropanenitrile)
N-allyl isothiocyanate
α-Cl-β-thiazolyl chloride
| Conditions | Yield |
|---|---|
| With N-chloro-succinimide; sulfuryl dichloride In dichloromethane | 64.5% |
| With N-chloro-succinimide; chlorine In dichloromethane | 57% |
| With N-chloro-succinimide; sulfuryl dichloride In 1,1-dichloroethane | 56.3% |
2-benzylsulfanyl-5-chloromethyl-thiazole
α-Cl-β-thiazolyl chloride
| Conditions | Yield |
|---|---|
| In dichloromethane for 2h; Chlorination; | 60% |
α-Cl-β-thiazolyl chloride
| Conditions | Yield |
|---|---|
| With sulfur dichloride In tetrachloromethane at 40℃; for 4h; Cyclization; | 50% |
| With thionyl chloride; sulphur dichloride In tetrachloromethane |
N-allyl isothiocyanate
α-Cl-β-thiazolyl chloride
| Conditions | Yield |
|---|---|
| With N-chloro-succinimide; sulfuryl dichloride In dichloromethane | 48% |
| With sulfuryl dichloride |
N-(2-chloroallyl)formamide
α-Cl-β-thiazolyl chloride
| Conditions | Yield |
|---|---|
| With thionyl chloride; sulfur dichloride for 24h; Cyclization; chlorination; Heating; | 42% |
| With thionyl chloride; sulphur dichloride | 42% |
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The IUPAC name of 2-Chloro-5-chloromethylthiazole is 2-chloro-5-(chloromethyl)-1,3-thiazole. With the CAS registry number 105827-91-6, it is also named as Thiazole, 2-chloro-5-(chloromethyl)-. The product's categories are halometyl; miscellaneous; API; thiazoles. It is white to pale yellow crystal or colorless liquid which is insoluble in water, soluble in dichloromethane, chloroform, carbon tetrachloride and other solvents.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.26; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.26; (4)ACD/LogD (pH 7.4): 1.26; (5)ACD/BCF (pH 5.5): 5.32; (6)ACD/BCF (pH 7.4): 5.32; (7)ACD/KOC (pH 5.5): 115.18; (8)ACD/KOC (pH 7.4): 115.18; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.583; (13)Molar Refractivity: 37.38 cm3; (14)Molar Volume: 111.7 cm3; (15)Polarizability: 14.82×10-24 cm3; (16)Surface Tension: 48.9 dyne/cm; (17)Enthalpy of Vaporization: 48.63 kJ/mol; (18)Vapour Pressure: 0.0126 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 166.936325; (21)MonoIsotopic Mass: 166.936325; (22)Topological Polar Surface Area: 41.1; (23)Heavy Atom Count: 8; (24)Complexity: 80.4.
Preparation of 2-Chloro-5-chloromethylthiazole: Adding 2-chloro-3-isothiocyanato-prop-1-ene and chloroform in the reaction flask, and then adding dropwise sulfuryl chloride at an internal temperature of 30 °C. After dropping, the reaction carries on at room temperature 2.5h and then the internal temperature rises to 36 °C, After the reaction, solvent and the remaining sulfuryl chloride are distilled to remove. The residue is dissolved in dichloromethane, and using NaHCO3 solution and water washing respectively, drying, distilling to remove the solvent (under vacuum) to get the products.
Uses of 2-Chloro-5-chloromethylthiazole: It is used as pharmaceutical and agrochemical intermediate. It is also used as intermediate of insecticides Thiamethoxam and Clothianidin.
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable gloves.
People can use the following data to convert to the molecule structure.
1. SMILES:ClCc1sc(Cl)nc1
2. InChI:InChI=1/C4H3Cl2NS/c5-1-3-2-7-4(6)8-3/h2H,1H2
3. InChIKey:VRMUIVKEHJSADG-UHFFFAOYAF
