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105827-91-6

Basic Information
CAS No.: 105827-91-6
Name: Thiazole,2-chloro-5-(chloromethyl)-
Molecular Structure:
Molecular Structure of 105827-91-6 (Thiazole,2-chloro-5-(chloromethyl)-)
Formula: C4H3Cl2NS
Molecular Weight: 168.04
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: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37
Transport Information:
PSA: 41.13000
LogP: 2.53530
Synthetic route
14214-31-4

2-chloro-3-isothiocyanato-1-propene

105827-91-6

α-Cl-β-thiazolyl chloride

Conditions
ConditionsYield
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%
196406-44-7

3-chloro-1-isothiocyanato-1-propene

105827-91-6

α-Cl-β-thiazolyl chloride

Conditions
ConditionsYield
With sulfuryl dichloride; sodium hydrogencarbonate91.2%
With sulfuryl dichloride; sodium carbonate In chloroform69.2%
With sulfuryl dichloride; sodium carbonate68.3%
With sodium carbonate In chloroform62.4%
With sulfuryl dichloride; sodium carbonate45.3%

5-(chloromethyl)-2-(phenylthio)thiazole

105827-91-6

α-Cl-β-thiazolyl chloride

Conditions
ConditionsYield
With hydrogenchloride; chlorine In water; chlorobenzene at 20 - 25℃; for 6h;90%
52829-72-8

5-methylene-1,3-thiazolidine-2-thione

105827-91-6

α-Cl-β-thiazolyl chloride

Conditions
ConditionsYield
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
33342-65-3

2-chloro-5-methyl-thiazole

105827-91-6

α-Cl-β-thiazolyl chloride

Conditions
ConditionsYield
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;
764-28-3

(E)-3,3'-(diazene-1,2-diyl)bis(2-methylpropanenitrile)

57-06-7

N-allyl isothiocyanate

105827-91-6

α-Cl-β-thiazolyl chloride

Conditions
ConditionsYield
With N-chloro-succinimide; sulfuryl dichloride In dichloromethane64.5%
With N-chloro-succinimide; chlorine In dichloromethane57%
With N-chloro-succinimide; sulfuryl dichloride In 1,1-dichloroethane56.3%
192439-48-8

2-benzylsulfanyl-5-chloromethyl-thiazole

105827-91-6

α-Cl-β-thiazolyl chloride

Conditions
ConditionsYield
In dichloromethane for 2h; Chlorination;60%

2-chloroallylisonitrile

105827-91-6

α-Cl-β-thiazolyl chloride

Conditions
ConditionsYield
With sulfur dichloride In tetrachloromethane at 40℃; for 4h; Cyclization;50%
With thionyl chloride; sulphur dichloride In tetrachloromethane
57-06-7

N-allyl isothiocyanate

105827-91-6

α-Cl-β-thiazolyl chloride

Conditions
ConditionsYield
With N-chloro-succinimide; sulfuryl dichloride In dichloromethane48%
With sulfuryl dichloride
188988-52-5

N-(2-chloroallyl)formamide

105827-91-6

α-Cl-β-thiazolyl chloride

Conditions
ConditionsYield
With thionyl chloride; sulfur dichloride for 24h; Cyclization; chlorination; Heating;42%
With thionyl chloride; sulphur dichloride42%
78-88-6

2,3-Dichloroprop-1-ene

540-72-7

sodium thiocyanide

105827-91-6

α-Cl-β-thiazolyl chloride

Conditions
ConditionsYield
Stage #1: 2,3-Dichloroprop-1-ene; sodium thiocyanide In acetonitrile at 85℃; for 6h;
Stage #2: With hydrogenchloride In dichloromethane; water for 6h; Solvent; Temperature; Electrochemical reaction;
75-04-7

ethylamine

105827-91-6

α-Cl-β-thiazolyl chloride

N-((2-chlorothiazol-5-yl)methyl)ethylamine

Conditions
ConditionsYield
In water; 1,2-dichloro-ethane at 20 - 50℃;98.5%
In ethanol; water at 0 - 20℃; for 7h;85%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In chloroform; water at 20℃;3.37 g
105827-91-6

α-Cl-β-thiazolyl chloride

153719-38-1

3,6-dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazin-4-amine

153719-23-4

thiamethoxam

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h;98%
Stage #1: 3,6-dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazin-4-amine With potassium carbonate In ethanol for 0.5h; Autoclave;
Stage #2: α-Cl-β-thiazolyl chloride In ethanol at 120℃; for 4h; Temperature; Autoclave;
95.2%
With N-ethyl-N,N-diisopropylamine; carbonic acid dimethyl ester at 20 - 40℃; for 1h; Temperature; Reagent/catalyst;94.3%
105827-91-6

α-Cl-β-thiazolyl chloride

108612-54-0

tert-butyl methyl(piperidin-4-yl)carbamate

tert-butyl N-methyl-N-{1-[(2-chlorothiazol-5-yl)methyl]piperidin-4-yl}carbamate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;98%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;92.7 g
105827-91-6

α-Cl-β-thiazolyl chloride

73874-95-0

(piperidin-4-yl)carbamic acid tert-butyl ester

tert-butyl N-{1-[(2-chlorothiazol-5-yl)methyl]piperidin-4-yl}carbamate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;98%
105827-91-6

α-Cl-β-thiazolyl chloride

1088445-95-7

5-(azidomethyl)-2-chlorothiazole

Conditions
ConditionsYield
With sodium azide In ethanol for 4h; Inert atmosphere; Reflux;97%
With sodium azide In ethanol Reflux;
With sodium azide In dimethyl sulfoxide at 25 - 40℃; for 18h;
With sodium azide In ethanol Reflux;
123-08-0

4-hydroxy-benzaldehyde

105827-91-6

α-Cl-β-thiazolyl chloride

338393-48-9

4-((2-chlorothiazol-5-yl)methoxy)benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In ethanol for 6h; Reflux;95.7%
With potassium carbonate In ethanol for 8h; Reflux;

tricaprylylmethyl ammoniumchloride

1634-04-4

tert-butyl methyl ether

7440-44-0

pyrographite

105827-91-6

α-Cl-β-thiazolyl chloride

145015-15-2

2-chloro-5-(hydroxymethyl)thiazole

Conditions
ConditionsYield
With sodium hydroxide; aq. NaOH; sodium formate In n-heptane94.4%
105827-91-6

α-Cl-β-thiazolyl chloride

120740-08-1

[(2-chloro-5-thiazolyl)methyl]amine

Conditions
ConditionsYield
With hexamethylenetetramine In chloroform for 3h; Heating;94.3%
With ammonium hydroxide In ethanol at 20℃;32.4%
With ammonium hydroxide; sodium hydroxide In ethanol; dichloromethane; acetonitrile
121-33-5

vanillin

105827-91-6

α-Cl-β-thiazolyl chloride

339018-41-6

3-methoxy-4-((2-chlorothiazol-5-yl)methoxy)benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In ethanol for 6h; Reflux;93.6%

3-methyl-4-nitroimino-1,3,5-oxadiazine

105827-91-6

α-Cl-β-thiazolyl chloride

153719-23-4

thiamethoxam

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 30 - 70℃;92.88%
Stage #1: 3-methyl-4-nitroimino-1,3,5-oxadiazine With tetrabutylammomium bromide; potassium carbonate In water; acetonitrile at 70℃; for 1h;
Stage #2: α-Cl-β-thiazolyl chloride In water; acetonitrile at 70℃; for 5h;
105827-91-6

α-Cl-β-thiazolyl chloride

74-89-5

methylamine

120740-06-9

N-(2-chloro-5-thiazolylmethyl)-N-methylamine

Conditions
ConditionsYield
In ethanol; water at 0 - 20℃; for 5h;92%
5465-96-3

2-(nitroimino)imidazolidine

105827-91-6

α-Cl-β-thiazolyl chloride

(EZ)-1-(2-chloro-1,3-thiazol-5-ylmethyl)-N-nitroimidazolidin-2-ylideneamine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Reflux;91.5%
With tetrabutylammomium bromide; potassium carbonate In toluene at 47℃; for 7h; Temperature;91.4%
With potassium carbonate In acetonitrile for 4h; Heating;66%
105827-91-6

α-Cl-β-thiazolyl chloride

1-[6-methyl-4-(4-methylphenyl)-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]-1-ethanone

1133378-44-5

1-[1-(2-chlorothiazol-5-yl-methyl)-2-(2-chlorothiazol-5-yl-methylsulfanyl)-4-methyl-6-(4-tolyl)-1,6-dihydropyrimidin-5-yl]ethanone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;91%
105827-91-6

α-Cl-β-thiazolyl chloride

141856-46-4

1-methyl-2-nitroimino-5-n-propyl-1,3,5-triazacyclohexane

C11H17ClN6O2S

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; Condensation;90%
105827-91-6

α-Cl-β-thiazolyl chloride

219806-93-6

5-acetyl-4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine

1133378-45-6

1-[1-(2-chlorothiazol-5-yl-methyl)-2-(2-chlorothiazol-5-yl-methylsulfanyl)-6-(4-methoxyphenyl)-4-methyl-1,6-dihydropyrimidin-5-yl]ethanone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;90%
105827-91-6

α-Cl-β-thiazolyl chloride

603-35-0

triphenylphosphine

1168140-08-6

((2-chlorothiazol-5-yl)methyl)triphenylphosphonium chloride

Conditions
ConditionsYield
In chloroform for 48h; Reflux;90%
105827-91-6

α-Cl-β-thiazolyl chloride

122454-29-9

tralopyril

4-bromo-2-(4-chlorophenyl)-1-(2-chloro-5-thiazolylmethyl)-5-trifluoromethylpyrrole-3-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Temperature;90%
1260230-40-7

5-(4-methyl-1,2,3-thiadiazol-5-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol

105827-91-6

α-Cl-β-thiazolyl chloride

1569752-99-3

5-(5-(((2-chlorothiazol-5-yl)methyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)-4-methyl-1,2,3-thiadiazole

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; under 10343.2 Torr; for 0.25h; Microwave irradiation;89%
16064-14-5

6-chloroquinazolin-4-one

105827-91-6

α-Cl-β-thiazolyl chloride

6-chloro-3-((2-chlorothiazol-5-yl)methyl)quinazolin-4(3H)-one

Conditions
ConditionsYield
Stage #1: 6-chloroquinazolin-4-one With tetra-(n-butyl)ammonium iodide; potassium hydroxide In toluene at 70℃; for 0.166667h;
Stage #2: α-Cl-β-thiazolyl chloride In toluene at 70℃; for 1h;
89%
105827-91-6

α-Cl-β-thiazolyl chloride

15264-63-8

5-(4-pyridinyl)-1,3,4-oxadiazole-2-thiol

2-(((2-chlorothiazol-5-yl)methyl)thio)-5-(pyridin-4-yl)-1,3,4-oxadiazole

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide under 10343.2 Torr; for 0.25h; Microwave irradiation; Heating;88%
105827-91-6

α-Cl-β-thiazolyl chloride

153719-38-1

3,6-dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazin-4-amine

thiamethoxam

Conditions
ConditionsYield
With potassium carbonate; cesium iodide In butanone at 60℃; for 10h;88%
144459-98-3, 31864-21-8

5-methylcarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidin-2(1H)-thione

105827-91-6

α-Cl-β-thiazolyl chloride

1029433-40-6

1-[1-(2-chlorothiazol-5-yl-methyl)-2-(2-chlorothiazol-5-yl-methylsulfanyl)-4-methyl-6-phenyl-1,6-dihydropyrimidin-5-yl]ethanone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;87%
105827-91-6

α-Cl-β-thiazolyl chloride

1-[4-(4-chlorophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]-1-ethanone

1133378-43-4

1-[6-(4-chlorophenyl)-1-(2-chlorothiazol-5-yl-methyl)-2-(2-chlorothiazol-5-yl-methylsulfanyl)-4-methyl-1,6-dihydropyrimidin-5-yl]ethanone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;87%
19414-86-9

methyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)-2-oxoacetate

105827-91-6

α-Cl-β-thiazolyl chloride

1383843-32-0

methyl 2-(1-((2-chlorothiazol-5-yl)methyl)-5-methoxy-2-methyl-1H-indol-3-yl)-2-oxoacetate

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 65℃; for 2h;87%
1245623-49-7

5-(4-chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

105827-91-6

α-Cl-β-thiazolyl chloride

1332502-88-1

5-(4-chlorophenyl)-2-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; for 1.5h;87%
128883-86-3

tert-butyl (1-methyl-1H-pyrazol-3-yl)carbamate

105827-91-6

α-Cl-β-thiazolyl chloride

tert-butyl N-[(2-chlorothiazol-5-yl)methyl]-N-(1-methylpyrazol-3-yl)carbamate

Conditions
ConditionsYield
Stage #1: tert-butyl (1-methyl-1H-pyrazol-3-yl)carbamate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h;
Stage #2: α-Cl-β-thiazolyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3h;
87%
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Standards and Recommendations

Purity: 98.0%

Analytical Methods

2-CHLORO-5-CHLOROMETHYLTHIAZOLE is isolated by conventional methods, for example by filtration, crystallization, distillation or chromatography or any suitable combination.

Specification

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