2-Chloro-5-chloromethylthiazole supplier

Name
2-Chloro-5-chloromethylthiazole
EINECS 429-830-5
CAS No. 105827-91-6
Article Data43
CAS DataBase
Density 1.503 g/cm³
Solubility insoluble in water, soluble in dichloromethane, chloroform, carbon tetrachloride and other solvents
Melting Point 31 °C
Formula C₄H₃Cl₂NS
Boiling Point 268.6 °C at 760 mmHg
Molecular Weight 168.047
Flash Point 116.3 °C
Transport Information
Appearance white to pale yellow crystal or colorless liquid
Safety 26-37
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
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

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%

: 196406-44-7
3-chloro-1-isothiocyanato-1-propene

: 105827-91-6
α-Cl-β-thiazolyl chloride

Conditions

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%

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

: 105827-91-6
α-Cl-β-thiazolyl chloride

Conditions

Conditions	Yield
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

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

: 33342-65-3
2-chloro-5-methyl-thiazole

: 105827-91-6
α-Cl-β-thiazolyl chloride

Conditions

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;

: 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

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%

: 192439-48-8
2-benzylsulfanyl-5-chloromethyl-thiazole

: 105827-91-6
α-Cl-β-thiazolyl chloride

Conditions

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

: 2-chloroallylisonitrile

: 105827-91-6
α-Cl-β-thiazolyl chloride

Conditions

Conditions	Yield
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

Conditions	Yield
With N-chloro-succinimide; sulfuryl dichloride In dichloromethane	48%
With sulfuryl dichloride

: 188988-52-5
N-(2-chloroallyl)formamide

: 105827-91-6
α-Cl-β-thiazolyl chloride

Conditions

Conditions	Yield
With thionyl chloride; sulfur dichloride for 24h; Cyclization; chlorination; Heating;	42%
With thionyl chloride; sulphur dichloride	42%

: 78-88-6
2,3-Dichloroprop-1-ene

: 540-72-7
sodium thiocyanide

: 105827-91-6
α-Cl-β-thiazolyl chloride

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide; aq. NaOH; sodium formate In n-heptane	94.4%

...Expand

: 105827-91-6
α-Cl-β-thiazolyl chloride

: 120740-08-1
[(2-chloro-5-thiazolyl)methyl]amine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

2-Chloro-5-chloromethylthiazole Standards and Recommendations

Purity: 98.0%

2-Chloro-5-chloromethylthiazole Analytical Methods

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

2-Chloro-5-chloromethylthiazole 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

Product Name

2-Chloro-5-chloromethylthiazole

Synthetic route

2-Chloro-5-chloromethylthiazole Standards and Recommendations

2-Chloro-5-chloromethylthiazole Analytical Methods

2-Chloro-5-chloromethylthiazole Specification

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