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Innovative Chemical Compound: 2-Chloro-5-chloromethylpyridine (CCMP)

Shandong Jihui Chemical Co., LTD : Deep cultivation of fine chemical industry, cast a diversified industrial pattern.

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2-Chloro-5-methylpyridine

CAS: 18368-64-4

Molecular Formula: C6H6ClN

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Description

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2-Chloro-5-methylpyridine – Introduction

18368-64-4 – Names and Identifiers

Name	2-Chloro-5-methylpyridine
Synonyms	6-CHLORO-3-PICOLINE 2-CHLORO-5-PICOLINE 2-chloro-5-methyl-pyridin 6-CHLORO-3-METHYL PYRIDINE 2-CHLORO-5-PICOLINE 2-CHLORO-5-METHYLPYRIDINE 2-CHLORO-5-METHYLPYRIDINE (2-CHLORO-5-PICOLINE)
CAS	18368-64-4
EINECS	418-050-0
InChI	InChI=1/C6H6ClN/c1-5-2-3-6(7)8-4-5/h2-4H,1H3
InChIKey	VXLYOURCUVQYLN-UHFFFAOYSA-N

18368-64-4 – Physico-chemical Properties

Molecular Formula	C6H6ClN
Molar Mass	127.57
Density	1.169 g/mL at 25 °C (lit.)
Melting Point	97 ºC (30 MMHG)
Boling Point	97 °C/30 mmHg (lit.)
Flash Point	195°F
Water Solubility	Slightly soluble in water.
Vapor Presure	0.736mmHg at 25°C
Appearance	Bright yellow liquid
Specific Gravity	1.169
Color	Clear light yellow to straw-yellow or light pink-orange
pKa	0.54±0.10(Predicted)
Storage Condition	Keep in dark place,Sealed in dry,Room Temperature
Refractive Index	n20/D 1.53(lit.)
MDL	MFCD00792460
Physical and Chemical Properties	Light yellow liquid
Use	Used as a pesticide intermediate

18368-64-4 – Risk and Safety

Risk Codes	R21/22 – Harmful in contact with skin and if swallowed. R38 – Irritating to the skin R52/53 – Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36/37/38 – Irritating to eyes, respiratory system and skin.
Safety Description	S23 – Do not breathe vapour. S25 – Avoid contact with eyes. S36/37 – Wear suitable protective clothing and gloves. S61 – Avoid release to the environment. Refer to special instructions / safety data sheets. S36 – Wear suitable protective clothing. S26 – In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany	2
RTECS	US6740000
HS Code	29333999

18368-64-4 – Reference Information

Use

Used as a pesticide intermediate
2-chloro-5-methylpyridine is an intermediate of imidacloprid and acetamiprid, referred to as monochloride, used to synthesize the next intermediate 2-chloro-5-chloromethylpyridine.

production method

there are many synthesis methods of 2-chloro-5-methylpyridine. according to the different raw materials used, there are mainly the following three routes. Using N-benzyl-N-acrylylacetamide as raw material, N-benzyl-N-acrylylacetamide and phosphorus oxychloride were stirred and reacted at 100 ℃ for 16h to obtain 2-chloro-5-methylpyridine with 67.5% yield. Aminopyridine is used as raw material. The methanol solution of 2-amino-5-methylpyridine is first saturated with hydrogen chloride, and then the mixture of methyl nitrite and hydrogen chloride is introduced to obtain 2-chloro-5-methylpyridine. Methyl nitrite can also be replaced by nitroso chloride or chlorobenzene as a solvent. Using 3-methylpyridine-N-oxide as raw material. Depending on the chlorinating agent used, there are four different ways to choose from. Phosphorus oxychloride is used as chlorinating agent. 3-methylpyridine-N-oxide reacts with phosphorus oxychloride in the presence of an organic base to produce 2-chloro-5-methylpyridine, and has a by-product 2-chloro-3-methylpyridine. Add a certain amount of 3-methylpyridine-N-oxide and solvent into the reaction kettle, add phosphorus oxychloride and organic phosphorus at -10 ℃, after dropping, react at -2 ℃ for 5h, hydrolyze, desolvate, distill to obtain crude products, and then freeze and crystallize to obtain fine monochloride. COCl2 can also be used instead of POCl3 as chlorinating agent. N,N-diethylamino phosphorus oxychloride as chlorinating agent. At room temperature, a dichloromethane solution containing 2-chloro-5-methylpyridine-N-oxide was treated with N,N-diethylaminooxyphosphorus and diisopropylamine dissolved in dichloromethane to obtain a mixture containing 2-chloro-5-methylpyridine-82%, 2-chloro-3-methylpyridine-12% in 83% yields. Phthalyl chloride is used as chlorinating agent. Phthalyl chloride was added dropwise to a mixture containing 3-methylpyridine-N-oxide, triethylamine and dichloromethane for reaction to obtain a mixture containing 2-chloro-5-methylpyridine 84% and 2-chloro-3-methylpyridine 16% with 85% yields. Organic salt is used as intermediate. 2-chloro-5-methylpyridine can also be prepared from n-propionaldehyde, methyl acrylate and morpholine. At present, some domestic enterprises also adopt this method.

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