2-Chloro-5-chloromethylpyridine
- Iupac Name：2-chloro-5-(chloromethyl)pyridine
- CAS No.: 70258-18-3
- Molecular Weight：162.013
- Modify Date.: 2022-11-29 04:09
- Introduction: 2-Chloro-5-chloromethylpyridine is used for the synthesis of various pharmaceutical compounds. It can also be used for the synthesis of new neonicotinoid compounds1, having insecticidal activity. It is the raw material of pesticide products such as imidacloprid, acetamiprid as well as bactericide and herbicide2,3.
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1. Names and Identifiers
- 1.1 Name
- 2-Chloro-5-chloromethylpyridine
- 1.2 Synonyms
(6-Chloro-3-pyridyl)methyl chloride 2-Chloro-5-(chloromethyl)pyridine 2-CHLORO-5-(CHLOROMETHYL)PYRIDINE[FOR IMIDACLOPRID] 2-CHLORO-5-CHLOROMETHYLPYRIDINE 2-CHLORO-5-CHLOROMETHYLPYRIDINE 2-Chloro-5-pyridylmethyl chloride 2-Chloropyridin-5-ylmethyl chloride 3-(Chloromethyl)-6-chloropyridine 5-(Chloromethyl)-2-chloropyridine 6-Chloro-3-(chloromethyl)pyridine imidacloprid impurity Pyridine, 2-chloro-5-(chloromethyl)- Pyridine, 2-chloro-5-(chloromethyl)- (9CI)
- 1.3 CAS No.
- 70258-18-3
- 1.4 CID
- 155479
- 1.5 EINECS(EC#)
- 615-091-8; 454-800-3
- 1.6 Molecular Formula
- C6H5Cl2N (isomer)
- 1.7 Inchi
- InChI=1S/C6H5Cl2N/c7-3-5-1-2-6(8)9-4-5/h1-2,4H,3H2
- 1.8 InChkey
- SKCNYHLTRZIINA-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=CC(=NC=C1CCl)Cl
- 1.10 Isomers Smiles
- C1=CC(=NC=C1CCl)Cl
2. Properties
- 2.1 Density
- 1.324
- 2.1 Melting point
- 37-42℃
- 2.1 Boiling point
- 249.8 °C at 760 mmHg
- 2.1 Refractive index
- 1.547
- 2.1 Flash Point
- >110℃
- 2.1 Precise Quality
- 160.98000
- 2.1 PSA
- 12.89000
- 2.1 logP
- 2.47380
- 2.1 Appearance
- beige moist crystals
- 2.2 Storage
- Ambient temperatures.
- 2.3 Chemical Properties
- beige moist crystals 2-Chloro-5-chloromethylpyridine Preparation Products And Raw materials Raw materials
- 2.4 Color/Form
- Beige
- 2.5 pKa
- -0.75±0.10(Predicted)
- 2.6 Water Solubility
- Insoluble in water.
- 2.7 StorageTemp
- Refrigerator
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- 18 g (0.1 mol) of 2-chloro-2-chloromethyl-4-cyanobutanal were addedDissolved in 50 ml of toluene, A solution of 33 g (1.1 eqiv)Solid phosgene toluene solution, The reaction was incubated at 50 ° C for 5 hours. Cooling crystallization, Acetamiprid intermediate 2-chloro-5-chloromethylpyridine, yield 97percent.Then methylated, esterified to synthesize acetamiprid original drug, Yield 95percent.Mix 9000g (about 50mol) of 2-chloro-2-chloromethyl-4-cyanobutyraldehyde and 32000ml of chlorobenzene, Dissolve 2870 g (about 9.66 mol) (CCl3)2CO3 with 14000 ml of chlorobenzene.Proportional to the use of the pump to drive the two materials simultaneously into the heating device, 0.1m2 continuous reactor equipped with reflux condenser and thermometer at the outletThe reactor outlet material temperature was controlled at 105°C.One-stage reactor outlet sampling, GC analysis, solvent peak deducted, Unreacted 2-chloro-2-chloromethyl-4-cyanobutyraldehyde 1.8percent, 2-chloro-5-chloromethylpyridine 87.5percent, (CCl3)2CO 31.6percent.After the material passes through the primary reactor, it is heated toA 0.15m2 secondary reactor equipped with a reflux condenser and thermometer at the outletControl and control the temperature between 105 ~ 110 °C.Secondary reactor outlet sampling, GC analysis, solvent peak deducted, Unreacted 2-chloro-2-chloromethyl-4-cyanobutanal 0.08percent, 2-chloro-5-chloromethylpyridine 92.1percent, (CCl3)2CO 31.1percent. Hydrogen chloride tail gas is absorbed by lye.After about 17 minutes, the material enters with mechanical stirring, reflux condenser, Thermometer 20000ml hydrolysis neutralizer with overflowA 10percent Na2CO3 solution was added to the bottle in proportion to control the pH to 7.5-8.Then divide the neutralized material into water, The aqueous layer was extracted twice with chlorobenzene, and the organic layer and the extract were combined and distilled after desolvation under reduced pressure.Collect fractions at 100 to 105 °C (750 mmHg vacuum), This gave 6763 g of 2-chloro-5-chloromethylpyridine. GC analysis, content 95.2percent, yield 79.5percent.Chloro-5-methylpyridine 350g, was added to a 500ml four-necked flask under stirring and heating 115-120 conditions, Into the chlorine reaction 5.5 hours, Control analysis of 2-chloro-5-dichloropyridine <3wtpercentAfter stopping the reaction cooling down, Analysis of feed solution 2-chloro-5-methyl pyridine, 2-Chloro-5-chloromethylpyridineAnd 2-chloro-5-dichloromethyl pyridine content, Chloro-5-chloromethylpyridine (calculated as 2-chloro-5-methylpyridine)The yield was 93.5percent.the above-obtained oil layer is mixed with 2-chloro-5-chloromethylpyridine of equal quality, 350 g of azobisisobutyronitrile, and chlorine, and the temperature of the mixture is maintained at 50-60° C., flowing through the ultraviolet light. In the tube reactor, the reaction was completed, 200 kg of water was washed, and the mixture was allowed to stand for delamination to obtain 105.6 kg of 2-chloro-5-chloromethylpyridine liquid having a purity of 99.6percent. The yield was 96.7percent (based on the conversion of 3-methylpyridine. ).Take the compound CCC 0.1mol, Dissolved in 20 ml of toluene, The oil bath was heated to 90 ° C, 6.6 g of catalyst N, N-dimethylformamide, A 40 ml portion of toluene solution containing 14.74 g (0.08 mol) of cyanuric chloride was added dropwise, Keep the temperature between 90-100 ° C, Dropping 2h, 100 for 30 minutes, Then cooled to 50 ° C, Add 10 ml of water, Then 10.7 g of an aqueous solution of 30percent NaOH was added dropwise at 20-50 ° C, The pH of the aqueous phase is about 8.0-10.0, Start filtering, The filter cake was rinsed with 10 ml of toluene, The separated filtrate was allowed to stand, The upper layer is toluene, De-dissolving, 18.4 g of a brown solid, GC internal standard detection containing CCMP 75.4percentYield 85.8percent.
4. Safety and Handling
- 4.1 Symbol
- GHS05;GHS07;
- 4.1 Hazard Codes
- C
- 4.1 Signal Word
- DANGER
- 4.1 Risk Statements
- R34
- 4.1 Safety Statements
- S25;S36/37/39;S45
- 4.1 Packing Group
- II
- 4.1 Hazard Declaration
- H302; H314
- 4.1 RIDADR
- UN 1759
- 4.1 Caution Statement
- P280-P305 + P351 + P338-P310
- 4.1 WGK Germany
- 3
- 4.1 Safety
-
Safty information about 2-Chloro-5-chloromethylpyridine (CAS NO.70258-18-3) is:
Hazard Codes:?
C,
Xi,
F
Risk Statements: 22-34-36-10?
R22:Harmful if swallowed.?
R34:Causes burns.?
R36:Irritating to eyes.?
R10:Flammable.
Safety Statements: 26-36/37/39-45-25-36-16?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S25:Avoid contact with eyes.?
S36:Wear suitable protective clothing.?
S16:Keep away from sources of ignition.
RIDADR: UN 3261 8/PG 2
WGK Germany: 3
Hazard Note: Corrosive/Harmful
HazardClass: LACHRYMATOR, CORROSIVE
PackingGroup: II
- 4.2 Specification
-
?2-Chloro-5-chloromethylpyridine , its cas register number is 70258-18-3. It also can be called?2-Chloro-5-(chloromethyl)pyridine ; Pyridine, 2-chloro-5-(chloromethyl)- .It is a?beige moist crystals.
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
Skin corrosion, Category 1B
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |   |
| Signal word | Danger |
| Hazard statement(s) | H302 Harmful if swallowed H314 Causes severe skin burns and eye damage |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P280 Wear protective gloves/protective clothing/eye protection/face protection. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
| Storage | P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
70258-18-3Total: 14 Synthesis Route
9. Other Information
- 9.0 Usage
- 2-Chloro-5-(chloromethyl)pyridine is used for the synthesis of various pharmaceutical compounds. It can also be used for the synthesis of new neonicotinoid compounds.
- 9.1 Storage Conditions
- 18 g (0.1 mol) of 2-chloro-2-chloromethyl-4-cyanobutanal were addedDissolved in 50 ml of toluene, A solution of 33 g (1.1 eqiv)Solid phosgene toluene solution, The reaction was incubated at 50 ° C for 5 hours. Cooling crystallization, Acetamiprid intermediate 2-chloro-5-chloromethylpyridine, yield 97percent.Then methylated, esterified to synthesize acetamiprid original drug, Yield 95percent.Mix 9000g (about 50mol) of 2-chloro-2-chloromethyl-4-cyanobutyraldehyde and 32000ml of chlorobenzene, Dissolve 2870 g (about 9.66 mol) (CCl3)2CO3 with 14000 ml of chlorobenzene.Proportional to the use of the pump to drive the two materials simultaneously into the heating device, 0.1m2 continuous reactor equipped with reflux condenser and thermometer at the outletThe reactor outlet material temperature was controlled at 105°C.One-stage reactor outlet sampling, GC analysis, solvent peak deducted, Unreacted 2-chloro-2-chloromethyl-4-cyanobutyraldehyde 1.8percent, 2-chloro-5-chloromethylpyridine 87.5percent, (CCl3)2CO 31.6percent.After the material passes through the primary reactor, it is heated toA 0.15m2 secondary reactor equipped with a reflux condenser and thermometer at the outletControl and control the temperature between 105 ~ 110 °C.Secondary reactor outlet sampling, GC analysis, solvent peak deducted, Unreacted 2-chloro-2-chloromethyl-4-cyanobutanal 0.08percent, 2-chloro-5-chloromethylpyridine 92.1percent, (CCl3)2CO 31.1percent. Hydrogen chloride tail gas is absorbed by lye.After about 17 minutes, the material enters with mechanical stirring, reflux condenser, Thermometer 20000ml hydrolysis neutralizer with overflowA 10percent Na2CO3 solution was added to the bottle in proportion to control the pH to 7.5-8.Then divide the neutralized material into water, The aqueous layer was extracted twice with chlorobenzene, and the organic layer and the extract were combined and distilled after desolvation under reduced pressure.Collect fractions at 100 to 105 °C (750 mmHg vacuum), This gave 6763 g of 2-chloro-5-chloromethylpyridine. GC analysis, content 95.2percent, yield 79.5percent.Chloro-5-methylpyridine 350g, was added to a 500ml four-necked flask under stirring and heating 115-120 conditions, Into the chlorine reaction 5.5 hours, Control analysis of 2-chloro-5-dichloropyridine <3wtpercentAfter stopping the reaction cooling down, Analysis of feed solution 2-chloro-5-methyl pyridine, 2-Chloro-5-chloromethylpyridineAnd 2-chloro-5-dichloromethyl pyridine content, Chloro-5-chloromethylpyridine (calculated as 2-chloro-5-methylpyridine)The yield was 93.5percent.the above-obtained oil layer is mixed with 2-chloro-5-chloromethylpyridine of equal quality, 350 g of azobisisobutyronitrile, and chlorine, and the temperature of the mixture is maintained at 50-60° C., flowing through the ultraviolet light. In the tube reactor, the reaction was completed, 200 kg of water was washed, and the mixture was allowed to stand for delamination to obtain 105.6 kg of 2-chloro-5-chloromethylpyridine liquid having a purity of 99.6percent. The yield was 96.7percent (based on the conversion of 3-methylpyridine. ).Take the compound CCC 0.1mol, Dissolved in 20 ml of toluene, The oil bath was heated to 90 ° C, 6.6 g of catalyst N, N-dimethylformamide, A 40 ml portion of toluene solution containing 14.74 g (0.08 mol) of cyanuric chloride was added dropwise, Keep the temperature between 90-100 ° C, Dropping 2h, 100 for 30 minutes, Then cooled to 50 ° C, Add 10 ml of water, Then 10.7 g of an aqueous solution of 30percent NaOH was added dropwise at 20-50 ° C, The pH of the aqueous phase is about 8.0-10.0, Start filtering, The filter cake was rinsed with 10 ml of toluene, The separated filtrate was allowed to stand, The upper layer is toluene, De-dissolving, 18.4 g of a brown solid, GC internal standard detection containing CCMP 75.4percentYield 85.8percent.
10. Computational chemical data
- Molecular Weight: 162.013g/mol
- Molecular Formula: C6H5Cl2N
- Compound Is Canonicalized: True
- XLogP3-AA: 2.2
- Exact Mass: 160.9799046
- Monoisotopic Mass: 160.9799046
- Complexity: 87.1
- Rotatable Bond Count: 1
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 1
- Topological Polar Surface Area: 12.9
- Heavy Atom Count: 9
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcYBiAAAGAAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAABgAAAHAIAAAAADAPBGmQ8gJIIEACgAjBnRACCgCAxByAI2CA4ZpgIIOLBk5GEIAhggADIyAYQAAAMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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