2-Chloro-5-Chloromethylpyridine (CCMP) CAS 70258-18-3

2-chloro-5-chloromethylpyridine (CCMP), dawb crystal, yog ib qho organic compound thiab ib qho tseem ceeb nruab nrab ntawm kev sib txuas ntawm cov tshuaj tua kab thiab tshuaj. Cov khoom lag luam uas muaj qhov muaj zog rhiab heev yog cov kua txiv kab ntxwv-liab kua nplaum, nrog cov ntxhiab tsw ntxhiab, soluble hauv ntau yam organic solvents thiab organic acids. Khaws rau hauv ib lub thawv ntim rau hauv qhov chaw txias, qhuav. Lub chaw cia khoom yuav tsum raug kaw thiab cov yuam sij yuav tsum khaws cia los ntawm cov kws tshaj lij thiab lawv cov neeg pabcuam. Kev khaws cia yuav tsum khaws cia kom deb ntawm oxidants. Nws yog siv los ua ib qho nruab nrab ntawm cov tshuaj tua kab imidacloprid thiab acetamiprid; 2-chloro-5-chloromethylpyridine yog ib qho nruab nrab ntawm cov tshuaj tua kab imidacloprid thiab acetamiprid.

Melting point {{0}} degree C (lit.), Boiling point 267.08 degree C (kwv yees ntxhib), Ceev 1.4411 (kwv yees ntxhib), Refractive index 1.6000 (kwv yees), Flash point> 230 degree f, Cia mob: ntxig cua, 2-8 degree C, Acidity coefficient (PKA) - 0.75 ± 0.10 (kwv yees), Daim ntawv moist crystals, xim beige, Solubility hauv dej, BRN 1635690, InChIKeySKCNYHLTRZIINA-UHFFFAOYSA-N .

Cov molecule no yog tsim los ntawm ib lub nplhaib pyridine thiab ib pawg chloroethane. Ntawm lub nplhaib pyridine, muaj cov tshuaj chlorine atom (Cl) txuas nrog cov pa roj carbon thib ob, thaum nyob hauv pawg chloroethane, muaj cov tshuaj chlorine atom (Cl) txuas nrog cov pa roj carbon atom, thiab cov methyl pawg (CH3) txuas nrog. tib carbon atom.
Tam sim no cia peb ua qhov kev ntsuam xyuas ntxaws ntxiv:
Pyridine nplhaib: Ib lub nplhaib pyridine yog rau lub nplhaib heterocyclic uas muaj rau cov pa roj carbon atom thiab ib lub atom nitrogen. Nyob rau hauv no molecule, lub nitrogen atom nyob rau ntawm qhov chaw nruab nrab. Cov pa roj carbon atoms ntawm lub nplhaib pyridine tuaj yeem suav los ntawm 1 txog 6, qhov twg thawj carbon atom txuas nrog nitrogen atom.
2nd carbon atom: 2nd carbon atom yog cov pa roj carbon atom txuas nrog chlorine atom ntawm lub nplhaib pyridine. Nws txuas nrog carbon atom 1 los ntawm carbon nitrogen ib daim ntawv cog lus.
Chloroethane pawg: Cov pab pawg chloroethane yog tsim los ntawm chlorine atom thiab methyl pawg. Cov tshuaj chlorine atom txuas nrog cov pa roj carbon atom ntawm pawg chloroethane, thiab pawg methyl txuas nrog tib cov pa roj carbon atom. Cov pab pawg chloroethane no tuaj yeem suav tias yog chloroethane molecule.

Cov kauj ruam tshwj xeeb rau cov synthesis ntawm2-chloro-5-chloromethylpyridine (CCMP)nyob rau hauv lub laboratory yog raws li nram no:

Demethylation: Sib tov 2-chloro-5-methylpyridine nrog rau qhov tsim nyog ntawm sodium hydroxide tov nyob rau hauv ib lub khob hauv qab thiab cua sov rau 100 degree.

C₆H₆ClN + NaOH → 2−Cl−5−Py + MeOH

Sulfation: Cov khoom tau txais nyob rau hauv cov kauj ruam dhau los yog reacted nrog sulfuric acid kom undergo sulfation.

2-Cl-5-Py + H₂YOG₄→ 2-Cl-5-ClMPy + H₂O

Sib cais thiab purification: Cov khoom tau muab rho tawm thiab crystallized, thiab ces recrystallized rau purification.

2-Cl-5-ClMPy+ H₂O → 2–Cl–5–ClMPy–H₂O

Recrystallization equation: 2-Cl-5-ClMPy + H₂O → 2−Cl−5−ClMPy + H₂O

Qhuav: Qhuav cov khoom purified kom tau cov khoom kawg.

2–Cl–5–ClMPy → 2–Cl–5–ClMPy + H₂O → 2–Cl–5–ClMPy

1. Ntxiv 2-chloro-5-methylpyridine thiab ib qho kev tsim nyog ntawm sodium hydroxide tov rau hauv lub khob ntim hauv qab thiab do kom sib npaug.

2. Muab lub khob ntim hauv qab rau hauv lub evaporator rotary, ua kom sov hauv cov roj da dej kom txog 100 degree, thiab tuav rau ob peb teev kom tso cai ua tiav cov tshuaj tiv thaiv ntawm 2-chloro-5-methylpyridine.

3. Tom qab cov tshuaj tiv thaiv tiav, ncuav cov tshuaj tiv thaiv rau hauv ib qho kev sib cais thiab ntxiv cov dej uas tsim nyog rau kev rho tawm. Tom qab txheej txheej, cais cov txheej txheem organic los ntawm theem aqueous.

4. Qhuav cov organic theem los ntawm lub tshuab ziab khaub ncaws silicone kom tshem tawm cov dej noo thiab impurities.

5. Ncuav cov hmoov nplej qhuav rau hauv ib lub lauj kaub, ntxiv ib qho tsim nyog ntawm sulfuric acid, thiab do sib npaug. Tom qab ntawd muab tso rau hauv ib qho dej khov da dej kom txias thiab cia nws crystallize.

6. Tom qab crystallization tiav lawm, lim cov muaju thiab ntxuav nrog dej txias me me. Qhuav cov crystals hauv qhov cub kom tau cov khoom kawg, 2-chloro-5-chloromethylpyridine.

3, khoom purification

Muab cov tau txais 2-chloro-5-chloromethylpyridine tso rau hauv lub raj mis uas hnyav, hnyav thiab sau cia.

Muab cov 2-chloro-5-chloromethylpyridine nyob rau hauv lub raj mis uas muaj qhov tsim nyog ntawm dichloromethane, thiab tom qab ntawd ua kem chromatography purification nrog silica gel.

Recrystallize cov purified 2-chloro-5-chloromethylpyridine rau kev ua kom huv ntxiv.

Qhuav lub purified 2-chloro-5-chloromethylpyridine kom tau cov khoom kawg.

Cov txheej txheem ntawm cyclization ntawm acetaldehyde rau synthesize 2-chloro-5-methylpyridine yeej muaj ntau yam tshuaj. Cov nram qab no yog cov kauj ruam ntxaws thiab sib npaug ntawm cov tshuaj sib npaug rau cov tshuaj tiv thaiv no:

1. Kev tsim cov N-oxide ntawm 2-chloro-5-methylpyridine los ntawm 3-methylpyridine li raw khoom

Qhov no tau txais los ntawm nitrification cov tshuaj tiv thaiv. Raws li kev ua ntawm nitric acid, C-5 txoj hauj lwm ntawm 3-methylpyridine yog nitrated, tsim N-oxide ntawm 2-chloro-5-methylpyridine.

3-MePy + HNO₃→ 2–Cl–5–MePyNO₂ + HNO₂

2. Cyclization ntawm pyrimidine nrog acetaldehyde kom tau txais 2-chloro-5-methylpyridine

Cov tshuaj tiv thaiv no yog cov tshuaj tiv thaiv condensation ntawm pyrimidine thiab acetaldehyde catalyzed los ntawm acid, tsim ib lub nplhaib tsib.

C₄H₄N₂ + C₃H₆CHO → 2−Cl−5−MePy + H₂O

3. Chlorination ntawm 2-chloro-5-methylpyridine

Qhov no yog ib qho tshuaj tiv thaiv electrophilic hloov pauv. Chlorine, ua ib qho electrophilic reagent, tawm tsam C-2 txoj hauj lwm hauv 2-chloro-5-methylpyridine los tsim 2,5-dichloromethylpyridine.

2-Cl-5-MePy + Cl₂→ 2,5–Cl2MePy

4. Chlorination ntawm 2, 5-Dichloromethylpyridine

Txuas ntxiv chlorinating 2,5-dichloromethylpyridine, hloov cov tshuaj chlorine ntawm txoj hauj lwm C-5 los tsim 2,3,5-trichloromethylpyridine.

2,5-Cl2MePy + Cl₂→ 2,3,5-Cl3MePy

5. Kev npaj ntawm 2-chloro-5-methylpyridine nyob rau hauv muaj carbon tetrachloride los yog ethyl wax

Qhov no yog cov kua-theem cov tshuaj tiv thaiv uas cuam tshuam nrog kev ua ntawm cov kuab tshuaj thiab azodiisocitrile ua tus pib. Cov kev sib npaug tshuaj tshwj xeeb yuav tsum tau txiav txim siab raws li qhov kev sim thiab kev ua haujlwm, tab sis tuaj yeem qhia tau hais tias: 2,3,5−Cl3MePy+RCOCl → 2−Cl− (RCO) MePy

Ntawm lawv, R=CCl4 lossis C18H37.

Cov kauj ruam no muab ib txoj hauv kev rau kev sib txuas lub hom phiaj2-chloro-5-chloromethylpyridine (CCMP)los ntawm cov khoom siv raw. Txawm li cas los xij, cov tshuaj tiv thaiv no yuav tsum tau ua raws li cov xwm txheej tshwj xeeb thiab tuaj yeem koom nrog lwm cov kauj ruam nruab nrab lossis kev cuam tshuam sab nraud. Yog li ntawd, ua ntej kev ua haujlwm tiag tiag, nws raug nquahu kom ua cov ntaub ntawv ntxaws ntxaws thiab kev sim ua ntej kev tshawb fawb.

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