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Cas Database

3678-62-4

3678-62-4

Identification

  • Product Name:2-Chloro-4-picoline

  • CAS Number: 3678-62-4

  • EINECS:222-951-2

  • Molecular Weight:127.573

  • Molecular Formula: C6H6ClN

  • HS Code:29349990

  • Mol File:3678-62-4.mol

Synonyms:2-chloro-4-methyl-pyridine;2-Chloro-4-methylpyridine;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi,HarmfulXn

  • Hazard Codes:Xi,Xn

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:2-Chloro-4-methylpyridine
  • Packaging:10g
  • Price:$ 125
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:2-Chloro-4-methylpyridine
  • Packaging:25g
  • Price:$ 220
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Chloro-4-methylpyridine >98.0%(GC)
  • Packaging:25g
  • Price:$ 66
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Chloro-4-methylpyridine >98.0%(GC)
  • Packaging:5g
  • Price:$ 23
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Chloro-4-methylpyridine
  • Packaging:25 g
  • Price:$ 16
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Chloro-4-methylpyridine
  • Packaging:100 g
  • Price:$ 56
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Chloro-4-methylpyridine
  • Packaging:500 g
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Chloro-4-methylpyridine 98%
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  • Manufacture/Brand:Sigma-Aldrich
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  • Manufacture/Brand:Oakwood
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Relevant articles and documentsAll total 20 Articles be found

Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions

Zhang, Xitao,Feng, Xiujuan,Zhang, Haixia,Yamamoto, Yoshinori,Bao, Ming

supporting information, p. 5565 - 5570 (2019/10/22)

A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.

Preparation method of non-transition metal-catalyzed 2-halogenated pyridine compound

-

Paragraph 0064-0066, (2018/10/11)

The invention provides a preparation method of a non-transition metal-catalyzed 2-halogenated pyridine compound. The 2-halogenated pyridine compound is an important component of many medicines and bioactive molecules and has important application in the fields of organic synthesis, medicinal chemistry and the like and wide market prospects. The invention relates to the preparation method of the non-transition metal-catalyzed 2-halogenated pyridine compound. According to the method, pyridine-2-carboxylic acid, derivatives of the pyridine-2-carboxylic acid, NaF, KF, CsF, TBAF, NaCl, KCl, CsCl, TBAC, NCS, NaBr, KBr, CsBr, Br2, TBAB, NBS, NaI, KI, CsI, I2 and NIS are used as raw materials, and under the presence of base and an accelerant and mild conditions, the 2-halogenated pyridine compoundis synthesized. The method has the advantages that the steps are simple, the raw materials are easy to obtain, the reaction conditions are mild and the like; the method has great use value and socialand economic benefits.

Method for producing 2-chloro-4-trifluoromethylpyridine

-

Paragraph 0023; 0027, (2017/09/19)

The invention discloses a method for producing 2-chloro-4-trifluoromethylpyridine, and belongs to the technical field of fine chemical synthesis. The method comprises the following steps: taking 2-amino-4-methylpyridine as a raw material, and successively carrying out diazotization, chlorination and fluoridation on the 2-amino-4-methylpyridine to obtain 2-chloro-4-trifluoromethylpyridine. The diazotization comprises the following steps: taking the 2-amino-4-methylpyridine as the raw material, and carrying out diazotization on the 2-amino-4-methylpyridine, sodium nitrite and hydrogen chloride in a reactor to obtain 2-chloro-4-methylpyridine. The chlorination comprises the following steps: taking the 2-chloro-4-methylpyridine as the raw material, feeding chlorine and carrying out chlorination to obtain 2-chloro-4-(trichloromethyl) pyridine as a main product and hydrogen chloride as a side product. The fluoridation comprises the following steps: taking the 2-chloro-4-(trichloromethyl) pyridine as the raw material, and carrying out fluoridation on the 2-chloro-4-(trichloromethyl) pyridine and anhydrous hydrogen fluoride in an autoclave to obtain the 2-chloro-4-trifluoromethylpyridine as a main product. Industrial production of the 2-chloro-4-trifluoromethylpyridine is realized.

Preparation of an Arenylmethylzinc Reagent with Functional Groups by Chemoselective Cross-Coupling Reaction of Bis(iodoazincio)methane with Iodoarenes

Shimada, Yukako,Haraguchi, Ryosuke,Matsubara, Seijiro

, p. 2395 - 2398 (2015/10/19)

Palladium-catalyzed cross-coupling reaction of bis(iodozincio)methane with iodoarenes carrying various functionalities such as ester, boryl, cyano, and halo groups proceeded chemoselectively to give the corresponding arenylmethylzinc species efficiently. The moderate reactivity of the gem-dizinc reagent imparted functional group tolerance to the process. The transformations from iodoheteroarenes were also performed; in the case of iodopyridine derivatives, the nickel-catalyzed reaction gave the corresponding organozinc species efficiently. The obtained arenylmethylzinc species underwent the copper-mediated coupling reaction with a range of organic halides.

Chemoselective sp 2-sp3 cross-couplings: Iron-catalyzed alkyl transfer to dihaloaromatics

Malhotra, Sushant,Seng, Pamela S.,Koenig, Stefan G.,Deese, Alan J.,Ford, Kevin A.

supporting information, p. 3698 - 3701 (2013/08/23)

The chemoselective functionalization of a range of dihaloaromatics with methyl, cyclopropyl, and higher alkyl Grignard reagents via iron-catalyzed cross-coupling is described. The site selectivity of C-X (X = halogen) activation is determined by factors such as the position of the halogen on the ring, the solvent, and the nucleophile. A one-pot protocol for the chemoselective synthesis of mixed dialkyl heterocycles is achieved solely employing iron catalysis.

Process route upstream and downstream products

Process route

4-methylpyridine-1-oxide
1003-67-4

4-methylpyridine-1-oxide

2-chloro-4-picoline
3678-62-4

2-chloro-4-picoline

4-picolylchloride hydrochloride
1822-51-1

4-picolylchloride hydrochloride

Conditions
Conditions Yield
With diisopropylamine; trichloromethyl chloroformate; In dichloromethane; at -40 - 20 ℃;
2-chloro-4-picoline
3678-62-4

2-chloro-4-picoline

(2-chloropyridin-4-yl)methanol
100704-10-7

(2-chloropyridin-4-yl)methanol

Conditions
Conditions Yield
4-methylpicolinic acid
4021-08-3

4-methylpicolinic acid

2-chloro-4-picoline
3678-62-4

2-chloro-4-picoline

Conditions
Conditions Yield
With tert-butylhypochlorite; sodium carbonate; sodium chloride; In toluene; at 80 ℃; for 20h; Schlenk technique;
71%
With tert-butylhypochlorite; dichloromethane; sodium hydrogencarbonate; at 60 ℃; for 20h; Green chemistry;
74 %Spectr.
2-Amino-4-methylpyridine
695-34-1

2-Amino-4-methylpyridine

2-chloro-4-picoline
3678-62-4

2-chloro-4-picoline

Conditions
Conditions Yield
With sodium nitrite; In hydrogenchloride;
58%
With hydrogenchloride; sodium nitrite; Yield given. Multistep reaction; 1.) concd. hydrochloric acid, 0 - 5 deg C; 2.) water;
With hydrogenchloride; dinitrogen trioxide; tetrabutyl-ammonium chloride; In dichloromethane; for 2h; Ambient temperature;
Multi-step reaction with 2 steps
1: 59 percent / sulphuric acid, sodium nitrite / H2O / 0 - 5 deg C, 45 min; 95 deg C, 15 min
2: 74 percent / phosphorus oxychloride / 2 h / 90 °C
With sulfuric acid; sodium nitrite; trichlorophosphate; In water;
With hydrogenchloride; sodium nitrite; In water; at 20 ℃; Industrial scale;
229.3 g
2-hydroksy-4-methyl-pyridine
13466-41-6,91914-05-5

2-hydroksy-4-methyl-pyridine

2-chloro-4-picoline
3678-62-4

2-chloro-4-picoline

Conditions
Conditions Yield
With sodium carbonate; In chloroform; water; trichlorophosphate;
98.7%
In trichlorophosphate;
In trichlorophosphate;
2-Amino-4-methylpyridine
695-34-1

2-Amino-4-methylpyridine

methyl nitrite
624-91-9

methyl nitrite

2-chloro-4-picoline
3678-62-4

2-chloro-4-picoline

2-methoxy-4-methyl-pyridine
100848-70-2

2-methoxy-4-methyl-pyridine

Conditions
Conditions Yield
2-Amino-4-methylpyridine; With hydrogenchloride; In methanol; at 10 - 30 ℃; for 1.5h;
methyl nitrite; In methanol; at 20 - 30 ℃; for 13h;
With sodium hydroxide; In water; at 30 ℃; pH=12;
69.5%
27.2%
2,4-dichloropyridine
26452-80-2

2,4-dichloropyridine

methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-chloro-4-picoline
3678-62-4

2-chloro-4-picoline

4-chIoro-2-methylpyridine
3678-63-5

4-chIoro-2-methylpyridine

Conditions
Conditions Yield
With iron(III)-acetylacetonate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; toluene; at 20 ℃; for 4h; chemoselective reaction; Inert atmosphere;
76%
With iron(III)-acetylacetonate; In tetrahydrofuran; toluene; at 20 ℃; for 2h; chemoselective reaction; Inert atmosphere;
50%
picoline
108-89-4

picoline

2-chloro-4-picoline
3678-62-4

2-chloro-4-picoline

Conditions
Conditions Yield
picoline; With n-butyllithium; 2-(N,N-dimethylamino)ethanol; In hexane; at 0 ℃; for 1h;
With hexachloroethane; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Further stages.;
80%
Multi-step reaction with 2 steps
1: xylene; sodium amide
2: sodium nitrite; hydrochloric acid; hydrogen chloride / -20 - -15 °C
With hydrogenchloride; sodium amide; xylene; sodium nitrite;
picoline
108-89-4

picoline

p-nitrophenyl isocyanide
1984-23-2

p-nitrophenyl isocyanide

2-chloro-4-picoline
3678-62-4

2-chloro-4-picoline

4-methyl-pyridine-2-carboxylic acid (4-nitro-phenyl)-amide

4-methyl-pyridine-2-carboxylic acid (4-nitro-phenyl)-amide

2-(4-methyl-pyridin-2-yl)-<i>N</i>-(4-nitro-phenyl)-2-oxo-acetamide

2-(4-methyl-pyridin-2-yl)-N-(4-nitro-phenyl)-2-oxo-acetamide

Conditions
Conditions Yield
picoline; With fluorine; In dichloromethane; at -78 - -50 ℃;
p-nitrophenyl isocyanide; In dichloromethane; at -50 - 0 ℃; for 4h;
71%
15%
4-methylpyridine-1-oxide
1003-67-4

4-methylpyridine-1-oxide

2-chloro-4-picoline
3678-62-4

2-chloro-4-picoline

Conditions
Conditions Yield
With trichlorophosphate; at 100 ℃;
64%
With trichlorophosphate; for 3h; Heating;
64%

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