39229-33-9|2-(2-Chloroethoxy)acetyl chloride| Ambeed

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Inaccessible (Haz class 6.1), International	USD 150+
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Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

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CAS No. :	39229-33-9
Formula :	C₄H₆Cl₂O₂
M.W :	157.00
SMILES Code :	O=C(Cl)COCCCl
MDL No. :	MFCD18379273

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H290-H335-H314
Precautionary Statements:	P234-P260-P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P390-P403+P233-P405-P406-P501
Class:	8
UN#:	3265
Packing Group:	Ⅱ

Yield	Reaction Conditions	Operation in experiment
82%	With thionyl chloride;N,N-dimethyl-formamide; at 60℃; for 1 - 16h;Product distribution / selectivity;	1.39 g (10.0 mmol) 2-<strong>[14869-41-1](2-chloro-ethoxy)-acetic acid</strong> are heated to 60° C. for 1 h with 1 drop of DMF in 8.0 ml of thionyl chloride and then evaporated down completely i. vac. The residue is added in 5 ml THF to a mixture of 1.18 g (10.0 mmol) 4-amino-benzonitrile and 4.5 ml (32.5 mmol) TEA in 20 ml THF at 0° C. and rinsed with 5 ml THF. Then the mixture is stirred for 16 h at ambient temperature. After evaporation i. vac. the residue is combined with ethyl acetate, washed with 2N hydrochloric acid and sat. sodium hydrogen carbonate solution and dried on sodium sulphate. After evaporation i. vac. the residue is purified by chromatography on silica gel (eluant gradient: petroleum ether/ethyl acetate=6:1-->3:1). Yield: 1.82 g (76percent) Rf value: 0.43 (silica gel, petroleum ether/ethyl acetate 1:1) C11H11ClN2O2 (238.67) Mass spectrum: (M-H)-=237/239 (chlorine isotopes); (c) 2-<strong>[14869-41-1](2-chloro-ethoxy)-acetic acid</strong>-chloride13.86 g (100 mmol) 2-<strong>[14869-41-1](2-chloro-ethoxy)-acetic acid</strong> are combined with 15 ml (207 mmol) thionyl chloride at ambient temperature and 3 drops of DMF are added. The mixture is stirred for 16 h at 60° C. Then it is evaporated down i. vac., the residue is distilled i. vac. and the overflow is collected at 75-78° C.Yield: 12.90 g (82percent)C4H6Cl2O2 (157.00)Mass spectrum: (M+H)+=157/159/161 (chlorine isotopes)
	With thionyl chloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 2.5h;	2-Chlorethoxyacetic acid (1.11 g, 8 mmol) is dissolved in dichloromethane (22 mL), and thereto are added thionyl chloride (1.17 mL, 16 mmol) and dimethylformamide (30 muL, 0.4 mmol) successively at room temperature. After stirring at room temperature for 2.5 hours, the mixture is concentrated, and the residue is dissolved in dichloromethane (22 mL). To the mixture are added methyl 4-aminobenzoate (661 mg, 4 mmol) and pyridine (674 muL, 8 mmol) under ice-cooling, followed by stirring overnight. The reaction solution is washed with dilute hydrochloric acid, dried, and concentrated. The residue is subjected to silica gel column chromatography to give ethyl 4-(2-chloroethoxyacetylamino)benzoate (540 mg, 23.6percent).
	With oxalyl dichloride; at 20℃; for 8h;	Step 2: 2-(2-Chloroethoxy)acetyl Chloride (c-3); oCl ^" ^ ClTo the acid, oxalyl chloride (50 mL), was added. The reaction was stirred at room temperature for 8 h. The solids were filtered and washed with DCM. The volatiles were removed and to give the product (560 mg), as a light yellow oil, which was used without further purification.1H NMR (400 MHz, CHLOROFORM-c/), delta ppm 3.67 (t, J=5.5 Hz, 2 H), 3.88 (t, J=5.7 Hz, 2 H), 4.52 (s, 2 H).

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CAS No.: 39229-33-9

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CAS No.: 39229-33-9

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[ 39229-33-9 ] Synthesis Path-Downstream 1~1

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	With thionyl chloride; at 60℃; for 1h;	2-(2-Chloroethoxy)acetyl chloride combined with thionyl chloride (9.51 ml, 130 mmol) and heated at 60 °C for lh. Thionyl chloride was removed in vacuum and resulting liquid was used without purification.
	With oxalyl dichloride; In dichloromethane; at 20℃; for 4h;	2-(2-Chloroethoxy)acetic acid (1.0 g, 7.2 mmol) was dissolved in dichloromethane (10.0 mL)Then oxalyl chloride (1.2 mL, 14 mmol) was added and stirred at room temperature for 4 hours.Evaporate the solvent under reduced pressure.The crude product was used directly in the next reaction.

Precautionary Statements-General
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Prevention
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P321
P322
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P378
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P401
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Physical hazards
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H271	May cause fire or explosion; strong oxidizer
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H290	May be corrosive to metals
Health hazards
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