intermediate for Clethodim

Name	(3-trans-Chloroallyl)oxyamine
Synonyms	intermediate for Clethodim (3-trans-Chloroallyl)oxyamine O-(3-Chloroallyl)hydroxylaMine (E)-O-(3-Chloroallyl)hydroxylamine O-(3-Chloro-2-propenyl)hydroxylamine O-(1-chloroprop-2-en-1-yl)hydroxylamine (E)-O-(3-Chloro-2-propenyl)hydroxylamine Hydroxylamine,O-[(2E)-3-chloro-2-propen-1-yl]-
CAS	87851-77-2
InChI	InChI=1/C3H6ClNO/c1-2-3(4)6-5/h2-3H,1,5H2

Molecular Formula	C3H6ClNO
Molar Mass	107.54
Density	1.155
Boling Point	209 ºC
Flash Point	80 ºC
Solubility	Chloroform (Slightly), Ethyl Acetate (Slightly)
Vapor Presure	0.798mmHg at 25°C
Appearance	Oil
Color	Clear Colourless
pKa	3.80±0.70(Predicted)
Storage Condition	Inert atmosphere,Store in freezer, under -20°C
Refractive Index	1.454

Overview	trans-3-chloro-2-propenyl hydroxylamine is an amine-based organic compound that can be used as a pharmaceutical synthesis intermediate.
preparation	3-bromo-2-chloropropene (1.4mL,13mmol,1.1 EQ) and 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU; 1.8mL,12mmol,1.0 equiv) was successively added to dichloromethane. Stirring of 2-hydroxyisoindoline-1, 3-dione (N-hydroxyphthalimide; 2.0g,12 mmol,1.0 equiv) in NN-dimethylformamide (DMF; 30 mL) in the solution. The resulting solution was changed from yellow to deep red to colorless in about 5 min and stirred at 230 C for 18 h. The reaction mixture was diluted with 1m aqueous hydrochloric acid (HCl; 300ml). The resulting white precipitate was vacuum filtered and washed with water to give a white powder (2.3g) which was dissolved in CH2Cl2(53ml). Hydrazine hydrate (570 μL,12mmol,1.1 equiv) was added and the resulting white suspension was stirred for 18h at 230 °c. The reaction mixture was vacuum filtered. The filtrate was diluted with 0.1M aqueous NaOH (200ml) and extracted with CH2Cl2(3 x 50ml). The combined organic layers were dried over Na2SO4, gravity filtered, and concentrated by rotary evaporation to give trans-3-chloro-2-propenyl hydroxylamine as a white semi-solid.
emergency	if trans-3-chloro-2-propenyl hydroxylamine is inhaled, please move the patient to fresh air; If skin contact, should remove contaminated clothing, with soap water and water thoroughly rinse the skin, if there is discomfort, see a doctor.

Last Update：2024-09-20 09:44:13

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