|
|
| | O-Benzylhydroxylamine hydrochloride Basic information |
| | O-Benzylhydroxylamine hydrochloride Chemical Properties |
| Melting point | 238 °C (subl.)(lit.) | | storage temp. | Inert atmosphere,2-8°C | | solubility | Soluble in DMSO and methanol. | | form | Crystalline Powder or Flakes | | color | White to almost white | | PH | 2.2～3.2 (10g/l, 25℃) | | Sensitive | Hygroscopic | | BRN | 3595440 | | InChI | InChI=1S/C7H9NO.ClH/c8-9-6-7-4-2-1-3-5-7;/h1-5H,6,8H2;1H | | InChIKey | HYDZPXNVHXJHBG-UHFFFAOYSA-N | | SMILES | C1(CON)=CC=CC=C1.Cl | | CAS DataBase Reference | 2687-43-6(CAS DataBase Reference) |
| Hazard Codes | Xi,Xn | | Risk Statements | 36/37/38-20/21/22 | | Safety Statements | 22-24/25-8-36-26 | | WGK Germany | 3 | | RTECS | NC3040000 | | F | 3 | | TSCA | Yes | | HS Code | 29280000 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Dam. 1
Skin Irrit. 2
Skin Sens. 1 |
| | O-Benzylhydroxylamine hydrochloride Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powde | | Uses | For use in the formation of nitrones from carbonyl compounds and their use in cycloaddition reactions. Used as a reagent used in the synthesis of hydroxylamines and hydroxyamates. Effective reagent used to prepare α-hydroxybenzylamines from α-hydroxyketones. | | Uses | O-Benzylhydroxylamine hydrochloride is a reagent used for the synthesis of hydroxylamines and hydroxyamates. | | Application | As a pharmaceutical intermediate, O-Benzylhydroxylamine hydrochloride is used in the synthesis of antibiotics, antiviral drugs, unnatural amino acids and antibody-drug conjugates (ADCs). It can introduce the benzyloxyamino group to optimize the efficacy and stability of target compounds. In addition, it also serves as an amide bond condensing agent, amino-protecting agent and protein cross-linking agent, and is applicable to the modification of polypeptides and biomolecules. | | Synthesis | Add the O-benzylacetoxime to a mixed solution of 17 g of methanol and 200 g of a 38% mass concentration hydrochloric acid solution; react for 210 minutes at a temperature of 36°C and a stirring speed of 90 rpm; then distill under reduced pressure at a temperature of 65°C until a solid precipitate out, and cool to room temperature. The solid was washed with petroleum ether (100mL×3) and dried under vacuum at 80°C for 8 hours to obtain 95.18g of the target product O-Benzylhydroxylamine hydrochloride, with a purity of 99.87%; the yield is 98.72%.
 | | Purification Methods | Recrystallise the hydrochloride from H2O or EtOH. [Beilstein 6 IV 2562.] | | References | [1] Journal of Organic Chemistry, 1997, vol. 62, # 26, p. 9177 - 9181
[2] Patent: US2014/378399, 2014, A1. Location in patent: Paragraph 0092
[3] Journal of Pharmacology and Experimental Therapeutics, 1999, vol. 288, # 2, p. 490 - 501
[4] Synthetic Communications, 1997, vol. 27, # 7, p. 1143 - 1147
[5] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 10, p. 3233 - 3241 |
| | O-Benzylhydroxylamine hydrochloride Preparation Products And Raw materials |
| Raw materials | 2-Propanone, O-(phenylmethyl)oxime-->Imidodicarbonic acid, 2-(phenylmethoxy)-, 1,3-bis(1,1-dimethylethyl) ester-->Acetamide, N-(phenylmethoxy)--->THIOCHROMAN-4-ONE-->N-Benzyloxybenzamide-->2-Butanone oxime-->O-Benzylhydroxylamine-->2-phenylmethoxyisoindole-1,3-dione-->Benzyl chloride-->Ethanimidic acid, N-(phenylmethoxy)-, ethyl ester | | Preparation Products | 2,3-DIPHENYLMALEIC ANHYDRIDE-->(S)-ethyl 4-(chloromethyl)-11,11-dimethyl-9-oxo-1-phenyl-2,10-dioxa-3,8-diazadodec-3-ene-7-carboxylate-->Carbamic acid, (phenylmethoxy)-, phenyl ester-->ETHYL 2-(BENZYLOXYAMINO)ACETATE |
|