Product Name

  • Name

    Oxybuprocaine hydrochloride

  • EINECS 227-808-8
  • CAS No. 5987-82-6
  • Article Data2
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point 158 - 162oC
  • Formula C17H29ClN2O3
  • Boiling Point 446.9 °C at 760 mmHg
  • Molecular Weight 344.882
  • Flash Point 224.1 °C
  • Transport Information
  • Appearance White crystalline powder
  • Safety 22-26-36
  • Risk Codes 36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 5987-82-6 (Oxybuprocaine hydrochloride)
  • Hazard Symbols HarmfulXn; IrritantXi
  • Synonyms Prestwick_896;Oxybuprocaine hydrochloride;Dorsacaine (TN);2-(4-amino-3-butoxy-benzoyl)oxyethyl-diethyl-azanium chloride;2-diethylaminoethyl 4-amino-3-butoxy-benzoate hydrochloride;Conjucaine;Benzoic acid,4-amino-3-butoxy-,2-(diethylamino) ethyl ester,monohydrochloride;Dorsacaine;Novesine;Oxybuprocaine hydrochloride (JP14);Benoxinate hydrochloride (USP);
  • PSA 64.79000
  • LogP 4.32950

Synthetic route

4-nitro-3-butoxybenzoic acid-2-(diethylamino)ethyl ester hydrochloride

4-nitro-3-butoxybenzoic acid-2-(diethylamino)ethyl ester hydrochloride

oxybuprocaine hydrochloride
5987-82-6

oxybuprocaine hydrochloride

Conditions
ConditionsYield
With iron(III) chloride; pyrographite; hydrazine hydrate In ethanol for 5h; Reflux;82.5%
ethyl 3-hydroxy-4-nitro-benzoate
717-01-1

ethyl 3-hydroxy-4-nitro-benzoate

oxybuprocaine hydrochloride
5987-82-6

oxybuprocaine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 14 h / 80 °C
2.1: sodium hydroxide / 1 h / 60 °C
3.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3.2: 6 h / 40 °C
4.1: pyrographite; hydrazine hydrate; iron(III) chloride / ethanol / 5 h / Reflux
View Scheme
ethyl 3-butoxy-4-nitrobenzoate

ethyl 3-butoxy-4-nitrobenzoate

oxybuprocaine hydrochloride
5987-82-6

oxybuprocaine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / 1 h / 60 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
2.2: 6 h / 40 °C
3.1: pyrographite; hydrazine hydrate; iron(III) chloride / ethanol / 5 h / Reflux
View Scheme
saccharin sodium salt
128-44-9

saccharin sodium salt

oxybuprocaine hydrochloride
5987-82-6

oxybuprocaine hydrochloride

oxybuprocaine saccharinate

oxybuprocaine saccharinate

Conditions
ConditionsYield
In ethanol at 20℃;100%
In ethanol at 20℃;97%
potassium acesulfame
55589-62-3

potassium acesulfame

oxybuprocaine hydrochloride
5987-82-6

oxybuprocaine hydrochloride

oxybuprocaine acesulfamate

oxybuprocaine acesulfamate

Conditions
ConditionsYield
In ethanol at 20℃;100%
In ethanol at 20℃;98%
oxybuprocaine hydrochloride
5987-82-6

oxybuprocaine hydrochloride

tetramethylammonium trifluoromethanethiolate

tetramethylammonium trifluoromethanethiolate

2-(diethylamino)ethyl 3-butoxy-4-isothiocyanatobenzoate

2-(diethylamino)ethyl 3-butoxy-4-isothiocyanatobenzoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.5h;90%

Oxybuprocaine hydrochloride Specification

The CAS registry number of Oxybuprocaine hydrochloride is 5987-82-6. The IUPAC name is 2-[(4-amino-3-butoxybenzoyl)oxy]-N,N-diethylethanaminium chloride. Its EINECS registry number is 227-808-8. In addition, the molecular formula is C17H29ClN2O3 and the molecular weight is 344.88. It should be stored in a airtight, cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 4.09; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.08; (4)ACD/LogD (pH 7.4): 2.3; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 12.36; (7)ACD/KOC (pH 5.5): 3.95; (8)ACD/KOC (pH 7.4): 65.54; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 38.77 Å2 ; (13)Flash Point: 224.1 °C; (14)Enthalpy of Vaporization: 70.51 kJ/mol; (15)Boiling Point: 446.9 °C at 760 mmHg; (16)Vapour Pressure: 3.51E-08 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin and harmful by inhalation, in contact with skin and if swallowed. You should not breathe dust and should wear suitable protective clothing during using it. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: [Cl-].O=C(OCC[NH+](CC)CC)c1cc(OCCCC)c(cc1)N
(2)InChI: InChI=1/C17H28N2O3.ClH/c1-4-7-11-21-16-13-14(8-9-15(16)18)17(20)22-12-10-19(5-2)6-3;/h8-9,13H,4-7,10-12,18H2,1-3H3;1H
(3)InChIKey: PRGUDWLMFLCODA-UHFFFAOYAC

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intravenous 4200ug/kg (4.2mg/kg)   Drugs in Japan Vol. -, Pg. 232, 1990.
guinea pig LD50 subcutaneous 21mg/kg (21mg/kg)   Drugs in Japan Vol. -, Pg. 232, 1990.
mouse LD50 intravenous > 6800ug/kg (6.8mg/kg)   Drugs in Japan Vol. -, Pg. 232, 1990.
mouse LD50 subcutaneous 42500ug/kg (42.5mg/kg)   Drugs in Japan Vol. 6, Pg. 154, 1982.
rabbit LD50 subcutaneous 30mg/kg (30mg/kg)   Drugs in Japan Vol. -, Pg. 232, 1990.
rabbit LD50 unreported 5600ug/kg (5.6mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 1957, 1974.
rat LD50 intravenous > 5600ug/kg (5.6mg/kg)   Drugs in Japan Vol. -, Pg. 232, 1990.
rat LD50 subcutaneous 60mg/kg (60mg/kg)   Drugs in Japan Vol. 6, Pg. 154, 1982.

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