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DL-Phenylephrine hydrochloride

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Name

DL-Phenylephrine hydrochloride

EINECS 205-835-6
CAS No. 154-86-9 Density N/A
PSA 52.49000 LogP 1.83790
Solubility N/A Melting Point 144°C
Formula C9H14ClNO2 Boiling Point 341.1 °C at 760 mmHg
Molecular Weight 203.669 Flash Point 163.4 °C
Transport Information N/A Appearance N/A
Safety 26-36/37/39 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 154-86-9 (DL-Phenylephrine hydrochloride) Hazard Symbols N/A
Synonyms

3-Hydroxy-a-[(methylamino)methyl]-, hydrochloride (9CI);

Article Data 1

DL-Phenylephrine hydrochloride Synthetic route

61-76-7, 154-86-9, 939-38-8, 20368-45-0

(-)-phenylephedrine hydrochloride

154-86-9

phenylephrine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 30.1℃; Rate constant;
154-86-9

phenylephrine hydrochloride

3-(1-Chloro-2-methylamino-ethyl)-phenol; hydrochloride

Conditions
ConditionsYield
With thionyl chloride In benzene62%
154-86-9

phenylephrine hydrochloride

541-41-3

chloroformic acid ethyl ester

[2-Hydroxy-2-(3-hydroxy-phenyl)-ethyl]-methyl-carbamic acid ethyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 1h;
154-86-9

phenylephrine hydrochloride

79060-88-1

sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate

C32H12BF24(1-)*C9H13NO2*H(1+)

Conditions
ConditionsYield
In chloroform
154-86-9

phenylephrine hydrochloride

110193-32-3

{2-Hydroxy-2-[3-(quinolin-2-ylmethoxy)-phenyl]-ethyl}-carbamic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran / 1 h
2: 11 percent / cesium carbonate / acetone / 48 h / Heating
View Scheme
154-86-9

phenylephrine hydrochloride

33543-61-2

3-<2-(methylamino)ethyl>phenol hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 62 percent / SOCl2 / benzene
2: H2 / Pd-black / ethanol / 20 °C
View Scheme
23979-41-1

(R)-2-(6-methoxy-2-naphthyl)propionic acid

154-86-9

phenylephrine hydrochloride

A

1280541-43-6

(S)-phenylephrine-(R)-naproxen

B

1280541-42-5

(R)-phenylephrine-(R)-naproxen

Conditions
ConditionsYield
Stage #1: phenylephrine hydrochloride With sodium hydroxide In methanol at 20℃; for 0.5h;
Stage #2: (R)-2-(6-methoxy-2-naphthyl)propionic acid In methanol at 25 - 60℃; for 1.5h; Product distribution / selectivity; Resolution of racemate;
154-86-9

phenylephrine hydrochloride

61-76-7

phenylephrine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / methanol / 0.5 h / 20 °C
1.2: 1.5 h / 25 - 60 °C / Resolution of racemate
2.1: hydrogenchloride / toluene; water / 0.5 h / 75 - 80 °C / pH < 2
2.2: 1 - 15 °C / pH ~ 9
3.1: hydrogenchloride / isopropyl alcohol / 0.5 h / 55 - 65 °C
View Scheme
154-86-9

phenylephrine hydrochloride

614-03-9

(S)-phenylephrine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / methanol / 0.5 h / 20 °C
1.2: 1.5 h / 25 - 60 °C / Resolution of racemate
2.1: sodium hydroxide / water
2.2: pH < 2
2.3: pH 9
View Scheme

DL-Phenylephrine hydrochloride Specification

The CAS registry number of DL-Phenylephrine hydrochloride is 154-86-9. This chemical is also named as 3-Hydroxy-a-[(methylamino)methyl]-, hydrochloride (9CI). Its EINECS registry number is 205-835-6. In addition, its molecular formula is C9H14ClNO2 and molecular weight is 203.67. Its systematic name is called 3-[1-hydroxy-2-(methylamino)ethyl]phenol hydrochloride (1:1).

Physical properties about DL-Phenylephrine hydrochloride are: (1)ACD/LogP: -0.03; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.05; (4)ACD/LogD (pH 7.4): -1.92; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 5; (12)Flash Point: 163.4 °C; (13)Enthalpy of Vaporization: 61.71 kJ/mol; (14)Boiling Point: 341.1 °C at 760 mmHg.

Uses of DL-Phenylephrine hydrochloride: it can be used to produce C9H12ClNO*ClH. It will need reagent SOCl2 and solvent benzene. The yield is about 62 %.

DL-Phenylephrine hydrochloride can be used to produce C9H12ClNO*ClH

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: Cl.OC(c1cc(O)ccc1)CNC
(2)InChI: InChI=1/C9H13NO2.ClH/c1-10-6-9(12)7-3-2-4-8(11)5-7;/h2-5,9-12H,6H2,1H3;1H
(3)InChIKey: OCYSGIYOVXAGKQ-UHFFFAOYAF

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 420mg/kg (420mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 89, Pg. 382, 1947.
mouse LDLo unreported 1gm/kg (1000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 162, Pg. 46, 1931.

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