Product Name

  • Name

    Chloropheniramine-d4

  • EINECS
  • CAS No. 132-22-9
  • Article Data20
  • CAS DataBase
  • Density 1.107g/cm3
  • Solubility 5.496g/L(37.5 oC)
  • Melting Point 25°C
  • Formula C16H19 Cl N2
  • Boiling Point 379°Cat760mmHg
  • Molecular Weight 274.793
  • Flash Point 183°C
  • Transport Information
  • Appearance
  • Safety Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. When heated to decomposition it emits toxic vapors of NOx and Cl−.
  • Risk Codes
  • Molecular Structure Molecular Structure of 132-22-9 (Chloropheniramine-d4)
  • Hazard Symbols
  • Synonyms Pyridine,2-[p-chloro-a-[2-(dimethylamino)ethyl]benzyl]-(8CI); (?à)-Chloropheniramine; (?à)-Chlorpheniramine;1-(p-Chlorophenyl)-1-(2-pyridyl)-3-dimethylaminopropane; 2-[p-Chloro-a-[2-(dimethylamino)ethyl]benzyl]pyridine;3-(p-Chlorophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamine; 4-Chloropheniramine;Allergican; Chloropheniramine; Chlorophenylpyridamine; Chloroprophenpyridamine;Chlorphenamine; Chlorpheniramine; Chlorprophenpyridamine; Haynon;RS-Chlorpheniramine;dl-1-(p-Chlorophenyl)-1-(2-pyridyl)-3-(dimethylamino)propane; g-(4-Chlorophenyl)-g-(2-pyridyl)propyldimethylamine
  • PSA 16.13000
  • LogP 3.81860

Synthetic route

3-(p-chlorophenyl)-3-(2-pyridyl)propanal
55486-47-0

3-(p-chlorophenyl)-3-(2-pyridyl)propanal

dimethyl amine
124-40-3

dimethyl amine

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In toluene at 120℃; under 38000 Torr; for 12h; catalytic reductive amination;100%
chloropheniramine nitrile
65676-21-3

chloropheniramine nitrile

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
With potassium hydroxide at 160℃; for 4h;95%
3-(4-chlorophenyl)-3-pyridin-2-yl-propan-1-ol
73486-85-8

3-(4-chlorophenyl)-3-pyridin-2-yl-propan-1-ol

dimethyl amine
124-40-3

dimethyl amine

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; bis[2-(diphenylphosphino)phenyl] ether In toluene at 20℃; Inert atmosphere; Reflux;81%
2-(4-chloro-phenyl)-4-dimethylamino-butyronitrile
73775-50-5

2-(4-chloro-phenyl)-4-dimethylamino-butyronitrile

acetylene
74-86-2

acetylene

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
(η5-cyclopentadienyl)-η4-cycloocta-1,5-dienecobalt(I) In toluene at 140℃; under 10640 Torr; for 36h;75%
1-(4-chlorophenyl-1-(2-pyridyl))ehylene
160911-84-2

1-(4-chlorophenyl-1-(2-pyridyl))ehylene

C12H12N2O4

C12H12N2O4

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 0.8C12H6N2O4(2-)*HO(1-)*Al(3+)*0.4CF3O3S(1-)*0.1Ir(3+)*0.2C11H8N(1-)*0.1Cl(1-) In acetonitrile at 20℃; for 6h; Inert atmosphere; Irradiation;36%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

p-chlorobenzyl cyanide
140-53-4

p-chlorobenzyl cyanide

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
With sodium amide; benzene anschl. mit <2-Chlor-aethyl>-dimethyl-amin und anschl. Erhitzen mit wss. H2SO4;
With sodium amide; benzene anschl. mit <2-Chlor-aethyl>-dimethyl-amin und anschl. Erhitzen mit NaOH in Butan-1-ol;
2-(4-chlorobenzyl)pyridine
4350-41-8

2-(4-chlorobenzyl)pyridine

2-(dimethylamino)ethyl chloride
107-99-3

2-(dimethylamino)ethyl chloride

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
With potassium amide
With sodium amide
Stage #1: 2-(4-chlorobenzyl)pyridine With sodium amide In tetrahydrofuran at 20 - 25℃; for 1h;
Stage #2: 2-(dimethylamino)ethyl chloride In tetrahydrofuran; toluene at 30 - 45℃; for 2h;
1-(4-chlorophenyl)-3-dimethylamino-1-propanone
2138-38-7

1-(4-chlorophenyl)-3-dimethylamino-1-propanone

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
With 2-pyridyllithium; diethyl ether
1t-(4-chloro-phenyl)-3-dimethylamino-1c-[2]pyridyl-propene
88848-63-9

1t-(4-chloro-phenyl)-3-dimethylamino-1c-[2]pyridyl-propene

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
With palladium on activated charcoal; acetic acid Hydrogenation;
(+-)-2-<4-chloro-phenyl>-4-dimethylamino-2-<2>pyridyl-butyric acid dimethylamide

(+-)-2-<4-chloro-phenyl>-4-dimethylamino-2-<2>pyridyl-butyric acid dimethylamide

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
With sulfuric acid; water
(+-)-2-<4-chloro-phenyl>-4-dimethylamino-2-<2>pyridyl-butyronitrile

(+-)-2-<4-chloro-phenyl>-4-dimethylamino-2-<2>pyridyl-butyronitrile

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
With sulfuric acid; water
(+-)-3-<4-chloro-phenyl>-3-<2>pyridyl-propionaldehyde diethylacetal

(+-)-3-<4-chloro-phenyl>-3-<2>pyridyl-propionaldehyde diethylacetal

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
With formic acid; water; N,N-dimethyl-formamide
2-bromo-pyridine
109-04-6

2-bromo-pyridine

(+-)-2-<4-chloro-phenyl>-4-dimethylamino-butyronitrile

(+-)-2-<4-chloro-phenyl>-4-dimethylamino-butyronitrile

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
With sodium amide; toluene anschl. mit wss. H2SO4;
2-(4-chlorobenzyl)pyridine
4350-41-8

2-(4-chlorobenzyl)pyridine

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: lithium diisopropylamide; HMPT / 2 h / 0 °C
1.2: 80 percent / HMPT / 3 h / -78 - 20 °C
2.1: 100 percent / 5 percent aq. HCl / methanol / 24 h / 20 °C
3.1: 100 percent / H2 / PtO2 / toluene / 12 h / 120 °C / 38000 Torr
View Scheme
1-(4-chlorophenyl-1-(2-pyridyl))ehylene
160911-84-2

1-(4-chlorophenyl-1-(2-pyridyl))ehylene

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 30 percent / Na / 6 h / 20 °C
2: aq. potassium tert-butoxide / diethyl ether / 25 °C
3: 70 percent / tetrabutylammonium periodate / dioxane / 20 h / Heating
4: 100 percent / H2 / PtO2 / toluene / 12 h / 120 °C / 38000 Torr
View Scheme
3-(p-chlorophenyl)-4,4-diethoxybutanenitrile
233760-10-6

3-(p-chlorophenyl)-4,4-diethoxybutanenitrile

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / (η5-cyclopentadienyl)<(1,5-η)-cyclooctadienyl>cobalt / toluene / 72 h / 120 °C / 9500 Torr
2: 100 percent / 5 percent aq. HCl / methanol / 24 h / 20 °C
3: 100 percent / H2 / PtO2 / toluene / 12 h / 120 °C / 38000 Torr
View Scheme
2-(4-chloro-phenyl)-3-[1,3]dioxolan-2-yl-propionaldehyde oxime

2-(4-chloro-phenyl)-3-[1,3]dioxolan-2-yl-propionaldehyde oxime

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: tetrabutylammonium hydrogen sulfate; carbon disulfide; 15 percent aq. NaOH / benzene / 0.5 h / 20 °C
2: 85 percent / (η5-cyclopentadienyl)<(1,5-η)-cyclooctadienyl>cobalt / toluene / 72 h / 120 °C / 9500 Torr
3: 100 percent / 5 percent aq. HCl / methanol / 24 h / 20 °C
4: 100 percent / H2 / PtO2 / toluene / 12 h / 120 °C / 38000 Torr
View Scheme
2-[1-(4-chloro-phenyl)-2-[1,3]dioxolan-2-yl-ethyl]-pyridine
233760-12-8

2-[1-(4-chloro-phenyl)-2-[1,3]dioxolan-2-yl-ethyl]-pyridine

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / 5 percent aq. HCl / methanol / 24 h / 20 °C
2: 100 percent / H2 / PtO2 / toluene / 12 h / 120 °C / 38000 Torr
View Scheme
4-(4-chloro-phenyl)-2-hydroxy-4-pyridin-2-yl-butyric acid

4-(4-chloro-phenyl)-2-hydroxy-4-pyridin-2-yl-butyric acid

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / tetrabutylammonium periodate / dioxane / 20 h / Heating
2: 100 percent / H2 / PtO2 / toluene / 12 h / 120 °C / 38000 Torr
View Scheme
N,N-dimethyl-4-(p-chlorophenyl)-4-(2-pyridyl)-2-hydroxybutanamide
233760-14-0

N,N-dimethyl-4-(p-chlorophenyl)-4-(2-pyridyl)-2-hydroxybutanamide

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. potassium tert-butoxide / diethyl ether / 25 °C
2: 70 percent / tetrabutylammonium periodate / dioxane / 20 h / Heating
3: 100 percent / H2 / PtO2 / toluene / 12 h / 120 °C / 38000 Torr
View Scheme
p-Chloro-N,N-dimethylcinnamylamine
42817-51-6

p-Chloro-N,N-dimethylcinnamylamine

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H2 / HRh(CO)(PPh3)3 / benzene / 24 h / 80 °C / 76000 Torr
2: NH2OH
3: 92 percent / CS2, n-Bu4N(1+)*HSO4(1-), 15percent aq. NaOH / CH2Cl2 / 0.5 h / Ambient temperature
4: 75 percent / (η5-cyclopentadienyl)<(1,5-η)-cyclopentadienyl>cobalt / toluene / 36 h / 140 °C / 10640 Torr
View Scheme
2-(4-Chloro-phenyl)-4-dimethylamino-butyraldehyde
158696-49-2

2-(4-Chloro-phenyl)-4-dimethylamino-butyraldehyde

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NH2OH
2: 92 percent / CS2, n-Bu4N(1+)*HSO4(1-), 15percent aq. NaOH / CH2Cl2 / 0.5 h / Ambient temperature
3: 75 percent / (η5-cyclopentadienyl)<(1,5-η)-cyclopentadienyl>cobalt / toluene / 36 h / 140 °C / 10640 Torr
View Scheme
2-(4-Chloro-phenyl)-4-dimethylamino-butyraldehyde oxime
158696-52-7

2-(4-Chloro-phenyl)-4-dimethylamino-butyraldehyde oxime

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / CS2, n-Bu4N(1+)*HSO4(1-), 15percent aq. NaOH / CH2Cl2 / 0.5 h / Ambient temperature
2: 75 percent / (η5-cyclopentadienyl)<(1,5-η)-cyclopentadienyl>cobalt / toluene / 36 h / 140 °C / 10640 Torr
View Scheme
pyridine
110-86-1

pyridine

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine hydrochloride; copper (II)-chloride
2: NaNH2
View Scheme
4-chlorobenzyl bromide
622-95-7

4-chlorobenzyl bromide

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine hydrochloride; copper (II)-chloride
2: NaNH2
View Scheme
p-chlorobenzyl cyanide
140-53-4

p-chlorobenzyl cyanide

Chlorpheniramine
132-22-9

Chlorpheniramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: cobaltocene / 4 h / 150 - 170 °C / Autoclave
2.1: sodium amide / tetrahydrofuran / 1 h / 20 - 25 °C
2.2: 2 h / 30 - 45 °C
View Scheme
2-(2-methylphenyl)pyridine
10273-89-9

2-(2-methylphenyl)pyridine

Chlorpheniramine
132-22-9

Chlorpheniramine

C28H29N3

C28H29N3

Conditions
ConditionsYield
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 50℃; for 72h; Inert atmosphere;81%
ethyl-2-thiourea
625-53-6

ethyl-2-thiourea

Chlorpheniramine
132-22-9

Chlorpheniramine

3-(4-ethylthiocarbamidophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
1378243-75-4

3-(4-ethylthiocarbamidophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine

Conditions
ConditionsYield
In isopropyl alcohol for 4h; Reflux;78%
1-(methyl)-thiourea
598-52-7

1-(methyl)-thiourea

Chlorpheniramine
132-22-9

Chlorpheniramine

3-(4-methylthiocarbamidophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
1378243-73-2

3-(4-methylthiocarbamidophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine

Conditions
ConditionsYield
In isopropyl alcohol for 4h; Reflux;75%
Chlorpheniramine
132-22-9

Chlorpheniramine

Chlorpheniramine-N-oxide

Chlorpheniramine-N-oxide

Conditions
ConditionsYield
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at -10℃; for 2h;72.37%
thiourea
17356-08-0

thiourea

Chlorpheniramine
132-22-9

Chlorpheniramine

3-(4-thiocarbamidophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
1377320-76-7

3-(4-thiocarbamidophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine

Conditions
ConditionsYield
In isopropyl alcohol for 4h; Reflux;67.7%
Chlorpheniramine
132-22-9

Chlorpheniramine

monophenylthiourea
103-85-5

monophenylthiourea

3-(4-phenylthiocarbamidophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
1378243-72-1

3-(4-phenylthiocarbamidophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine

Conditions
ConditionsYield
In isopropyl alcohol for 4h; Reflux;67%
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Chlorpheniramine
132-22-9

Chlorpheniramine

C18H21N3

C18H21N3

Conditions
ConditionsYield
Stage #1: ethyl 2-cyanoacetate; Chlorpheniramine With N-(2-methylnaphthalen-1-yl)-N’-(pyridin-2-ylmethyl)oxalamide; copper(I) bromide; sodium t-butanolate In isopropyl alcohol at 105℃; for 24h; Schlenk technique; Inert atmosphere;
Stage #2: With water In isopropyl alcohol at 105℃; for 12h; Schlenk technique; Inert atmosphere; Cooling;		66%
ethylenethiourea
1483-58-5

ethylenethiourea

Chlorpheniramine
132-22-9

Chlorpheniramine

3-(4-allylthiocarbamidophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine

3-(4-allylthiocarbamidophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine

Conditions
ConditionsYield
In isopropyl alcohol for 4h; Reflux;65%
indole
120-72-9

indole

Chlorpheniramine
132-22-9

Chlorpheniramine

(±)-3-(4-(1H-indol-3-yl)phenyl)-N,N-dimethyl-3-(pyridin-2-yl)propan-1-amine

(±)-3-(4-(1H-indol-3-yl)phenyl)-N,N-dimethyl-3-(pyridin-2-yl)propan-1-amine

Conditions
ConditionsYield
With Cy-DHTP*HBF4; palladium diacetate; lithium tert-butoxide In toluene at 20 - 110℃; for 49h; Inert atmosphere; Sealed tube;53%
Chlorpheniramine
132-22-9

Chlorpheniramine

chlorpheniramine-d4

chlorpheniramine-d4

Conditions
ConditionsYield
With deuterosulfonic acid In water-d2 at 120℃; for 6h;50%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

triphenylphosphine
603-35-0

triphenylphosphine

Chlorpheniramine
132-22-9

Chlorpheniramine

(2-(1-(4-chlorophenyl)-3-(dimethylamino)propyl)pyridin-4-yl)triphenylphosphonium trifluoromethanesulfonate

(2-(1-(4-chlorophenyl)-3-(dimethylamino)propyl)pyridin-4-yl)triphenylphosphonium trifluoromethanesulfonate

Conditions
ConditionsYield
Stage #1: trifluoromethylsulfonic anhydride; Chlorpheniramine at -78℃; Inert atmosphere;
Stage #2: triphenylphosphine Inert atmosphere; Cooling;
Stage #3: Alkaline conditions; Inert atmosphere; regioselective reaction;		40%
at -78 - 20℃; Alkaline conditions;40%
...Expand
Chlorpheniramine
132-22-9

Chlorpheniramine

A

2-(4-chlorobenzoyl)pyridine
6318-51-0

2-(4-chlorobenzoyl)pyridine

B

C16H17ClN2O
1449714-76-4

C16H17ClN2O

Conditions
ConditionsYield
With copper(l) iodide; oxygen; acetic acid In dimethyl sulfoxide at 120℃; for 16h;A 13%
B 26%
Chlorpheniramine
132-22-9

Chlorpheniramine

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester
21085-72-3

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

((2R,3R,4S,5S,6S)-6-Carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-[3-(4-chloro-phenyl)-3-pyridin-2-yl-propyl]-dimethyl-ammonium; chloride
145823-27-4

((2R,3R,4S,5S,6S)-6-Carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-[3-(4-chloro-phenyl)-3-pyridin-2-yl-propyl]-dimethyl-ammonium; chloride

Conditions
ConditionsYield
With XAD-2 ion-exchange resin; sodium hydrogencarbonate In chloroform; water for 96h; Ambient temperature;15%
Chlorpheniramine
132-22-9

Chlorpheniramine

L-chlorpheniramine
32188-09-3

L-chlorpheniramine

Conditions
ConditionsYield
With C18H18O6
Chlorpheniramine
132-22-9

Chlorpheniramine

(S)-chlorpheniramine

(S)-chlorpheniramine

Conditions
ConditionsYield
Stage #1: Chlorpheniramine With sec.-butyllithium; (-)-sparteine In diethyl ether at -78℃; for 2h;
Stage #2: With deuteromethanol at -78℃;

Chlorpheniramine Chemical Properties

Chemistry informtion about Chlorpheniramine (CAS NO.132-22-9) is:
IUPAC Name:  3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
Synonyms: Chlorpheniramine ; Dl-Chlorpheniramine
MF: C16H19ClN2
MW: 274.79
Density: 1.107 g/cm3
Flash Point: 183 °C
Boiling Point: 379 °C at 760 mmHg
Enthalpy of Vaporization: 62.7 kJ/mol 
Vapour Pressure: 6.04E-06 mmHg at 25°C
Following is the molecular structure of Chlorpheniramine (CAS NO.132-22-9) is:

Chlorpheniramine Uses

 Chlorpheniramine (CAS NO.132-22-9) is often combined with phenylpropanolamine to form an allergy medication with both antihistamine and decongestant properties.

Chlorpheniramine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 125mg/kg (125mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 92, Pg. 1339, 1972.
mouse LD50 intravenous 20mg/kg (20mg/kg)   Medizinische Welt. Vol. 17, Pg. 2791, 1966.
mouse LD50 oral 121mg/kg (121mg/kg)   Medizinische Welt. Vol. 17, Pg. 2791, 1966.
mouse LD50 subcutaneous 160mg/kg (160mg/kg)   Bollettino Chimico Farmaceutico. Vol. 111, Pg. 293, 1972.
rabbit LD50 intravenous 22mg/kg (22mg/kg)   Medizinische Welt. Vol. 17, Pg. 2791, 1966.
rat LD50 oral 118mg/kg (118mg/kg)   Medizinische Welt. Vol. 17, Pg. 2791, 1966.

Chlorpheniramine Consensus Reports

Reported in EPA TSCA Inventory.

Chlorpheniramine Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. When heated to decomposition it emits toxic vapors of NOx and Cl−.

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