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1078-21-3

Basic Information
CAS No.: 1078-21-3
Name: Benzenepropanoic acid, b-(aminomethyl)-
Molecular Structure:
Molecular Structure of 1078-21-3 (Benzenepropanoic acid, b-(aminomethyl)-)
Formula: C10H13NO2
Molecular Weight: 179.24
Synonyms: Hydrocinnamicacid, b-(aminomethyl)- (6CI,7CI,8CI);3-Phenyl-4-aminobutanoic acid;4-Amino-3-phenylbutyricacid;DL-4-Amino-3-phenylbutanoic acid;DL-b-Phenyl-g-aminobutyric acid;Fenibut;Fenigam;Fenigama;P-GABA;PhGABA;Phenibut;Phenigam;Phenybut;Phenygam;b-Phenyl-GABA;b-Phenyl-g-aminobutyricacid;g-Amino-b-phenylbutyric acid;
EINECS: 214-079-6
Density: 1.161 g/cm3
Melting Point: 194.0-202 °C
Boiling Point: 327.8 °C at 760 mmHg
Flash Point: 152.1 °C
Solubility: Free soluble in water
Appearance: white to off-white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes:
Safety:
Transport Information:
PSA: 63.32000
LogP: 2.70590
Synthetic route
41441-41-2

4-nitro-3-phenylbutanoic acid

1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 60℃; under 45004.5 Torr;98%

4-(1,3-dioxoisoindolin-2-yl)-3-phenyl-N-(quinolin-8-yl)butanamide

1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 130℃; for 24h; Sealed tube;95%
2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine
52450-32-5

2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine

1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
With hydrogenchloride
4-phenylpyrrolidin-2-one

4-phenylpyrrolidin-2-one

1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
With hydrogenchloride Heating;
14387-18-9

3-cyano-3-phenyl propionic acid

1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In acetic acid under 15200 Torr;
(+-)-3-phenyl-glutaramic acid

(+-)-3-phenyl-glutaramic acid

1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium hypobromide
7647-01-0

hydrogenchloride

72976-16-0

3-phenyl-glutaric acid dihydrazide

110-46-3

isopentyl nitrite

A

B

1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
at 25℃; Kochen mit Bromwasserstoffsaeure;
benzyl alcohol

benzyl alcohol

1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium hypochlorite; potassium bromide / water; dichloromethane / 0.21 h / 0 °C
2.1: potassium tert-butylate / toluene; methanol / 0.17 h / 20 °C / 4500.45 Torr / Inert atmosphere
2.2: 0.11 h / 25 °C / 4500.45 Torr / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 1 h / 50 °C / 6000.6 Torr
4.1: lithium hydroxide; water / toluene / 1 h / 50 °C / 3750.38 Torr
5.1: hydrogen; palladium 10% on activated carbon / methanol / 60 °C / 45004.5 Torr
View Scheme
100-52-7

benzaldehyde

1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium tert-butylate / toluene; methanol / 0.17 h / 20 °C / 4500.45 Torr / Inert atmosphere
1.2: 0.11 h / 25 °C / 4500.45 Torr / Inert atmosphere
2.1: tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 1 h / 50 °C / 6000.6 Torr
3.1: lithium hydroxide; water / toluene / 1 h / 50 °C / 3750.38 Torr
4.1: hydrogen; palladium 10% on activated carbon / methanol / 60 °C / 45004.5 Torr
View Scheme
103-26-4

methyl cinnamate

1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 1 h / 50 °C / 6000.6 Torr
2: lithium hydroxide; water / toluene / 1 h / 50 °C / 3750.38 Torr
3: hydrogen; palladium 10% on activated carbon / methanol / 60 °C / 45004.5 Torr
View Scheme
34687-03-1

4-nitro-3-phenylbutanoic acid methyl ester

1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hydroxide; water / toluene / 1 h / 50 °C / 3750.38 Torr
2: hydrogen; palladium 10% on activated carbon / methanol / 60 °C / 45004.5 Torr
View Scheme
1078-21-3

4-amino-3-phenylbutanoic acid

446-52-6

2-Fluorobenzaldehyde

20577-61-1

methyl 2,4-dioxopentanoate

4-[3-acetyl-2-(2-fluoro-phenyl)-4-hydroxy-5-oxo-2,5-dihydro-pyrrol-1-yl]-3-phenyl-butyric acid

Conditions
ConditionsYield
In ethanol; water at 20℃; for 12h; Condensation;78%
24424-99-5

di-tert-butyl dicarbonate

1078-21-3

4-amino-3-phenylbutanoic acid

189014-01-5

4-((tert-butoxycarbonyl)amino)-3-phenylbutanoic acid

Conditions
ConditionsYield
With sodium hydroxide In water; tert-butyl alcohol at 0 - 20℃;73%
1078-21-3

4-amino-3-phenylbutanoic acid

100-51-6

benzyl alcohol

C17H19NO2*(x)ClH

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; for 16h;66%
1078-21-3

4-amino-3-phenylbutanoic acid

54648-79-2

N,N'-diisopropyl-O-methylisourea

129453-46-9

C13H19NO2

Conditions
ConditionsYield
In methanol for 120h; Ambient temperature;65%
85-44-9

phthalic anhydride

1078-21-3

4-amino-3-phenylbutanoic acid

4-(1,3-dioxoisoindolin-2-yl)-3-phenylbutanoic acid

Conditions
ConditionsYield
In ethanol for 3h; Reflux;62%
1078-21-3

4-amino-3-phenylbutanoic acid

1198-97-6

4-phenylpyrrolidin-2-one

Conditions
ConditionsYield
With potassium hydroxide
1078-21-3

4-amino-3-phenylbutanoic acid

77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium hydroxide / ethanol / 65 - 75 °C
2: ethanol / 65 - 75 °C
3: acetic acid / ethanol
4: Heating
View Scheme
1078-21-3

4-amino-3-phenylbutanoic acid

4-[(2-amino-2-oxoethyl)amino]-3-phenylbutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium hydroxide / ethanol / 65 - 75 °C
2: ethanol / 65 - 75 °C
3: acetic acid / ethanol
View Scheme
1078-21-3

4-amino-3-phenylbutanoic acid

4-[bis(2-amino-2-oxoethyl)amino]-3-phenylbutanoic acid sodium salt

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium hydroxide / ethanol / 65 - 75 °C
2: ethanol / 65 - 75 °C
3: acetic acid / ethanol
4: sodium hydroxide / ethanol / 65 - 75 °C
5: ethanol / 65 - 75 °C
View Scheme
1078-21-3

4-amino-3-phenylbutanoic acid

C10H12NO2(1-)*K(1+)

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 65 - 75℃;
1078-21-3

4-amino-3-phenylbutanoic acid

C12H15N2O3(1-)*K(1+)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol / 65 - 75 °C
2: ethanol / 65 - 75 °C
View Scheme
1078-21-3

4-amino-3-phenylbutanoic acid

C12H15N2O3(1-)*Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium hydroxide / ethanol / 65 - 75 °C
2: ethanol / 65 - 75 °C
3: acetic acid / ethanol
4: sodium hydroxide / ethanol / 65 - 75 °C
View Scheme
1078-21-3

4-amino-3-phenylbutanoic acid

N-(4-hydroxy-2-phenylbutyl)-2H-benzo[e][1,2,4]thiadiazine-3-carboxamide 1,1-dioxide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydroxide / water; tert-butyl alcohol / 0 - 20 °C
2.1: potassium carbonate / tetrahydrofuran / 0.25 h / 20 °C
2.2: 20 °C
3.1: hydrogenchloride / ethyl acetate / 3 h / 20 °C
4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C
5.1: sodium hydroxide / 3 h / 20 °C
6.1: borane-THF / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
View Scheme
1078-21-3

4-amino-3-phenylbutanoic acid

437708-57-1

tert-butyl (3-amino-2-phenylpropyl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanol / 3 h / Reflux
2: triethylamine; diphenyl phosphoryl azide / 1,4-dioxane / 100 °C
3: hydrazine hydrate / ethanol / 2 h / 80 °C
View Scheme
1078-21-3

4-amino-3-phenylbutanoic acid

tert-butyl (3-(1,1-dioxido-2H-benzo[e][1,2,4]thiadiazine-3-carboxamido)-2-phenylpropyl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: ethanol / 3 h / Reflux
2.1: triethylamine; diphenyl phosphoryl azide / 1,4-dioxane / 100 °C
3.1: hydrazine hydrate / ethanol / 2 h / 80 °C
4.1: sodium hydrogencarbonate / dichloromethane / 0.17 h / 20 °C
4.2: 1 h / 20 °C
View Scheme
1078-21-3

4-amino-3-phenylbutanoic acid

N-(3-amino-2-phenylpropyl)-2H-benzo[e][1,2,4]thiadiazine-3-carboxamide 1,1-dioxide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: ethanol / 3 h / Reflux
2.1: triethylamine; diphenyl phosphoryl azide / 1,4-dioxane / 100 °C
3.1: hydrazine hydrate / ethanol / 2 h / 80 °C
4.1: sodium hydrogencarbonate / dichloromethane / 0.17 h / 20 °C
4.2: 1 h / 20 °C
5.1: hydrogenchloride / ethyl acetate / 2 h / 20 °C
View Scheme
1078-21-3

4-amino-3-phenylbutanoic acid

25271-46-9

methyl 4-amino-3-phenylbutanoate hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water; tert-butyl alcohol / 0 - 20 °C
2.1: potassium carbonate / tetrahydrofuran / 0.25 h / 20 °C
2.2: 20 °C
3.1: hydrogenchloride / ethyl acetate / 3 h / 20 °C
View Scheme
1078-21-3

4-amino-3-phenylbutanoic acid

methyl 4-(1,1-dioxido-2H-benzo[e][1,2,4]thiadiazine-3-carboxamido)-3-phenylbutanoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water; tert-butyl alcohol / 0 - 20 °C
2.1: potassium carbonate / tetrahydrofuran / 0.25 h / 20 °C
2.2: 20 °C
3.1: hydrogenchloride / ethyl acetate / 3 h / 20 °C
4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C
View Scheme
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    4-amino-3-phenylbutanoic acid hydrochloride

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The 4-Amino-3-phenylbutyric acid , with cas registry number of 1078-21-3, has other registry number which is 35568-37-7. It is also called Benzenepropanoic acid, beta-(aminomethyl)- . Its IUPAC name and systematic name are the same wich is also called 4-amino-3-phenylbutanoic acid . This chemical belongs to several classification codes including (1) Anticonvulsants ; (2) Central Nervous System Agents ; (3) Central Nervous System Depressants ; (4) Central Nervous System Stimulants ; (5) Convulsants ; (6) Drug / Therapeutic Agent ; (7) GABA agents ; (8) Human Data ; (9) Hypnotics and sedatives ; (10) Neurotransmitter Agents ; (11) Psychotropic Drugs ; (12) Tranquilizing agents.

Physical properties about this chemical are: (1) ACD/LogP: 0.97 ; (2) # of Rule of 5 Violations: 0 ; (3) ACD/LogD (pH 5.5): -1.54 ; (4) ACD/LogD (pH 7.4): -1.53 ; (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) Polar Surface Area: 29.54 Å2 ; (13) Index of Refraction: 1.563 ; (14) Molar Refractivity: 50.17 cm3 ; (15) Molar Volume: 154.3 cm3 ; (16) Surface Tension: 51.2 dyne/cm ; (17) Density: 1.161 g/cm3 ; (18) Flash Point: 152.1 °C ; (19) Enthalpy of Vaporization: 60.18 kJ/mol ; (20) Boiling Point: 327.8 °C at 760 mmHg ; (21) Vapour Pressure: 7.98E-05 mmHg at 25°C.

Uses of  4-Amino-3-phenylbutyric acid : this chemical can used to produce other chemicals. Here is a example, it can react with 2-fluoro-benzaldehyde and 2,4-dioxo-pentanoic acid methyl ester to produce 4-[3-acetyl-2-(2-fluoro-phenyl)-4-hydroxy-5-oxo-2,5-dihydro-pyrrol-1-yl]-3-phenyl-butyric acid .


This reaction is a Condensation. It needs solvents ethanol, water at the temperature of 20 ℃ for 12 hours. The yield is about 78%.

When you are using this chemical, please be cautious about it as the following:
Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: somnolence, hallucinations, distorted perception. Used as a mood elevator and tranquilizer. When heated to decomposition it emits toxic fumes of NOx.

You can still convert the following datas into molecular structure:
(1) SMILES:O=C(O)CC(c1ccccc1)CN;
(2) InChI:InChI=1/C10H13NO2/c11-7-9(6-10(12)13)8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13) ;
(3) InChIKey:DAFOCGYVTAOKAJ-UHFFFAOYAE

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 5mg/kg (5mg/kg) BEHAVIORAL: SLEEP
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Bulletin of Experimental Biology and Medicine Vol. 57, Pg. 52, 1964.
mouse LD50 intraperitoneal 900mg/kg (900mg/kg)   Bulletin of Experimental Biology and Medicine Vol. 57, Pg. 52, 1964.
rat LD50 intraperitoneal 700mg/kg (700mg/kg)   Bulletin of Experimental Biology and Medicine Vol. 57, Pg. 52, 1964.

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