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1134-47-0

Basic Information
CAS No.: 1134-47-0
Name: Baclofen
Article Data: 16
Molecular Structure:
Molecular Structure of 1134-47-0 (Baclofen)
Formula: C10H12ClNO2
Molecular Weight: 213.664
Synonyms: Hydrocinnamicacid, b-(aminomethyl)-p-chloro- (7CI,8CI);4-Amino-3-(4-chlorophenyl)butanoic acid;4-Amino-3-(4-chlorophenyl)butyricacid;4-Amino-3-(p-chlorophenyl)butyric acid;Ba 34647;Baclon;C34647Ba;CIBA Ba 34647;DL-4-Amino-3-p-chlorophenylbutanoic acid;DL-Baclofen;Lioresal;b-(4-Chlorophenyl)-g-aminobutyric acid;b-(Aminomethyl)-p-chlorohydrocinnamicacid;b-(p-Chlorophenyl)-g-aminobutyric acid;
EINECS: 214-486-9
Density: 1.285 g/cm3
Melting Point: 208-210 ºC
Boiling Point: 364.3 ºC at 760 mmHg
Flash Point: 174.1 ºC
Solubility: 1 M HCl: 50 mg/mL
Appearance: white to very faintly yellow solid
Hazard Symbols: ToxicT,HarmfulXn
Risk Codes: 61-25-36/37/38-42/43-20/21/22
Safety: 53-22-36/37/39-45-52-26
Transport Information: UN 2811 6.1/PG 3
PSA: 63.32000
LogP: 2.55730
Synthetic route

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

1134-47-0

4-amino-3-(4-chlorophenyl)butanoic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 130℃; for 24h; Sealed tube;97%

3-(4-chlorophenyl)-4-((((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)carbonyl)amino)butanoic acid

1134-47-0

4-amino-3-(4-chlorophenyl)butanoic acid

Conditions
ConditionsYield
With sodium L-ascorbate; fluorescein free acid In aq. phosphate buffer for 0.5h; pH=7.4; Irradiation;87%
22518-27-0

4-(4-chlorophenyl)pyrrolidin-2-one

1134-47-0

4-amino-3-(4-chlorophenyl)butanoic acid

Conditions
ConditionsYield
With hydrogenchloride; water In water for 16h; Reflux;81%
With hydrogenchloride for 2h; Heating;54%
1141-23-7

3-(p-chlorophenyl)glutaramic acid

1134-47-0

4-amino-3-(4-chlorophenyl)butanoic acid

Conditions
ConditionsYield
With sodium sulfamate; sodium hypobromide at -5 - 55℃; for 2.16667h;79.4%

(E)-3-(4-chlorophenyl)-3-cyanoacrylic acid

1134-47-0

4-amino-3-(4-chlorophenyl)butanoic acid

Conditions
ConditionsYield
With ammonia; hydrogen In water at 25 - 30℃; for 6h;70%
927207-26-9

ethyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(4-chlorophenyl)butanoate

1134-47-0

4-amino-3-(4-chlorophenyl)butanoic acid

Conditions
ConditionsYield
With hydrogenchloride; hydrazine hydrate In ethanol Heating;58%

Baclofen hydrochloride

1134-47-0

4-amino-3-(4-chlorophenyl)butanoic acid

Conditions
ConditionsYield
With ammonium hydroxide In methanol at 60℃; for 2h; pH=6.9 - 7;41%
21133-98-2

ethyl 3-(4-chlorophenyl)-3-hydroxybutanoate

1134-47-0

4-amino-3-(4-chlorophenyl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) p-toluenesulfonic acid, 2.) 10percent NaOH / 1.) toluene, reflux, 3 h, 2.) reflux, 2 h
2: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h
3: 16 percent / NH3 / tetrahydrofuran / 3 h
4: 65 percent / 1 M NH4OH / 1 h / 70 °C
5: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature
6: 54 percent / 6 M HCl / 2 h / Heating
View Scheme
Multi-step reaction with 6 steps
1: 1.) p-toluenesulfonic acid, 2.) 10percent NaOH / 1.) toluene, reflux, 3 h, 2.) reflux, 2 h
2: 37 percent / N-bromosuccinimide / CCl4 / 48 h / Heating
3: 16 percent / NH3 / tetrahydrofuran / 3 h
4: 65 percent / 1 M NH4OH / 1 h / 70 °C
5: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature
6: 54 percent / 6 M HCl / 2 h / Heating
View Scheme
81187-89-5, 21758-07-6

(E)-3-(4-chlorophenyl)but-2-enoic acid

1134-47-0

4-amino-3-(4-chlorophenyl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h
2: 16 percent / NH3 / tetrahydrofuran / 3 h
3: 65 percent / 1 M NH4OH / 1 h / 70 °C
4: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature
5: 54 percent / 6 M HCl / 2 h / Heating
View Scheme
Multi-step reaction with 5 steps
1: 37 percent / N-bromosuccinimide / CCl4 / 48 h / Heating
2: 16 percent / NH3 / tetrahydrofuran / 3 h
3: 65 percent / 1 M NH4OH / 1 h / 70 °C
4: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature
5: 54 percent / 6 M HCl / 2 h / Heating
View Scheme
99-91-2

para-chloroacetophenone

6--benzo<1.3>dioxol-5-ylamine

6--benzo<1.3>dioxol-5-ylamine

1134-47-0

4-amino-3-(4-chlorophenyl)butanoic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 240 g / Zn / benzene / Heating
2: 1.) p-toluenesulfonic acid, 2.) 10percent NaOH / 1.) toluene, reflux, 3 h, 2.) reflux, 2 h
3: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h
4: 16 percent / NH3 / tetrahydrofuran / 3 h
5: 65 percent / 1 M NH4OH / 1 h / 70 °C
6: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature
7: 54 percent / 6 M HCl / 2 h / Heating
View Scheme
Multi-step reaction with 7 steps
1: 240 g / Zn / benzene / Heating
2: 1.) p-toluenesulfonic acid, 2.) 10percent NaOH / 1.) toluene, reflux, 3 h, 2.) reflux, 2 h
3: 37 percent / N-bromosuccinimide / CCl4 / 48 h / Heating
4: 16 percent / NH3 / tetrahydrofuran / 3 h
5: 65 percent / 1 M NH4OH / 1 h / 70 °C
6: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature
7: 54 percent / 6 M HCl / 2 h / Heating
View Scheme
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    CAS 1134-47-0 Name Baclofen MW 213.66100 MF C10H12ClNO2 Appearance White to very pale yellow solid Appearance:White powde

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Specification

1. Introduction of Baclofen
Baclofen is one kind of white powder or white to very faintly yellow solid. The IUPAC Name of this chemical is 4-Amino-3-(4-chlorophenyl)butanoic acid. Its Classification Code is Central Nervous System Agents ;  Drug / Therapeutic Agent ; GABA Agents ; GABA agonists ; Human Data ; Muscle relaxants, central ; Neuromuscular Agents ; Neurotransmitter Agents ; Peripheral Nervous System Agents ; Relaxant [muscle]. The Product Categories of this chemical is Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts ; Active Pharmaceutical Ingredients ; Intermediates & Fine Chemicals ; Pharmaceuticals ; GABA/Glycine receptor ; GABA.

2. Properties of Baclofen
Physical properties about Baclofen are:
(1)Polar Surface Area: 29.54 Å2; (2)Index of Refraction: 1.576; (3)Molar Refractivity: 55.06 cm3; (4)Molar Volume: 166.2 cm3; (5)Surface Tension: 53 dyne/cm; (6)Density of Baclofen: 1.285 g/cm3; (7)Flash Point: 174.1 °C; (8)Enthalpy of Vaporization: 64.41 kJ/mol; (9)Boiling Point: 364.3 °C at 760 mmHg; (10)Vapour Pressure: 6.01E-06 mmHg at 25°C.

3. Structure Descriptors of Baclofen
(1)InChI: InChI=1S/C10H12ClNO2/c11-9-3-1-7(2-4-9)8(6-12)5-10(13)14/h1-4,8H,5-6,12H2,(H,13,14);
(2)InChIKey: InChIKey=KPYSYYIEGFHWSV-UHFFFAOYSA-N;
(3)Smiles: c1cc(ccc1C(CC(=O)O)CN)Cl.

4. Toxicity of Baclofen

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 571ug/kg (0.571mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA Annals of Pharmacotherpy. Vol. 27, Pg. 883, 1993.
man TDLo oral 4286ug/kg (4.286mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
American Journal of Emergency Medicine. Vol. 4, Pg. 552, 1986.
man TDLo oral 14mg/kg (14mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: COMA
Journal of Toxicology, Clinical Toxicology. Vol. 20, Pg. 59, 1983.
man TDLo oral 3429mg/kg (3429mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY OBSTRUCTION
Journal of Toxicology, Clinical Toxicology. Vol. 32, Pg. 291, 1994.
man TDLo unreported 857ug/kg/2D-I (0.857mg/kg) BRAIN AND COVERINGS: CHANGES IN SURFACE EEG

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Italian Journal of Neurological Sciences. Vol. 12, Pg. 323, 1991.
mouse LD50 intravenous 31mg/kg (31mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 2069, 1979.
mouse LD50 oral 200mg/kg (200mg/kg)   Drugs in Japan Vol. 6, Pg. 576, 1982.
mouse LD50 subcutaneous 103mg/kg (103mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 181, 1980.
rat LD50 intravenous 78mg/kg (78mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 181, 1980.
rat LD50 oral 145mg/kg (145mg/kg)   Drugs in Japan Vol. 6, Pg. 576, 1982.
rat LD50 subcutaneous 115mg/kg (115mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 181, 1980.
women TDLo oral 8mg/kg (8mg/kg) CARDIAC: PULSE RATE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Postgraduate Medical Journal. Vol. 57, Pg. 580, 1981.
women TDLo oral 9mg/kg (9mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Postgraduate Medical Journal. Vol. 56, Pg. 865, 1980.
women TDLo oral 18mg/kg (18mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Journal of Toxicology, Clinical Toxicology. Vol. 22, Pg. 11, 1984.
women TDLo parenteral 25ug/kg/2D-I (0.025mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: COMA
International Journal of Clinical Pharmacology, Therapy and Toxicology. Vol. 29, Pg. 274, 1991.

5. Safety information of Baclofen

Hazard Codes:  T,Xn
Risk Statements: 61-25-36/37/38-42/43-20/21/22 
R61:May cause harm to the unborn child. 
R25 :Toxic if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R42/43:May cause sensitization by inhalation and skin contact. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 53-22-36/37/39-45-52-26 
S53:Avoid exposure - obtain special instructions before use. 
S22:Do not breathe dust. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S52:Not recommended for interior use on large surface areas. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: MW5084200
HazardClass: 6.1(b)
PackingGroup: III
Poison by ingestion, subcutaneous and intravenous routes. Human systemic effects by ingestion: blood pressure lowering, coma, muscle weakness, pulse rate decrease, respiratory depression. When heated to decomposition it emits toxic fumes of Cl and NOx. A muscle relaxant.

6. Uses of Baclofen
Baclofen can be used as Specific GABA-B receptor agonist. Muscle relaxant (skeletal). It is primarily used to treat spasticity and is in the early research stages for use for the treatment of alcoholism. In addition, research has shown baclofen to be effective in the treatment of alcohol dependence and withdrawal, by inhibiting both withdrawal symptoms and cravings.

7. Production of Baclofen
You can condense the chlorobenzaldehyde with ethyl acetoacetate to get the chloro benzylidene-double-ethyl acetoacetate. Then you can get the for chlorinated phenyl glutaric acid after the chloro benzylidene-double-ethyl acetoacetate hydrolysis. Glutaric acid imide chlorophenyl, the last open-loop degradation on chlorobenzene aminobutyric acid then concentrated ammonia amination generate. Its final open-loop, the degradation of specific methods of operation are as follows: 42.25gβ-(p-chlorophenyl) glutaric acid imide was added under stirring to the aqueous solution containing 8.32 g of sodium hydroxide in 200ml. The mixture is heated at 50 ° C for 10min, cooled to 10-15 ° C, 200ml aqueous solution containing 40.9g of sodium hydroxide was added dropwise, 20min, add 38.8g bromide, stirred at 20-25 ° C 8H, carefully neutralized with concentrated hydrochloric acid and the reaction mixturewas adjusted to pH 7, and then settle out fine β-(p-chlorophenyl)-γ-amino - butyric acid was crystallized and then recrystallized from water, m.p. 206-208 ° C.