Valproic Acid supplier | CasNO.99-66-1

Name
2-Propylpentanoic acid
EINECS 202-777-3
CAS No. 99-66-1
Article Data55
CAS DataBase
Density 0.926 g/cm³
Solubility slightly soluble in water
Melting Point 120 - 130oC
Formula C₈H₁₆O₂
Boiling Point 220 °C at 760 mmHg
Molecular Weight 144.214
Flash Point 116.6 °C
Transport Information UN 1230 3/PG 2
Appearance Colorless liquid
Safety 26-45-36/37-16
Risk Codes 22-36/37/38-39/23/24/25-23/24/25-11
Molecular Structure
Hazard Symbols Xn,T,F
Synonyms Divalproex;Valericacid, 2-propyl- (6CI,7CI,8CI);2-Propylvaleric acid;4-Heptanecarboxylic acid;44089;Acetic acid, dipropyl-;DPA;Depakine;Depakine-chrono;Dipropylacetic acid;Ergenyl;Mylproin;NSC 93819;Stavzor;Valproic acid;n-Dipropylacetic acid;2-Propylpentanoic acid;
PSA 37.30000
LogP 2.28740

Synthetic route

: 33433-82-8, 98378-05-3, 119923-11-4
valproic acid calcium salt

: 99-66-1
valproic acid

Conditions

Conditions	Yield
With hydrogenchloride In water	98%

: magnesium valproate

: 99-66-1
valproic acid

Conditions

Conditions	Yield
With hydrogenchloride In water	98%

: 1636-27-7
di-n-propylmalonic acid

: 99-66-1
valproic acid

Conditions

Conditions	Yield
copper(I) oxide In acetonitrile at 90 - 100℃; for 12 - 15h; Product distribution / selectivity;	97.7%
With poly-4-vinylpyridine In N,N-dimethyl-formamide for 0.05h; microwave irradiation;	88%
at 180 - 200℃;

: 2430-27-5
valpromide

: 99-66-1
valproic acid

Conditions

Conditions	Yield
With phthalic anhydride at 240 - 250℃; under 3040 Torr; for 0.75h; Hydrolysis;	92%
With hydrogenchloride at 100℃; for 72h; Product distribution; various times of reaction, also various reagents and enzymes;	54%

: 22632-59-3
methyl 2-propylvalerate

: 99-66-1
valproic acid

Conditions

Conditions	Yield
With 2C33H37N*H2O7S2; water at 80℃; for 48h;	92%
With 2C33H37N*H2O7S2; water at 60℃;	80 %Spectr.

: 2-[(E)-prop-1-enyl]pent-2-enoic acid

: 99-66-1
valproic acid

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 23h;	88%

: 13310-75-3
di-N-propyl acetonitrile

: 99-66-1
valproic acid

Conditions

Conditions	Yield
With sodium perborate at 240℃; for 1h;	82.5%
With benzene-1,2-dicarboxylic acid at 240℃; under 3040 Torr; for 1h;	74%
With sodium hydroxide

: 106-95-6
allyl bromide

: 109-52-4
valeric acid

: 99-66-1
valproic acid

Conditions

Conditions	Yield
Multistep reaction.;	82%

: 71-23-8
propan-1-ol

: 624-24-8
methyl valerate

: 99-66-1
valproic acid

Conditions

Conditions	Yield
Stage #1: propan-1-ol; methyl valerate With (NCOP)IrHCl; potassium tert-butylate at 60℃; for 12h; Glovebox; Schlenk technique; Sealed tube; Inert atmosphere; Stage #2: With hydrogenchloride In water for 5h; Glovebox; Schlenk technique; Sealed tube; Inert atmosphere;	74%

: 2,3-epoxy-3-(1-propyl)-hexanenitrile

: 99-66-1
valproic acid

Conditions

Conditions	Yield
With water; lithium bromide In N,N-dimethyl-formamide; acetonitrile at 91℃; for 48h;	49%

: 142-82-5
n-heptane

: 201230-82-2
carbon monoxide

A: 149-57-5
2-Ethylhexanoic acid

B: 116454-37-6, 128441-06-5, 1188-02-9
2-methylheptanoic acid

C: 99-66-1
valproic acid

Conditions

Conditions	Yield
With potassium peroxodisulfate; Cu(1,10-phenanthroline)(1,2-ethanediphosphonic acid); water In acetonitrile at 60℃; under 15201 Torr; for 4h; Autoclave; High pressure; Overall yield = 29.1 %;	A 10.5% B 12.4% C 5.3%

...Expand

: 917-64-6
methyl magnesium iodide

: 6065-63-0
2,2-dipropyl-malonic acid diethyl ester

: 99-66-1
valproic acid

Conditions

Conditions	Yield
und durch Behandeln des Reaktionprodukts mit Barytwasser, neben Aceton;

: 917-64-6
methyl magnesium iodide

: 6065-63-0
2,2-dipropyl-malonic acid diethyl ester

A: 99-66-1
valproic acid

B: 67-64-1
acetone

Conditions

Conditions	Yield
Verseifung des Reaktionsproduktes;

...Expand

: 76002-02-3
ethyl 2-acetyl-2-propylpentanoate

: 99-66-1
valproic acid

Conditions

Conditions	Yield
With potassium hydroxide
With sodium hydroxide In water at 80℃; for 20h;	3.1 g

: 18295-59-5
2-propylpentanal

: 99-66-1
valproic acid

Conditions

Conditions	Yield
With ammonium hydroxide; silver nitrate

: 18325-74-1
4-ethoxycarbonyl-1,6-heptadiene

: 99-66-1
valproic acid

Conditions

Conditions	Yield
With ethanol; hydrogen bromide Kochen des Reaktionsprodukts mit Zinkstaub, Verseifen des entstandenen Aethylesters mit Natronlauge;

: 6065-63-0
2,2-dipropyl-malonic acid diethyl ester

: methylmagnesium iodide

A: 99-66-1
valproic acid

B: 67-64-1
acetone

Conditions

Conditions	Yield
Verseifung des Reaktionsprodukts;

...Expand

: 592-76-7
1-Heptene

: 201230-82-2
carbon monoxide

A: 149-57-5
2-Ethylhexanoic acid

B: 116454-37-6, 128441-06-5, 1188-02-9
2-methylheptanoic acid

C: 99-66-1
valproic acid

Conditions

Conditions	Yield
(i) BF3*H2SO4, (ii) H2O; Multistep reaction;
With sulfuric acid at -5℃; under 76000 Torr;

...Expand

: 17022-31-0
ethyl 2-propylpentanoate

: 99-66-1
valproic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol
With sodium hydroxide In methanol; water for 3h; Reflux;

: 6065-63-0
2,2-dipropyl-malonic acid diethyl ester

: 99-66-1
valproic acid

Conditions

Conditions	Yield
(i) aq. KOH, (ii) (decarboxylation); Multistep reaction;

: 14686-14-7
trans-3-heptene

: 201230-82-2
carbon monoxide

A: 149-57-5
2-Ethylhexanoic acid

B: 99-66-1
valproic acid

Conditions

Conditions	Yield
With hydrogenchloride; oxygen; copper dichloride; palladium dichloride In tetrahydrofuran under 760 Torr; for 18h; Ambient temperature; Yield given. Yields of byproduct given;

...Expand

: 58844-38-5
di-n-propylketene

: 99-66-1
valproic acid

Conditions

Conditions	Yield
With water In acetonitrile at 20℃; Rate constant; var. H2O conc.;

: 225118-08-1
2-propyl-pentanoic acid [methyl-(4-nitro-benzenesulfonyl)-amino]-methyl ester

A: 99-66-1
valproic acid

B: 4-chloro-N-hydroxymethyl-N-methyl-benzenesulfonamide

Conditions

Conditions	Yield
With sodium perchlorate; water In acetonitrile at 25℃; Rate constant; also in base and acid buffers;

oxime of α,α-dipropyl-acetoacetic acid ethyl ester: oxime of α,α-dipropyl-acetoacetic acid ethyl ester

: 99-66-1
valproic acid

Conditions

Conditions	Yield
With ethanol; sodium

: 64-17-5
ethanol

: 2-(1-hydroxyimino-ethyl)-2-propyl-valeric acid ethyl ester

sodium: sodium

A: 52030-03-2
1-methyl-2-propyl-pentylamine

B: 2-(1-amino-ethyl)-2-propyl-pentan-1-ol

C: 99-66-1
valproic acid

D: 52030-22-5
3-propyl-hexan-2-one oxime

...Expand

: 105540-70-3
6-allyl-non-8-enoic acid

sodium hydroxide: sodium hydroxide

A: 99-66-1
valproic acid

B: 64-19-7
acetic acid

Conditions

Conditions	Yield
at 280℃;

...Expand

: 76002-02-3
ethyl 2-acetyl-2-propylpentanoate

KOH-solution: KOH-solution

A: 64-17-5
ethanol

B: 99-66-1
valproic acid

C: 64-19-7
acetic acid

...Expand

: 76002-02-3
ethyl 2-acetyl-2-propylpentanoate

sodium amalgam: sodium amalgam

A: 64-17-5
ethanol

B: 99-66-1
valproic acid

C: 64-19-7
acetic acid

D alkali: alkali

...Expand

: 174842-80-9
(N-methylbenzamido)methyl 2-propylpentanoate

: 99-66-1
valproic acid

Conditions

Conditions	Yield
With NADPH-generating system; rat liver homogenate at 37℃; Enzyme kinetics; Hydrolysis; Enzymatic reaction;

: 99-66-1
valproic acid

: 2936-08-5
valproyl chloride

Conditions

Conditions	Yield
With thionyl chloride In toluene Heating;	100%
With thionyl chloride at 10 - 20℃; for 4h;	94%
With thionyl chloride In N,N-dimethyl-formamide Reflux;	93.6%

: 99-66-1
valproic acid

: 1069-66-5
sodium valproate

Conditions

Conditions	Yield
With sodium hydroxide In water Product distribution / selectivity;	100%
With sodium hydroxide In water at 20℃;	100%
With sodium hydroxide In toluene	97.7%
With sodium hydroxide In ethanol; ethyl acetate Reflux; Industrial scale;	75.5%
With sodium hydroxide

: 99-66-1
valproic acid

: (S)-allylglycine methyl ester hydrochloride

: 1048107-04-5
(S)-methyl 2-(2-propylpentanamido)pent-4-enoate

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h;	100%

: 99-66-1
valproic acid

: 1313484-36-4
C14H26O7

: C22H40O8

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 19h; Inert atmosphere;	100%

: 99-66-1
valproic acid

: valproic acid

Conditions

Conditions	Yield
Stage #1: valproic acid With d8-isopropanol; 10% Pt/activated carbon; water-d2 at 120℃; for 24h; Stage #2: With water; sodium hydroxide at 70℃; for 24h; Reagent/catalyst;	100%

: 51862-24-9
2-chloro-1-ferrocenylethanone

: 99-66-1
valproic acid

: 2‐oxo‐2‐ferrocenylethyl 2‐propylpentanoate

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 12h; Reflux;	100%

: 2‐iodoethylferrocene

: 99-66-1
valproic acid

: 2‐ferrocenylethyl 2‐propylpentanoate

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 2h; Reflux;	100%

: 2-bromo-1-(ferrocen-1-yl)ethan-1-one

: 99-66-1
valproic acid

: 2‐oxo‐2‐ferrocenylethyl 2‐propylpentanoate

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 2h; Reflux;	100%

: 162382-19-6
4‐iodobutylferrocene

: 99-66-1
valproic acid

: 4‐ferrocenylbutyl 2‐propylpentanoate

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 2h; Reflux;	100%

: 2‐iodoacetylferrocene

: 99-66-1
valproic acid

: 2‐oxo‐2‐ferrocenylethyl 2‐propylpentanoate

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetonitrile Reflux;	100%

: 99-66-1
valproic acid

: 3‐iodopropylferrocene

: 3‐ferrocenylpropyl 2‐propylpentanoate

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 2h; Reflux;	100%

: 99-66-1
valproic acid

: 100-46-9
benzylamine

: 22635-28-5
N-benzyl-2-propylpemtanamide

Conditions

Conditions	Yield
With 4,5,6,7-tetrachlorobenzo[d][1,3,2]dioxaborole In o-xylene for 24h; Heating;	99%

: 99-66-1
valproic acid

: 1907-33-1
lithium tert-butoxide

: 93391-29-8
lithium valproate

Conditions

Conditions	Yield
In hexane for 1h; Product distribution / selectivity;	99%
In ethanol; hexane for 1h; Product distribution / selectivity;	77%

: 99-66-1
valproic acid

: 51660-44-7
2-propylpentanoic anhydride

Conditions

Conditions	Yield
With triethylamine; chlorophosphoric acid diphenyl ester In dichloromethane at 20℃;	97%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20 - 25℃;	82%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	80%

: 99-66-1
valproic acid

: 77-86-1
2-amino-2-hydroxymethyl-1,3-propanediol

: 923953-12-2
valproic acid tromethamine salt

Conditions

Conditions	Yield
In methanol at 20℃; for 0.5h;	97%

: 99-66-1
valproic acid

: divalproex sodium

Conditions

Conditions	Yield
With sodium hydroxide In di-isopropyl ether at 20 - 50℃; for 1h; Product distribution / selectivity;	96.65%
With sodium hydroxide In tert-butyl methyl ether at 20 - 50℃; for 1h; Product distribution / selectivity;	94.79%
With sodium hydroxide In dichloromethane at 20 - 40℃; for 1h; Product distribution / selectivity;	93%

: 99-66-1
valproic acid

: 107-06-2
1,2-dichloro-ethane

: 99174-91-1
2-bromo-2-propyl pentanoic acid ethyl ester

Conditions

Conditions	Yield
With thionyl chloride; bromine In ethanol; water; N,N-dimethyl-formamide	96.5%

: 2‐bromoethylferrocene

: 99-66-1
valproic acid

: 2‐ferrocenylethyl 2‐propylpentanoate

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 5h; Reflux;	95%

: 3‐bromopropylferrocene

: 99-66-1
valproic acid

: 3‐ferrocenylpropyl 2‐propylpentanoate

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 5h; Reflux;	95%

: 99-66-1
valproic acid

: 129826-46-6
4‐bromobutylferrocene

: 4‐ferrocenylbutyl 2‐propylpentanoate

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 5h; Reflux;	95%

: 99-66-1
valproic acid

: 1069-66-5
sodium valproate

: divalproex sodium

Conditions

Conditions	Yield
In acetonitrile Product distribution / selectivity; Heating / reflux;	93.75%
In acetone at 50℃; for 0.166667h;

: 186581-53-3, 908094-01-9
diazomethane

: 99-66-1
valproic acid

: 22632-59-3
methyl 2-propylvalerate

Conditions

Conditions	Yield
In diethyl ether for 0.5h; Ambient temperature;	93%

: 99-66-1
valproic acid

: 322468-25-7
((R)-2-O-benzyl-glyceryl)-2-bromoethyl-methylphosphate

: 322468-34-8
(3-O-[2-propyl pentanoyl]-(R)-2-O-benzylglyceryl)-2-bromoethyl-methyl phosphate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 2h;	92%

: 99-66-1
valproic acid

: 68076-36-8
1-amino-4-[(tert-butyloxycarbonyl)amino]butane

: 868566-95-4
[4-(2-propyl-pentanoylamino)-butyl]-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide)	92%

: 99-66-1
valproic acid

: 21209-51-8
N-benzyloxycarbonyl-L-serine benzyl ester

: 852055-98-2
C26H33NO6

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 20h;	92%

Valproic Acid Specification

Valproic Acid, an acidic chemical compound, has found clinical use as an anticonvulsant and mood-stabilizing drug. With the CAS NO. 99-66-1, it is also called 2-Propylpentanoic acid; 2-n-Propylpentanoicacid; 2-n-Propylvalericacid; 2-Propylpentansαure; 2-Propylvaleriansαure; 2-propyl-valericaci; 44089. Valproic acid, 2-propylvaleric acid, is synthesized by the alkylation of cyanoacetic ester with two moles of propylbromide, to give dipropylcyanoacetic ester. Hydrolysis and decarboxylation of the carboethoxy group gives dipropylacetonitrile, which is hydrolyzed into valproic acid.

Physical properties about Valproic Acid are: (1)ACD/LogP: 2.579; (2)ACD/LogD (pH 5.5): 1.81; (3)ACD/LogD (pH 7.4): 0.02; (4)ACD/BCF (pH 5.5): 9.23; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 103.54; (7)ACD/KOC (pH 7.4): 1.68; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 5; (11)Index of Refraction: 1.435; (12)Molar Refractivity: 40.635 cm³; (13)Molar Volume: 155.592 cm³; (14)Polarizability: 16.109 10-24cm³; (15)Surface Tension: 31.8439998626709 dyne/cm; (16)Density: 0.927 g/cm³; (17)Flash Point: 116.564 °C; (18)Enthalpy of Vaporization: 50.287 kJ/mol; (19)Boiling Point: 219.999 °C at 760 mmHg; (20)Vapour Pressure: 0.0439999997615814 mmHg at 25°C

Uses of Valproic Acid: This medication is used to treat seizure disorders, mental/mood conditions (such as manic phase of bipolar disorder), and to prevent migraine headaches. It works by increasing the amount of a certain natural substance in the brain.

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
3. Wear suitable protective clothing and gloves;
4. Keep away from sources of ignition - No smoking;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10);
(2)InChIKey=NIJJYAXOARWZEE-UHFFFAOYSA-N;
(3)SmilesC(CCC)(CCC)C(O)=O;

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	oral	375mg/kg (375mg/kg)	CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP LUNGS, THORAX, OR RESPIRATION: CYANOSIS VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	Critical Care Medicine. Vol. 21, Pg. 299, 1993.
child	TDLo	oral	412mg/kg (412mg/kg)	LUNGS, THORAX, OR RESPIRATION: DYSPNEA CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP BEHAVIORAL: COMA	Journal of Analytical Toxicology. Vol. 20, Pg. 55, 1996.
child	TDLo	oral	10500mg/kg/30 (10500mg/kg)	GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS GASTROINTESTINAL: NAUSEA OR VOMITING	American Journal of Diseases of Children. Vol. 138, Pg. 912, 1984.
child	TDLo	unreported	1800mg/kg/60D (1800mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS	Lancet. Vol. 1, Pg. 1196, 1980.
guinea pig	LD50	oral	824mg/kg (824mg/kg)		"Pharmacodynamie de l'Acide Dipropylacetique Vol. -, Pg. 39, 1968.
human	TDLo	oral	13333ug/kg/D- (13.333mg/kg)	BEHAVIORAL: SLEEP	New England Journal of Medicine. Vol. 301, Pg. 435, 1979.
man	LDLo	oral	736mg/kg (736mg/kg)	LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES	Journal of Analytical Toxicology. Vol. 22, Pg. 537, 1998.
man	TDLo	oral	21mg/kg/2D-I (21mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Neurology. Vol. 37, Pg. 886, 1987.
man	TDLo	oral	429mg/kg (429mg/kg)	BEHAVIORAL: COMA	Journal of Toxicology, Clinical Toxicology. Vol. 38, Pg. 219, 2000.
mouse	LD50	intraperitoneal	470mg/kg (470mg/kg)		Chimica Therapeutica. Vol. 3, Pg. 430, 1968.
mouse	LD50	oral	1098mg/kg (1098mg/kg)		European Patent Application. Vol. #78785,
mouse	LD50	subcutaneous	860mg/kg (860mg/kg)		"Pharmacodynamie de l'Acide Dipropylacetique Vol. -, Pg. 38, 1968.
rabbit	LD50	intraperitoneal	1200mg/kg (1200mg/kg)		"Pharmacodynamie de l'Acide Dipropylacetique Vol. -, Pg. 39, 1968.
rat	LD50	oral	670mg/kg (670mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
women	TDLo	oral	100mg/kg/10D- (100mg/kg)	BEHAVIORAL: GENERAL ANESTHETIC BRAIN AND COVERINGS: ENCEPHALITIS BRAIN AND COVERINGS: CHANGES IN SURFACE EEG	Journal of Toxicology, Clinical Toxicology. Vol. 38, Pg. 219, 2000.
women	TDLo	oral	330mg/kg (330mg/kg)	BEHAVIORAL: COMA BRAIN AND COVERINGS: CHANGES IN SURFACE EEG LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	American Journal of Emergency Medicine. Vol. 18, Pg. 508, 2000.

Product Name

2-Propylpentanoic acid

Synthetic route

Valproic Acid Specification

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