627-00-9

Basic information

• Product Name: 4-CHLOROBUTYRIC ACID
• Synonyms: 4-Chlorobutanoic acid;4-chloro-butanoicaci;4-Chlorobutanoicacid;4-chloro-Butanoicacid;Butyric acid, 4-chloro-;Cl(CH2)3COOH;gamma-Chloro-n-butyric acid;GAMMA-CHLOROBUTYRIC ACID
• CAS NO: 627-00-9
• Molecular Formula: C₄H₇ClO₂
• Molecular Weight: 122.55
• EINECS: 210-977-7
• Product Categories: omega-Chlorocarboxylic Acids;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;C1 to C5;Carbonyl Compounds;Carboxylic Acids
• Mol File: 627-00-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 12-16 °C(lit.)
• Boiling Point: 196 °C22 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.24 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000131mmHg at 25°C
• Refractive Index: n20/D 1.451(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Ether
• PKA: 4.52(at RT℃)
• BRN: 1700264
• CAS DataBase Reference: 4-CHLOROBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLOROBUTYRIC ACID(627-00-9)
• EPA Substance Registry System: 4-CHLOROBUTYRIC ACID(627-00-9)

Safety Data

• Hazard Codes: C
• Statements: 22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 627-00-9(Hazardous Substances Data)

Usage

Chemical Properties

Dark brown liquid

Uses

4-Chlorobutanoic Acid is an impurity of Levetiracetam(L331500) which is (S)-enantiomer of Etiracetam (E932970) and the ethyl analog of Piracetam (P500800). Used as an anticonvulsant. Neuroprotective & Neuroresearch Product.

Synthesis Reference(s)

Journal of the American Chemical Society, 92, p. 5274, 1970 DOI: 10.1021/ja00720a076The Journal of Organic Chemistry, 21, p. 883, 1956 DOI: 10.1021/jo01114a016

InChI:InChI=1/C4H7ClO2/c5-3-1-2-4(6)7/h1-3H2,(H,6,7)

Synthetic route

allyl 4-chlorobutyrate (4897-91-0) → γ-chlorobutyric acid (627-00-9)

Conditions	Yield
[(cyclopentadienyl)bis(acetonitrile)(triphenylphosphine)ruthenium(II)] hexafluorophosphate In methanol at 25℃; for 12h;	97%

4-butanolide (96-48-0) → γ-chlorobutyric acid (627-00-9)

Conditions	Yield
With hydrogenchloride; calcium chloride at 100℃; for 72h;	80%
With hydrogenchloride
With hydrogenchloride
With hydrogenchloride; dodecatungstosilic acid In water at 20℃; under 760.051 Torr; for 2h; Reagent/catalyst;

thiophene (188290-36-0) + 4-Chlorobutanoyl chloride (4635-59-0) → γ-chlorobutyric acid (627-00-9) + 4-chloro-1-(thien-2-yl)-1-butanone (43076-59-1)

Conditions	Yield
aluminium trichloride; nitromethane In carbon disulfide for 3h; Ambient temperature;	A 17% B 75%

4-Chlorobutyronitrile (628-20-6) → γ-chlorobutyric acid (627-00-9)

Conditions	Yield
With copper(II) sulfate at 240℃; for 1h;	65%

2-pyrrolidinon (616-45-5) → but-3-enoic acid (625-38-7) + γ-chlorobutyric acid (627-00-9)

Conditions	Yield
With hydrogenchloride; sodium nitrite
With hydrogenchloride; sodium nitrite

4-chloro-butyric acid ethyl ester (3153-36-4) → γ-chlorobutyric acid (627-00-9)

Conditions	Yield
With hydrogenchloride

N-nitroso-dihydro-2(3H)-pyrrolidinone (54634-49-0) → but-3-enoic acid (625-38-7) + γ-chlorobutyric acid (627-00-9)

Conditions	Yield
With hydrogenchloride

4-Chloro-1-butanol (928-51-8) → γ-chlorobutyric acid (627-00-9)

Conditions	Yield
With nitric acid
With chromium(VI) oxide; sulfuric acid

4-(4-nitrophenoxy)butanoic acid (28341-54-0) → γ-chlorobutyric acid (627-00-9)

potassium cyanide (151-50-8) + 1,3-chlorobromopropane (109-70-6) → γ-chlorobutyric acid (627-00-9)

Conditions	Yield
Verseifen des entstandenen γ-Chlor-butyronitrils mit konz.Salzsaeure unter Druck und Ueberfuehren der gebildeten Saeuren in γ-Butyrolacton,danach Addition von Chlorwasserstoff;

butyric acid (107-92-6) → γ-chlorobutyric acid (627-00-9)

Conditions	Yield
With tetrachloromethane; sulfuryl dichloride; dibenzoyl peroxide im Dunkeln;

cyclopropanecarboxylic acid (1759-53-1) → γ-chlorobutyric acid (627-00-9)

Conditions	Yield
With hydrogenchloride; diethyl ether at 0℃;

1,1,4-trichlorobut-1-ene (17219-57-7) → γ-chlorobutyric acid (627-00-9)

Conditions	Yield
With sulfuric acid

4-Chlorobutanoyl chloride (4635-59-0) → γ-chlorobutyric acid (627-00-9)

Conditions	Yield
With potassium fluoride; acetic acid

4-chloro-butyric acid ethyl ester (3153-36-4) → γ-chlorobutyric acid (627-00-9) + ethene (74-85-1)

Conditions	Yield
In gas at 360.1 - 390.2℃; under 49 - 209 Torr; Rate constant; Kinetics; Thermodynamic data; E(act);

2-pyrrolidinon (616-45-5) + hydrogenchloride (7647-01-0) + water (7732-18-5) + NaNO2 → but-3-enoic acid (625-38-7) + γ-chlorobutyric acid (627-00-9)

chlorine (7782-50-5) + butyric acid (107-92-6) → γ-chlorobutyric acid (627-00-9) + 3-chlorobutyric acid (625-68-3, 1951-12-8) + 2-chlorobutanoic acid (4170-24-5)

Conditions	Yield
Einwirkung von γ-Strahlen.Irradiation;
im Licht (λ: 350-400 nm).Irradiation;

tetrachloromethane (56-23-5) + sulfuryl dichloride (7791-25-5) + butyric acid (107-92-6) + dibenzoyl peroxide (94-36-0) → γ-chlorobutyric acid (627-00-9) + 3-chlorobutyric acid (625-68-3, 1951-12-8) + 2-chlorobutanoic acid (4170-24-5)

Conditions	Yield
im Dunkeln;
im Dunkeln;

hydrogenchloride (7647-01-0) + 4-chloro-butyric acid ethyl ester (3153-36-4) → γ-chlorobutyric acid (627-00-9)

butyric acid (107-92-6) → γ-chlorobutyric acid (627-00-9) + 3-chloro-butyric acid ; 2-chloro-butyric acid

Conditions	Yield
With chlorine im UV-Licht;

5-Chloro-dihydro-2(3H)-furanone (36603-83-5) → 4-butanolide (96-48-0) + γ-chlorobutyric acid (627-00-9) + 2-buten-4-olide (497-23-4)

Conditions	Yield
With palladium on activated carbon at 130℃; under 760.051 Torr; for 4h; Reagent/catalyst; Temperature;

γ-chlorobutyric acid (627-00-9) + 1-bromo-6-hexanol (4286-55-9) → C10H18BrClO2

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 2h;	100%

γ-chlorobutyric acid (627-00-9) + Benzophenone oxime (574-66-3) → diphenylmethanone O-(4-chlorobutanoyl) oxime

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

γ-chlorobutyric acid (627-00-9) + tributylphosphine (998-40-3) → tri-n-butyl(3-carboxypropyl)phosphonium chloride (64750-78-3)

Conditions	Yield
at 60℃; for 0.25h; Microwave irradiation; Inert atmosphere;	99%

γ-chlorobutyric acid (627-00-9) → 4-Chlorobutanoyl chloride (4635-59-0)

Conditions	Yield
With thionyl chloride Heating;	97%
With thionyl chloride In benzene for 0.5h; Heating; water-bath;	58%
With thionyl chloride

1-Butylimidazole (4316-42-1) + γ-chlorobutyric acid (627-00-9) → 1-butyl-3-(3-carboxypropyl)-1H-imidazol-3-ium chloride (1050516-60-3)

Conditions	Yield
at 120℃; for 8h;	96%

γ-chlorobutyric acid (627-00-9) + 4-t-amylphenol (80-46-6) → 4-(4-tert-pentylphenoxy)-γ-butyric acid + phenol (108-95-2)

Conditions	Yield
	A n/a B 92.6%

γ-chlorobutyric acid (627-00-9) + para-xylene (106-42-3) → 4-(p-xylyl)butyric acid (1453-06-1)

Conditions	Yield
With aluminium trichloride at 20 - 50℃; for 3h; Friedel-Crafts reaction;	92%

γ-chlorobutyric acid (627-00-9) + 5-methoxy-2-(3-phenylisoxazol-5-yl)phenol (1186130-66-4) → 4-(5-methoxy-2-(3-phenylisoxazol-5-yl)phenoxy)butanoic acid (1350176-24-7)

Conditions	Yield
With potassium carbonate In acetone Williamson type O-alkylation; Reflux;	90.65%

γ-chlorobutyric acid (627-00-9) + cholesterol (57-88-5) → cholesterine γ-Cl-butyrate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;	88%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	88%
With dmap; dicyclohexyl-carbodiimide In dichloromethane

γ-chlorobutyric acid (627-00-9) + 4-Chloro-3,5-dimethylphenol (88-04-0) → 6-chloro-3-(2-chloroethyl)-2-(3-chloropropyl)-5,7-dimethyl-4H-chromen-4-one

Conditions	Yield
With titanium tetrachloride In neat (no solvent) at 100℃; for 6h; Inert atmosphere;	86%

5,6-dimethoxy-2-[(pyridin-4-yl)methylene]-1-indanone (4803-74-1) + γ-chlorobutyric acid (627-00-9) → 1-(3-carboxypropyl)-4-[(5,6-dimethoxy-1-indanone-2-ylidene)methyl]pyridinium chloride

Conditions	Yield
In acetonitrile at 80℃; for 48h;	86%

γ-chlorobutyric acid (627-00-9) + 4-methylphenyl methylsulfide (623-13-2) → (p-tolylthio)methyl 4-chlorobutanoate

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In methanol; acetonitrile at 20℃; for 6h; Inert atmosphere; Electrochemical reaction;	85%

γ-chlorobutyric acid (627-00-9) + 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-1-ethanol (58905-18-3) → C14H14Cl3N3O2

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 13h; Reflux;	83%

γ-chlorobutyric acid (627-00-9) + C82H125CoN15O15P → C85H132CoN14O17P

Conditions	Yield
Stage #1: C82H125CoN15O15P With ammonium bromide; zinc In ethanol for 0.333333h; Inert atmosphere; Stage #2: γ-chlorobutyric acid In ethanol for 3h; Inert atmosphere;	82%

γ-chlorobutyric acid (627-00-9) + Magnolol (528-43-8) → 4'-O-(4-chlorobutyl)magnolol

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	81.2%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;	81.2%

γ-chlorobutyric acid (627-00-9) + phenylmethanethiol (100-53-8) → 4-benzylsulfanyl-butyric acid (3679-50-3)

Conditions	Yield
With sodium hydride In various solvent(s) 1.) 0 deg C, 30 min, 2.) r.t., 18 h;	81%

γ-chlorobutyric acid (627-00-9) → 4-azidobutanoic acid (54447-68-6)

Conditions	Yield
With sodium azide In water for 24h; Reflux;	81%

γ-chlorobutyric acid (627-00-9) + Magnolol (528-43-8) → 4'-di-(4-chlorobutyl)magnolol

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	80.5%

γ-chlorobutyric acid (627-00-9) + potassium phtalimide (1074-82-4) → 4-phthalimidobutyric acid (3130-75-4)

Conditions	Yield
In water; N,N-dimethyl-formamide	80%
In water; N,N-dimethyl-formamide	80%

γ-chlorobutyric acid (627-00-9) + sodium hydrogencarbonate (144-55-8) → allyl 4-chlorobutyrate (4897-91-0)

Conditions	Yield
With toluene-4-sulfonic acid In hexane; water	79%

γ-chlorobutyric acid (627-00-9) + triphenylphosphine (603-35-0) → (3-carboxy-propyl)triphenylphosphonium chloride (60633-18-3)

Conditions	Yield
In toluene at 180℃; for 3h;	78%
In neat (no solvent) at 180℃; for 2h;	61%

γ-chlorobutyric acid (627-00-9) → C4H7O2(1+)*F6Sb(1-)

Conditions	Yield
With silver hexafluoroantimonate In trifluoroacetic acid at 20℃; for 3h;	75%

γ-chlorobutyric acid (627-00-9) + 2-phenyl-acrylic acid methyl ester (1865-29-8) → methyl 6-chloro-2-phenylhexanoate

Conditions	Yield
With titanium(IV) dioxide In acetonitrile for 48h; Inert atmosphere; Irradiation; Cooling;	74%

γ-chlorobutyric acid (627-00-9) + poly(methacrylic acid) (79-41-4) → 7-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 4-(methacryloyloxy)butyrate (1187392-93-3)

Conditions	Yield
With sodium iodide; triethylamine In N-methyl-acetamide; water	73%

γ-chlorobutyric acid (627-00-9) + 1,4-bis(piperazin-1-yl)-2,3,5,6-tetrafluorobenzene → 4-(4-{4-[4-(3-carboxy-propyl)-piperazin-1-yl]-2,3,5,6-tetrafluoro-phenyl}-piperazin-1-yl)-butyric acid

Conditions	Yield
With triethylamine Heating;	70%

γ-chlorobutyric acid (627-00-9) + 7-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 4-chlorobutyrate (1187392-90-0) + sodium methacrylate (5536-61-8) → 7-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 4-(methacryloyloxy)butyrate (1187392-93-3)

Conditions	Yield
With sodium iodide In N-methyl-acetamide; water	70%

γ-chlorobutyric acid (627-00-9) + N-methyl-p-toluenesulfonylamide (640-61-9) → N-methyl-N-tosyl-4-chlorobutyramide (1445317-18-9)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃;	70%

Upstream product

• 54634-49-0 N-nitroso-dihydro-2(3H)-pyrrolidinone 
• 628-20-6 4-Chlorobutyronitrile 
• 28341-54-0 4-(4-nitrophenoxy)butanoic acid 
• 107-92-6 butyric acid 
• 1759-53-1 cyclopropanecarboxylic acid 
• 188290-36-0 thiophene 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 7782-50-5 chlorine 
• 56-23-5 tetrachloromethane 
• 7791-25-5 sulfuryl dichloride 
• 94-36-0 dibenzoyl peroxide 
• 36603-83-5 5-Chloro-dihydro-2(3H)-furanone 
• 4897-91-0 allyl 4-chlorobutyrate 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 64581-96-0 C₁₃H₂₁AsO₂Si 
• 51317-85-2 4-chloro-1-(2-hydroxy-5-methylphenyl)butan-1-one 
• 2323-82-2 γ-Chlor-buttersaeure-octylester 
• 78224-78-9 3-(4-chlorobutyrylthio)-4-phenyl-3-isothiazoline-5-thione 
• 542-76-7 3-Chloropropionitrile 
• 49637-21-0 4-(pyrrolidin-1-yl)butanoic acid hydrochloride 
• 15163-30-1 α-Dodecyldimethylammonio-ω-propanecarboxylate 
• 1453-06-1 4-(p-xylyl)butyric acid 
• 3130-75-4 4-phthalimidobutyric acid 
• 57010-67-0 4-chloro-1-(3,4-dimethoxyphenyl)-1-butanone 
• 108-95-2 phenol 
• 180743-24-2 p-isopropenylphenyl γ-chlorobutyrate 
• 33550-22-0 Tributylzinn γ-chlorobutyrat 
• 2403-66-9 2-(3-hydroxypropyl)benzimidazole 

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