29882-07-3

Basic information

• Product Name: 4-Chlorobutanal dimethyl acetal
• Synonyms: 4-CHLOROBUTANAL DIMETHYL ACETAL;4-CHLOROBUTYRALDEHYDE DIMETHYL ACETAL;4-chloro-1,1-dimethoxybutane;4-CHLORO BUTYALDEHYDE DIMETHYL ACETAL;4-CHLOROBUTANAL DIMETHYL ACETAL (FOR SUMATRIPTAN AND OTHER TRIPTANS);1-Chloro-4,4-dimethoxybutane;4,4-Dimethoxybutyl Chloride;4-Chlorobutanal Dimethyl Acetal 90%
• CAS NO: 29882-07-3
• Molecular Formula: C₆H₁₃ClO₂
• Molecular Weight: 152.62
• EINECS: 249-924-8
• Product Categories: All Aliphatics;Aliphatics;Other Products
• Mol File: 29882-07-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 120 °C / 40mmHg
• Flash Point: 43°C(lit.)
• Appearance: colorless liquid
• Density: 1.04
• Vapor Pressure: 2.15mmHg at 25°C
• Refractive Index: 1.4270-1.4310
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform, Methanol
• Stability: Moisture Sensitive
• CAS DataBase Reference: 4-Chlorobutanal dimethyl acetal(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chlorobutanal dimethyl acetal(29882-07-3)
• EPA Substance Registry System: 4-Chlorobutanal dimethyl acetal(29882-07-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-36
• RIDADR: 1993
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 29882-07-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless Liquid

Uses

4-Chlorobutanal Dimethyl Acetal 90% is a compound useful in organic synthesis and other chemical processes. It is used as an intermediate in the synthesis of aripiprazole, buspirone, and NAN-190 via reductive alkylation of piperazine derivatives with aldehydes

InChI:InChI=1/C6H13ClO2/c1-8-6(9-2)4-3-5-7/h6H,3-5H2,1-2H3

Synthetic route

4-chlorobutyraldehyde (6139-84-0) + trimethyl orthoformate (149-73-5) → 4-chlorobutanal dimethyl acetal (29882-07-3)

Conditions	Yield
With toluene-4-sulfonic acid; triethylamine In neat (no solvent) at 20℃;	84%
With toluene-4-sulfonic acid In methanol

methanol (67-56-1) + 4-chloro-butyric acid ethyl ester (3153-36-4) → 4-chlorobutanal dimethyl acetal (29882-07-3)

Conditions	Yield
Stage #1: 4-chloro-butyric acid ethyl ester With hydrogenchloride; diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 1h; Stage #2: methanol With sulfuric acid for 18h;	78%

methanol (67-56-1) + 4-chloro-1-acetoxy-1-butene (763101-16-2) → 4-chlorobutanal dimethyl acetal (29882-07-3)

Conditions	Yield
With amberlyst-15 Heating;	74%
Amberlyst 15 acidic ion-exchange resin Heating / reflux;	74.4%

4-chlorobutyraldehyde (6139-84-0) + 2,2-dimethoxy-propane (77-76-9) → 4-chlorobutanal dimethyl acetal (29882-07-3)

Conditions	Yield
With toluene-4-sulfonic acid	50%

methanol (67-56-1) + 4-chlorobutyraldehyde (6139-84-0) → 4-chlorobutanal dimethyl acetal (29882-07-3)

Conditions	Yield
With thio-xanthene-9-one for 1.5h; Irradiation; Sealed tube; Green chemistry;	33%
With sulfuric acid for 1h; Yield given;

tetramethylorthosilicate (681-84-5) + 4-Chlorobutanoyl chloride (4635-59-0) → 4-chlorobutanal dimethyl acetal (29882-07-3)

Conditions	Yield
With Pd-BaSO4; hydrogen

4-Chlorobutanoyl chloride (4635-59-0) + trimethyl orthoformate (149-73-5) → 4-chlorobutanal dimethyl acetal (29882-07-3)

Conditions	Yield
With Pd-BaSO4; hydrogen

methanol (67-56-1) + Cyclopropanecarboxaldehyde (1489-69-6) → 4-chlorobutanal dimethyl acetal (29882-07-3)

Conditions	Yield
With hydrogenchloride

methanol (67-56-1) + 4-Chlorobutanoyl chloride (4635-59-0) → 4-chlorobutanal dimethyl acetal (29882-07-3)

Conditions	Yield
With Pd-BaSO4; sulfuric acid; nitrogen; hydrogen 1.) toluene, reflux, 6 h, 2.) room temperature, 0.5 h; Yield given. Multistep reaction;

tetramethylorthosilicate (681-84-5) + 4-chloro-butyryl bromide → 4-chlorobutanal dimethyl acetal (29882-07-3)

Conditions	Yield
With Pd-BaSO4; hydrogen

trimethyl orthoformate (149-73-5) + 4-chloro-butyryl bromide → 4-chlorobutanal dimethyl acetal (29882-07-3)

Conditions	Yield
With Pd-BaSO4; hydrogen

4-chlorobutanal dimethyl acetal (29882-07-3) + tetramethylene glutarimide (1075-89-4) → 8-(4,4-dimethoxybutyl)-8-azaspiro[4.5]decane-7,9-dione (1359159-58-2)

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In dimethyl sulfoxide at 80℃; for 4h;	96%

phthalimide (136918-14-4) + 4-chlorobutanal dimethyl acetal (29882-07-3) → dimethyl acetal of γ-phtalimidobutyrylaldehyde (86492-19-5)

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In dimethyl sulfoxide at 75℃; for 2.5h;	95%

7-hydroxy-3,4-dihydro-2-(1H)-quinolinone (22246-18-0) + 4-chlorobutanal dimethyl acetal (29882-07-3) → 7-(4,4-dimethoxybutoxy)-3,4-dihydro-1H-quinolin-2-one (1359159-57-1)

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In dimethyl sulfoxide at 115℃; for 4h;	95%

cis-hexahydro-pyrrolo[3,4-b]pyrrole-5-carboxylic acid methyl ester (1378811-99-4) + 4-chlorobutanal dimethyl acetal (29882-07-3) → (cis)-1-(4,4-Dimethoxy-butyl)-hexahydro-pyrrolo[3,4-b]pyrrole-5-carboxylic acid methyl ester

Conditions	Yield
With sodium iodide; sodium carbonate In 1,2-dimethoxyethane	94%

4-chlorobutanal dimethyl acetal (29882-07-3) + 5-vinylpyridin-2(1H)-one (1147938-98-4) → C13H19NO3

Conditions	Yield
With potassium carbonate; potassium iodide In methanol for 21h; Inert atmosphere; Reflux;	89%

4-chlorobutanal dimethyl acetal (29882-07-3) + dimethyl amine (124-40-3) → 4-(N,N-dimethylamino)butyraldehyde dimethyl acetal (19718-92-4)

Conditions	Yield
In water 1.) r.t., 15 min, 2.) 62 deg C, 1 h;	87%
In water at 20℃;	84%

4-chlorobutanal dimethyl acetal (29882-07-3) + 2-amino-3-(3,4-dimethoxybenz-1-yl)propanoic acid methyl ester (78392-35-5) → (5S,10bS)-methyl 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboxylate (1269617-12-0)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 4h; Pictet-Spengler cyclisation; Inert atmosphere; Molecular sieve; stereoselective reaction;	82%

4-chlorobutanal dimethyl acetal (29882-07-3) → 4-Hydroxy-4-methyl-2-pentanone (123-42-2) + 4-iodobutyraldehyde dimethyl acetal (91988-32-8) + 4-iodobutyraldehyde (77406-93-0)

Conditions	Yield
With sodium iodide In acetone at 56℃; for 10h;	A n/a B 80% C n/a

4-chlorobutanal dimethyl acetal (29882-07-3) + (S)-2-amino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester (78083-80-4) → (5S,10bS)-methyl 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboxylate (1269617-12-0) + (5S,10bR)-methyl 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboxylate (1269617-13-1)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 4h; Pictet-Spengler cyclisation; Inert atmosphere; Molecular sieve; optical yield given as %de; stereoselective reaction;	A 80% B 18%

4-chlorobutanal dimethyl acetal (29882-07-3) + 7-hydroxy-1H-quinolin-2-one (70500-72-0) → 7-(4,4-dimethoxybutoxy)quinolin-2(1H)-one

Conditions	Yield
Stage #1: 7-hydroxy-1H-quinolin-2-one With potassium carbonate In N,N-dimethyl-formamide at 25 - 35℃; for 0.5h; Stage #2: 4-chlorobutanal dimethyl acetal In N,N-dimethyl-formamide at 70 - 75℃; for 10h;	80%
With tetrabutylammomium bromide; potassium carbonate In dimethyl sulfoxide at 20 - 70℃; for 20h;

4-chlorobutanal dimethyl acetal (29882-07-3) → 4-azido-1,1-dimethoxybutane (114819-95-3)

Conditions	Yield
With sodium azide; tetraoctylammonium chloride In water for 6h; Heating;	79%

morpholine (110-91-8) + 4-chlorobutanal dimethyl acetal (29882-07-3) → 4-(Morpholin-4-yl) Butanal Dimethyl Acetal (175459-02-6)

Conditions	Yield
In water; ethyl acetate	78%

4-chlorobutanal dimethyl acetal (29882-07-3) + 4-((1-pyrrolidinylsulfonyl)methyl)phenylhydrazine → 1-[[3-(2-aminoethyl)-1H-indol-5-yl]methylsulfonyl]pyrrolidine (181178-24-5)

Conditions	Yield
Stage #1: 4-chlorobutanal dimethyl acetal With hydrogenchloride In methanol; water at 20℃; for 1h; Large scale; Stage #2: 4-((1-pyrrolidinylsulfonyl)methyl)phenylhydrazine In methanol; water Large scale; Further stages;	75%

4-chlorobutanal dimethyl acetal (29882-07-3) + Ethyl nipecotate (71962-74-8) → ethyl 1-(4,4-dimethoxybutyl)piperidine-3-carboxylate

Conditions	Yield
With potassium carbonate In acetone at 70℃; for 62h; Darkness;	74%

4-chlorobutanal dimethyl acetal (29882-07-3) + methyl-alpha-D-glucopyranoside (97-30-3) → C11H19ClO6

Conditions	Yield
With camphor-10-sulfonic acid In acetonitrile at 70℃; Molecular sieve;	70%

(S)-benzyl 2-amino-3-(3,4-dimethoxyphenyl)propanoate + 4-chlorobutanal dimethyl acetal (29882-07-3) → (5S,10bS)-benzyl 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboxylate (1269617-18-6) + (5S,10bR)-benzyl 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboxylate (1269617-19-7)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 4h; Pictet-Spengler cyclisation; Inert atmosphere; Molecular sieve; optical yield given as %de; stereoselective reaction;	A 60% B 31%

4-chlorobutanal dimethyl acetal (29882-07-3) + (2S)-N(H)-2-2-<(N-benzyl-N-methylamino)methyl>pyrrolidine (177948-63-9) → (2S)-4-<3-<(N-benzyl-N-methylamino)methyl>pyrrolidin-1-yl>butanal dimethyl acetal (1026912-47-9)

Conditions	Yield
With sodium carbonate; sodium iodide In 1,2-dimethoxyethane for 18h; Heating;	57%

4-chlorobutanal dimethyl acetal (29882-07-3) + 4-(1,2,4-triazol-4-yl)phenylhydrazine (154594-16-8) → 2-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]ethylamine

Conditions	Yield
With ammonia; hydrogenchloride In methanol; ethanol; dichloromethane; water	49%

1H-imidazole (288-32-4) + 4-chlorobutanal dimethyl acetal (29882-07-3) → 1-(4,4-dimethoxybutyl)-1H-imidazole

Conditions	Yield
With sodium hydride In tetrahydrofuran for 18h; Inert atmosphere; Reflux;	48%

methanol (67-56-1) + [4-(methoxycarbonyl)phenyl]hydrazine hydrochloride (6296-89-5) + 4-chlorobutanal dimethyl acetal (29882-07-3) → 6-methoxycarbonyltryptamine

Conditions	Yield
Stage #1: [4-(methoxycarbonyl)phenyl]hydrazine hydrochloride; 4-chlorobutanal dimethyl acetal In ethanol; water for 18h; Stage #2: methanol With thionyl chloride at 80℃;	47%

4-chlorobutanal dimethyl acetal (29882-07-3) + (3R)-N(H)-3-(benzyloxy)pyrrolidine (177948-70-8) → (3R)-4-<3-(benzyloxy)pyrrolidin-1-yl>butanal dimethyl acetal (177947-68-1)

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 48h; Heating;	44%
With sodium carbonate; sodium iodide In 1,2-dimethoxyethane

4-chlorobutanal dimethyl acetal (29882-07-3) + potassium carbonate (584-08-7) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → 4-(4-tert-Butyloxycarbonyl)piperazin-1-yl Butanal Dimethyl Acetal (175459-01-5)

Conditions	Yield
In water; N,N-dimethyl-formamide	42%

4-chlorobutanal dimethyl acetal (29882-07-3) + 4-(1,2,4-triazol-1-ylmethyl)phenylhydrazine (144035-22-3) → 2-<5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl>ethylamine (144035-23-4)

Conditions	Yield
With hydrogenchloride In ethanol for 4h; Heating;	38%

4-chlorobutanal dimethyl acetal (29882-07-3) + 4-hydrazinobenzonitrile hydrochloride (2863-98-1) → 3-(2-aminoethyl)-5-cyano-1H-indole hydrochloride

Conditions	Yield
In ethanol; water for 18h; Heating;	35%

4-chlorobutanal dimethyl acetal (29882-07-3) + 4-ethoxycarbonylphenylhydrazine hydrochloride (40566-85-6) → 2-(5-Carboethoxy-1H-indol-3-yl)ethylamine (7272-54-0)

Conditions	Yield
In ethanol; water for 2h; Heating;	34.4%
In ethanol; water

Upstream product

• 67-56-1 methanol 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 6139-84-0 4-chlorobutyraldehyde 
• 149-73-5 trimethyl orthoformate 
• 3153-36-4 4-chloro-butyric acid ethyl ester 
• 763101-16-2 4-chloro-1-acetoxy-1-butene 
• 681-84-5 tetramethylorthosilicate 
• 77-76-9 2,2-dimethoxy-propane 
• 1489-69-6 Cyclopropanecarboxaldehyde 

Downstream Products

• 101831-71-4 3-(2-aminoethyl)-5-cyano-1H-indole hydrochloride 
• 144432-39-3 3-(2-aminoethyl)-5-(5-benzyl-1,1-dioxo-1,2,5-thiadiazolidin-2-yl)-1H-indole 
• 1269617-18-6 (5S,10bS)-benzyl 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboxylate 
• 1269617-19-7 (5S,10bR)-benzyl 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline-5-carboxylate 
• 741690-16-4 3-[(4,4-dimethoxybutyl)thio]-4-methyl-5-phenyl-4H-1,2,4-triazol 
• 77192-22-4 methyl 6,6-dimethoxy-2-(diphenyloxophosphoranyl)-2-trimethylsilylmethylhexanoate 
• 77192-23-5 6,6-dimethoxy-2-(diphenyloxophosphoranyl)-2-trimethylsilylmethylhexan-1-ol 
• 59627-58-6 3-methylenecyclohexyl methyl ether 
• 138714-23-5 1,3-Dimethoxy-methylcyclohexan 
• 19060-15-2 4-aminobutyraldehyde dimethyl acetal 
• 177947-68-1 (3R)-4-<3-(benzyloxy)pyrrolidin-1-yl>butanal dimethyl acetal 
• 223453-22-3 (3R)-4-(3-benzyloxymethyl)pyrrolidin-1-ylbutanal dimethyl acetal 
• 165605-52-7 N-[4-(1-{2-[3-(2-Amino-ethyl)-1H-indol-5-yl]-ethyl}-2,5-dioxo-imidazolidin-4-ylmethyl)-phenyl]-methanesulfonamide 
• 165605-56-1 N-[3-(1-{2-[3-(2-Amino-ethyl)-1H-indol-5-yl]-ethyl}-2,5-dioxo-imidazolidin-4-ylmethyl)-phenyl]-acetamide 

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