627-27-0

Basic information

• Product Name: 3-Buten-1-ol
• Synonyms: 1-Buten-4-ol;3-buten-1-0l;3-Buten-1-O1;3-butene-1-0l;3-Butenol;3-Butenyl alcohol;BUTEN-(3)-O1-(L);CH2=CHCH2CH2OH
• CAS NO: 627-27-0
• Molecular Formula: C₄H₈O
• Molecular Weight: 72.11
• EINECS: 210-991-3
• Product Categories: Alcohol& Phenol& Ethers;API intermediates;omega-Unsaturated Alkanols;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;Acyclic;Alkenes;Building Blocks;Chemical Synthesis;Organic Building Blocks;pharmaceutical industry;Pharmaceutical intermediates
• Mol File: 627-27-0.mol
• Article Data: 167

Chemical Properties

• Melting Point: -31.44°C (estimate)
• Boiling Point: 112-114 °C(lit.)
• Flash Point: 90 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.838 g/mL at 25 °C(lit.)
• Vapor Pressure: 10.6mmHg at 25°C
• Refractive Index: n20/D 1.421(lit.)
• Storage Temp.: Flammables area
• PKA: 15.04±0.10(Predicted)
• Explosive Limit: 2-28%(V)
• Water Solubility: SOLUBLE
• Stability: Stable. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents. Flammable.
• BRN: 1633504
• CAS DataBase Reference: 3-Buten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Buten-1-ol(627-27-0)
• EPA Substance Registry System: 3-Buten-1-ol(627-27-0)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1987 3/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 627-27-0(Hazardous Substances Data)

Usage

Description

3-Buten-1-ol is a homoallyl alcohol. It is employed in a study of the Mn-catalyzed hydrohydrazination of olefins. It is also used in a study of the conversion of propargylic acetates to ethers catalyzed by ferric chloride1. It can also be used as a starting reagent in asymmetric total synthesis of natural seimatopolide B. It was also used in the synthesis of catalytic bimetallic nanoparticles2.

Chemical Properties

liquid

Uses

3-Buten-1-ol is an aliphatic primary alcohol used as a reagent in organic synthesis.

Uses

3-Buten-1-ol is employed in a study of the Mn-catalyzed hydrohydrazination of olefins. Also used in a study of the conversion of propargylic acetates to ethers catalyzed by ferric chloride.

Uses

Employed in a study of the Mn-catalyzed hydrohydrazination of olefins. Also used in a study of the conversion of propargylic acetates to ethers cataylzed by ferric chloride.

General Description

3-Buten-1-ol is a homoallyl alcohol that can be prepared by the dehydration of 1,4-butanediol using cerium catalyst. The intramolecular hydrogen bonding of 3-buten-1-ol has been studied using FT-IR and 1H NMR spectroscopic data. Its microwave spectrum has been recorded and analyzed. The alkylation reaction of 3-buten-1-ol using titanium-organoaluminum system has been studied. Its gas-phase enthalpy of formation has been reported to be -147.3 ± 1.8kJ mol-1.

Synthesis

The synthesis of?3-Buten-1-ol is as follows:After adding 24.3 g (1 mol) of magnesium turnings, 50 g of diethyl ether and 1 ml of dibromoethane in a 500 mL four-necked flask,A solution of 62.5 g of vinyl chloride (1 mol) dissolved in 200 g of diethyl ether was added dropwise to magnesium and diethyl ether, and the micro reflux was controlled, and the dropwise addition was completed, and the mixture was kept under a micro reflux for 2 hours, and the temperature was lowered to -5 °C;Then 44 g (1 mol) of ethylene oxide was dissolved in 60 g of diethyl ether. Ethylene oxide is added dropwise to the vinylmagnesium chloride solution prepared above, control the temperature -5-5 degrees, and stir at this temperature for 1 hour. Sampling gas phase analysis until the reaction is complete; pour the reaction solution into a 1000 mL beaker, Add 200mL of ice water and add ammonium chloride until the residual magnesium disappears. Control the temperature 0-10 ° C, stir for 1 hour after the addition, add salt to saturation, static layering. The organic layer was separated and washed twice with 100 ml of saturated brine, and a polymerization inhibitor was added. The product is subjected to rectification to obtain 53 g of 3-buten-1-ol, and the content is 99.2%. The yield was 73.6%.

InChI:InChI=1/C4H8O/c1-2-3-4-5/h2,5H,1,3-4H2

Synthetic route

1-butyn-4-ol (927-74-2) → homoalylic alcohol (627-27-0)

Conditions	Yield
With 2,6-bis[1-(2,6-diisopropylphenylimino)ethyl]pyridine cobalt(II) dichloride; diethoxymethylane; sodium triethylborohydride In neat (no solvent) at -78 - 40℃; for 1h;	97%
With hydrogen In methanol at 20℃; under 760.051 Torr; for 4.5h; Green chemistry;	92%
With hydrogen In methanol under 760.051 Torr; for 5h;	87%

formaldehyd (50-00-0) + allyldibutyltin chloride (64549-05-9) → homoalylic alcohol (627-27-0)

Conditions	Yield
In water at 20℃; for 0.0833333h;	97%

1-(4-methoxybenzyloxy)-3-butene (142860-83-1) → homoalylic alcohol (627-27-0)

Conditions	Yield
With t-butyl bromide In acetonitrile for 1h; Reflux; chemoselective reaction;	93%

Cyclopropylmethanol (2516-33-8) → homoalylic alcohol (627-27-0) + cyclobutanol (2919-23-5)

Conditions	Yield
With hydrogenchloride In water for 3h; Heating;	A 3% B 92%
With hydrogenchloride In water at 100℃; for 3h;	A n/a B 57%
With hydrogenchloride In water at 100℃; for 0.00166667h;

formaldehyd (50-00-0) + allyl bromide (106-95-6) → homoalylic alcohol (627-27-0)

Conditions	Yield
Stage #1: formaldehyd; allyl bromide With zinc In ethyl acetate at 75℃; for 5h; Large scale; Stage #2: With ammonium chloride for 2h; Large scale;	87%
With magnesium In diethyl ether for 6h; Heating;	72%
With magnesium In diethyl ether	39%
Stage #1: allyl bromide With tin In water at 20℃; for 0.166667h; Green chemistry; Stage #2: formaldehyd In water at 20℃; for 3h; Green chemistry;	75 %Chromat.
With ammonium chloride; zinc In tetrahydrofuran at 20℃; for 2.5h; Inert atmosphere;

Butane-1,4-diol (110-63-4) → homoalylic alcohol (627-27-0)

Conditions	Yield
With hydrogen at 350℃; Reagent/catalyst;	85.9%
With 1-hexadecylcarboxylic acid at 330 - 345℃; under 760 Torr; for 32h;	50%
With Er2O3 nanoparticles HT-150-24 at 350℃; for 5h;
Heating;
With yttria-stabilized zirconia at 325℃; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;

Butane-1,4-diol (110-63-4) → tetrahydrofuran (109-99-9) + homoalylic alcohol (627-27-0)

Conditions	Yield
With hydrogen at 350℃; for 0.6h; Reagent/catalyst; Temperature; Flow reactor;	A n/a B 85.9%
With Mg and Yb-containing organic foam into the binaryoxides at 350℃; Reagent/catalyst; Temperature; Inert atmosphere;	A n/a B 71.1%
With Er2O3 nanoparticles CM-1000 at 350℃; for 5h;
at 350℃; Reagent/catalyst; Flow reactor; Inert atmosphere;

epoxybutene (930-22-3) → homoalylic alcohol (627-27-0)

Conditions	Yield
With formic acid; tributyl-amine; tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In water at 50 - 120℃; for 4.5 - 26h; Product distribution / selectivity;	85.8%
With formic acid; tributyl-amine; tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In tetrahydrofuran; water at 62℃; for 1.21667 - 2.56667h; Product distribution / selectivity;	78.5%
With ammonium formate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tributylphosphine In 1,4-dioxane for 2h; Heating;	100 % Chromat.

3-chlorotetrahydrofuran (19311-38-7) → homoalylic alcohol (627-27-0)

Conditions	Yield
With sodium In diethyl ether	84%
With diethyl ether; sodium

(2R,3R)-2-But-3-enyloxy-3-heptadecafluorooctyl-tetrahydro-pyran → homoalylic alcohol (627-27-0)

Conditions	Yield
With methanol; toluene-4-sulfonic acid In tetrahydrofuran at 70℃; for 24h; deprotection of alcoholic OH;	78%

D,L-1,2,4-butanetriol (3068-00-6) → homoalylic alcohol (627-27-0)

Conditions	Yield
With rhenium(VII) oxide; triphenylphosphine at 165℃; for 1h;	77%
With rac-3-octanol at 170℃; for 1h;	28%

2-But-3-enyl-benzo[1,3,2]dioxaborole → homoalylic alcohol (627-27-0)

Conditions	Yield
With hydroxide; dihydrogen peroxide	76%

oxirane (75-21-8) + chloroethylene (75-01-4) → homoalylic alcohol (627-27-0)

Conditions	Yield
Stage #1: chloroethylene With magnesium In diethyl ether; ethylene dibromide for 2h; Reflux; Stage #2: oxirane In diethyl ether; ethylene dibromide at -5 - 5℃; for 1h; Temperature; Solvent;	73.6%

vinylmagnesium chloride (3536-96-7) + 2-bromoethanol (540-51-2) → homoalylic alcohol (627-27-0)

Conditions	Yield
copper(I) bromide In tetrahydrofuran at -40 - 3℃; for 2.5h;	72%

Butane-1,4-diol (110-63-4) → tetrahydrofuran (109-99-9) + homoalylic alcohol (627-27-0) + (E/Z)-2-buten-1-ol (6117-91-5)

Conditions	Yield
With hydrogen at 350℃; for 0.6h; Reagent/catalyst; Flow reactor;	A n/a B 69.9% C n/a

but-3-enoic acid (625-38-7) → homoalylic alcohol (627-27-0)

Conditions	Yield
With lithium aluminium tetrahydride	50%
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride

formaldehyd (50-00-0) + allylmagnesium bromide (2622-05-1) → homoalylic alcohol (627-27-0)

Conditions	Yield
Grignar reaction;	46%
With diethyl ether

cyclobutanecarbonyl m-chlorobenzoyl peroxide (70458-21-8) → homoalylic alcohol (627-27-0) + Cyclopropylmethanol (2516-33-8) + 3-butenyl m-chlorobenzoate (70458-29-6) + cyclobutyl m-chlorobenzoate (70458-27-4) + cyclopropylmethyl m-chlorobenzoate (70458-28-5) + cyclobutanol (2919-23-5)

Conditions	Yield
With acetic acid; potassium iodide In tetrachloromethane at 26℃; Rate constant; on silica;	A 4.3% B 9.6% C 19.5% D 11.8% E 45.5% F 6.5%
With acetic acid; potassium iodide In neat (no solvent) at 26℃; Rate constant; on silica;
With acetic acid; potassium iodide In chloroform at 55℃; Rate constant;
With acetic acid; potassium iodide In tetrachloromethane at 55℃; Rate constant;

cyclobutanecarbonyl m-chlorobenzoyl peroxide (70458-21-8) → homoalylic alcohol (627-27-0) + 3-butenyl m-chlorobenzoate (70458-29-6) + cyclobutyl m-chlorobenzoate (70458-27-4) + cyclopropylmethyl m-chlorobenzoate (70458-28-5)

Conditions	Yield
With acetic acid; potassium iodide In tetrachloromethane at 26℃; Further byproducts given;	A 4.3% B 19.5% C 11.8% D 45.5%

1-bromo-4-butene (5162-44-7) → homoalylic alcohol (627-27-0)

Conditions	Yield
With sodium carbonate for 15h; Heating;	45%

formaldehyd (50-00-0) + 3-chloroprop-1-ene (107-05-1) → homoalylic alcohol (627-27-0)

Conditions	Yield
With magnesium In diethyl ether for 2h; Heating;	45%

(E)-N-benzylidenebenzenesulfonamide (130552-90-8) + allyl-trimethyl-silane (762-72-1) → homoalylic alcohol (627-27-0) + N-(1-phenylbut-3-en-1-yl)benzenesulfonamide (217947-24-5)

Conditions	Yield
With indium(III) chloride; chloro-trimethyl-silane In nitromethane at 20℃; for 6h; Sakurai-Hosomi reaction;	A 8 % Spectr. B 40%

Ti(OCH2CH(CH2)2)4 → homoalylic alcohol (627-27-0) + Cyclopropylmethanol (2516-33-8) + Di-(1-butenyl)ether (trans/trans) (22597-56-4) + bis(cyclopropylmethyl) ether (74976-40-2) + allylcarbinyl cyclopropylcarbinyl ether (74976-38-8)

Conditions	Yield
In gas byproducts: CH2CH(CH2)2, CH2(CH)2CH2; decomposition at a pressure of 0.01 mm Hg at 550°C; further compounds: (CH2)2CHCHO (trace), TiO2, H2 (<0.5%), C (4%); NMR; GC; mass spectra;	A 37% B 23% C 12% D 10% E 18%

formaldehyd (50-00-0) + propene (187737-37-7) → homoalylic alcohol (627-27-0)

Conditions	Yield
In water at 220℃; under 6000.6 Torr; for 10h; Reagent/catalyst; Autoclave;	2.47%
at 246℃;
In 1,4-dioxane at 149.84℃; for 4h;

oxirane (75-21-8) + tetrahydrofuran (109-99-9) + vinyl magnesium bromide (1826-67-1) → homoalylic alcohol (627-27-0)

oxirane (75-21-8) + vinylmagnesium chloride (3536-96-7) → homoalylic alcohol (627-27-0)

Conditions	Yield
With tetrahydrofuran

oxirane (75-21-8) + vinyl magnesium bromide (1826-67-1) → homoalylic alcohol (627-27-0)

Conditions	Yield
With tetrahydrofuran

(RS)-3-bromotetrahydrofuran (19311-37-6) → homoalylic alcohol (627-27-0)

Conditions	Yield
With diethyl ether; magnesium und Zersetzen mit Wasser;
With diethyl ether; sodium und Zersetzen mit Wasser;

4-methyl-1,3-dioxane (1120-97-4) → homoalylic alcohol (627-27-0)

Conditions	Yield
With tricalcium diphosphate; water at 350℃;

homoalylic alcohol (627-27-0) + p-toluenesulfonyl chloride (98-59-9) → but-3-enyl 4-methylbenzenesulfonate (778-29-0)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃;	100%
With potassium hydroxide In diethyl ether at 20℃; for 3h;	99%
With dmap; triethylamine In dichloromethane at 20℃; for 3h; Inert atmosphere;	99%

homoalylic alcohol (627-27-0) + methanesulfonyl chloride (124-63-0) → 4-methanesulfonyloxy-1-butene (40671-34-9)

Conditions	Yield
With triethylamine In dichloromethane at -15℃; for 1h; Green chemistry;	100%
With triethylamine In dichloromethane at -15℃; for 1.5h;	100%
With triethylamine In dichloromethane at 0℃; for 5h;	98%

3,4-dihydro-2H-pyran (110-87-2) + homoalylic alcohol (627-27-0) → 2-(3-butenyloxy)tetrahydropyran (59574-65-1)

Conditions	Yield
With toluene-4-sulfonic acid In diethyl ether for 5h; Ambient temperature;	100%
In dichloromethane at 0℃; for 2h;	95%
With hydrogenchloride at 20℃; Addition;	91%

homoalylic alcohol (627-27-0) + benzoyl chloride (98-88-4) → 3-butenyl benzoate (18203-32-2)

Conditions	Yield
With triethylamine In dichloromethane	100%
With triethylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	91%
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	91%

homoalylic alcohol (627-27-0) + tert-butylchlorodiphenylsilane (58479-61-1) → 4-tert-butyldiphenylsilyloxy-1-butene (135006-32-5)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	100%
With 1H-imidazole In N,N-dimethyl-formamide for 17h; Ambient temperature;	99%

homoalylic alcohol (627-27-0) + acetylacetone (123-54-6) → (Z)-4-But-3-enyloxy-pent-3-en-2-one

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;	100%

homoalylic alcohol (627-27-0) + sodium 4-methylbenzenesulfinate (824-79-3) → 3-Iodo-4-(toluene-4-sulfonyl)-butan-1-ol

Conditions	Yield
With iodine In water; ethyl acetate at 20℃; for 2.5h; iodosulfonization;	100%

homoalylic alcohol (627-27-0) + p-Methoxybenzyl bromide (2746-25-0) → 1-(4-methoxybenzyloxy)-3-butene (142860-83-1)

Conditions	Yield
Stage #1: homoalylic alcohol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: p-Methoxybenzyl bromide In tetrahydrofuran at 0℃; for 1h;	100%
Stage #1: homoalylic alcohol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: p-Methoxybenzyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 0 - 20℃; for 17h; Inert atmosphere;	100%
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 12h;	96%

homoalylic alcohol (627-27-0) + p-methoxybenzyl chloride (824-94-2) → 1-(4-methoxybenzyloxy)-3-butene (142860-83-1)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide	100%
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 20h; Inert atmosphere; Schlenk technique;	97%
Stage #1: homoalylic alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.333333h; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; mineral oil at 0 - 20℃; for 3h;	96%

N-hydroxyphthalimide (524-38-9) + homoalylic alcohol (627-27-0) → 2-(but-3-en-1-yloxy)isoindoline-1,3-dione (80042-17-7)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 2.5h; Inert atmosphere;	100%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 4.5h; Mitsunobu Displacement; Inert atmosphere;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 16.5h;

homoalylic alcohol (627-27-0) + triisopropylsilyl chloride (13154-24-0) → 1-triisopropylsiloxy-3-butene (169310-77-4)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere;	100%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	98%
With 1H-imidazole In tetrahydrofuran at 20℃; for 5.5h;	95%

homoalylic alcohol (627-27-0) + n-octanoic acid chloride (111-64-8) → but-3-enyl octanoate (1070316-20-9)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;	100%

homoalylic alcohol (627-27-0) + Octanal (124-13-0) → cis-2-heptyl-4-fluorotetrahydro-2H-pyran

Conditions	Yield
With Et4NF*5HF at 20℃; for 0.166667h; Prins reaction; stereoselective reaction;	100%
With Et4NF*5HF at 20℃; for 0.166667h; Prins cyclization; stereoselective reaction;

homoalylic alcohol (627-27-0) + 4-nitrobenzaldehdye (555-16-8) → cis-4-fluoro-2-(4-nitrophenyl)tetrahydro-2H-pyran

Conditions	Yield
With Et4NF*5HF at 20℃; for 0.333333h; Prins reaction; stereoselective reaction;	100%
With HSO4- exchanged Amberlyst A26 resin-supported hydrogen fluoride In 1,2-dichloro-ethane at 20℃; for 5h; diastereoselective reaction;	82%
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone complex with hydrogen fluoride In dichloromethane at 20℃; for 3h; diastereoselective reaction;	81%
With Et4NF*5HF at 20℃; for 0.333333h; Prins cyclization; stereoselective reaction;

homoalylic alcohol (627-27-0) + benzaldehyde (100-52-7) → cis-4-fluoro-2-phenyltetrahydro-2H-pyran

Conditions	Yield
With Et4NF*5HF at 20℃; for 0.333333h; Prins reaction; stereoselective reaction;	100%
With HSO4- exchanged Amberlyst A26 resin-supported hydrogen fluoride In 1,2-dichloro-ethane at 20℃; for 5h; diastereoselective reaction;	83%
With titanium(IV) fluoride In dichloromethane at 20℃; for 2.5h; Prins cyclization reaction;	82%
With tetrafluoroboric acid diethyl ether In dichloromethane at 23℃; for 20h; diastereoselective reaction;	76%
With Et4NF*5HF at 20℃; for 0.333333h; Prins cyclization; stereoselective reaction;

4-nitro-phenol (100-02-7) + homoalylic alcohol (627-27-0) → 1‐(but‐3‐en‐1‐yloxy)‐4‐nitrobenzene (40742-21-0)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction; Reflux;	100%

homoalylic alcohol (627-27-0) + meta-nitrophenol (554-84-7) → 1-but-3-enyloxy-3-nitrobenzene (374588-08-6)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran	100%

homoalylic alcohol (627-27-0) + O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → 1-(4-methoxybenzyloxy)-3-butene (142860-83-1)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In toluene for 0.25h; Inert atmosphere;	100%
With lanthanum triflate In toluene at 20℃; Inert atmosphere;

homoalylic alcohol (627-27-0) + acrolein (107-02-8) → (E)-5-hydroxypent-2-enal (112596-89-1)

Conditions	Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; for 24h;	100%

homoalylic alcohol (627-27-0) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 4-(2,2-diethoxyethoxy)but-1-ene (1343915-25-2)

Conditions	Yield
Stage #1: homoalylic alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: Bromoacetaldehyde diethyl acetal In tetrahydrofuran; mineral oil at 0 - 68℃; for 66h; Inert atmosphere;	100%
Stage #1: homoalylic alcohol With sodium hydride In water at 0℃; for 1h; Stage #2: Bromoacetaldehyde diethyl acetal In water at 0 - 80℃; for 24h; Temperature;	100%
Stage #1: homoalylic alcohol In tetrahydrofuran at 0℃; for 1h; Stage #2: Bromoacetaldehyde diethyl acetal In tetrahydrofuran at 70℃; for 48h; Temperature;	96.3%
Stage #1: homoalylic alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: Bromoacetaldehyde diethyl acetal In tetrahydrofuran; mineral oil at 0 - 68℃; for 66h;	77 g

homoalylic alcohol (627-27-0) + 2-bromo-N-(2-methoxyphenyl)benzenesulfonamide (924107-85-7) → 2-bromo-N-(but-3-en-1-yl)-N-(2-methoxyphenyl)benzenesulfonamide (1582316-68-4)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 3.16667h; Mitsunobu Displacement;	100%

homoalylic alcohol (627-27-0) + C16H17BrN2O3S (1286918-84-0) → 2-bromo-N-(but-3-en-1-yl)-N-(2-morpholinophenyl)benzenesulfonamide (1582316-69-5)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 3.16667h; Mitsunobu Displacement;	100%

homoalylic alcohol (627-27-0) + 2-bromo-N-(2-nitrophenyl)benzenesulfonamide (1304050-40-5) → 2-bromo-N-(but-3-en-1-yl)-N-(2-nitrophenyl)benzenesulfonamide (1582316-72-0)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 3.16667h; Mitsunobu Displacement;	100%

homoalylic alcohol (627-27-0) → N-(3-butenyl)phthalimide (52898-32-5)

Conditions	Yield
With phthalimide; di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 3.03333h;	100%

homoalylic alcohol (627-27-0) + diethyl (1-((4-methylphenyl)sulfonamido)prop-1-en-1-yl)phosphonate → (E)-diethyl (1-((N-(but-3-en-1-yl)-4-methylphenyl)sulfonamido)prop-1-en-1-yl)phosphonate

Conditions	Yield
With tributylphosphine; di-isopropyl azodicarboxylate In tetrahydrofuran; toluene at 20℃; for 1h; Mitsunobu Displacement; Inert atmosphere;	100%

homoalylic alcohol (627-27-0) + L-valine (72-18-4) + toluene-4-sulfonic acid (104-15-4) → (S)-1-(but-3-en-1-yloxy)-3-methyl-1-oxobutan-2-aminium 4-methylbenzenesulfonate

Conditions	Yield
In water; toluene for 24h; Reflux; Dean-Stark;	100%

homoalylic alcohol (627-27-0) + 2-oxo-4-phenylbutyric acid (710-11-2) → but-3-en-1-yl 3-phenylpropanoate (327620-61-1)

Conditions	Yield
With 3-nitro(diacetoxyiodo)benzene In dichloromethane at 20℃; for 8h; Sealed tube; Darkness; chemoselective reaction;	100%

homoalylic alcohol (627-27-0) + ethyl α-nitrocinnamate (18315-80-5, 18315-86-1, 16508-09-1) → ethyl 3-phenyl-2-nitropropionate (16782-23-3)

Conditions	Yield
With lithium hexamethyldisilazane at -78℃; Michael Addition;	100%

homoalylic alcohol (627-27-0) + N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-fluoro-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzenesulfonamide (1403480-28-3) → 2-(but-3-en-1-yloxy)-N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-Nmethylphenylsulfonamido)-2-methylbutyl)-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzenesulfonamide (1403480-44-3)

Conditions	Yield
Stage #1: homoalylic alcohol With sodium hydride at 0℃; for 0.333333h; Stage #2: N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-fluoro-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzenesulfonamide In tetrahydrofuran at 0℃;	99%
Stage #1: homoalylic alcohol With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: N-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-4-(4-fluoro-N-methylphenylsulfonamido)-2-methylbutyl)-2-fluoro-N-((2S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-5-nitrobenzenesulfonamide In tetrahydrofuran at 0℃; for 2.75h;	99.5%

homoalylic alcohol (627-27-0) → 3,4-dichloro-butan-1-ol (38300-63-9)

Conditions	Yield
With Oxone; sodium chloride In dichloromethane; water at 0℃; for 0.5h; Darkness; diastereoselective reaction;	99%
With chlorine
With tetrachloromethane; chlorine at -20℃;

Upstream product

• 62726-91-4 D-ALPHA-TOCOPHEROL QUINONE 
• 6272-69-1 methyl 3-[4-(ethylamino)phenyl]propanoate 
• 627-26-9 (2E)-2-Butenenitrile 
• 6272-68-0 2-(cyclohexylcarbamimidoyl)-1-hydroxy-1-oxodiazanium 
• 6272-66-8 AZODIFORMAMIDINE DINITRATE 
• 62726-18-5 (2E,4E,10Z)-N-(2-methylpropyl)docosa-2,4,10-trienamide 
• 62726-15-2 [pentachloro-29H,31H-phthalocyaninato(2-)-N29,N30,N31,N32]copper 
• 62726-09-4 delta(1)-tetrahydrocannabinol glucuronide 
• 62726-03-8 2-methoxy-4-nitrobenzamide 
• 6272-60-2 triethyl 7-(naphthalen-1-yl)-4-oxoheptane-1,5,5-tricarboxylate 
• 6272-58-8 9,9,10,10,11,11-hexamethyl-10,11-dihydrotetraphen-8(9H)-one 
• 6272-57-7 9-(2-methylcyclohex-1-en-1-yl)phenanthrene 
• 6272-56-6 [1-(pyren-1-yl)ethyl]propanedioic acid 
• 6272-55-5 7,8,9,10-TETRAHYDRO-BENZO[A]PYREN-7-OL 

Downstream Products

• 6272-70-4 3-{4-[(2-chloroethyl)(ethyl)amino]phenyl}propanoic acid 
• 6272-72-6 2-[ethyl(2-hydroxyethyl)amino]-1,2-bis(4-methoxyphenyl)ethanone 
• 6272-73-7 3-[(1,2-diphenylethyl)amino]heptan-4-ol 
• 6272-74-8 lapirium chloride 
• 6272-75-9 3-methyl-2-[2-(3-methyloctahydroisoquinolin-2(1H)-yl)ethyl]-1,2-dihydroisoquinoline 
• 6272-78-2 4-ethoxy-N-[1-(4-methoxyphenyl)-2-phenylethyl]aniline 
• 6272-82-8 butyl N,N-diprop-2-en-1-ylcarbamimidate 
• 6272-83-9 N-[(2Z)-3-(2-ethoxyethyl)-6-nitro-1,3-benzothiazol-2(3H)-ylidene]furan-2-carboxamide 
• 6272-85-1 4-(2,5-dioxopyrrolidin-1-yl)-N-[(2Z)-3-(2-ethoxyethyl)-6-nitro-1,3-benzothiazol-2(3H)-ylidene]benzamide 
• 6272-86-2 ethyl(4-iodophenyl)arsinic acid 
• 6272-87-3 ethyl 4,6-dimethyl-3-nitro-2-oxo-2H-pyran-5-carboxylate 
• 6272-88-4 2,4-DiaMino-7-hydroxy-6-pteridineacetic Acid Ethyl Ester 
• 62728-88-5 RHODIUM(II) TRIMETHYLACETATE 
• 62728-89-6 RHODIUM(II) HEXANOATE DIMER 

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• 1120-97-4  4-methyl-1,3-dioxane 
• 598-32-3  2-hydroxy-3-butene 
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• 50-00-0  formaldehyd 
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• 100-52-7  benzaldehyde