497-06-3

Basic information

• Product Name: 3-BUTENE-1,2-DIOL
• Synonyms: 1,2-Dihydroxy-3-butene;1-Butene-3,4-diol;3-buten-1,2-diol;Erythrol;EPB(TM) DIOL;BUT-3-ENE-1,2-DIOL;3,4-DIHYDROXY-1-BUTENE;3-BUTENE-1,2-DIOL
• CAS NO: 497-06-3
• Molecular Formula: C₄H₈O₂
• Molecular Weight: 88.11
• EINECS: 207-835-1
• Product Categories: Acyclic;Alkenes;Organic Building Blocks;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 497-06-3.mol
• Article Data: 42

Chemical Properties

• Melting Point: 15.1°C (estimate)
• Boiling Point: 196.5 °C(lit.)
• Flash Point: 222 °F
• Appearance: /
• Density: 1.047 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.102mmHg at 25°C
• Refractive Index: n20/D 1.462
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.68±0.20(Predicted)
• BRN: 1633578
• CAS DataBase Reference: 3-BUTENE-1,2-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BUTENE-1,2-DIOL(497-06-3)
• EPA Substance Registry System: 3-BUTENE-1,2-DIOL(497-06-3)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 497-06-3(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

Different sources of media describe the Uses of 497-06-3 differently. You can refer to the following data:
1. Decomposition product of Erythritol.
2. 3,4-Dihydroxy-1-butene can be used:As a reactant to synthesize cyclic organic carbonates by continuous flow procedure.To prepare substituted oxazolidinone ligands used to target medicinally relevant RNAs.

General Description

3,4-Dihydroxy-1-butene, also known as 3-butene-1,2-diol (BDdiol), is a metabolite of 1,3-butadiene. It forms the precursor for synthesizing different chiral building blocks. BDdiol can undergo oxidation to form hydroxymethylvinyl ketone (HMVK). 1,2-epoxy-3-butene (EB) on hydrolysis in the presence of epoxide hydrolases (EH) forms BDdiol.

InChI:InChI=1/C4H8O2/c1-2-4(6)3-5/h2,4-6H,1,3H2

Synthetic route

4-vinyl-1,3-dioxolan-2-one (4427-96-7) → methanol (67-56-1) + 3,4-butenediol (497-06-3)

Conditions	Yield
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); potassium carbonate In isopropyl alcohol at 140℃; Glovebox;	A > 99 %Chromat. B 96%
With [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](bromo)(carbonyl)(hydride)iron(II); potassium tert-butylate; isopropyl alcohol In tetrahydrofuran at 140℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;	A 82 %Chromat. B 85%

epoxybutene (930-22-3) → 3,4-butenediol (497-06-3) + 1,4-butenediol (821-11-4, 6117-80-2, 110-64-5)

Conditions	Yield
With water; molybdenum-containing silicate at 25℃; for 5h; Product distribution / selectivity;	A 93% B 4%
With water; vanadium-containing silicate at 25℃; for 5h; Product distribution / selectivity;	A 87% B 5%
With water; tungsten-containing silicate at 25℃; for 5h; Product distribution / selectivity;	A 81% B 2%
With sodium perchlorate; water at 25℃; Rate constant; Mechanism;	A 96 % Chromat. B 4 % Chromat.
With water; lithium iodide In 1-methyl-pyrrolidin-2-one at 80℃; Product distribution; Further Variations:; Catalysts; Temperatures; reaction time;

1,4-butenediol (821-11-4, 6117-80-2, 110-64-5) → 3,4-butenediol (497-06-3)

Conditions	Yield
With sulfuric acid; mercury(II) sulfate In water at 90 - 95℃; for 4h;	75.6%
With sulfuric acid; mercury(II) sulfate In water for 1.5h; Heating;	52%
With sulfuric acid; water; mercury(II) sulfate for 1.5h; Isomerization; Heating;

1,4-butenediol (6117-80-2) → 3,4-butenediol (497-06-3)

Conditions	Yield
With sulfuric acid; mercury(II) sulfate In water at 50℃; for 0.05h; microwave oven;	66%
With sulfuric acid; mercury(II) sulfate In water at 50℃; for 0.0833333h; Rearrangement; Irradiation;	66%
With sulfuric acid; mercury(II) sulfate In water at 100℃; for 3h;	65%

epoxybutene (930-22-3) → 3,4-butenediol (497-06-3)

Conditions	Yield
With sulfuric acid for 3h; Heating;	58%
With water at 20℃; Product distribution; Rate constant; in the presence of H2SO4 and further acids, further temperatures;
With sulfuric acid

buta-1,3-diene (106-99-0) → 3,4-butenediol (497-06-3) + 1,4-butenediol (821-11-4, 6117-80-2, 110-64-5)

Conditions	Yield
With oxygen In ethyl acetate at 60℃; under 7500.75 Torr; for 60h; Temperature; Reagent/catalyst; Solvent; Pressure;	A 51% B 39%

epoxybutene (930-22-3) → 3,4-butenediol (497-06-3) + (E)-2-butene-1,4-diol (821-11-4)

Conditions	Yield
With water

trans-1,4-dichlorobut-2-ene (110-57-6) → 3,4-butenediol (497-06-3) + (E)-2-butene-1,4-diol (821-11-4)

Conditions	Yield
With sodium carbonate
With sodium carbonate at 90 - 95℃;

1,4-dibromo-2-butene (6974-12-5) → 3,4-butenediol (497-06-3)

(E)-1,4-dibromobutene (821-06-7) → 3,4-butenediol (497-06-3) + (E)-2-butene-1,4-diol (821-11-4)

Conditions	Yield
With sodium carbonate at 90 - 95℃;

meso-erythritol (909878-64-4) → 3,4-butenediol (497-06-3)

2,3-dimethylbutene (590-19-2) → 3,4-butenediol (497-06-3)

Conditions	Yield
With iodo silver benzoate und Verseifen des entstandenen 4-Jod-buten-(1)-ol-(3)-benzoats;

1-chloro-2-hydroxy-3-butene (671-56-7) → 3,4-butenediol (497-06-3)

Conditions	Yield
With sodium hydrogencarbonate

buta-1,3-diene (106-99-0) → 3,4-butenediol (497-06-3) + (E)-2-butene-1,4-diol (821-11-4)

Conditions	Yield
With sodium perchlorate In water; acetonitrile (electrolysis);

Formic acid (2S,3R)-4-formyloxy-2,3-dihydroxy-butyl ester → 3,4-butenediol (497-06-3) + 1,4-butenediol (6117-80-2)

Conditions	Yield
With sodium methylate In methanol Ambient temperature; Yield given;

epoxybutene (930-22-3) → 3,4-butenediol (497-06-3) + 1,2:3,4-Diepoxybutane (564-00-1, 1464-53-5, 30031-64-2, 30419-67-1, 34897-03-5, 298-18-0)

Conditions	Yield
With tert.-butylhydroperoxide; molybdenum resinate In toluene at 110℃;

epoxybutene (930-22-3) → 2,5-dihydrofuran (1708-29-8) + trans-Crotonaldehyde (123-73-9) + 3,4-butenediol (497-06-3) + (E)-2-butene-1,4-diol (821-11-4) + 4-iodo-2-butene-1-ol

Conditions	Yield
With potassium iodide; USY zeolite In various solvent(s) at 74.85℃; for 24h; Product distribution; Mechanism; var. nucleophiles and acids; var. solv. and time;

epoxybutene (930-22-3) + H2SO4-containing water → 3,4-butenediol (497-06-3)

Conditions	Yield
Erhitzen des Reaktionsgemisches zum Sieden;

buta-1,3-diene (106-99-0) + iodo silver benzoate complex → 3,4-butenediol (497-06-3)

Conditions	Yield
Verseifung des Reaktionsprodukts;

monoformate of erythrol → 3,4-butenediol (497-06-3)

Conditions	Yield
With barytes

trans-1,4-dichlorobut-2-ene (110-57-6) + aqueous natrium carbonate → 3,4-butenediol (497-06-3) + (E)-2-butene-1,4-diol (821-11-4)

1-chloro-2-hydroxy-3-butene (671-56-7) + NaHCO3 → epoxybutene (930-22-3) + 3,4-butenediol (497-06-3) + (E)-2-butene-1,4-diol (821-11-4)

cis-1,4-dibromo-2-butene (18866-73-4) + diluted natrium carbonate → 2,5-dihydrofuran (1708-29-8) + 3,4-butenediol (497-06-3) + 1,4-butenediol (6117-80-2) + crotonaldehyde (123-73-9)

Conditions	Yield
at 90 - 95℃; Hydrolysis;

1,4-dibromo-2-butene (6974-12-5) + diluted natrium carbonate → 3,4-butenediol (497-06-3) + 1,4-butenediol (821-11-4, 6117-80-2, 110-64-5) + crotonaldehyde (123-73-9)

buta-1,3-diene (106-99-0) → 3,4-butenediol (497-06-3) + erythritol,DL-threitol

Conditions	Yield
With Methyl formate; dihydrogen peroxide

(E)-2-butene-1,4-diol (821-11-4) → 3,4-butenediol (497-06-3)

Conditions	Yield
trimethylsilylperrhenate In dichloromethane at 20℃; Rearrangement;

epoxybutene (930-22-3) + molybdenum-containing silicate → 3,4-butenediol (497-06-3)

Conditions	Yield
In tetrahydrofuran; water

epoxybutene (930-22-3) → 3,4-butenediol (497-06-3) + C8H14O3 (1058721-17-7)

Conditions	Yield
With sodium hydroxide Title compound not separated from byproducts.;

buta-1,3-diene (106-99-0) → furan (110-00-9) + 3,4-butenediol (497-06-3) + 1,4-butenediol (821-11-4, 6117-80-2, 110-64-5) + acrolein (107-02-8) + crotonaldehyde (123-73-9)

Conditions	Yield
With 1-vanado,11-molybdophosphoric acid; dihydrogen peroxide In water; acetonitrile at 40℃; for 2h; Gas phase;	A 30 μmol B 59 μmol C 7.5 μmol D 238 μmol E 3.7 μmol
With 5H(1+)*Mo10O40PV2(5-)*9H2O; dihydrogen peroxide In water; acetonitrile at 50℃; for 2h; Gas phase;	A 23 μmol B 17 μmol C 5 μmol D 99 μmol E 12 μmol
With 1-vanado,11-molybdophosphoric acid; dihydrogen peroxide In water; acetonitrile at 50℃; for 2h; Kinetics; Gas phase;	A 59 μmol B 42 μmol C 15 μmol D 282 μmol E 5.1 μmol

3,4-butenediol (497-06-3) + 1-penten (109-67-1) → 1,2-dihydroxy-3-heptene

Conditions	Yield
With 1,2,3-trimethoxybenzene; Grubbs catalyst first generation In dichloromethane for 6h; Heating / reflux;	100%

3,4-butenediol (497-06-3) + 1,1-dimethoxyethylene (922-69-0) → C12H24O6 (1092455-60-1)

Conditions	Yield
at 20℃; for 12h; Inert atmosphere; neat (no solvent);	100%

3,4-butenediol (497-06-3) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-((tert-butyldimethylsilyl)oxy)but-3-en-2-ol (136917-96-9, 136984-28-6, 119125-28-9)

Conditions	Yield
With 1H-imidazole In dichloromethane for 4h;	99%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 21h;	97%
In tetrahydrofuran at 20℃; for 9h;	95%

3,4-butenediol (497-06-3) + methylthiol (74-93-1) → 4-methylsulfanyl-butane-1,2-diol (57070-84-5)

Conditions	Yield
dimethyl 2,2'-azobis(isobutyrate) at 0 - 40℃; under 367.786 - 1838.93 Torr; for 4h; Product distribution / selectivity;	98%
With triethyl borane at -10 - 20℃; for 0.0833333h;	96%
2,2'-azobis(isobutyronitrile) at 0 - 40℃; under 367.786 - 1838.93 Torr; for 2 - 4h; Product distribution / selectivity;	67 - 94 %Chromat.

3,4-butenediol (497-06-3) + p-toluenesulfonyl chloride (98-59-9) → 2-hydroxy-3-butenyl-4-methyl-1-benzenesulfonate (138332-13-5)

Conditions	Yield
With di(n-butyl)tin oxide; triethylamine In dichloromethane; water at 20℃;	97%
With pyridine In chloroform	94.3%
With pyridine In dichloromethane at 20℃; for 33h;	62%

3,4-butenediol (497-06-3) + tert-butylchlorodiphenylsilane (58479-61-1) → (+/-)-1-(tert-butyldiphenylsilyloxy)-2-hydroxy-3-butene (177032-63-2)

Conditions	Yield
With 1H-imidazole In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;	95%
With dmap; triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; regioselective reaction;	95%
With dmap; triethylamine In tetrahydrofuran at 20℃; silylation;	88%

3,4-butenediol (497-06-3) + chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) → 1-[(dimethyl(1,1,2-trimethylpropyl)silyl)oxy]-3-butene-2-ol (136917-98-1)

Conditions	Yield
With 1H-imidazole In dichloromethane at 0℃; for 1.5h;	95%

3,4-butenediol (497-06-3) → vinyl ethylene sulfite

Conditions	Yield
With thionyl chloride at 5℃; for 2h; Temperature; Solvent;	93.2%

3,4-butenediol (497-06-3) + 2-Chloro-2-oxo-1,3,2-dioxaphospholane (6609-64-9) → C8H14O8P2

Conditions	Yield
Stage #1: 3,4-butenediol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-Chloro-2-oxo-1,3,2-dioxaphospholane In dichloromethane at 0 - 20℃; for 12h;	93%

3,4-butenediol (497-06-3) + 2-chloro-1,3,2-dioxaphospholan (822-39-9) → C8H14O6P2

Conditions	Yield
In dichloromethane at 0 - 20℃; for 12h;	93%

3,4-butenediol (497-06-3) + carbonic acid dimethyl ester (616-38-6) → 4-vinyl-1,3-dioxolan-2-one (4427-96-7)

Conditions	Yield
Stage #1: 3,4-butenediol; carbonic acid dimethyl ester With sodium methylate; sodium carbonate; magnesium sulfate for 0.5h; Stage #2: With sodium methylate; sodium carbonate at 60℃; for 5h; Temperature;	92.7%
With tetrabutylammomium bromide at 180℃; under 8250.83 Torr; for 0.05h; Flow reactor;	67%
With cross-linked with 1percent DVB polystyrene-bound 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 160℃; under 8250.83 Torr; Reagent/catalyst; Solvent; Temperature; Flow reactor;	87 %Chromat.

3,4-butenediol (497-06-3) + tert-butyldimethylsilyl chloride (18162-48-6) → 3,4-bis(tert-butyldimethylsilanyloxy)but-1-ene (172290-42-5)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide	92%
With 1H-imidazole In tetrahydrofuran at 20℃; for 72h;	58%

(-)-(R)-(1-methoxy-2,2,2-triphenylethyl)dimethylsilane (952652-05-0) + 3,4-butenediol (497-06-3) → (1'R)-1-[(1-methoxy-2,2,2-triphenylethyl)dimethylsilyloxy]but-3-en-2-ol (952652-10-7)

Conditions	Yield
Stage #1: (-)-(R)-(1-methoxy-2,2,2-triphenylethyl)dimethylsilane With bromine In dichloromethane at -78℃; Stage #2: 3,4-butenediol With dmap; triethylamine In dichloromethane at 0 - 23℃; for 1h; Further stages.;	92%

3,4-butenediol (497-06-3) + t-butyldimethylsiyl triflate (69739-34-0) → 3,4-bis(tert-butyldimethylsilanyloxy)but-1-ene (172290-42-5)

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane	90%

3,4-butenediol (497-06-3) + benzaldehyde (100-52-7) → 1,2-benzylidene-3-buten-1,2-diol (62999-50-2)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 3h; Condensation; Heating;	90%

3,4-butenediol (497-06-3) + acetyl chloride (75-36-5) → 1,2-diacetoxy-3-butene (18085-02-4)

Conditions	Yield
With pyridine In diethyl ether 1.) room temp., 14 h; 2.) reflux, 6 h;	88%
With pyridine; Petroleum ether

3,4-butenediol (497-06-3) + 4-nitro-benzoyl chloride (122-04-3) → 4-Nitro-benzoic acid 2-hydroxy-but-3-enyl ester (184845-06-5)

Conditions	Yield
With pyridine In dichloromethane	88%

3,4-butenediol (497-06-3) + trityl chloride (76-83-5) → (+/-)-1-(trityloxy)but-3-en-2-ol (89543-83-9)

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; regioselective reaction;	88%
With pyridine; dmap for 3h; Heating;	65%
With dmap; triethylamine In toluene at 0 - 40℃; Industry scale;
With dmap; triethylamine In n-heptane; ethyl acetate; toluene

3,4-butenediol (497-06-3) + 2,4-dimethyl-3-cyclohexenecarboxaldehyde (68039-49-6) → 2-(2,4-dimethylcyclohex-3-enyl)-4-vinyl-[1,3]dioxolane (1411949-22-8)

Conditions	Yield
	86%

2-Methylbutyraldehyde (96-17-3, 57456-98-1) + 3,4-butenediol (497-06-3) → 2-secbutyl-4-vinyl-[1,3]dioxolane (1411949-07-9)

Conditions	Yield
In cyclohexane; water	86%

3,4-butenediol (497-06-3) + Diphenylphosphine oxide (4559-70-0) → 4-(diphenyl-phosphinoyl)-butane-1,2-diol

Conditions	Yield
triethyl borane In methanol; hexane at 20℃; for 2h;	85%

thiophosgene (463-71-8) + 3,4-butenediol (497-06-3) → 4-vinyl-1,3-dioxolane-2-thione (1198600-65-5)

Conditions	Yield
With pyridine; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;	85%

3,4-butenediol (497-06-3) → 2-oxo-but-3-enoic acid (56842-76-3)

Conditions	Yield
With oxygen; sodium hydroxide; 5% Bi/4% Pd/1% Pt on active charcoal In water at 30℃; for 4.5h; pH=7.5; Product distribution / selectivity;	85%

3,4-butenediol (497-06-3) + trichloroacetonitrile (545-06-2) → but-1-ene-3,4-diylbis(trichloroacetimidate) (1408232-59-6)

Conditions	Yield
Stage #1: 3,4-butenediol With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.5h; Molecular sieve; Stage #2: trichloroacetonitrile In dichloromethane for 0.5h;	85%

3,4-butenediol (497-06-3) + cycloxexanone dimethyl ketal (933-40-4) → 2,2-pentamethylene-4-vinyl-1,3-dioxolane (62999-51-3)

Conditions	Yield
With toluene-4-sulfonic acid In cyclohexanone; benzene Heating;	84%

3,4-butenediol (497-06-3) + 3,5,5-trimethyl hexanal (5435-64-3) → 2-(2,4,4-trimethylpentyl)-4-vinyl-[1,3]dioxolane (1411949-38-6)

Conditions	Yield
	83%

3,4-butenediol (497-06-3) + 4-tercbutyl-cyclohexanone (98-53-3) → 8-tertbutyl-2-vinyl-1,4-dioxaspiro-[4.5]-decane (1411949-53-5)

Conditions	Yield
	79%

Upstream product

• 930-22-3 epoxybutene 
• 96-26-4 dihydroxyacetone 
• 1826-67-1 vinyl magnesium bromide 
• 909878-64-4 meso-erythritol 
• 1421929-85-2 (±)-1-(4-methoxybenzyloxy)but-3-en-2-ol 
• 141-46-8 Glycolaldehyde 
• 4427-96-7 4-vinyl-1,3-dioxolan-2-one 
• 106-99-0 buta-1,3-diene 
• 821-11-4 trans-butene-1,4-diol 
• 6974-12-5 1,4-dibromo-2-butene 
• 18866-73-4 cis-1,4-dibromo-2-butene 
• 671-56-7 1-chloro-2-hydroxy-3-butene 
• 110-57-6 trans-1,4-dichlorobut-2-ene 
• 821-11-4 1,4-butenediol 

Downstream Products

• 17177-50-3 (+/-)-(1,2-Dihydroxyethyl)oxirane 
• 62214-39-5 (2S)-but-3-ene-1,2-diol 
• 86106-09-4 (R)-(+)-3,4-dihydroxy-1-butene 
• 6974-12-5 1,4-dibromo-2-butene 
• 123-73-9 crotonaldehyde 
• 821-11-4 trans-butene-1,4-diol 
• 4437-51-8 3,4-hexanedione 
• 123-38-6 propionaldehyde 
• 5077-67-8 1-Hydroxy-2-butanone 
• 6968-16-7 rac-threitol 
• 144-62-7 oxalic acid 
• 2319-57-5 1,2,3,4-butanetetrol 
• 90802-14-5 4-chlorobutane-1,2,3-triol 
• 22554-74-1 (+/-)-trans-tetrahydrofuran-3,4-diol 

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