(R)-(-)-1,3-Butanediol supplier

Name
(R)-(-)-1,3-Butanediol
EINECS 228-532-0
CAS No. 6290-03-5
Article Data51
CAS DataBase
Density 1.001 g/cm³
Solubility Fully miscible in water.
Melting Point 0ºC
Formula C₄H₁₀O₂
Boiling Point 207 °C at 760 mmHg
Molecular Weight 90.1222
Flash Point 121.1 °C
Transport Information
Appearance Colorless to light yellow liquid
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1,3-Butanediol,(R)-;1,3-Butanediol, (R)-(-)- (8CI);(-)-1,3-Butanediol;(3R)-1,3-Butanediol;(R)-1,3-Butanediol;L-Butane-1,3-diol;
PSA 40.46000
LogP -0.25040

Synthetic route

: 105-45-3
acetoacetic acid methyl ester

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
Stage #1: acetoacetic acid methyl ester With ruthenium trichloride; C102H72NO9P3 for 0.5h; Stage #2: With diphenyl hydrogen phosphate; hydrogen at 80℃; under 37503.8 - 45004.5 Torr; Reagent/catalyst; Temperature; Pressure; Sealed tube;	99.4%

: 590-90-9
1-Hydroxy-3-butanone

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3; hydrogen In methanol at 50℃; under 38000 Torr; for 24h;	98%
With hydrogen; dichloro(benzene)ruthenium(II) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In ethanol at 30℃; under 76000.1 Torr; for 40h; Yields of byproduct given. Title compound not separated from byproducts;	96%
With methanol; phosphate buffer at 30℃; for 6.5h; Candida boidinii KK912 (IFO 10574);	60%

: 108-05-4
vinyl acetate

: 18826-95-4, 107-88-0
1.3-butanediol

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
Stage #1: vinyl acetate; 1.3-butanediol With ChirazymeTM L-2 In diethyl ether at 20℃; for 30h; Stage #2: With sodium methylate In methanol at 20℃; for 2h;	90%

: 79464-76-9
(2S,4R)-4-methyl-2-phenyl-1,3-dioxane

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With hydrogen; palladium dihydroxide In ethyl acetate	87%

: 24915-95-5
Ethyl (R)-3-hydroxybutanoate

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 1h; Ambient temperature;	86%
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 0.5h;	85.6%
Stage #1: Ethyl (R)-3-hydroxybutanoate With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 3h; Inert atmosphere; Stage #2: With water In diethyl ether	81%

: 625-72-9
(R)-3-hydroxybutyric acid

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 5h;	85%

: 32082-74-9
(R)-4-methyloxetan-2-one

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With sodium tetrahydroborate; ethanol at 20℃;	85%
With sodium tetrahydroborate In ethanol at 20℃;	79%

poly[(R)-3-hydroxybutanoate]: poly[(R)-3-hydroxybutanoate]

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
Stage #1: poly[(R)-3-hydroxybutanoate] With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Inert atmosphere; Reflux; Stage #2: With water; sodium hydroxide In tetrahydrofuran; diethyl ether at 0℃;	84%

: 112635-76-4, 108585-47-3
(S)-ethyl 3,4-dihydroxybutanoate

: 98-59-9
p-toluenesulfonyl chloride

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
Stage #1: (S)-ethyl 3,4-dihydroxybutanoate With triethylamine In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride In dichloromethane at 20℃; for 10h; Inert atmosphere; Stage #3: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 8h; Inert atmosphere; chemoselective reaction;	82%

: 77876-45-0
(R)-4-methyl-1,3-dioxan

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With hydrogenchloride; (2,4-dinitro-phenyl)-hydrazine for 12h;	75%

: 115404-95-0
(2R,6S,7S,10R)-7-Isopropyl-2,10-dimethyl-1,5-dioxa-spiro[5.5]undecane

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 14h; Ambient temperature;	53%

: 24830-94-2
D-allo-threonine

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
Multistep reaction;

: 18826-95-4, 107-88-0
1.3-butanediol

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
Multistep reaction;
at 30℃; for 72h;

: 590-90-9
1-Hydroxy-3-butanone

A: 24621-61-2
1,3-butanediol

B: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With hydrogen; RuCl2[(R)-BINAP] In ethanol under 53200 Torr; for 42h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; acetic acid; Raney nickel modified with R,R-tartaric acid In tetrahydrofuran at 80℃; under 66195.7 Torr; for 14h; Title compound not separated from byproducts;
With hydrogen; TA-NaBr-MR-Ni In tetrahydrofuran; acetic acid under 66195.7 Torr; Product distribution;

: 75052-43-6
1,3-butanedioldicarbanilate

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In 1,4-dioxane at 80℃; for 3h; Heating;	2.5 g

: 115346-84-4
Benzoic acid (R)-3-[(2S,5R)-2-isopropyl-5-methyl-1-(2-oxo-2-phenyl-ethyl)-cyclohexyloxy]-butyl ester

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With sodium hydroxide In methanol Heating; Yield given;

: 115404-95-0
(2R,6S,7S,10R)-7-Isopropyl-2,10-dimethyl-1,5-dioxa-spiro[5.5]undecane

A: 24621-61-2
1,3-butanediol

B: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol Ambient temperature; Yield given;

: 141859-92-9
4-Hydroxy-2-butanone dimethylsilylether

A: 24621-61-2
1,3-butanediol

B: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With potassium carbonate; (-)-1,2-bis[(2R,5R)-2,5-diisoprohylphospholano]benzene 1) CH2Cl2, 2 h, 20-25 deg C, 2) MeOH, 4 h; Multistep reaction. Title compound not separated from byproducts;

: 117631-61-5
(S)-4-Benzenesulfonyl-butane-1,3-diol

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With Ra-Ni

: 3-hydroxybutyl β-D-galactopyranoside

A: 10257-28-0
D-Galactose

B: 24621-61-2
1,3-butanediol

C: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With phosphoric acid; β-galactosidase from Escherichia coli at 40℃; for 0.25h; Product distribution; selectivity; influence of incubation time, temperature, microbial source, enzyme activity; other galactopyranosides;

...Expand

: 186378-98-3
(2S,4R)-2-(4-methoxyphenyl)-4-methyl-1,3-dioxane

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With ethandithiol; camphor-10-sulfonic acid In dichloromethane Ambient temperature; Yield given;

: 77877-38-4
(3'R,4S)-3-(3'-hydroxybutanoyl)-4-(1-methylethyl)-2-oxazolidinone

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran

: 18826-95-4, 107-88-0
1.3-butanediol

A: 24621-61-2
1,3-butanediol

B: 6290-03-5
(R)-butane-1,3-diol

C: 590-90-9
1-Hydroxy-3-butanone

Conditions

Conditions	Yield
With phosphate buffer; pKK-CPA1 In water at 30℃; for 24h; pH=6.5; Isomerization;

...Expand

: 590-90-9
1-Hydroxy-3-butanone

yeast: yeast

: 6290-03-5
(R)-butane-1,3-diol

: hexyl 4-chloroacetoacetate

A: 24621-61-2
1,3-butanediol

B: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
Stage #1: hexyl 4-chloroacetoacetate With bakers' yeast; phenylthioethylene In ethanol; water at 20℃; for 96h; Reduction; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 17h; Reduction; dehalogenation; Title compound not separated from byproducts;

: 18826-95-4, 107-88-0
1.3-butanediol

A: 24621-61-2
1,3-butanediol

B: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With E. coli cells expressing CpSADH In phosphate buffer at 30℃; for 40h; pH=6.8; Product distribution; Further Variations:; pH-values; concentrations; Enzymatic reaction;

: 4740-77-6
2,6-dimethyl-1,3-dioxan-4-ol

A: 24621-61-2
1,3-butanediol

B: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With sodium tetrahydroborate In 1-methyl-pyrrolidin-2-one; methanol at 4℃; Inert atmosphere; optical yield given as %ee;

: 3976-69-0
Methyl (R)-3-hydroxybutyrate

: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With hydrogen; C52H53BN2P2Ru In tetrahydrofuran at 80℃; under 37503.8 Torr; for 16h; Product distribution / selectivity;	n/a
With lithium aluminium tetrahydride

: 3976-69-0
Methyl (R)-3-hydroxybutyrate

A: 24621-61-2
1,3-butanediol

B: 6290-03-5
(R)-butane-1,3-diol

Conditions

Conditions	Yield
With RuH(η1-BH4)(dppp)((R,R)-dpen); hydrogen In tetrahydrofuran at 80℃; under 37503.8 Torr; for 16h; Autoclave;

: 6290-03-5
(R)-butane-1,3-diol

: 58479-61-1
tert-butylchlorodiphenylsilane

: (R)-4-(tert-butyldiphenylsilyloxy)-2-methylbutan-1-ol

Conditions

Conditions	Yield
With 1H-imidazole; dmap In dichloromethane at 0 - 20℃; for 18h;	100%
With dmap; water; triethylamine In dichloromethane for 12h;	70%
With 1H-imidazole In dichloromethane at 25℃; for 1h; Inert atmosphere;
With triethylamine In dichloromethane at 20℃; for 15h;

: 6290-03-5
(R)-butane-1,3-diol

: 1125-88-8
benzaldehyde dimethyl acetal

: 79464-76-9
(2S,4R)-4-methyl-2-phenyl-1,3-dioxane

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane for 3h; Heating;	98%

: 6290-03-5
(R)-butane-1,3-diol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1642119-85-4
(5R)-2,2,3,3,5,9,9,10,10-nonamethyl-4,8-dioxa-3,9-disilaundecane

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane for 6h;	98%
With 1H-imidazole In dichloromethane at 20℃;	98%
With 1H-imidazole In dichloromethane at 0 - 25℃; for 24h; Inert atmosphere;	90%

: 6290-03-5
(R)-butane-1,3-diol

: 77943-38-5
(2R)-4-[(methylsulfonyl)oxy]butan-2-yl methanesulfonate

Conditions

Conditions	Yield
following procedure published for the racemic compound;	97%

: 6290-03-5
(R)-butane-1,3-diol

: 40615-36-9
4,4'-dimethoxytrityl chloride

: (R)-(-)-1-O-(4,4'-dimethoxytrityl)-1,3-butanediol

Conditions

Conditions	Yield
With pyridine at 20℃; for 6h;	97%
With pyridine at 0 - 20℃; for 6h;	97%

: 6290-03-5
(R)-butane-1,3-diol

: 76-83-5
trityl chloride

: 113522-45-5
(R)-4-(triphenylmethoxy)butan-2-ol

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 6h;	96%
With pyridine; dmap at 20℃; for 48h;	92%
With triethylamine In dichloromethane at 0 - 20℃;	89.1%
With pyridine Ambient temperature;

: 6290-03-5
(R)-butane-1,3-diol

: 1125-88-8
benzaldehyde dimethyl acetal

: 116757-62-1
(R)-3-O-benzyl-1,3-butanediol

Conditions

Conditions	Yield
Stage #1: (R)-butane-1,3-diol; benzaldehyde dimethyl acetal With camphor-10-sulfonic acid In dichloromethane Stage #2: With diisobutylaluminium hydride In toluene	94%

: 6290-03-5
(R)-butane-1,3-diol

: 124-63-0
methanesulfonyl chloride

: (R)-3-hydroxybutyl methanesulfonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	92%

: 6290-03-5
(R)-butane-1,3-diol

: 124-63-0
methanesulfonyl chloride

: 77943-38-5
(2R)-4-[(methylsulfonyl)oxy]butan-2-yl methanesulfonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane 1.) - 20 deg C, 2.) -20 deg C -> 25 deg C;	91%
With triethylamine In dichloromethane at 0 - 20℃; for 2.25h;	89%
With triethylamine In dichloromethane at 0 - 20℃; for 2.25h;	89%
With triethylamine In dichloromethane at 0 - 20℃; for 5h;

: 6290-03-5
(R)-butane-1,3-diol

: 5949-05-3
(S)-Citronellal

: (-)-(2S,4R,2'S)-2-2',6'-dimethylhept-5'-enyl-4-methyl-1,3-dioxane

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; calcium carbonate In tetrahydrofuran 1.) 30 min, -60 deg C, 2.) 14.5 h, 0 deg C;	90%

: 6290-03-5
(R)-butane-1,3-diol

: 2385-77-5
(R)-Citronellal

: (-)-(2S,4R,2'R)-2-2',6'-dimethylhept-5'-enyl-4-methyl-1,3-dioxane

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; calcium carbonate In tetrahydrofuran 1.) 30 min, -60 deg C, 2.) 14.5 h, 0 deg C;	90%

: 6290-03-5
(R)-butane-1,3-diol

: 80617-15-8
(E)-3-(3,5-Dichloro-4'-fluoro-biphenyl-2-yl)-propenal

: 120185-77-5
(2S,4R)-2-[(E)-2-(3,5-Dichloro-4'-fluoro-biphenyl-2-yl)-vinyl]-4-methyl-[1,3]dioxane

Conditions

Conditions	Yield
toluene-4-sulfonic acid In benzene Heating; azeotropic removal of water;	90%

: 27856-66-2
O,O,O,O-tetraacetylsecologaninn

: 6290-03-5
(R)-butane-1,3-diol

: (4S,5R,6S)-4-((2S,4R)-4-Methyl-[1,3]dioxan-2-ylmethyl)-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	87.9%

: 6290-03-5
(R)-butane-1,3-diol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 136918-09-7
(R)-4-((tert-butyldimethylsilyl)oxy)butan-2-ol

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane for 27h; Ambient temperature;	87%
With dmap; triethylamine In dichloromethane at 20℃;	85%
Stage #1: (R)-butane-1,3-diol With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	85%

: 6290-03-5
(R)-butane-1,3-diol

: 35963-20-3
(R)-10-camphorsulfonic acid

: 91-00-9
Benzhydrylamine

: (2S)-1-(diphenylmethyl)-2-methylazetidinium [(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonate

Conditions

Conditions	Yield
Stage #1: (R)-butane-1,3-diol With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine In acetonitrile at -35 - -30℃; for 3.83333h; Inert atmosphere; Stage #2: Benzhydrylamine In acetonitrile at -35 - 45℃; for 2.66667h; Stage #3: (R)-10-camphorsulfonic acid In methanol at 10 - 20℃; for 0.25h;	86%
Stage #1: (R)-butane-1,3-diol With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine In acetonitrile at -35 - -30℃; for 0.833333h; Stage #2: (R)-10-camphorsulfonic acid; Benzhydrylamine In acetonitrile at -30 - 45℃;	65%

...Expand

: 6290-03-5
(R)-butane-1,3-diol

: [(1R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid

: 91-00-9
Benzhydrylamine

: (2S)-1-(diphenylmethyl)-2-methylazetidinium [(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonate

Conditions

Conditions	Yield
Stage #1: (R)-butane-1,3-diol With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine In acetonitrile at -35 - -30℃; for 3.83333h; Inert atmosphere; Stage #2: Benzhydrylamine In acetonitrile at -35 - 45℃; for 2.5h; Inert atmosphere; Stage #3: [(1R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid In methanol at -10 - 20℃; for 2.25h;	86%

...Expand

: 6290-03-5
(R)-butane-1,3-diol

: 66774-71-8
Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester

: (20S)-des-A,B-8β-(benzoyloxy)-20-<(2'S,4'R)-4'-methyl-1',3'-dioxan-2'-yl>pregnane

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In tetrahydrofuran for 16h; Ambient temperature;	85%

: 6290-03-5
(R)-butane-1,3-diol

: 98-88-4
benzoyl chloride

: 59694-08-5, 79413-96-0, 82659-86-7, 82598-19-4
Benzoesaeure<(R)-3-hydroxybutyl>ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 10h;	85%
With triethylamine In dichloromethane at 0 - 20℃; for 10h; Inert atmosphere;	81%
With pyridine In dichloromethane at -40℃; for 3h;	72%

: 6290-03-5
(R)-butane-1,3-diol

: 65236-83-1
phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-α-D-mannopyranoside

: 1126292-23-6
(3R)-1,3-bis(2',3',4',6'-tetra-O-benzoyl-α-D-mannopyranosyloxy)butane

Conditions

Conditions	Yield
With N-iodo-succinimide; trifluorormethanesulfonic acid In dichloromethane at 0℃; for 0.05h; Inert atmosphere; Molecular sieve;	85%

(R)-(-)-1,3-Butanediol Chemical Properties

Molecular Structure of (R)-(-)-1,3-Butanediol (6290-03-5):

EINECS: 228-532-0
IUPAC Name: Butane-1,3-diol
Molecular Formula: C₄H₁₀O₂
Molecular Weight: 90.121000 g/mol
XLogP3-AA: -0.4
H-Bond Donor: 2
H-Bond Acceptor: 2
Canonical SMILES: CC(CCO)O
InChI: InChI=1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3
InChIKey: PUPZLCDOIYMWBV-UHFFFAOYSA-N
Freely Rotating Bonds: 4
Index of Refraction: 1.437
Molar Refractivity: 23.6 cm³
Molar Volume: 89.9 cm³
Surface Tension: 37.1 dyne/cm
Density: 1.001 g/cm³
Flash Point: 121.1 °C
Boiling Point: 207 °C at 760 mmHg
Enthalpy of Vaporization: 51.56 kJ/mol
Vapour Pressure: 0.0541 mmHg at 25 °C
Water Solubility: 2.204e+005 mg/L at 25 °C
Refractive Index: 1.44
Sensitive: Hygroscopic
Alpha: -31 º (c=1 in EtOH )
BRN: 1718944

(R)-(-)-1,3-Butanediol Safety Profile

Safety Information of (R)-(-)-1,3-Butanediol (6290-03-5):
Hazard Codes: Xi
Hazard Note: Irritant
Risk Statements: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
WGK Germany: 3
RTECS: EK0440000
F: 3-10

(R)-(-)-1,3-Butanediol Specification

(R)-(-)-1,3-Butanediol (6290-03-5) is also known as 1,3-Butanediol ; (+/-)-1,3-Butylene glycol ; 1,3-Butylene glycol ; 1,3-Dihydroxybutane ; Butane-1,3-diol ; Methyl trimethylene glycol with appearance of colorless to light yellow liquid.

Product Name

(R)-(-)-1,3-Butanediol

Synthetic route

(R)-(-)-1,3-Butanediol Chemical Properties

(R)-(-)-1,3-Butanediol Safety Profile

(R)-(-)-1,3-Butanediol Specification

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