7564-64-9

Basic information

• Product Name: 3-METHYLPENTANE-1,3,5-TRIOL
• Synonyms: 3,5-Pentanetriol,3-methyl-1;5-pentanetriol,3-methyl-3;1,3,5-TRIHYDROXY-3-METHYLPENTANE;3-METHYLPENTANE-1,3,5-TRIOL;3-METHYL-1,3,5-PENTANETRIOL;Methylpentanetriol;3-METHYL-1 3 5-PENTANETRIOL TECH. 80%;3-METHYLPENTANE-1,3,5-TRIOL 80+%
• CAS NO: 7564-64-9
• Molecular Formula: C₆H₁₄O₃
• Molecular Weight: 134.17
• EINECS: 231-466-5
• Product Categories: Alcohols;Monomers;Polymer Science;Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 7564-64-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 216 °C0.5 mm Hg(lit.)
• Flash Point: 113 °C
• Appearance: /
• Density: 1.112 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.89E-05mmHg at 25°C
• Refractive Index: n20/D 1.475(lit.)
• Storage Temp.: Room Temperature
• Solubility: Chloroform (Heated), DMSO (Soluble), Methanol (Slightly)
• PKA: 14.43±0.29(Predicted)
• CAS DataBase Reference: 3-METHYLPENTANE-1,3,5-TRIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLPENTANE-1,3,5-TRIOL(7564-64-9)
• EPA Substance Registry System: 3-METHYLPENTANE-1,3,5-TRIOL(7564-64-9)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 7564-64-9(Hazardous Substances Data)

Usage

Uses

3-Methyl-1,3,5-pentanetriol is used in the synthesis of Mevalonolactone (M339040), in the synthesis of vitamins and isoprenoids such as steroids.

InChI:InChI=1/C6H14O3/c1-6(9,2-4-7)3-5-8/h7-9H,2-5H2,1H3

Synthetic route

3-Methyl-1,5-bis-(tetrahydro-pyran-2-yloxy)-pentan-3-ol → 3-methyl-1,3,5-pentanetriol (7564-64-9)

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

dimethyl 3-hydroxy-3-methylglutarate (56652-39-2) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With boron trifluoride-tetrahydrofuran complex for 18h; Heating;	88%

meglutol (503-49-1) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 16h;	45%
Multi-step reaction with 2 steps 1: 91 percent / SOCl2 / 0 °C 2: 88 percent / BF3*THF / 18 h / Heating View Scheme

mevalonolactone (674-26-0) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran
With lithium aluminium tetrahydride In tetrahydrofuran for 18h; Reflux;	2.1 g

1,1-diallylethanol (25201-40-5) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
(i) O3, CH2Cl2, (ii) LiAlH4, THF; Multistep reaction;
With ozone 1.) -50 deg C, 20-30 min; Yield given. Multistep reaction;

1,1-diallylethanol (25201-40-5) → (R/S)-3-methyl-5-hexene-1,3-diol (114580-75-5) + 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With lithium aluminium tetrahydride; ozone Product distribution; 1.) CH2Cl2, -78 deg C, 7 min; 2.) THF, RT, 12 h; different ozonolysis temperature;
With lithium aluminium tetrahydride; ozone 1.) CH2Cl2, -78 deg C, 7 min; 2.) THF, RT, 12 h; Yield given. Multistep reaction. Yields of byproduct given;

4-(β-hydroxyethyl)-4-methyl-1,3-dioxane (2018-45-3) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With oxalic acid at 150℃; under 4484 Torr; for 2.5h;

[1,3]oxathiolane-2,2-diyl-bis-acetic acid diethyl ester (86447-05-4) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 90 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 2: 100 percent / p-toluenesulphonic acid / CH2Cl2 / 4 h / 0 °C 3: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 4: 1) Mg / 1) ether, 2) 0 deg C, 15 min 5: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

2,2'-(1,3-oxathiolane-2,2-diyl)bisethanol (86447-06-5) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / p-toluenesulphonic acid / CH2Cl2 / 4 h / 0 °C 2: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 3: 1) Mg / 1) ether, 2) 0 deg C, 15 min 4: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

2,2-bis[2-(tetrahydropyran-2-yloxy)ethyl]-1,3-oxathiolane (86447-07-6) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 2: 1) Mg / 1) ether, 2) 0 deg C, 15 min 3: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

1,5-bis(tetrahydropyran-2-yloxy)pentan-3-one (86447-08-7) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) Mg / 1) ether, 2) 0 deg C, 15 min 2: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

diethyl 1,3-acetonedicarboxylate (105-50-0) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions

Yield

Multi-step reaction with 6 steps 1: 92 percent / BF3*Et2O / CH2Cl2 / 6 h / Ambient temperature 2: 90 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 3: 100 percent / p-toluenesulphonic acid / CH2Cl2 / 4 h / 0 °C 4: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 5: 1) Mg / 1) ether, 2) 0 deg C, 15 min 6: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

(R)-mevalonolactone (19115-49-2) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
In tetrahydrofuran

3-methyl-1,3,5-pentanetriol (7564-64-9) + benzaldehyde (100-52-7) → 1,3-O,O-benzylidene-3-methylpentane-1,3,5-triol (877308-88-8)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 60℃; for 18h;	100%
With toluene-4-sulfonic acid In toluene at 60℃; for 24h;	63%

3-methyl-1,3,5-pentanetriol (7564-64-9) → mevalonolactone (674-26-0)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 4h; Ambient temperature;	92%
With aluminum oxide; sodium bromite In dichloromethane for 1.5h; Ambient temperature;	85%
With peracetic acid; sodium bromide In ethyl acetate at 39.9℃; for 2h;	83%
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate In acetonitrile at 22℃; for 6h;	83%

3-methyl-1,3,5-pentanetriol (7564-64-9) → meglutol (503-49-1)

Conditions	Yield
In acetic acid butyl ester; nitric acid	85%

3-methyl-1,3,5-pentanetriol (7564-64-9) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 1,5-bis-dimethoxytrityloxy-3-methyl-pentan-3-ol (1033113-30-2)

Conditions	Yield
With dmap In pyridine at 0 - 20℃;	78%

3-methyl-1,3,5-pentanetriol (7564-64-9) + p-toluenesulfonyl chloride (98-59-9) → 3-hydroxy-3-methylpentane-1,5-diyl bis(4-methylbenzenesulfonate)

Conditions	Yield
With dmap; triethylamine In acetonitrile at 0 - 20℃; for 5h; Inert atmosphere;	73%

3-methyl-1,3,5-pentanetriol (7564-64-9) + 2,2-dimethoxy-propane (77-76-9) → 1,3-O,O-isopropylidene-3-methylpentane-1,3,5-triol (154066-61-2)

Conditions	Yield
With camphor-10-sulfonic acid In acetone at 20℃; for 24h;	66%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 80 - 90℃; for 3h;	42.5%

3-methyl-1,3,5-pentanetriol (7564-64-9) + epichlorohydrin (106-89-8) → 3-Methyl-1,5-bis-oxiranylmethoxy-pentan-3-ol

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 40℃; for 6h;	65%

3-methyl-1,3,5-pentanetriol (7564-64-9) + C6H11BO2 + sodium hydride (7646-69-7) → C10H16BO3(1-)*Na(1+)

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	63%

3-methyl-1,3,5-pentanetriol (7564-64-9) + tert-butyldimethylsilyl chloride (18162-48-6) → 5-{[tert-butyl(dimethyl)silyl]oxy}-3-methylpentane-1,3-diol (861389-35-7)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	50%

3-methyl-1,3,5-pentanetriol (7564-64-9) + Trimethylhydroquinone (700-13-0) → 2-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)ethanol (79907-48-5)

Conditions	Yield
With hydrogenchloride; zinc(II) chloride In 1,4-dioxane; toluene at 100℃; for 6h;	47%

pyridine (110-86-1) + Mn3O((CH3)3CCO2)6(pyridine)3 + 3-methyl-1,3,5-pentanetriol (7564-64-9) + tetramethyl ammoniumhydroxide (75-59-2) + acetonitrile (75-05-8) → (Me4N)2[MnIII13MnIV2O10(OH)2(3-methyl-1,3,5-pentanetriol(-3H))4(2-hydroxymethyl-3-methylbutane-1,3-diol(-3H))2((CH3)3CCO2)8(py)2]((CH3)3CCO2)2H*2py*2H2O

Conditions	Yield
for 1h;	25%

3-methyl-1,3,5-pentanetriol (7564-64-9) → 3-hydroxy-3-methylcadaverine (133213-14-6)

Conditions	Yield
With hydrogen azide; triphenylphosphine; 2,2'-azobis(isobutyronitrile) In tetrahydrofuran; benzene 1) RT, 1h, 2) 50 deg C, 3h; Yield given;

3-methyl-1,3,5-pentanetriol (7564-64-9) → (S)-mevalonolactone (19022-60-7) + (R)-mevalonolactone (19115-49-2)

Conditions	Yield
In water at 30℃; for 72h; Gluconobacter scleroideus IAM 1842; Yield given. Title compound not separated from byproducts;
In water at 30℃; Product distribution; different Gluconobacters and time of incubation;

3-methyl-1,3,5-pentanetriol (7564-64-9) → 1,3-O,O-isopropylidene-5-O-(t-butyldiphenylsilyl)-3-methylpentane-1,3,5-triol (877308-89-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent / camphorsulphonic acid / acetone / 24 h / 20 °C 2: 85 percent / triethylamine; DMAP / CH2Cl2 / 12 h / 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → 1,3-O,O-benzylidene-5-O-(t-butyldiphenylsilyl)-3-methylpentane-1,3,5-triol (877308-90-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / p-toluenesulphonic acid monohydrate / toluene / 24 h / 60 °C 2: 90 percent / triethylamine; DMAP / CH2Cl2 / 12 h / 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → 5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,3-diol

Conditions	Yield
Multi-step reaction with 3 steps 1: 63 percent / p-toluenesulphonic acid monohydrate / toluene / 24 h / 60 °C 2: 90 percent / triethylamine; DMAP / CH2Cl2 / 12 h / 20 °C 3: 85 percent / ZnBr2 / CH2Cl2 / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 66 percent / camphorsulphonic acid / acetone / 24 h / 20 °C 2: 85 percent / triethylamine; DMAP / CH2Cl2 / 12 h / 20 °C 3: 86 percent / ZnBr2 / CH2Cl2 / 1 h / 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → 5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-pentanal

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / triethylamine / CH2Cl2 / 20 °C 2: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / -78 - 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → ethyl (2E)-7-bromo-5-(methoxymethoxy)-5-methylhept-2-enoate

Conditions

Yield

Multi-step reaction with 6 steps 1: 50 percent / triethylamine / CH2Cl2 / 20 °C 2: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / -78 - 20 °C 3: 60 percent / CH2Cl2 / -78 - 20 °C 4: 79 percent / diisopropylethylamine / CH2Cl2 / 0 - 20 °C 5: 81 percent / hydrogen fluoride; pyridine / tetrahydrofuran / 0 - 20 °C 6: 45 percent / carbon tetrabromide; triphenylphosphine / CH2Cl2 / 0 - 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → ethyl (2E)-7-hydroxy-5-(methoxymethoxy)-5-methylhept-2-enoate (861389-37-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 50 percent / triethylamine / CH2Cl2 / 20 °C 2: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / -78 - 20 °C 3: 60 percent / CH2Cl2 / -78 - 20 °C 4: 79 percent / diisopropylethylamine / CH2Cl2 / 0 - 20 °C 5: 81 percent / hydrogen fluoride; pyridine / tetrahydrofuran / 0 - 20 °C View Scheme

Upstream product

• 674-26-0 mevalonolactone 
• 25201-40-5 1,1-diallylethanol 
• 2018-45-3 4-(β-hydroxyethyl)-4-methyl-1,3-dioxane 
• 19115-49-2 (R)-mevalonolactone 
• 503-49-1 meglutol 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 86447-08-7 1,5-bis(tetrahydropyran-2-yloxy)pentan-3-one 
• 86447-07-6 2,2-bis[2-(tetrahydropyran-2-yloxy)ethyl]-1,3-oxathiolane 
• 86447-06-5 2,2'-(1,3-oxathiolane-2,2-diyl)bisethanol 
• 86447-05-4 [1,3]oxathiolane-2,2-diyl-bis-acetic acid diethyl ester 
• 56652-39-2 dimethyl 3-hydroxy-3-methylglutarate 

Downstream Products

• 877308-88-8 1,3-O,O-benzylidene-3-methylpentane-1,3,5-triol 
• 117896-69-2 1-phenyl-4-hydroxypiperidine 
• 19125-34-9 1-phenylpiperidin-4-one 
• 871026-48-1 3,5-dihydroxy-3-methylpentyl benzoate 
• 503-49-1 meglutol 
• 154170-47-5 5-benzyloxy-3-methylpentane-1,3-diol 
• 154066-62-3 4-(2-Benzyloxy-ethyl)-2,2,4-trimethyl-[1,3]dioxane 
• 87137-49-3 methyl (RS)-5-benzyloxy-3-hydroxy-3-methylpentanoate 
• 101268-70-6 (RS)-5-benzyloxy-3-hydroxy-3-methylpentanoic acid 
• 60018-14-6 (S)-(-)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol 
• 877308-90-2 1,3-O,O-benzylidene-5-O-(t-butyldiphenylsilyl)-3-methylpentane-1,3,5-triol 
• 877308-89-9 1,3-O,O-isopropylidene-5-O-(t-butyldiphenylsilyl)-3-methylpentane-1,3,5-triol 
• 674-26-0 mevalonolactone 

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