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MilliporeSigma

296678

(S)-(−)-1,2,4-Butanetriol

98%

Synonym(s):

(2S)-(-)-Butane-1,2,4-triol, (S)-(-)-1,2,4-Trihydroxybutane

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$690.00

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About This Item

Linear Formula:
HOCH2CH2CH(OH)CH2OH
CAS Number:
42890-76-6
Molecular Weight:
106.12
UNSPSC Code:
12352001
NACRES:
NA.22
PubChem Substance ID:
24857865
MDL number:
MFCD00063213
Beilstein/REAXYS Number:
1719408

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Product Name

(S)-(−)-1,2,4-Butanetriol, 98%

InChI

1S/C4H10O3/c5-2-1-4(7)3-6/h4-7H,1-3H2/t4-/m0/s1

SMILES string

OCC[C@H](O)CO

InChI key

ARXKVVRQIIOZGF-BYPYZUCNSA-N

assay

98%

optical activity

[α]19/D −28±2, c = 1 in methanol

optical purity

ee: 99% (GLC)

refractive index

n20/D 1.475 (lit.)

bp

150 °C/0.04 mmHg (lit.)

density

1.19 g/mL at 25 °C (lit.)

functional group

hydroxyl

Quality Level

100

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(S)-(−)-1,2,4-Butanetriol 98%

Sigma-Aldrich

296678

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Sigma-Aldrich

237639

(2R,3R)-(−)-2,3-Butanediol

(S)-(−)-1-Phenylethanol 97%

Sigma-Aldrich

685836

(S)-(−)-1-Phenylethanol

(S)-(−)-α-Methylbenzyl isocyanate 98%

Sigma-Aldrich

220566

(S)-(−)-α-Methylbenzyl isocyanate

assay

98%

assay

97%

assay

97%

assay

98%

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

refractive index

n20/D 1.475 (lit.)

refractive index

n20/D 1.433 (lit.)

refractive index

-

refractive index

n20/D 1.5145 (lit.)

density

1.19 g/mL at 25 °C (lit.)

density

0.987 g/mL at 25 °C (lit.)

density

1.012 g/mL at 20 °C (lit.)

density

1.045 g/mL at 20 °C (lit.)

bp

150 °C/0.04 mmHg (lit.)

bp

77.3-77.4 °C/10 mmHg (lit.)

bp

88-89 °C/10 mmHg (lit.)

bp

55-56 °C/2.5 mmHg (lit.)

optical activity

[α]19/D −28±2, c = 1 in methanol

optical activity

[α]23/D −13.2°, neat

optical activity

[α]22/D -44.0°, neat

optical activity

[α]20/D −10°, neat

Application

(S)-(-)-1,2,4-Butanetriol may be used as a starting material in the enantioselective total syntheses of (+)-azimine and (+)-carpaine.[1]
It can also be used to prepare the following organic building blocks:
  • (+)-3,4-epoxy-1-butanol[2]
  • (2S,4S)-4-(hydroxymethyl)-2-ferrocenyl-1,3-dioxane[3]
  • (S)-1,2,4-triacetoxybutane via acetylation with acetic anhydride[4]
  • (S)-1,2,4-tris-(3,5-dinitrobenzoy1oxy)butane via esterification with 3,5-dinitrobenzoyl chloride[4]

General description

(S)-(-)-1,2,4-Butanetriol can be prepared via reduction of (S)-malic acid in the presence of borane-dimethyl sulfide.[4]

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG1938
BCCH1969
SHBK8570
BCBZ3224
BCBP9613V

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Enantioselective total synthesis of (+)-azimine and (+)-carpaine.
Sato T, et al.
Organic Letters, 5(21), 3839-3842 (2003)
An efficient asymmetric synthesis of 2-substituted ferrocenecarboxaldehydes
Riant O, et al
The Journal of Organic Chemistry, 62(20), 6733-6745 (1997)
Asymmetric Michael addition of thiophenol to maleic acid esters
Yamashita H and Mukaiyama T
Chemistry Letters (Jpn), 14(3), 363-366 (1985)
Facile access to (S)-1, 2, 4-butanetriol and its derivatives.
Hanessian S, et al.
Canadian Journal of Chemistry, 62(11), 2146-2147 (1984)

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