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Isopropyl-beta-D-thiogalactopyranoside

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Name

Isopropyl-beta-D-thiogalactopyranoside

EINECS 206-703-0
CAS No. 367-93-1 Density 1.37 g/cm3
PSA 115.45000 LogP -1.07210
Solubility soluble in water Melting Point 105 ºC
Formula C9H18O5S Boiling Point 438.4 ºC at 760 mmHg
Molecular Weight 238.305 Flash Point 219 ºC
Transport Information N/A Appearance white crystalline powder
Safety 23-24/25-36/37-22-36/37/39-27-26 Risk Codes 19-40-66-36/37/38
Molecular Structure Molecular Structure of 367-93-1 (Isopropyl-beta-D-thiogalactopyranoside) Hazard Symbols HarmfulXn,IrritantXi
Synonyms

Galactopyranoside,isopropyl 1-thio- (7CI);Galactopyranoside, isopropyl 1-thio-, b-D- (8CI);IPTG;Isopropyl 1-thio-b-D-galactopyranoside;Isopropyl thio-b-D-galactopyranoside;Isopropyl thio-b-D-galactoside;Isopropyl b-thiogalactopyranoside;Isopropyl b-thiogalactoside;

Article Data 15

Isopropyl-beta-D-thiogalactopyranoside Synthetic route

55692-87-0

isopropyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopiranoside

367-93-1

isopropyl β-D-thiogalactopyranoside

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; pH=10;98%
With sodium methylate In methanol for 0.5h;90%
With sodium methylate In methanol at 20℃; for 5h; pH=10;81%
29587-08-4

2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl-aethylxanthat

75-26-3

isopropyl bromide

367-93-1

isopropyl β-D-thiogalactopyranoside

Conditions
ConditionsYield
With methanol; potassium carbonate at 60℃; for 5h; Reagent/catalyst; Temperature;92%

isopropylthio-6-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbonate)-β-D-galactopyranoside

367-93-1

isopropyl β-D-thiogalactopyranoside

Conditions
ConditionsYield
With sodium L-ascorbate; fluorescein free acid In aq. phosphate buffer for 0.5h; pH=7.4; Irradiation;75%
10257-28-0

D-Galactose

75-33-2

2-propanethiol

367-93-1

isopropyl β-D-thiogalactopyranoside

Conditions
ConditionsYield
Stage #1: D-Galactose; 2-propanethiol With aluminum (III) chloride; acetic anhydride at 5 - 10℃;
Stage #2: With sodium methylate In methanol Reagent/catalyst;
74.3%
25878-60-8

D-galactose pentaacetate

75-33-2

2-propanethiol

367-93-1

isopropyl β-D-thiogalactopyranoside

Conditions
ConditionsYield
Stage #1: D-galactose pentaacetate; 2-propanethiol With boron trifluoride diethyl etherate In dichloromethane at 0 - 5℃; for 2h;
Stage #2: With sodium methylate In methanol
45.2%
75-33-2

2-propanethiol

4163-60-4

β-D-galactose peracetate

367-93-1

isopropyl β-D-thiogalactopyranoside

Conditions
ConditionsYield
Stage #1: 2-propanethiol; β-D-galactose peracetate With boron trifluoride diethyl etherate In dichloromethane at 0 - 5℃; for 2h;
Stage #2: With sodium methylate In methanol
45.2%
75-33-2

2-propanethiol

3068-32-4

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

367-93-1

isopropyl β-D-thiogalactopyranoside

Conditions
ConditionsYield
With potassium ethoxide Behandeln des Reaktionsprodukts mit Natriummethylat in Methanol;
4163-60-4

β-D-galactose peracetate

367-93-1

isopropyl β-D-thiogalactopyranoside

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / BF3*Et2O / CH2Cl2 / 1.5 h / 20 °C
2: 81 percent / CH3ONa / methanol / 5 h / 20 °C / pH 10
View Scheme
Multi-step reaction with 4 steps
1: thiourea; boron trifluoride diethyl etherate / dichloromethane / 12 h / 20 °C
2: sodium metabisulfite / dichloromethane; water / Reflux
3: potassium carbonate / acetone / 20 °C
4: sodium methylate / methanol / 20 °C / pH 10
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: BF3*OEt2 / CH2Cl2 / 0.17 h / Ambient temperature
2: 72 percent / NaOMe / methanol / 1 h / Ambient temperature
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) NaH, Molekularsieb 4 A, 2) 0.1 M BF3*OEt2, Molekularsieb 4 A / 1) CH2Cl2, 30 min, RT, 2) CH2Cl2, 30 min, RT
2: 90 percent / 0.5 M CH3ONa / methanol / 0.5 h
View Scheme

Isopropyl-beta-D-thiogalactopyranoside Specification

The Isopropyl-β-D-thiogalactopyranoside , with appearance of white crystalline powder, belongs to the classes of (1) Substrates ; (2) 13C & 2H Sugars ; (3) Biochemistry ; (4) Galactose ; (5) Glycosides ; (6) Sugars ; (7) Thioglycosides ; (8) Enzyme substrates ; (9) Carbohydrates & Derivatives ; (10) Carbohydrates . Besides its cas registry number of 367-93-1, it also has other registry number which is 30323-26-3. Its BRN registry number is 4631. Its systematic name is called propan-2-yl 1-thio-beta-D-galactopyranoside . And its IUPAC name is called (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-propan-2-ylsulfanyloxane-3,4,5-triol . This chemical is stable but incompatible with strong oxidizing agents.

Physical properties about this chemical are: (1) # of Rule of 5 Violations: 0 ; (2) ACD/BCF (pH 5.5): 1 ; (3) ACD/BCF (pH 7.4): 1 ; (4) ACD/KOC (pH 5.5): 6.7 ; (5) ACD/KOC (pH 7.4): 6.7 ; (6) #H bond acceptors: 5 ; (7) #H bond donors: 4 ; (8) #Freely Rotating Bonds: 7 ; (9) Polar Surface Area: 71.45 Å2 ; (10) Index of Refraction: 1.577 ; (11) Molar Refractivity: 57.43 cm3 ; (12) Molar Volume: 173 cm3 ; (13) Surface Tension: 63.9 dyne/cm ; (14) Density: 1.37 g/cm3 ; (15) Flash Point: 219 °C ; (16) Enthalpy of Vaporization: 80.25 kJ/mol ; (17) Boiling Point: 438.4 °C at 760 mmHg ; (18) Vapour Pressure: 1.58E-09 mmHg at 25°C ; (19) Melting point: 105 oC ; (20) Alpha: -31 °(c=1, water).

When you are using this chemical, please be cautious about it as the following:
The Isopropyl-β-D-thiogalactopyranoside should be stored at the temperature of -20°C. This chemical is irritating to eyes, respiratory system and skin. It may form explosive peroxides. Repeated exposure may cause skin dryness or cracking. It also has limited evidence of a carcinogenic effect. If you will use this material, wear suitable protective clothing, gloves and eye/face protection. Avoid contact with skin and eyes. Do not breathe gas, fumes, vapor, spray, and dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After use it, take off immediately all contaminated clothing.

You can still convert the following datas into molecular structure:
(1) SMILES:S(C(C)C)[C@@H]1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)CO;
(2) InChI:InChI=1/C9H18O5S/c1-4(2)15-9-8(13)7(12)6(11)5(3-10)14-9/h4-13H,3H2,1-2H3/t5-,6+,7+,8-,9+/m1/s1;
(3) InChIKey:BPHPUYQFMNQIOC-NXRLNHOXBD

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